I had spent my post-college years as a growth marketer while blogging on the side. Growth marketing paid the bills, but writing was my calling, and I often wondered if I would ever have the guts to stop dabbling and pursue it seriously.

I had already tried going full-time with my blog when I was twenty-five, but it wasn’t enough. In my mind, real writers didn’t churn out essays and newsletters; they wrote books.

With my twenties slipping away, writing a book became my white whale. I didn’t need to write a bestseller; I just wanted to write something I was proud to hold and share with others.

For years, I had pushed my writing dreams aside in favor of a stable career. But my fear of not achieving my ambitions began to outweigh my desire for financial security.

In part, that’s because I couldn’t shake the irrational suspicion that I might not make it to my 30th birthday. If that were true, I had less than two years to write my book. Otherwise, I would end up on my deathbed filled with morphine and regret. And I only wanted the morphine.

So, I made the leap. I left my job to write a good book before I turned thirty.

On the first day of my new path, I printed out an email exchange with author Steven Pressfield, who had given me feedback on my book idea. I smiled when I read his final piece of advice:

“Sometimes it’s best to plunge right in.”

Beneath the email, I placed a photo of a penguin diving into frigid waters. I was excited and optimistic about taking my own plunge.

I just wish I had known what was waiting for me in the waters below.

Free Fall

A year later, wine and laughs flowed freely between me and my partner Steph. We were celebrating the 80,000-word book draft I submitted to a developmental editor.

We talked about how the draft had taken longer than expected, concluding that all of the time I spent trading options, watching television, and researching was not a wasted effort. Those activities were simply the tax I paid for learning how to navigate the oddities of the writer’s life. And now that I had a full draft and this wisdom, finishing the book before my 30th birthday would be no problem.

The next step was to review the draft with Linda, an editor specializing in memoirs. In the hours leading up to the call, I nervously watched Linda’s icon race through the manuscript containing raw accounts of my life’s most difficult experiences. What would she think, and could she help me finish this thing?

After we introduced ourselves, Linda shared her initial impressions:

“You have some interesting plot points. But…it’s really flat. This is not going to change lives. It doesn’t speak to anyone. I think you should write an entirely different book.”

As Linda spoke, I felt my chest constrict. Her words were landing like a precision strike on my psyche, rather than the constructive feedback I was expecting. I felt a sudden, sickening sense of vertigo, as if the ground beneath me had given way. The manuscript I had poured my heart into, the dream I so desperately desired, was crumbling before me.

I wanted to shut my laptop and run. What did LINDA know anyway? But I also knew that running away would not help me finish the book. And I needed to finish. So as I learned to do as a kid, I suppressed my emotions, pretended to be okay, and listened to what she had to say.

Linda explained that I had two paths. The first path was to continue working on the memoir I set out to write. This path involved nuking all but one good chapter in my draft and learning how to write in a more descriptive style that would resonate with readers. This would probably take at least another year, and even with that work, the book may not land.

The second path was to write an entirely different book. Linda pointed out that I’m good at finding and sharing nuggets of wisdom. My existing blog audience comes to me for these nuggets, not my life story, and I would be better off offering readers a prescriptive self-help book. The call ended with me more confused than when we started.

Steph asked me how the call went. I told her that I didn’t feel great about what Linda said, but thought her feedback was directionally correct. As a next step, I would work on the two paths she gave me in parallel before deciding which one to take. There was still a lot more work to be done — a lot more than I had expected — but this was just part of the journey.

She knew I was hurting and disappointed, but respected my need to believe I could power my way through this setback. But over the next few weeks, it became clear that the hard-nosed pragmatism that had helped me navigate many of life’s setbacks would not work here.

One problem was that I was confused. I thought I was writing one book, but now I was being advised to write another. If I continued with my first idea, was I going to end up with a shitty and embarrassing memoir? Was I okay with that outcome? And if I went down the second route, did I have to let go of a year’s worth of work and begin again? That seemed impossible.

And then there was the fact that every time I sat down to write, I felt numb. My optimism and excitement about the project had faded. I wanted to watch television and drink wine and forget that I had ever tried to write a book. But it was too late to give up now. I had already told so many people about the book and built my identity around becoming an author.

Noticing my confusion and the rapid decline in my spirits, Steph suggested that I take a break from the book. I could always pick it back up once I felt better. Her suggestion — like almost everything about my life since the book review call — irritated me. Didn’t she know that I had to finish the book? How would taking a break solve the problem? I just needed to keep going.

I didn’t appreciate how bad my inner world had become until I went surfing on a warm spring day. Surfing had been my zendo for the last few years. I could enter the water angry and distraught and emerge with a zen-like appreciation for the simple beauty of a grain of sand. There was no emotional problem that could not be solved by a vigorous surf session.

I paddled out to the lineup and sat on my board, a leaden heaviness sitting on my eyes. As waves rolled in, I felt no motivation to chase them. The heaviness spread to my chest and arms, as if invisible weights were pinning me to my board. I wondered why I was out in this stupid ocean, doing this pointless sport I sucked at.

I looked at the other surfers, desperately wanting to inhabit their lives, convinced their struggles couldn’t compare to mine. I sat, waiting for the healing powers of the ocean and sun to cleanse me. But relief never came.

Instead, the corners of my mouth dropped downward, and I wept.

As tears raced down my cold cheeks, I held my breath and looked around me, hoping the other surfers would not notice a loser like me in the lineup. My mind chimed in: “How pathetic. You’re surfing and have a great life, and you’re crying and feeling sorry for yourself. What a joke.”

I gave up on catching waves and rode a wall of whitewater on my belly until I reached the shore. As I sat on the beach, I could no longer deny the truth: I was depressed. Not even surfing, my silver bullet for emotional regulation, could bring levity and light back into my life.

No, this was a different beast. It was the same one that led my mom to take her own life a few years earlier. I was in uncharted territory, facing a darkness I had never known before. Stoicism, pragmatism, and the other isms that had worked so well in the past were no match for this beast. I had no idea what to do in the face of such a formidable opponent.

I realized that whatever was happening was about more than my confusion and frustration about the book. The review call may have sent me over the precipice, but it was not the cause of this depression. I had been walking toward the edge for at least a year, and now I was in free fall.

As I moved my trembling fingers through the damp sand beneath me, my fear of not finishing the book gave way to my terror about the depression that gripped me. I had to find a way through or risk losing myself entirely.

Descending into Darkness

After the busted surf session, I was stuck in a groove of misery, lacking the insight, energy, or confidence to find my way out. Depression, I realized, was not a problem I could solve with my mind alone. That’s because my mind was the source of the problem. Instead of offering solutions, it whispered a scary suggestion: you can end this.

Losing control of my mind and will to live was terrifying, like being trapped in a car with no brakes on a twisting mountain road. If I was going to stop the car safely, I needed to tap into the part of me that recoiled at the word suicide being etched in my gravestone.

From living through my mom’s descent into the darkness, I knew that suicide was a selfish act. When you end your life, it’s the ones you love who pay the price. They’re left with the burden of grief, unanswerable questions, and guilt while you rest peacefully in the grave.

I didn’t want my friends and family to pay that price, but I also wondered if I had a choice. Both my mom and grandfather had committed suicide. Was I destined to follow the same path?

If anything was clear, it was that I needed a hard reset. My usual coping techniques like surfing, exercise, journaling, and meditation were not enough. I needed to find something potent enough to pull me out of this groove.

Having watched my mom battle depression for 10 years, I was deeply skeptical of the traditional solutions offered by the mental health system — pharmacological interventions, past-focused therapy, electroshock treatments, and psych wards. While these interventions worked for some people, they accelerated my mom’s demise. I couldn’t risk having a similar experience.

Unconventional healing modalities held more appeal. A friend had recently found his way out of a similar rut with a few months of ketamine therapy. While I thought ketamine was likely to help, the high cost of treatment and my lack of a stable income made this path unfeasible.

As I grappled with the pros and cons of various paths forward, I realized that I would never escape this rut by continuing my same routine in Southern California. What I needed was a change of scenery, a reminder that joy, beauty, and meaning were still possible.

I told Steph that I wanted to take a trip to see if it would help restore my sense of self. We decided that Bali was a good place to go. It was far away, fun, and perhaps the medicine I needed.

Bottoming Out

Traveling 8,700 miles across the globe was not the miraculous remedy I had hoped it would be. That first week in Bali, I remained the same lost, exhausted, and frustrated person I had been in Encinitas. Apparently, Confucius was right: Wherever you go, there you are.

At this point though, I was used to my depressed state. It seemed like the new normal, and so what if it continued for a few more weeks or months?

This line of thinking would have been fine if I had been the only person on the trip. But Steph was in Bali too, and she wanted to have an enjoyable reunion with the place she used to call home.

For as much as she wanted me to get better, her patience with my negative state was waning. I understood where she was coming from. Not only had I been a downer at home, but I was now the type of travel companion that I would advise people to avoid at all costs.

Still, I had no idea how to get better and felt like my biggest supporter was abandoning me when I needed her the most.

We decided to travel north to stay at a resort in the jungle. Maybe a few days outside the busyness of Canggu would bring us together. But that first night, we got into a shouting match that made me think that there was a good chance that I would lose myself and my partner to this depression.

I went to breakfast alone the next morning, hoping that the sunshine and plate of tropical fruit would wash away the tension from the previous night. As I was about to leave, I was relieved to see Steph arrive. We were supposed to tour the organic coffee plantation on the property, and I wasn’t sure if she would join me.

The tour featured a bubbly Balinese guide who led us through lush, jungle-like fields as he discussed the origins and operations of the plantation. On our walk to the roasting facility where we would sample the local coffee, we strolled into a small, open-aired room.

Two women with grey hair and deep wrinkles sat on the floor in front of a wooden table, their nimble fingers sifting through thousands of coffee beans with surprising speed. I asked the guide what they were doing. He explained that all exported coffee beans needed to look perfect. Otherwise, foreign buyers (like me) would not be satisfied.

The women were examining each bean and sorting them into two piles: those that were good enough for foreigners and those that would go to locals who weren’t so concerned about the shape of their beans.

While Steph and the rest of the group moved on to the coffee tasting, I felt compelled to stay behind and watch the women work. Despite their tedious task and buzzing flies, subtle smiles graced their sun-worn faces. One of the women looked up at me and beamed, making me feel welcome in a place where I was nothing but a gawking intruder.

I thought about all of the lattes I had consumed so mindlessly over the years. Never once had I paused to think about everything that had to happen for me to enjoy my morning coffee. And now the truth was here in front of me: every single bean I had consumed had been hand-sorted by people like these women, who likely earned less in a year than I did on my best days.

As I watched their hands move effortlessly through the never-ending pile of beans, I sighed and felt the tension in my neck release. The room brightened, and a small smile washed over my face. For the first time in months, the darkness that had engulfed me began to dissipate.

I thought about how lucky I was to be born in America, to have received a good education, and to be able to do work that mattered to me. I thought about the book, my white whale, and how it hadn’t unfolded as I had hoped. It suddenly seemed silly how much pressure I had put on myself and how miserable I had become in failing to meet my arbitrary expectations.

Buddhist Pema Chodron says, “The most difficiult times for many of us are the ones we give ourselves.”

Is that what was happening to me? Did my misery stem from some unnecessary story I created about how my life should be? And could I simply revise that story and move on?

I waved goodbye to the two women and headed to the coffee tasting, feeling a glimmer of hope about the future. My self-loathing still had a strong grip on me, but the pressure had decreased just enough so that I could start breathing again.

And as hope-infused oxygen began to enter my lungs, I knew the worst part of this depression was over. I had no idea what would happen with the book or my life, but I at least felt like everything would eventually be okay. The task was now to find a way to hold on to that feeling.

Surrendering to the Rip

Six months after the Bali trip, I woke up in an Airbnb in San Diego. My friends were still sleeping off a late night of drinking. I downed a banana and two cups of coffee before scrambling out the door with a wetsuit, surfboard, and container filled with my mom’s ashes.

It was my 30th birthday and the sixth anniversary of my mom’s death. For the last two years, I had envisioned this day as a special moment where I would be surrounded by loved ones and holding a copy of my first book as I entered my third decade of life.

But there was no book to hold, and I was forced to confront the gap between my expectations and reality on the bleary-eyed drive to a new surf break.

I thought back to what happened after my depression loosened its grip on the coffee plantation in Bali. I had returned home feeling like myself again and with a renewed vigor to write the book from a more informed and grounded place.

I started by re-reading my original manuscript, concluding that the story I had tried to tell was too big and would take years to make it good. I decided to discard most of that draft and write a smaller chunk of the story in a more descriptive, emotionally resonant way.

To improve my memoir-writing skills, I devoured niche memoirs and took notes on the type of writing I liked. As I put those lessons into practice, I asked other writers for feedback. Not only did these people help me improve my work, but they made writing a more fun and less isolating pursuit than it had previously been.

I also started writing a prescriptive self-help book. That gave me another book to pour my energy into when the memoir became difficult. And because the writing style was similar to how I had blogged for years, the words came more easily.

All of this effort gave me a sense that I was moving somewhere, that within a short period, I would certainly be able to finish one book if not two. That sense of progress was motivating and filled me with the confidence I had lost after the manuscript review with Linda.

Reflecting on the “progress” from the last six months on the drive to the surf, I realized that all I had to show for my efforts was a discarded manuscript and fragments of new book ideas. I had done many things, but my dispersed efforts left me no real pathway to finishing anything.

And now that I had arrived at my 30th birthday, my deadline for being a real writer with a published book, with no book in hand, it was hard to deny the reality of the situation. I wasn’t on the cusp of finishing a book. I was a flailing writer who talked about writing a book and who had no clear path to actually finishing one. In fact, I felt less certain about what I was doing than when I started two years earlier.

When I arrived at the surf break, I got out of the car with a heavy feeling in my face and chest. As I put my wetsuit on in the cool December air, my head throbbed from the previous night’s activities and the weight of the realization about where I was in my quest to finish the book.

I grabbed my board and mom’s ashes and made my way down the beach. As my bare feet hit the cool Pacific Ocean, I closed my eyes and imagined my mom’s spirit joining me on the surf that I hoped would cleanse me of the disaster that the book had become. I sprinkled her ashes into the ocean, set the empty container on the beach, and began paddling out. I may not be an author, but at least I had my mom with me in the Pacific.

On my way to the lineup of this punchy beach break, wall after wall of whitewater halted my efforts. I paddled for 10 minutes without making much progress and began to wonder if I was going to catch a wave today. I took a breath and looked to my right. Two other surfers were cruising out without much effort. Ah, there’s a rip. I paddled twenty yards to my right, found my way into the rip current, and arrived at the lineup without taking any more waves on the head.

As a surfer, you learn to look out for rip currents, which are powerful bands of water that pull you out to sea. If you’re caught in a rip current that you don’t want to be in, your instinct is to try to paddle against it. But resisting the rip is unwise. Since the sea is stronger than you, fighting it only burns your limited energy and increases your chances of drowning.

Instead of fighting the rip, it’s better to let it take you until it ends or to swim parallel to the shoreline until you’re out of it. Then you can go about business as usual.

While the rip zipped me to the lineup on my 30th birthday surf, I realized that for many reasons, writing the book had become like paddling against a rip current. As I paddled harder, I thought I was inching closer to my dream of being a published author. But I was wrong.

I was stuck in a rip, and the more I fought the insurmountable force, the more exhausted I became. My depression before Bali was a warning sign. And the last six months of effort were my last bits of energy. I was exhausted and had lost sense of what I was doing.

Writing the book was not the dream I thought it would be. As the rip of becoming an author tired me out, the book became a constant source of anxiety and insecurity. Whatever confidence I had in myself as a writer had dissolved into a not-so-subtle self-doubt.

Continuing along the same path was only to lead to peril, not the outcome I had hoped for. It took me getting to my deadline without a book in hand to wake up to what was happening.

By this point, I knew what I had to do. I had to let the book go and surrender to the rip. That way, I could make it back to shore without drowning.

But I was scared to give up on the book. I had quit my job, poured two years into writing, and told all of my friends that I would be an author. My ego and identity were wrapped up in an ambition that I had failed to fulfill.

What did it say about me if I gave up?

I wasn’t sure, but it was the only path forward. I had exhausted myself into surrender.

Rethinking Ambition

“You sensed that you should be following a different path, a more ambitious one, you felt that you were destined for other things but you had no idea how to achieve them and in your misery you began to hate everything around you.” — Dostoyevsky

A few weeks after my birthday, I stopped working on any of the book ideas and stopped telling people I was writing a book. Giving up on the book was not so much a decision as it was a slow acceptance that I no longer had the will or strength to fight. Perhaps I would return to the project someday, but for now, I needed to take an indefinite break and move on with my life.

For the next few months, I deliberately avoided setting goals or expectations for myself. I was afraid of what would happen without my core ambition, but wanted to live life as it came and see what emerged. I wasn’t ready to attach myself to a new professional pursuit.

What emerged first was an intensifying love story with surfing. Each session left me feeling healthy, content, and liberated from the pressure I had put on myself with writing. Spending weekdays chasing lines of energy in the Pacific Ocean transported me back to the freedom of childhood. Sunshine, birds, and warm showers suddenly seemed profound.

Surfing was fascinating, in part, because I had no idea where it was taking me. I knew I had fun, enjoyed improving, and felt better when I did it, but there was no finish line to cross or external achievement that I could show to other people. It was inherently rewarding, like writing a journal entry that you know no one else will ever read. And that was enough reason to keep doing it.

My relationships outside of surfing also began to flourish during this period. With more time and energy on my hands, I said “yes” to all invites from new and existing friends. As my social web grew wider and deeper, I realized how much of my life satisfaction came from the people around me. I began to value good laughs with friends more than even creative work.

When friends or strangers asked me what I did with my days, I now said I was a flaneur, a surfer, or a house husband. I got used to the unimpressed looks I received in rooms where people were gushing about their big ambitions. I was happy to be happy and living a simple life without any orientation other than enjoying the day at hand.

The only thing that made me uneasy during this period was how happy I seemed to be without any particular ambition driving my life forward. It was unfamiliar and odd to feel satisfied without any external purpose to hold onto.

Up until this point in my life, ambition was my driving force. Growing up, ambition meant studying hard to get into the best school possible. Once I did that, it meant excelling in college so that I could get a high-paying job in finance. When I did that, it meant saving money and finding meaningful work.

These shifting ambitions were my source of fuel. They motivated me to work hard and gave me a sense of direction when life turned dark. And when I accomplished what I set out to do, I grew more confident in my ability to build the life I wanted.

But then the ambition of writing the book came, and unlike my other ambitions, the toil did not lead to the spoils. It led to disappointment and depression. I struggled to make sense of the situation while it was happening, though I knew there was no one to blame but myself.

As far as I was concerned, there was no legitimate excuse for not finishing. I had everything I needed to complete the mission and still came up short. It felt like an unforgivable and indulgent waste of two years that destroyed my self-confidence and filled me with self-loathing. The only reason I let go was because I had exhausted myself into surrender, not because I wanted to do it.

I expected the post-book life to be difficult, but then something unexpected happened. In the months following the surrender, the striving and judgmental layer of my mind began to soften. I no longer berated myself for being a failed author. Through surfing, being with friends, and navigating the world without any real direction, I had unintentionally found a pathway to the equanimity I thought the book would bring me.

Letting go of my dream was, in a weird way, exactly what I needed to enter a new season of life. And that new season seemed to have less to do with hard-charging ambition than it did with realizing that my satisfaction came from non-ambitious places.

Today, as an example, I woke up to the sounds of birds, surfed for three hours, and worked on this essay at a new cafe. I picked up groceries at Costco, sat in traffic, and video-chatted with friends before cooking dinner for my wife. Honestly, it felt like a perfect day.

And today was not a reprieve from an otherwise busy life. It followed the rhythm of how I’ve lived for the last 18 months. I wake up without any firm plans and try to map my activities to the evolving needs of my mind and body as the day progresses. Repeating this cycle leaves me feeling relatively happy and relaxed most of the time.

Almost nothing I do is ambitious in any classical sense, nor will it lead to any impressive creations, large financial returns, or invitations to come on podcasts. And while I’m okay with this, for now, my formerly ambitious self still has unanswered questions about this path:

Am I wasting my potential? How long can I keep this up? Is this enough?

Basically, despite feeling pretty good, part of me still wonders if I’ve become a hedonistic man-child who is throwing his life away. It’s a fair question, though I’ve come to see that this questioning comes from the narrow scripts we have about what it means to live well.

In Turning Pro, the writing hero Steven Pressfield who advised me to “plunge right in” to my book, offers a take on ambition that resonates with the part of me that’s suspicious about my current path,

“Ambition, I have come to believe, is the most primal and sacred fundament of our being. To feel ambition and to act upon it is to embrace the unique calling of our souls. Not to act upon that ambition is to turn our backs on ourselves and on the reason for our existence.”

When I started my blog seven years ago, I would gobble up this type of self-help hype talk. I loved well-packaged ideas and distilling life into its essential truths. But now, I look at Pressfield’s idea of ambition and wonder what I found so profound.

His words now sound less like Truth than they do some clever prose that makes ambition out to be the God that it certainly is not. For some people or seasons of life, feeling big ambition and acting on it may be a good move. But if I’ve learned anything since giving up the book, it’s that you can be perfectly happy without striving for anything other than to take care of your basic needs.

My ambition, if you want to call it that, seems to have shifted away from external goals and toward listening to the whims of a given day. Some days, I want to be a better surfer. Other days, I want to be as healthy as I can. Other days, I want to be a great husband and friend.

The throughline of these shifting desires, though, is that I want to enjoy my life. And my pathway to doing so is not aiming toward some goal, but rather living a fluid existence filled with activities I enjoy and people I love.

In Gift From the Sea, Anne Morrow Lindbergh shares a view that counters Pressfield’s and that helps explain some of the change that’s happened in my relationship with ambition,

“Perhaps one can shed at this stage in life as one sheds in beach-living; one’s pride, one’s false ambitions, one’s mask, one’s armor. Was that armor not put on to protect one from the competitive world? If one ceases to compete, does one need it? Perhaps one can at last in middle age, if not earlier, be completely oneself. And what a liberation that would be!”

I think Lindberg is on to something. Perhaps all of my former ambitions, including the book, were armor that protected me in a world obsessed with achievement. And once I let go of the book, my primary armor, without replacing it, I began to become more of myself.

And that self, it turns out, is not the Ivy leaguer, Wall Street Banker, Startup Grinder, Great Book Author I’ve been or tried to be at various points of my life. Those were simply masks I wore, and now that they’re gone, it turns out I’m a simpler and less ambitious guy than I fancied myself to be at one point. Failing to finish the book helped me see and accept that surprising truth.

If I have any ambition these days, it has no specific aim. Rather, it’s an orientation toward living fully, without really knowing what that means, that is helping me let go of all of the false ambitions that have driven me up to this point.

And like a tide that goes out and reveals the contours of a previously hidden and vibrant reef, perhaps I’m finally starting to see what’s underneath all of that armor that I carried for so long.

The reef, I know, is not yet fully exposed. Maybe that will happen with time; maybe it won’t. I’m okay either way. I’ve grown to enjoy walking this weird and unpredictable path in the dark.

Keep Nosara Green. Leave Only Footprints.

It reminded me of Leave No Trace, an environmental conservation philosophy that encourages people to leave nature as they found it. Basically, leave only footprints.

I trekked onward and noticed the sounds of leaves and sticks breaking beneath me. With each step, the jungle path became more matted and lifeless than it had once been. The change was almost imperceptible, but it was happening.

It occurred to me that no matter how hard we try to minimize our impact, we can never leave nature quite as we found it. Even our footprints transform the places we walk.

The impact of small actions in the natural world is obvious, hence the popularity of ideas like Leave No Trace. But we seem to forget that this dynamic also occurs outside of nature.

As we navigate careers, conversations, and the responsibilities of life, our goal is not to leave no trace. In fact, we often want to leave the biggest trace we can imagine. We strive for an impact large enough to create a positive legacy, garner adulation, and imbue our lives with meaning.

But in our relentless striving to leave our mark, we forget something important. We forget that it’s the tiny footprints we leave behind, not our grand plans, that actually change the people and world around us.

The importance of footprints became clear to me a few years ago. I was writing a memoir and interviewed friends and family to get a better understanding of myself.

At the end of the interviews, I always asked: What’s something you know about me that I don’t know about myself? 

I hoped this question would reveal my blind spots through the people who knew the best and worst parts of me. Most people said something unmemorable, but my friend Dror said something that shook me:

“You would be a great dad.”

A tight ball formed in my chest and remained long after the interview ended.

At the time, I had never seriously considered being a dad, let alone a good one. In part, that’s because I had a complicated relationship with male role models.

My biological father was a drunk gambler who disappeared when I was two years old. In his absence, my mom fell for a rotating cast of sketchy and selfish men. My grandfather is likely the only reason I didn’t end up in jail. He was a good man who showed up when it counted.

But even with my grandfather’s influence, the idea of fatherhood never sat well with me. I always assumed that I would be no better than my father or the men my mom brought around.

It’s with this backdrop that Dror offered those six penetrating words: you would be a great father. I don’t know if he remembers what he said, but he left a footprint that changed my life. 

His words opened a door that allowed me to reconsider my self-image and ideas about fatherhood. Over the next few years, I began to understand that I was not the same as my father or my mom’s other love interests. I was not destined to leave my kids in the dust or exist as an unreliable outlaw.

I could have been like these men, but I made different choices. And as Dror helped me understand, those choices mattered. Perhaps I could be a half-decent father.

I don’t have children, so the jury’s still out on the great dad thesis. But no matter what happens, it’s clear that Dror’s footprint nudged my life in a better direction.

Looking back, I can think of dozens of similar examples. Each event started with something as simple as kind words or an act of generosity from people who took their footprints seriously. And those small acts made a profoundly positive difference in my life.

Taking your footprints seriously requires you to believe that the little things count, even when you can’t see the outcome. That’s because the impact of your footprints, unlike the dollars you donate, is not measurable or predictable.

Footprints are like a gust of wind at sea. That gust can start a chain reaction of energy that moves thousands of miles across the ocean. The energy slowly builds until it has transformed into a wave that arrives to the delight of a surfer looking for his next ride. The wave crashes onto the shore, subtly changing the sandy ocean bottom and the spirit of the surfer who will re-enter land life with a smile.

Every day, we leave behind dozens of footprints that have the potential to be like this gust of wind. Those footprints could be the attitude we bring to work, the presence we offer to loved ones, or the curiosity we bring to a conversation. These subtle acts are less about what we do and more about how we show up in the world.

Trusting that how you show up matters is an act of humility and faith. No one will put you on a magazine cover for being consistently kind, patient, and generous. And you will never quite know when you change someone’s life. Yet, you show up anyway.

We’ve all heard of or met people who make a name for themselves by saying that they care about this or that cause. But behind closed doors, they are mean-spirited and uncharitable. Magazines love these people and don’t care to mention the muddy footprints they’ve left around the world.

But it’s that mud, not the praise, that will define their lives.

We all reach the end of our time at some point. It’s at this moment when the seriousness with which we took our footprints will matter most. Hooked up to a series of tubes, we will no longer be blinded by the legacy, fame, and admiration we once craved. Those desires will have faded and lived on with the young.

With clear heads, we will finally have time to think about the millions of footprints we made as we traversed the world. And hopefully, we will be satisfied with the traces we left behind.

Mom would be 56 years old today, and I wonder what her life would have become.

I like to imagine that she would be living her dream: a slow and sunny life on the sandy shores of Florida. But I can only speculate about how her story may have unfolded. She passed away six years ago after a decade of teetering on the edge of darkness.

I know that Mom would not have liked that she was nearing sixty. She was fond of being young and would have resisted the wrinkles, aches, and extra paddling of midlife.

But then again, I can’t even know this with any certainty. What if Mom’s fierce resistance to aging had loosened its grip by now? What if she had a newfound appreciation for the accumulated wisdom in each of her wrinkles? I’m again left to wonder.

Losing someone you love leaves you with many unanswered questions. You’re perpetually suspended in a state of not knowing. That’s a particularly uncomfortable place to be if you have a strong desire to control your world.

The only thing you have to grasp onto is the fading memory of who the person once was. But that memory is an imperfect glimpse at the past that offers no real answers or comfort.

Birthdays of lost loved ones are interesting moments in the grieving process. They can surface memories and questions that don’t come up on other days. And even if you want to live the day like it’s nothing special, people remind you that this day is not ordinary.

On Mom’s birthday, I receive supportive texts from friends and family. They seem to think that I will be in shambles. But so far, that has not been my experience. Mom’s birthday has felt like any other day.

With time, I’ve come to believe that grief does not walk a predictable path. Grief is more like floating down an uncharted river than hiking a well-known trail. You don’t know what will come, when it will arrive, or how long it will last. You float and hope everything turns out okay.

On some days, often when you least expect it, grief will knock on your door with angry fists. And on other days, you won’t even think about the person you lost. In such an uncertain environment, staying sane requires you to learn to let go and accept life as it unfolds.

While Mom’s birthday has not been difficult in the ways that other people expect, I still treat it as a sacred day. Instead of going about my usual routine, I go into the day without any goals, work, or pressure. My only intention is to spend the day as I want.

In a sense, her birthday is a dedicated day for me to float down the river of grief and see what emerges. A few years ago, that float took me on an unexpected ride.

On March 3, 2020, I woke up in Encinitas, California. I drank coffee, grabbed my surfboard, and walked barefoot down Neptune Avenue. I watched the waves from the top of the wooden steps that led down to Grandview, the break where I was learning to surf.

The setup was perfect — small, clean, and uncrowded waves. I zipped up my wetsuit and paddled out expecting to have a great session. The surf gods had other plans for me. I spent an hour missing waves, faceplanting, and banana peeling on the takeoff.

Leaving the dreamy surf a little frustrated, I headed to a restorative yoga class to settle down. A solo lunch and lazy afternoon of reading and looking at the wind-swept ocean followed. As the afternoon progressed, I noticed something interesting. The waves were cleaning up, opening up a window for another session. This time, I would surf without any expectations.

During the first 30 minutes of the session, I scored two beautiful, long lefts and rode them to completion. I then duffed it on a few rights but laughed it off. While waiting for the next set, a fin emerged from the water three feet in front of me. My legs curled up onto my board until I saw fins all around me. 

Dolphins. I exhaled and smiled.

There were at least six dolphins and likely more I couldn’t see. My eyes suddenly darted to the horizon where a large, dark line had formed. A set wave was moving in my direction.

I paddled toward the peak, turned around, and popped up once I felt the board lift. Stoked that I had not faceplanted, I was now racing down the face of a peeling right-hander.

Twenty feet ahead of me, I noticed a fin in the water. A dolphin had joined me for the ride! Time slowed as we cruised together in harmony for the next 20 seconds. When the wave closed out, I took a belly ride to shore while the dolphin rejoined her friends. 

As I sat on the beach, salty tears dripped down my face as little bumps formed on my arms.

I thought back to a trip Mom and I took to Clearwater Beach on the Gulf Coast of Florida. We took a boat out one day to see dolphins. Mom held my arm and giggled as a pod of dozens of dolphins followed the boat and played in its wake. It was one of the last times I saw her truly happy.

Then I thought of the blue sticky note that Mom put on her bathroom mirror a few months before she passed. It read: Clearwater Beach Surf Shop. The note was a reminder of the dream she was working toward. She wanted to work at a surf shop in Clearwater and get a shack with an extra bedroom for me to visit.

I wondered if my recent decision to move to Encinitas and spend my days surfing had anything to do with Mom’s unlived dream. I wasn’t sure. But I did know that being in the ocean made me feel more connected with her, especially when I saw dolphins.

As my mind raced between the past and the present, I knew deep in my heart and soul that it was Mom who had joined me on that wave.

That knowing was absolute. I didn’t need to believe in reincarnation, God, or anything else to know its truth. I felt Mom’s energy and strength flow through me and the body of the dolphin.

It’s been four years since that day, and I’m left to make sense of the experience.

The first question: Was it real?

It’s difficult to know. 

It felt real, but I may be like the child who confuses the shadows of the night for monsters in the closet. Just a grieving man confusing a coincidence for a paranormal connection with his late mother.

I have sympathy for this interpretation. Yet that sympathy doesn’t penetrate the part of me that knows that this experience was real. As real as anything explainable with math or physics anyway.

During my life, I’ve had a handful of experiences that follow a similar rhythm. Something happens, and that something shatters my understanding of what’s possible. As I’ve had more of these moments, I’ve learned that I can either accept or reject what happened, but I can’t explain it. Words and the limitations of the rational mind can’t capture such experiences.

I’ve also learned that knowing the “realness” of these events is not important.

Illusions or not, these experiences point toward something worth knowing. In a sense, they remind us that there is something core to life that we may never fully understand. We can begin to understand it, but not through the narrow lens of science and intellectualism. Its only with faith and humility that we can begin to understand.

Each of these experiences has occurred in wildly different ways. However, they have all given me what feels like a glimpse of the all-knowing interconnectedness that ties reality together.

People use concepts like God, mystical experiences, and consciousness to hint at this interconnectedness. But like my words, these concepts are insufficient. They are only loose approximations of what it’s like to have encounters with the ineffable.

My ability to notice these encounters seems to have accelerated on my 25th birthday. That was the day I held my mom’s hand as she took her final breath. The absurdity and pain of that day seemed to crack open a doorway to more moments like the wave at Grandview.

Before that day, I was bound by mental and spiritual shackles. I would have seen my ride with the dolphin as nothing more than an enjoyable and lucky event. But with my shackles loosened in the wake of Mom’s death, my heart opened to supernatural interpretations of these moments. And with time, I’ve begun to see the wisdom embedded within these previously off-limits interpretations.

As I’ve reflected on my ride with the dolphin, it’s become clear that it was more than a cathartic moment of reconnection with Mom. That experience, with the help of time and reflection, helped me understand that Mom’s love endures even in the absence of her physical presence.

The aftermath of that wave felt like the many times when I was afraid as a kid and received one of Mom’s hugs. Her comforting embrace reminded me that her invulnerable love would always be with me. The wave had a similar effect, reminding me that Mom didn’t need to be in this world for her love to endure.

Today, another one of Mom’s birthdays will come and go. I still don’t know how her story would have unfolded and can’t share new moments with her. I wish I could.

But thanks to that experience on the wave I will never forget, I have something that allows me to rest easy. I know, deep in my heart, that Mom’s love will always be with me.

And what more could a man without his mother ask for?

Solitude is precious.

That’s what comes to mind as I lean back on my forearms and nuzzle my toes into the soft sand of Playa Carmen. It’s the first discernable thought I’ve had in a few hours. Now that the unbearable heat of a Costa Rican afternoon has loosened its grip, my mind is working again.

All around me, friends gather in small circles to share laughs and light beers. Surfers snag their final waves of the day, performing as much for themselves as for the land-dwellers who watch them. Cicadas buzz loudly in celebration of the sun’s descent below the horizon.

I’ve spent the last two weeks bopping down the coast of Costa Rica discovering the textures and rhythms of unfamiliar waves. Friends have appeared here and there, but I have been on a primarily solo expedition to deepen my ongoing love story with the ocean.

At least that’s what I thought when I began this trip.

But as I sit on this beach, alone and typing furiously on my phone with no desire to communicate with anyone but the voice inside my mind, it feels like there is something other than the pursuit of waves that is emerging from this trip.

I’m not unfamiliar with the rhythms of solo travel. I spent multi-month periods of my twenties hopping around foreign lands, floating like a dandelion in the wind to wherever life took me. I enjoyed that aimless and solitary period. I had no home base and was on a mission to figure out who I was and what I wanted. Solo travel was indispensable to the process of self-discovery.

But now, these self-inflicted periods of solitude seem out of place. I live in a city I enjoy, am happily married, and believe that the only thing that matters at the end of life is that we share it with loved ones. Yet from time to time, I still hear the call to hit the road and see what happens.

I often listen to that call, knowing that it’s a signal that something needs to be worked out. I’m just not always sure what that something is. The trip always reveals the answer.

Last year, the call took me to the surf-filled coast of France and Spain, where I spent two weeks exploring new waves, puttering around, and enjoying good food. 

It was only when I returned home from Europe that I realized how that trip helped me unlock a new relationship with creativity. Solitude allowed me to re-examine my stale relationship with writing, and I came back with a renewed vigor for sharing ideas. That was not the intention of the trip. It’s just what happened, and the feeling endures to this day.

But what is this Costa Rica trip all about?

On the surface, it was completely unnecessary. I had no real reason to be in Costa Rica outside of my love for surfing and distaste for the moderately cold and rainy winter days of Northern California. That reason was enough to book a plane ticket, but I was curious to see if something more profound emerged.

I think I’m starting to see what that something is, and I’m slowly finding it in the many feelings of discomfort that I’ve had while navigating life near the equator on my own.

Being alone, now that I’m married and settled in San Francisco, is not as comfortable as it used to be. When I was young and had no real home, drifting around felt more normal. Not just to me, but to people who heard my story. People don’t turn their heads when a lost soul in his twenties is basking in solitude, but some people do when you’re married. 

Oh, you’re married, why isn’t your wife with you? Is she okay with you being here?

Answering these questions isn’t difficult, but the fact that they’re now being asked reminds me that something has changed. And while I think such questions are often a projection onto me of what people believe life after marriage has to be, they are a good forcing function to make sure I’m still doing something I want to do and not repeating the wandering escapism of my youth.

The experience is also different for me. I now feel that solo trips make me miss out on things I enjoy back home. I see packs of travelers laughing and drinking and sharing stories with people they love. I watch lovers embrace during sunsets. I feel like an aging, stone-faced wallflower when I see young people enjoying the bliss of their first year on the road.

These feelings and experiences raise questions that weren’t as relevant during my earlier years: Why am I here? Should I be at home? Am I too old for these trips?

This trip has also surfaced the nagging insecurities of an earlier version of me. In some ways, I feel like I’m a new kid at school trying to navigate the oddities of a middle school lunch.

As I pass through my days, I look around awkwardly, hoping that the cool kids will welcome me to their table and tell me how glad they are that I’ve arrived. I want to feel like a person worth knowing, someone with people to see and things to do. But this type of emotional validation does not make it into my days. 

And so I’m left alone to sit with my questions and insecurities.

This experience is particularly noticeable in the surf towns I like to visit these days. I wake up at dawn to squeeze the maximum juice out of the morning surf window. It’s an unbelievably exciting and energizing period for me. I really am living my dream. But after that session is done, I eat a well-deserved meal and my thumbs start twiddling.

If you’re not surfing, tropical surf towns aren’t very exciting places. As the heat picks up around 11 am, sluggishness consumes my mind and body. All I can seem to do is sit lazily in the shade or retreat to an air-conditioned room. From there, I wait.

What am I waiting for? Mostly for the sun to set, which on some days offers a window where the wind drops and the ocean cleans up to allow another round of surfing.

But whether or not that window opens up, I’m left with hours of uncomfortable moments.

I think this discomfort is the point of this trip.

The uncomfortable quiet of my experience is something that I need to feel. For what reason? I’m not sure yet. But the awkwardness, isolation, and silence — the things that I spend so much of my life trying not to feel — appear to have good and healing properties.

I can think of a few benefits to these feelings.

The first is that they help me remember why it’s worth having loved ones and friends in this life. I realize how nice it is to have these people around. They really do make life worth living. 

Not only do they give me the sense that I am someone, but they are joint gatekeepers of the mundane, sad, and profound experiences we share. And simply having shared memories of those experiences is a deep source of joy and connection in my life.

In the absence of the people who enrich my life with meaning and purpose, another benefit of discomfort bubbles to the surface. I have the chance to explore who I am without these people and the comfort of feeling that I belong.

In Letters to a Stoic, Seneca says:

“Set aside a certain number of days, during which you shall be content with the scantiest and cheapest fare, with coarse and rough dress, saying to yourself the while: ‘Is this the condition that I feared?’ 

While Seneca is talking about practicing financial poverty as a reminder of how little you need, my solo expedition offers something similar. By creating an environment in which I’m forced to practice social poverty and feel all the feels of solitude, I’m remembering just how little I need to be and feel okay in the world.

While I’ve had many uncomfortable moments, they have not killed me. Nor have they stripped me of satisfaction. On most days, I wake up with a healthy dose of stoke and find myself sleeping well at night. Knowing that I can still be content living with the ups and downs of being alone in an unfamiliar place is a good reminder. Wherever I am and whoever I’m with, I am indeed okay.

Feeling gratitude for loved ones and knowing how little I need for contentment are valuable lessons, but they’re too reductive. They don’t quite get at the beating heart of this experience. There is something deeper to solitude. 

This something is difficult to describe, but it feels like entering the clear and sunny eye of a hurricane. In the chaos of the violent storm that surrounds me, I’m realizing that I can still tap into the equanimity that is always there at the core if I can just remember that it exists and muster the courage to get there.

Yes, that’s part of it. Solitude is helping me remember something fundamental to the experience of living an imperfect and sometimes difficult existence.

And remembering that has a similar effect as a vigorous surf session. After hours of intense paddling, underwater demolition, and brief moments of bliss, my body buzzes with the invulnerable knowledge that everything I need is always with me. Striving and yearning disappear as I trot like a barefooted zen zombie along the beach.

This is how I’m starting to feel as I get closer to the end of this period of solitude, and it’s similar to how I’ve felt during other such periods.

Solitude, in a weird way, is slowly washing away the accumulated muck of the life I know that has taken me far from the simple core of existence where true equanimity rests. As the muck begins to clear, I’m starting to see myself and the life I’ve built more clearly.

This process only seems to work if I surrender fully to the experience. Surrendering involves feeling it all — the lulls of the day, periods of peace, and longing for what I know.

Surrendering is not easy. When my legs start moving or the call to drink alcohol arrives or I grab for my phone, it takes courage to avoid distracting the discomfort away.

The distractions come in seemingly benign forms — a podcast I should listen to, making plans for the next day, and so on. I’ve learned with time that these distractions are a form of self-sabotage. While they may alleviate short-term discomfort with what seem like productive or harmless actions, they subtly subvert the process of rebirth and growth that solitude offers.

The most difficult part of avoiding the distractions comes when my mind starts asking hairy questions: Is anyone back home thinking of me? What am I doing here without loved ones? Why am I not a part of the friends huddled together and enjoying the sun’s final act of the day?

So far, I’ve allowed my mind to race without numbing it with distractions.

Being booze-free for the first time in my life, taking headphone-free walks, and regular meditation have helped. But no tricks or techniques can take away the small stings of discomfort. So like a meditating zen-master who ignores the fly that has landed on his eyebrow and continues to focus on the rhythms of his breath, I trudge forward knowing the discomfort is part of the experience.

Now that I’m sitting on this beach and beginning to understand what this period of solitude may be about, I can’t help but wonder if all of this was necessary. Did I need to isolate myself in a foreign land, embrace discomfort, and limit distractions to get here?

And is here even a better place than wherever I was before?

Maybe, but it’s impossible to know.

What I do know, however, is that solitude has helped me in the past and appears to continue to have some function in my new life. In a sense, these self-induced periods of being alone seem to facilitate a process that will allow me to return to the life I know with soft, still eyes. 

Like the water and sunlight of Spring help plants emerge in full stride after a harsh winter, solitude is an elixir that helps me remember my core during the many seasons of life.

For most people, I doubt it’s necessary or possible to venture to foreign lands for weeks or months at a time to experience this opening and re-alignment of mind, body, and spirit. My guess is that even a few hours or a day of solitude in the place you call home can at least nudge you in the direction I’m talking about.

And yet, how often do we create space for even an hour to explore the wisdom of solitude?

But I also know that a longer adventure, if you can make it work, certainly forces your hand. With nowhere to hide, all of the frenetic energy that tells you to be somewhere else and to cover up the acne of existence starts to melt away. In its wake, there is now room for something new.

In a world that has hijacked and monetized our attention at nearly every waking (and even sleeping) moment, we have been convinced that we must know what’s going on and constantly striving to be somewhere else and someone different. There is no escape unless we actively fight against this pressure to do anything but be alone.

It may be more difficult today than 50 or 200 years ago to be alone, but our strained relationship with solitude is not a modern problem. While writing Gift from the Sea in the 1950s, writer Anne Morrow Lindberg shares her observations about solitude from the sandy shores of Florida:

“We seem so frightened today of being alone that we never let it happen. Even if family, friends, and movies should fail, there is still the radio or television to fill up the void.”

Sounds familiar, doesn’t it? Lindberg goes on to describe why she has resisted these forces and made her way to the coast of Florida for a few weeks of alone time:

“Only when one is connected to one’s own core is one connected to others, I am beginning to discover. And, for me, the core, the inner spring, can best be refound through solitude.”

Like Lindberg, whose work I discovered on the sandy shores of Costa Rica, I’m realizing that being alone is slowly helping me to reconnect with my core. Yes, that’s it.

When I return home soon, I suspect I will see the fruits of this re-connection not only in the inner stillness that has begun to replace the discomforts that solitude has surfaced but in a deeper connection with all those people who graciously allowed me to go on this adventure and re-emerge into their lives.

And perhaps that’s what this whole trip has been all about.

I want to tell you a story about how an unexpected encounter with nature changed everything.

In the summer of 2021, my girlfriend Steph and I spent all of July working on a course designed to help people use technology to get more out of their time. By the time launch day rolled around, we were exhausted but had pocketed $20,000.

I decided that we should use those course winnings on a trip to Alaska. The Last Frontier seemed like a great place to unwind and recharge, and I planned a two-week trip that included epic hikes, a glacier tour, whale watching, salmon fishing, and good food.

As we boarded our first-class flight to Anchorage and took a sip of the free champagne, my mind fantasized about a magical Alaskan experience that would deepen our budding romance.

But as war strategists say, no plan survives contact with reality. 

The first few days of our trip were not the romantic fairy tale I had imagined. Upon landing in Anchorage, we spent our time quibbling about this and that as we drove through landscapes that belonged in a Bob Ross painting.

On the third day, we woke up at dawn to ride bikes through Denali National Park. I thought this biking adventure might turn things around, but during the first 10 miles, we continued bickering. If we had not been the only two people biking in the park, we probably would have parted ways and enjoyed the alone time.

I started wondering if we were going to have to cut our trip short, and that’s when life handed us an unplanned gift in the form of a snacking grizzly bear.

When we were five miles from the end of our bike ride, a tour bus driver stopped and rolled down the window. He said a bear was munching on berries close to the road about a quarter mile ahead. There was no way to predict how he would react to us, so he advised us to stop biking and go back. Before we could ask him the many questions we now had, he drove away and left us to fend for ourselves.

We were less than prepared for this news. While each of us had spent time in nature, we were not the type of people who carried first-aid kids, went overnight camping, or knew what the hell you do when a bear decides to eat lunch on your path.

But this little snafu proved to be the medicine we needed. As the reality of dealing with a wild grizzly bear sunk in, the tension and quarreling dissipated. With our lives on the line, we had to drop the drama and start working as a team on a mission to survive.

We agreed that we could not turn back. That involved biking 10 miles (mostly uphill), and neither of us had the water supply or quads for such an endeavor. That meant we either had to convince the next bus to let us on or that we had to bike past the bear. The team preferred the bus option.

We had no cell phone service or knowledge about the bus schedules, so while we waited for another bus to come, we moved closer to the bear to observe him. He would get sick of eating berries and move on at some point, right? Well, apparently not. This guy went on munching for the better part of an hour, ignoring our pleas for him to move on.

A bus eventually came and we waved it down. The driver said he couldn’t take us onboard, so we asked him about biking past the bear. He said it wasn’t smart, but we could give it a go and see what happens. He wished us luck and kept driving. Thanks man.

To his credit, his cheeky answer was another gift. Given our ignorance about the situation, his lack of a hard no for going past the bear gave us the confidence we needed to try it out. Steph and I hugged each other, exchanged nervous glances, and agreed not to look the bear in the eyes.

With that, we began to peddle, quickly realizing that we were moving uphill into a fierce wind. Neither of us was moving more than a few miles an hour, but we weren’t turning back now. I reached the bear first and tried not to look at him, but he looked up for the first time and gave me a long stare. I looked at him and realized just how big bears are. 

My heart thumped a little faster as I prayed that he didn’t chase me down. I looked back to see that he now had his eyes on Steph. She had fallen back quite a bit, and it wasn’t until she was a couple hundred yards past the bear that I took a breath. Mr. Bear seemed unphased and resumed his adventures in Berrylandia. We both peddled hard for a half mile and finally stopped to discuss what had happened.

We laughed about how stupid we were and how helpless we would be if the bear came after us. But he didn’t, and it was nice to feel the rush of connection that comes from dicey moments. The quibbles of the past few days already seemed like they were from another part of our lives. All that mattered was that we were together and safe.

As we prepared for the last few miles of the journey, we caught our breath and passed an apple back and forth. Right as I handed the apple to Steph for the final bite, I saw something emerge from the woods about 50 yards away. It was moving fast and toward us.

Another grizzly, much bigger and more active than the other one. Oh boy.

My eyes bulged and I told Steph to come to me. A bear was walking toward us. She giggled and told me to stop joking until she looked back and froze in silence. I considered telling her to run, but she appeared unable to move her legs. My mind turned off as my instincts took over.

My arms raised high above my head and a series of tribal-sounding chants emerged from my mouth. I don’t know where these sounds came from or what they were, but I’m sure I could not make those noises again. Upon hearing these sounds, the bear immediately changed course. He made a hard right, darting into the woods on the other side of the road. My chants continued as I watched the trees closely. A bus driver pulled up thirty seconds later.

I pleaded for him to take us on the bus, and after deliberating for too long, he relented, helped us load our bikes, and cursed us for being dumb enough to bike through the park. The bears had become a lot more active with fewer people visiting Denali during the pandemic. Didn’t we know?

I had never been so happy to enter a hot, packed bus of chatty middle-aged tourists. As I sat down, the image of that bear walking toward us remained burned in my mind. Some passengers asked me what happened, but I was not ready to speak. Steph told the story while I remained in awe about the size of the grizzly, the sounds that came out of me, and our proximity to a violent death.

Let go or be dragged

When I’m surfing and the ocean holds me underwater, I often think of the Buddhist saying: “let go or be dragged.” It’s a reminder to let go of the desire to breathe, relax, and wait for the ocean to allow me to resurface. It always does. Over time, I’ve learned to shortcircuit my desire to fight the ocean. That’s an unwinnable battle that only makes the experience worse.

While I’ve learned to let go in the water, I sometimes forget to apply this idea to land life. 

The Alaska trip is a good example. I had an idea in my head about what our trip should be. The plan was to have the BEST TRIP EVER, and when reality deviated from those expectations, I resisted. And that resistance dragged me and Steph further away from enjoying our time.

But sometimes life has a few tricks in its book that force you to let go of your expectations. In our case, that trick came in the form of two Alaskan grizzlies. While neither bear did anything other than be a bear wandering around, the experience of being that close to and helpless against a bear in the wild put everything into perspective.

I don’t — and I doubt Steph does either — remember what we were even quibbling about at the start of the trip. Almost certainly something silly. 

But I do remember the joy and gratitude that bubbled to the surface after we came out unscathed from the encounters with the bears. The opportunity to continue enjoying this life and the experience of being together, even for one more day, felt like a gift.

After the bears, all expectations went out the window. I let go of all my ideas about the trip and simply lived out the experience of being in Alaska with someone I love and everything that came with it. And once I let go of the plans and expectations and started living more fully in the moment, one of the more magical and unexpected events of our relationship played out.

At the end of the first week of our trip, I woke up groggy and exhausted. We were supposed to go on an all-day trek up to a glacier, and I didn’t feel like going. I nearly bowed out until I thought about how those bears had given us a second chance to live more fully. So I got myself together, and Steph and I headed for the trek to the Harding Icefield.

After five hours of intense hiking, we reached a stunning view of a glacier that stretched for miles and looked like it belonged to some land other than Earth. As we sat down to enjoy some snacks, I surprised us both by taking out the ring that I had carried around for the last 9 months and asked Steph to marry me.

She said yes.

Some locals sensed love in the air and followed us to take pictures of the proposal.

Making sense of the experience

Looking back on the proposal, marriage, and many good times that followed, I can’t help but consider the role of those grizzlies.

I had no plans of proposing on that trip or on the day that it happened. Sure, I carried a ring, but I figured I might use it in the next 5 years if and when the moment felt right. Even 15 minutes before the proposal, the idea had not crossed my mind.

In my attempts to make sense of it all, I like to think about what John Lennon said In “Beautiful Boy (Darling Boy):” “Life is what happens to you while you’re busy making other plans.” 

I didn’t know what he meant until the Alaskan journey that led to an unplanned proposal. You see, it was the bears that allowed me to let go of my original plan and focus on simply being present with life as it unfolded. And paying attention to the full beauty of our experience together is what gave me the courage to take the leap with Steph at that glacier.

As I noodle on that experience now, it’s humbling to realize how the random unfolding of life leads us in directions that no plans can account for.

I mean, had we started biking 20 minutes earlier on that day in Denali, maybe we would not have seen any bears. Maybe we would have been killed by a bear. Maybe we would have continued quibbling and missed the chance to start over and take our relationship to the next level.

I can’t know for sure because you can never know the counterfactual. All you know is what happened, and the rest is conjecture.

What I do know now is that regardless of how it happened, the process of letting go is what allowed us to stop getting dragged during our vacation and to embrace the unpredictable twists and turns of the experience. We needed to chill and roll with it to allow the beautiful moments to emerge.

Zooming out beyond that trip, it’s clear that so many of the most important forks of life follow a similar path. There is some plan, and while I grasp onto it with all I have, the randomness of the world causes me to lose my grip and chart a new path.

Whether that randomness comes in the form of people, things, experiences, or bears that I did not forecast, these deviations all play a role in moving life in a new direction. Sometimes that direction is a good one; other times it isn’t. And often we don’t even know whether it’s good or bad until enough time has passed for us to connect the dots backward.

What I take from these experiences is that my desire for control over my life and the world is a fool’s errand. Life does not offer certainty or control, no matter how much we want it. There are no guarantees in this world. None. And when you begin to see that this is the fundamental, unalterable nature of life, you can learn to let go and surrender to the unknown.

I think this is what Lennon meant when he said, “life is what happens to you while you’re busy making other plans.” He was reminding us that life is fundamentally unpredictable and uncontrollable. No matter how diligent we are with our planning, intentions, and goals, there will be surprises that muck it all up.

That doesn’t mean that we shouldn’t try to plan or direct our lives, but it does mean that we should remain open to the flow of life that does not care about our plans. Or at the very least, we should recognize that life becomes easier and more enjoyable when we stop resisting.

To do otherwise is no different than fighting a wave that will hold you down as long as it wants. If you’ve ever found yourself in that situation, you understand that the wave is not what will kill you; it’s the panic and fear and grasping to get to the surface that does you in.

It’s only in learning to let go that we can finally be free to exist as we were meant to be.

Too many adults become serious people.

Serious about work. Serious about politics. Serious about mowing their lawns. Serious about everything!

I want to make a case against being so serious, but first, I must make a distinction. I have no qualms with people who take the act of living seriously. Life is brief, and I commend anyone who tries to make the most of their time.

The seriousness I’m talking about is different. It’s a pernicious form of seriousness that emerges the day you accept the myth that life has to get harder, busier, and less enjoyable with time. This seriousness is bad news. 

It’s a wet blanket on adulthood that suffocates the childlike looseness and curiosity that makes life worth living. And it’s the loss of that looseness and curiosity that worries me.

This worry comes from direct experience, so let’s begin there.

Serious dude to mellow bumpkin

If you met me today, you might be surprised to learn that I was once a very serious guy. It was the kind of seriousness that I now resist, but that made sense at the time.

You see, my early life was heavy. Or at least it felt that way. I had to escape poverty, and that felt like serious business. I didn’t see any room for error or games in that pursuit. I only had room for focused effort, hypervigilance, and prayers for a lucky break.

For the first 25 years of my life, I felt like I was climbing a mountain and could not stop to take a breath until I had basic financial freedom. My ongoing battle with poverty meant that I never fully relaxed. I had many wonderful times, but it’s now clear that there was a limit on my joy meter.

Once I had some cash in the bank, my situation changed. The cash didn’t solve everything, but it turned the pressure down. It was as if I reached a flat spot with a beautiful vista on my climb up the mountain. I finally had time to breathe and widen my focus. 

As I enjoyed the view, something (probably a self-help charlatan) told me to stop climbing the mountain. It was time to regroup and take a look at my inner world. I could always keep climbing later on if I needed to do so.

That decision to pause upended my life, sending me into a difficult process of unlearning, decompressing, and shifting my identity. While I didn’t know it at the time, I was learning to live without the ferocious focus and seriousness that directed my youth.

Little by little, my inner and outer world began to soften. I started laughing more, connecting with a wider group of people, enjoying simple moments, and perhaps most importantly, taking myself less seriously. Collectively, these changes made nearly everything about life more enjoyable.

By my 30th birthday, my orientation toward the world had shifted radically. I was open to the random unfolding of life and felt very little connection to my past. I no longer felt obligated to do anything other than show up fully. I was at ease.

This was a strange orientation to have, especially considering where I started. For a long time, a part of me resisted this shift. It felt indulgent and unserious and like I was heading down a lame path. But at some point, the perpetually striving part of my serious self faded away and transformed into a silly curiosity that felt like enough on its own.

The other strange part of this transition away from seriousness is that I was moving in the opposite direction from many of my friends. As I started feeling more like a kid discovering the world for the first time, friends seemed to gravitate towards the more rigid and responsibility-focused idea of adulthood that everyone is always talking about.

But my own meandering experience was enough to convince me that not only is it possible to avoid the pull toward seriousness with age, but that it can be a rewarding shift if you can find a way to make it work. And that’s the next part of the equation: how does this type of loosening coexist with the unavoidable responsibilities of adulthood over time?

Can you stay loose?

These days, a lot of friends ask me when I’ll stop living like a kid and start being a real adult again. Embedded within the question is the idea that living in this way simply cannot last. At some point, one has to become serious again. Or so they seem to think.

But my answer for the moment is always the same: so far it’s working, and I don’t know if or when that will change. Why shake up a formula that’s working?

I think this question comes up a lot because it’s not immediately obvious how a loose orientation toward the world is compatible with the real and serious business of adulthood: paying the bills, working toward goals, taking care of kids, being a good partner, trying to do good in the world, and so on.

But even though it’s not obvious, it’s certainly possible. I still lead a fairly normal life where bills get paid, necessary work gets done, and responsibilities are taken care of. The difference is just in the spotlight that I put on certain areas of life.

I spend most of my days chasing waves, exchanging small talk with strangers, and avoiding self-created stress and striving. Practically speaking, that means that previous areas of focus like increasing my net worth, moving up the career ladder, and maximizing my potential have taken a lower priority.

Now, an open question is whether or not this reorientation of priorities is good for the long term. It’s certainly possible that I’m on a path that will leave me with deathbed regrets.

But while it’s possible, it doesn’t feel likely.

One guidepost I use to think about whether this path has legs is thinking about what I’ve valued most in my 31 years of life. I’m not old, but three decades of life is enough data to get a sense of what worked and what didn’t work.

And when I think about my life in those terms, what I’m most proud of are the times when I stopped striving, pulled out a big floaty, and waded down the river of life.

The moments where I had one too many drinks and lots of giggles about nonsense with friends and strangers. The endless days I’ve spent checking surf reports and flapping around the ocean. The years I’ve spent traveling without purpose and reading books. These are the moments I cherish.

Before I leaned into the looseness, the moments I cherished looked quite different. I was proud of getting into a great university, making a good living, solving problems, building systems at startups, and other classic markers of achievement. Those pursuits now feel like they were done by some other person and are no longer interesting to me.

With time, they seem more like means to an end than a representation of my life or who I am. They were mechanisms for enabling the freedom I now have to enjoy a simpler existence. And to my surprise, that simpler existence seems closer to what I want and more satisfying than my younger self would have guessed. At least for now.

As to how these ideas hold up or change over time, I have no idea. Given the magnitude of shifts in thinking and values over the last decade, I can only imagine that similar unpredictable shifts will happen over the coming years.

A thought experiment for you

By this point, I think you have a sense of why I’m in favor of taking a less serious approach than is considered normal for adulthood. And while I’ve shared my path to this conclusion, I’d like to explore how this idea of resisting the pull toward seriousness could be useful for you. Or at the very least, I’d like you to consider what rejiggering the balance between seriousness and play looks like throughout your life.

To do so, let’s imagine that you’re accompanied by a two-year-old child on a morning walk.

While you lock the front door, you hear the child cry out with joy. She’s pointing at a beautiful yellow flower near the garden. Before you get to the end of the driveway, she’s giggling at a squirrel eating a nut at the base of an oak tree. As you walk down the street, she grabs your leg firmly as she sees a cat emerge from under a car.

The entire walk is like this. Pure discovery and presence.

Now imagine that you took the same walk without the child. What would you see and think about on your walk?

If you’re in the mode of being a serious adult, perhaps by the time you get to the end of the driveway, you may have seen some weeds that need to be pulled or bird poop on the car that needs cleaning.  You may also be thinking about the many things that you have to do today.

You throw in Airpods, queue up a podcast, and go on walking to avoid further irritation.

This is a bit of a silly example, but do you see the point?

During your solo walk, you’re thinking about adult stuff. The things you need to do, the problems you need to solve, and so on. Maybe you’re thinking about good stuff too like an awesome date you had or how you’re stoked about a new promotion. It doesn’t matter.

The point is that you’re likely lost in some story in your head. You’re not in the moment, and you’re missing all of the wonderful stuff of life — the sunflower, the squirrel, and everything else the child notices. And maybe those seem like trivial observations, but I think being a person who can notice that type of thing enhances nearly every area of life.

The child is the opposite of most adults. She is not lost in some story about what her life is or what it needs to be. She’s simply living, fully present with the seemingly infinite novelty, joy, and pain that exist when you’re experiencing the world for the first time.

If there is any takeaway from this essay, it’s that you can (and may benefit from) seeing the world more like the child. Instead of being engrossed in the incessant dialogue of the adult mind, try to see the world with fresh eyes. Even if you can do it only once a week, that’s better than nothing.

The philosopher Jiddu Krishnamurti once said, “The day you teach the child the name of the bird, the child will never see that bird again.”

Krishnamurti gets to the core of my quibbles with allowing yourself to become too serious. As you navigate life, the tendency is to start to think you understand and know things. You develop ideas, names, and concepts for all that you encounter. You see a tree and it’s not interesting because it’s just a tree and who cares? You have plans, goals, and ambitions to get to. Nonsense!

You don’t need to lose your childlike curiosity as you age. And remaining loose doesn’t mean that you have to be enamored by every tree you see. But what if you could nudge yourself toward being a person who can appreciate small pleasures like a beautiful tree or a cool breeze on a sunny morning?

What might a subtle shift like that do for your life?

I don’t know why this is happening, and I’m not here to play the blame game. Adults want more friends and need real answers, not another dissertation about the root causes of adult loneliness.

Below, I share a few ideas and techniques that have helped me build a socially vibrant life as an adult. Not everything that has helped me will help you, but I suspect that some of it will.

Okay, you get it. Let’s get to the good stuff so you can stop listening to a stranger on the internet and find more friends to share life with.

Don’t be a hermit

We played a game called “hermit” in my fraternity. If you were asked (forced) to play, you had to grab six beers, sit in a corner of the room, and stare at the wall in silence until you finished your beers. Hermit is a great game for getting drunk, but no one makes friends playing the game.

Making friends in adulthood follows a similar dynamic. Friendship is built on shared experience, and you can’t have that shared experience if you play the adult version of hermit, which is to stay at home, DoorDash your ice cream, and watch Friends for the fourth time.

So if you’re serious about making more friends, pick up a sharpie and write “I WILL NOT BE A HERMIT” on your bathroom mirror. Then, go out into the world in whatever ways you can manage.

Work from the same cafe for a week and practice chatting with the baristas. Say hello to people at the dog park. Say yes to any invitations you get. Do anything but sit in your house expecting that people will knock on your door and cure your loneliness. No one is coming to save you.

Now that you’re motivated to leave the house, let’s talk about how to be with people.

Don’t be dull

You’re a weirdo. I’m a weirdo. We’re all weirdos. Not weirdos in a creepy way, but people with beating hearts and blushing faces and eccentric beliefs and interests.

Don’t hide your quirks from people. Tell a stranger that you think Bukowski is a beast of a man, but that his poetry makes your blood pump. Let a colleague know that you want to open a food truck that serves pupusas and peanut butter pie. Don’t settle for dull, surface-level talk.

Sharing what makes you tick helps you in three ways. The first is that you can exist in the world as YOU, not some shell of a person who walks through life afraid to be who they are. The second is that you find kindred spirits. And third, sharing your interests makes you more interesting, and being interesting is worth at least 25 likeability points.

But Calvin, what if people think I’m weird? You’re going to have to get over that. Some people will think you’re weird, but who cares? We’re all heading for the grave one day. It’s better to be a weirdo with friends than dull and lonely in your brief moment on this spinning rock.

Park your ego at home

People don’t care that you went to Princeton, traveled the world, and now make a living as a fledgling writer. Let your grandma tell that tale. No one worth knowing cares about what you’ve done or what you own; they care about who you are.

Who you are is revealed by how you behave. Are you present, curious, positive, honest, kind, reliable, and overall a good lad who will show up in both the good times and the bad? If so, you’ll make more real friends than the stuffy credentialites who sip espresso martinis and ask, “So…what do you do?”

Get curious

Pretend that every person you meet is God herself. You can’t impress God. She already knows all of your good deeds and dirty secrets. The best you can do is to learn from her.

When you believe that everyone is a god who can teach you something, you will stop being a judgmental asshat and start finding points of connection with more people.

Store clerks, cab drivers, used-book store dwellers, naive youths, temporary lovers, and snoopy neighbors will suddenly become wells of wisdom and friendship.

Most of these people will not become friends, but some of them will.

Don’t fret about bad impressions

It feels crummy when you say the wrong thing at a party or are irritable and “off your game” when meeting new people. I’ve had many restless nights in bed replaying the tape in my head about how I could have done something differently in a social encounter.

However, time has revealed that almost all of my fretting about social stumbles has been a big waste of time and energy.

No one becomes your friend because you present yourself perfectly. The people who you want to stick around enjoy your company even when you’re not as charming or affable or funny or graceful as you want to be. They like you despite (and sometimes because) of your quirks.

So if you flub something up, dwell on it for a bit, but let it go as fast as you can and go on living.

Find the forums that work for you

There are endless ways to meet people, but depending on your interests and personality, you will find it easier to form friendships in some contexts than others.

Some people love meeting friends of friends; other people dig meeting strangers. Some people enjoy one-off events; others enjoy regular meetups over shared hobbies. Some people love going out for drinks; others thrive at intimate dinner parties and poetry readings.

Don’t worry about whether you’re an extrovert, introvert, or whateververt. There is no “right” or “best” way to meet new people or nurture relationships. All that matters is that you find what feels good to you.

If you don’t know what you like, pour yourself a glass of whiskey, try many activities over the next six months, and pay attention. Stop doing the stuff you don’t like, and double down on the forums that you enjoy.

Be responsive and flexible

The early stages of friendship are fragile. You and the other person are feeling each other out. If there is an initial flame, nurture it with gasoline. Respond to texts, send memes, share invites, and change your schedule to make time for the person.

Don’t be a “sorry for the delay, but I’m a bad texter and have been busy” type of person. Your lack of responsiveness will suck the air out of the flame of friendship and leave dog poo on its doorstep. And you will be left standing in the stinky ashes wondering why you still don’t have friends.

Avoid lukewarm connections

Friendship is a decision between you and another person to make the time and space to get to know the weirdest parts about each other. For this process to work, you both need to be into it.

Sadly, that’s not always the case. Sometimes you think someone is awesome, but they don’t think the same about you. Other times, someone likes you, but you’re kinda “meh” on them. And sometimes, you’re both only hanging around because it’s convenient.

Don’t waste time on any of these variations of lukewarm connections. These sluggish relationships will suck the limited time and energy you have, preventing you from building the rewarding relationships that are available if you find the courage and patience to build them.

And if someone you like doesn’t like you, don’t take it personally. You may not be their cup of tea, or they may already have a vibrant social life. The reason does not matter. What matters is that you don’t waste time with people who don’t want to have you in their lives.

Even when it’s fast, it’s slow

In college, you can make friends quickly. Making friends as an adult is different. People are busy, spread out, and often less open to letting new people into their lives.

They’re also in different stages of their lives. Some people are in grind at work mode, others are in young parent mode, and others are drifting souls who aren’t sure if they’ll be in the same town a month from now.

The complex social landscape of adulthood means that adult friendships take more time to build. It often takes at least a year to build enough trust and shared experience with a new person to call them a real friend.

So don’t get too worried if you’ve been trying for a few months and don’t have new besties. That’s normal!

Don’t forget: people are lonely as hell!

Do you know what this picture is? It’s the sad and lonely inner world that plagues most people in our hyper-connected and fast-moving era.

Modern life gives us free porn and burgers in bed, but it is also overwhelming and leads many of us into an isolating spiral of worry, comparison, and doubt. And if you stay in that spiral for too long, you may begin to believe that you’re the only lonely person out there.

The good news is that you’re not the only one. Not even close. Most people are spiraling and want more friends to share this crazy life with.

So as a final tip, do yourself a favor: Stop feeling bad about yourself and the current state of your social life. There is a vast world of fellow lonely souls who want to connect with people like you. If you want proof, put on some pants and interact with the real world.

Talk to 10 strangers. Host a dinner party. Organize a morning run. Take a drawing course. Just get out there. You’ll be surprised by the warm reception you’ll receive. And little by little, your social life will become more vibrant. I promise.

Alright, I’m done babbling for now. Put your phone down and get after it.

I’m going to tell you a story about how birds changed my life. Yes, that’s right, birds.

My path to the birds began in the spring of 2019. I started waking up at three in the morning and could not get back to sleep. My mind had many questions for me, and they could not wait until the morning:

Is your girlfriend good for you? Is this the right job? Why did you say that joke at dinner?

I don’t know Mr. Brain, but can we revisit this in a few hours? I need to get more sleep!

The restless nights turned into uneasy days. Simple problems suddenly felt less solvable. I laughed less often and had a gnawing tightness in my chest. And my thinking, typically clear and grounded, turned into a circular and muddy web of looming worries about this and that.

At 26 years old, I was familiar with these symptoms. They were signs that change was on the horizon. What change? Only God knew. Like a storm that’s still far out at sea, I only knew that something was coming. As to how bad it would be, time would tell.

In truth, I was not too worried about this particular storm. Sure, there were a few cracks in the foundation of my life, but no water flowed into the house just yet. With enough journaling, meditating, and traveling, I thought I could seal the cracks before the storm arrived.

But then I received a call from Rob, my right-hand man at work. Rob’s agreeable nature and bookish proclivities made my life both easier and more fun. His call came a few days before we were supposed to meet in Lisbon to lead a week-long event for 50 people.

Rob had bad news. His grandfather had fallen ill and was not going to make it. He would still come to Lisbon, but after that, he was leaving the company to pursue his dream of becoming the next Hemingway. He had realized that life was too short to do anything else.

His story struck a chord. Eighteen months earlier, I had lost my mom to suicide. And a few years before that, I lost a mentor to cardiac arrest. I understood what Rob meant when he said that life was too short to delay his dreams. And I began to wonder if I could really sweep my looming problems under the rug. Wasn’t life too short to ignore the call for change when it arrived?

Ten days later, Rob and I headed to a rooftop bar to celebrate the end of the event in Lisbon. One drink turned into another and another and another, and five hours later, we were deep into a discussion about the brevity of life and what we were both going to do next.

“I’m going to miss working together. I’m not sure if I want to do this without you,” I said.

“You’ll be alright. What else would you do anyway?”

“I’m not sure, but I’m heading to the Azores Islands for a week to figure it out.”

As we said goodbye, Rob said he was heading to France to take a class with his favorite writer. I told him to remember me when he was famous and left to catch a flight to São Miguel Island.

Waking Up to the Birdsong

On my third day in the Azores, I woke up at dawn in a small surf hostel. I had spent the last two days with Apa, a squat and affable local surf instructor. He taught me how to read waves on day one, and on day two, we took longboards out in sloppy, two-foot summer surf. At the end of the session, Apa said, “Don’t be so stiff. Be more like a monkey.”

I had my next session with Apa in four hours. I needed more sleep, but my mind wanted to rehash all of my troubles. Instead of fighting it, I cut my losses and tip-toed to the kitchen to make coffee. I scooped grounds from a weathered bag, placed them in a fresh filter, and filled the tank with water. As I waited for the coffee to brew, my mind peppered me with questions:

What are you even doing on this island? Do you really want to be with this girl? How are you going to afford rent if you quit your job?

It had now been two months of these questions and I still had no answers. By this point, I had stopped looking. My experience with prior existential tailspins had taught me one thing: When my mind is lost in circular ruminations, it is not the place where I will find the path forward. I had to live my way forward. Patience and action, not thinking, would illuminate the path.

And I suppose that’s why I was in the Azores. I was here to live, to temporarily escape my responsibilities and create space for whatever came next.

A sputtering sound broke my mental trance. The coffee was ready. I poured a cup and headed for the front door. As I stepped outside, the cool cement soothed my bare feet. The sun peaked through a cloudy sky and found a home on the right side of my face. I closed my eyes.

My mind drifted to a familiar exercise. I visualized myself on a map. Starting with a flat image of the world, I zoomed across Europe and toward the middle of the Atlantic Ocean to find the spot where I now stood on São Miguel Island.

I realized that I was thousands of miles from anyone I knew. That meant that no one on the island had any expectations of me. Anonymity offered a comforting paradox: By isolating myself from everything I knew, I was free to do and be whatever I wanted.

I had visited 30 countries over the last three years and used this visualization exercise to ground myself in unfamiliar lands. It was like a secret game that only I knew and that often filled me with gratitude about passing my twenties on an unfettered adventure around the world.

And today, that game was helping me see that I had the shield of anonymity on my side. The problems of the “me” that existed around the people I knew did not have to be here with the “me” on this island.

The sun broke through the clouds, covering my entire face and chest in a warm bath. I began to feel the carefree joy of a golden retriever who has nothing to do but chase a yellow ball and return it to its owner. The chatter in my mind faded into a barely discernable whisper as I let out a long, hearty exhale that eased the tension in my forehead.

And that’s when I heard them. Chirp, chirp. Chirp, chirp.

The soundscape transformed into a beautiful melody of hundreds of birds both near and far. They grew louder and louder as my attention narrowed.

Was this birdsong for me?

The song had a cheerful tone, almost as if these birds were grateful to be alive on this sunny morning. But birds don’t feel happiness, do they? Maybe they do. I would never know.

I opened my eyes. Where were all these birds? I could not see them, yet they were certainly around. I imagined how nice it would be to be a bird. To glide freely through the air, unbounded by the silly human concerns that sat on me like a wet blanket during the past few months.

It occurred to me then that surfing, like the life of a bird, offered me an escape from the constraints of land life. When I entered the ocean, I danced freely with the energy of the waves.

Like a bird gliding to its nest in the wind, surfing required me to be fully present and integrated with the world around me. The tides, winds, and swells determined my fate. Surfing catapulted me into a world where the problems of my land life did not exist. I became one with nature, and nothing else mattered.

A small bird with a light brown body and a black head sailed above me and landed on a tree in the yard. I took a breath of crisp morning air and released it in my second long exhale of the day. This time, the tension in my shoulders dissipated and my lips curled into a soft smile.

As I looked at my new bird friend and listened to the collective birdsong, something within me said: Don’t worry Cal. Everything will be okay. It was as if my mom had come down from heaven to give me the loving embrace I needed to let go of all of my existential unease. All that remained was the stillness of knowing that I am loved and interwoven with the natural world.

I still had some things to figure out, but my anxiety about the task had faded. Today, I would not solve anything. I would simply be like a monkey on the wave, and that would be enough.

Finding the Birdsong in All Places

I traveled to Lisbon, Denver, Boise, and New York over the following weeks. Every morning, I ventured outside and listened for the birds, hoping that I could find some semblance of the stillness I experienced on that day in the Azores. And the birds were always there. Not just on remote islands, but in small and large cities around the world. Even in New York City!

Once I started hearing them, it was hard to believe I had not heard them before. I must have been in the presence of the birdsong thousands of times, and yet, I never heard it. How was that possible?

I realized that hearing the birds had very little to do with where I was. The presence of the birdsong was a mirror of my internal state. When I was trapped in the madness of my mind, there were no birds. When I was present with the world around me, the birds returned. They were always there; I wasn’t.

It’s now been four years since I heard those birds in the Azores. The storm that was brewing in the spring and summer of 2019 wreaked more havoc than I originally thought. I blew up the foundations of my career, romantic life, and home within a month of leaving São Miguel Island. Those were painful changes, but they led me to the places that I needed to go.

I’m now living in San Francisco, married, and settled in a new career. I surf four times a week and still think of Apa as I do my best to “be like a monkey” on the waves. Many storms have come and gone since the day I heard the birds, and I realize that there are many more storms to come. But I also now have a ritual that grounds me during the calm and chaotic moments of life.

That ritual is my morning visit with the birds. This morning, for instance, I woke up hungover and irritated with myself for having one too many drinks. I made an espresso and walked outside into a fog-filled morning. I took a deep breath and started paying attention.

In front of me, I noticed a large spider with a brown belly who had built a home on my aging wooden deck. He was wrapping up an unlucky fly who would surely be a tasty lunch. A cool breeze slid across my face and moved toward a tree with dark purple leaves that swayed gracefully in the warm morning light. In the distance, I heard a wind chime sing.

And then they arrived. Chirp, chirp. Chirp, chirp.

The birds were here again, and like a baby playing peekaboo with a friendly uncle, I was just as surprised they were here today as I was on that day in the Azores. I closed my eyes and allowed the morning birdsong to wash away my hungover agitation and thoughts about all that I had to do on this day.

I simply listened, and their song reminded me that everything would be okay.

Embracing Gökotta

I recently learned that my morning ritual has a name. It’s called gökotta, an untranslatable Swedish word that means “to wake up at dawn to go outside and listen to the birds sing.” I’m happy to have a name for this wonderful practice and to know that I’m not the only one doing it.

Embracing gökotta has changed my life for the better. Unlike the endless supply of lame, self-help hacks that promise more productivity with less stress, gökotta has fundamentally reshaped and deepened my relationship with the world.

Gökotta is a way of being, a simple practice that reminds me of the transformative and always-available pleasures of nature.

It’s a few minutes of stillness during which I can begin the day unchained from the prison of my mind and become more attuned to the small details of where I am. It’s a gentle nudge to remember that I’m never really alone and that everything will work out in the end.

Just as focusing on the breath is a way for meditators to connect with the present moment, gökotta is a pathway for reminding me that I am a part of an interconnected web of life that is far more vast and beautiful than I could ever understand or communicate with words. It is a test of my presence and willingness to surrender to what is always around if I simply listen.

And now that you know about gökotta, perhaps it can be a pathway to help you live more fully as well.

As a kid, you’re rewarded for following the rules.

If you do your homework and eat your broccoli, you get to swim in a pool of Chunky Munky ice cream and play Call of Duty until your eyeballs fall out. If not, you’re grounded!

This “follow the rules or else” song and dance may be an effective way to raise children; however, it leaves many people unprepared for the task of creating an enjoyable life in adulthood.

That’s because adulthood has no real rules.

Once you enter the “real world,” the fixed boundaries of childhood disappear. You can take infinite paths, and you can walk each path on one leg, barefoot, or backwards in a pink fedora.

Figuring out how to spend your life is unlike any task you faced growing up. There are no correct paths or guarantees of ice creamed filled swimming pools along the way. And no parent, teacher, or cult leader can give you the answer. Only you can decide what to do.

And if you mess it up, you risk becoming a cranky old fool who yells at teenage cashiers for refusing to take expired coupons. Damn kids never respect their elders.

So what do you do if you want to enjoy life and avoid becoming a coupon-clipping curmudgeon?

You play Calvinball!

Calvinball is a game with only one rule: it can never be played the same way twice. Like life, it’s a free-for-all adventure in which you can make up and change the rules as you go.

Wait…Calvin, did you invent a game, name it after yourself, and then write about it?

No, dear reader. I’m not that big of a navel-gazer. Calvinball was invented by a blonde boy named Calvin and his pet tiger Hobbes in Bill Watterson’s cartoon series, Calvin and Hobbes.

And yes, I admit that I’m partial to the game because I’m a blonde guy named Calvin. But I digress, and it’s time we get back to the regular programming.

Now that you know about Calvinball, I’d like to tell you why treating your life like a game of Calvinball is the best way to spend your time on this spinning rock.

Seeing the world clearly

The creator of Calvinball, Bill Watterson, once said, “People have asked how to play Calvinball. It's pretty simple: you make up the rules as you go."

Making up the rules as you go may seem like a naive way to approach your life, and it is. But it’s also the most effective way to build a life that fulfills and evolves with your quirky desires.

When you play Calvinball, you see the world as it is. By breaking the spell of childhood that dupes you into believing that life has fixed rules and correct answers, you see that every person, including you, can play a different game with different rules.

The task then becomes to make up the rules that work for you. As you begin this process and encounter obstacles, continuing to play Calvinball will help you in three ways.

Becoming adaptable

Imagine you’ve spent seven years in an unfulfilling career as a corporate lawyer and realize that facilitating M&A transactions just doesn’t do it for you. You want to follow your real passion: to be a sex therapist who helps married couples keep it spicy in the bedroom.

In a world of fixed rules, you may decide to continue being a lawyer. Maybe you think “it’s too late” to start a new career or that you can’t “waste” the money you spent on law school. Or hell, maybe you’re afraid the new career will let your parents discover that you’ve had sex.

As a Calvinballer (yes, that means someone who plays Calvinball), you would see what a silly decision that would be.

Is it really ever too late to start a new career? Is the point of life never to waste money? Is it that bad if your parents know that at 32 years old you are no longer a virgin?

No, no, and hell no.

In Calvinball, you can edit the rules whenever you want. And choosing to make up rules that allow you to switch careers is better than spending 30 years doing something you don’t enjoy.

So what do you do when you’re considering a big life change? You play Calvinball!

Staying curious

Living under the illusion that the world has fixed rules, many adults lose their curiosity. They see their lives as static, decaying shells of some carefree past that will never return. They stop exploring, making new friends, or believing that their lives can be different than they are today. It sucks, but it is what it is.

Playing Calvinball helps you avoid this false and depressing mental trap. As a Calvinballer, you know that you can change the context and rules of your life when something is not working. You understand that no matter what has happened in the past, you still have an infinite world of known and unknown possibilities available to you.

Like a two-year-old discovering the beauty of a blooming flower or the pangs of a hot stovetop for the first time, you maintain a curious, exploratory spirit. You know that you’re never too old to make new friends, start skateboarding, or move to South Africa.

So what do you do when you feel that the doors of life have closed? You play Calvinball!

Having fun

When you believe there is a correct way to live, adulthood feels like serious business. You’re an important person with important things to do, and there’s simply no time to take a break from all of this important stuff. Jeez, sorry for wasting your time with small talk, Mr. Important Person.

What a lame way to live. What’s the point of all your goals, achievements, and possessions if you’re not having fun?

As a Calvinballer, you won’t have this problem. When life starts to feel too serious or stressful, you switch it up and start a new game. You know that even if you want to achieve big things in the world, you can still take a few detours and have fun along the way.

So what do you do when life starts to feel too serious? That’s right, you play Calvinball!

Parting Thoughts

Figuring out how to create an enjoyable life is like Calvinball. It’s a game that’s best played by making up the rules as you go.

By giving you the freedom to make up the rules as you go, treating your life like Calvinball opens the door to a more adaptable, curious, and fun existence. And seriously, who doesn’t want that?

As you walk your unique path and stumble upon undesirable roads, remember that you are never stuck. Every day is an opportunity to rewrite the rules.

And if you’re ever in doubt, just play Calvinball!

P.S. I’ll leave you with the Calvinball theme song.

"Other kids' games are all such a bore!

They've gotta have rules and they gotta keep score!

Calvinball is better by far!

It's never the same!

It's always bizarre!

You don't need a team or a referee!

You know that it's great, 'cause it's named after me!"

- Bill Watterson from Calvin and Hobbes

He’s paid well, has a kind boss and smart peers, and takes enough vacation. But he’s felt unfulfilled for some time. Something is off, and he asked me what to do.

I told him what he already knows: “The job sounds great on paper, but it’s not working out. It seems sensible to quit. What’s stopping you?”

The money is good. He’s not sure if he can get another job like this one. His colleagues may think he gave up. He feels he should be grateful for having a job when people are struggling.

“Those are fine considerations,” I said. “But what do you want?”

After a long pause, he said, “Hmm, I don’t know. I haven’t really thought about that.”

And that’s when it hit me. My friend wants to make an important life decision. He’s paralyzed by doubt and hoping that someone else can give him the answer. But even the wisest friend can’t bring him any closer to an answer because he’s asking the wrong questions.

He’s focused on how he should feel about his job, how his career move might be perceived by others, and how he may never be able to have this level of money or prestige again.

But he’s not confronting the only question that matters: What do you want?

The Central Task of Adulthood

Figuring out what you want is the central task of adulthood, and it’s not an easy one.

Once you leave formal schooling, you’re catapulted into a world with infinite possibilities. You no longer have to show up at school to avoid detention or ace tests to make your parents proud. You’re finally unshackled from the training wheels of life, and now you get to decide what the hell to do.

You expect this freedom to be liberating. You get to decide where to live, how you’ll make money, and hell, you can even decide how much ice cream you’ll eat this weekend. No more nagging parents or irritating classmates to hold you back. Free at last.

But as you begin to direct your life, you quickly learn that adulthood is harder than you expected. You realize that you can (as many people do) screw up your life by making bad decisions. It becomes clear that it’s not so easy to balance your many needs.

The burden of having real responsibility can weigh on you. And little by little, your naive excitement turns into a dark cloud of fear and doubt. When this happens, your focus shifts away from figuring out what you want and toward a different set of questions:

What if I mess it up? What if I don’t live up to my potential? What if I marry the wrong person?

These are valid concerns. But if you give them too much attention, you may end up like my friend, unaware of what you want and unable to make important life decisions. And that’s not a good place to be if you want to enjoy your time on this spinning rock.

So what should you do? How do you know what you really want?

While I don’t have all of the answers, I can offer some tricks of the trade and help you avoid common traps that prevent you from knowing what you want and how to get it. These ideas should give you a good foundation for learning how to steer the ship of your life in the right direction. At the end of our exploration, I will return to the question of what my friend should do.

Caution: Safety is an Illusion

When you realize that you can mess up your life, you may look for a safe path that prevents you from ending up on your deathbed with regrets. This desire for safety leads you into the comforting current of cultural gravity, the invisible set of forces that move you along socially-approved paths.

Like a riptide that sweeps you out to sea, cultural gravity’s current will bring you along the default path. In a capitalist, career-obsessed society like the United States, the default path nudges you to pursue careers that allow you to preserve optionality, stockpile cash, and garner adulation via achievement.

The default path offers an alluring proposition: If you follow the rules and work hard, you will live a good, respectable life that ends with a blissful period of unlimited pisco sours on the beach. The embedded promise of this path is that you will not squander your life.

But it turns out that the default path is not a risk-free antidote to the difficult problem of figuring out what to do with your life. For every person who is satisfied with the default path, there are droves of people who wake up one day to the unbearable hangover of a midlife crisis, regret, and existential frustration.

Taking the default path is not safe. It’s more like opting into a game of Russian roulette, where the cost of losing is wasting your one chance to enjoy your life.

Despite the many faults of the default path, the lesson is not that you should avoid it. It may work for you; it may not. The lesson is that there are no paths that can guarantee that you will move through life without any risk of messing it up. Creating a life worth living is like embarking on an ocean crossing. There is no route or amount of preparation that can ensure you won’t get caught in a violent storm.

So the first step in figuring out what you want is to know that safety is an illusion. This knowledge does give you an answer, but it does help you resist the temptation to simply do what other people are doing and assume that it will work out. Knowing this will help you remain more curious about the diversity of paths available and skeptical of anyone who claims to have an answer for how you should live.

Try More Stuff

To begin to understand what you want, you need to know what you don’t want. And the only way to figure out what you don’t want is to try more stuff.

As soon as you can, expose yourself to as many new things as possible. Travel. Change jobs. Date around. Read voraciously. Interview old people. Try new hobbies. Follow the whims of your heart.

People may call you non-commital and directionless during your exploratory period. Ignore them. What they don’t understand and what you won’t understand until later is that meandering for enough time is the only reliable way to create a higher-resolution map of your desires.

When you explore in an unfettered way, a beautiful order begins to arise from the chaos. Little by little, as you expose yourself to the many paths the world has to offer, you begin to understand the nuances of what you want and don’t want.

You’ll know you’re making progress when you discover that you’re no longer interested in mindlessly pursuing wealth, status, happiness, security, and other generic desires.

As you move beyond surface-level desires, you start to see the quirky details of what you want more clearly. You know that you want to live in Oaxaca, teach yoga, and marry an artist named Paul. Your clarity is real and actionable because it’s not built on a mirage of safety or the shaky promise of the default path. It’s built on the strong inner foundation that formed during your time exploring.

And one day you’ll think back to your post-college self. That person had a 10-year plan for riches, success, and happiness. You were going to be a hedge fund tycoon in New York City who married her college sweetheart and spent summers on the coast of Italy. You were so sure that was the right path.

Now look at you. You’re teaching yoga in Mexico with Paul by your side. A few years ago, you didn’t even know you could live like this. As you reflect on how your life unfolded, you’ll be humbled by how wrong you were when you were young and grateful that you had the courage to deviate from the original plan.

Many people don’t find that courage. They make a plan and stick to it, even when it’s not working. They allow inertia, fear, or stubbornness to keep them on a mediocre path. And since they never had an exploratory period that clarified their desires, they freeze up when thinking about making a change. And their lives remain smaller than they could otherwise be.

So if you’re serious about figuring out what you want, don’t try to think your way to an answer. Stay curious and try more stuff. Trust that your meandering will help you learn about yourself and eventually guide you to a more enjoyable path.

Beware of Tradeoffs

I’ve been a solopreneur for two years. I make enough money and don’t have a boss, zoom meetings, or pesky colleagues. I surf four times a week and travel whenever I want.

Sounds pretty good, right?

Well, it depends on what you value. It’s great for me because I’m optimizing for time freedom so that I can pass the days of my fading youth as I wish. But in choosing this path, I’ve given up some important things.

My income is unstable and lumpy. I don’t have colleagues to learn from or laugh with. I rarely get validation and have no clear next steps to follow.

The downsides of my path would make many people miserable. I know this because I tried to live this same way in my mid-twenties and ended up anxious and unhappy. I learned the hard way that my need for financial stability at that time was more important than my desire to have an empty calendar. I took the loss and returned to full-time work six months later.

The truth is that no path has it all, and everything worth having comes with a cost. Time freedom requires uncertainty. Entrepreneurship requires risk. Marriage requires tough conversations.

When making big life decisions like where to live, what to do for work, and who to spend your life with, you need to understand the trade that you’re making with each path.

You need to know what you’re getting, what you’re giving up, and how the various tradeoffs will impact your satisfaction. You won’t always have the full picture, but thinking in these terms can help you avoid some mistakes.

Like me, you will still mess up along the way. That’s okay. What you learn from those mistakes may help you later on. That became apparent two years ago when I was thinking about leaving my stable job at a venture studio to try being a solopreneur for the second time.

Thanks to what I learned from making a similar decision in my mid-twenties, I understood the trade. I knew that I would gain freedom and lose security, money, and prestige. I felt good about that trade because I wanted time freedom more than what I had to give up to have it. And so far, it’s working out.

Be Wary of Advice

Imagine you’re a marketing executive in your mid-thirties. You’ve enjoyed your career and can optimize landing pages better than anyone. But for 10 years, you’ve fantasized about quitting your job to head to a cabin in the woods to write poetry.

As a kid, you found comfort in the words of Dickinson, Wordsworth, and Rilke. Now you’re ready to join these bold souls in giving a voice to the human experience. Before making the leap, you want to ensure that your pivot to poetry is not a naive fantasy that will lead you into a hellscape of financial ruin and depression. So like my friend who is thinking about leaving his job, you decide to talk to a few friends.

While asking other people what to do may seem harmless, it can lead you astray in three ways.

1. Most people give you advice, and what you need is counsel.

When you ask people for help, most people give you advice. Advice is when someone tells you what they would do. And since you’re not that person, it’s rarely useful to hear what they would do. You want to know what you should do.

Counsel, on the other hand, is when someone helps you figure out what you think. Counsel is invaluable because it helps you clarify your thoughts and tap into your inner wisdom about what you should do.

If you have friends who know how to give you counsel, hold onto them dearly. These people are angels who offer a non-judgmental, listening ear that will help you find the best path forward.

2. You may not have the right people in your life.

Friends and family are indispensable parts of living a great life, but depending on who you surround yourself with, your loved ones may lead you in the wrong direction.

One common problem is not having any people in your life who have experience with the decision you’re making. If your friends are all marketers who enjoy the default path, don’t ask them about quitting your job to write poetry. They won’t understand, and what they offer may lead to confusion and a loss of confidence in your intuition.

Or you may encounter another problem. Friends and family like you for who you are today. They do not want you to move to the woods, change, or be anything other than what they know and love. And when you ask them what to do, they may unconsciously encourage you to stay put.

This is not an intentional or malicious attempt to keep you from being happy. It’s just how people are, and this dynamic can make it more likely that you stay trapped in the inertia of your current situation.

3. Everybody comes with biases.

If you ask a philosopher what to do, he will tell you to imagine you’re on your deathbed and to consider what your older self will have wished you did. A rationalist will tell you to use time-tested frameworks or weigh your options in a spreadsheet. And a spiritual person will encourage you to find the answer in ayahuasca, journaling, meditation, and knowledge of moon cycles.

Everyone you talk to comes with a specific lens on the world, and so does their advice. And while their ideas can be useful fodder, they can also muddy your thinking or take you down unhelpful rabbit holes.

There is nothing wrong with talking with other people about your decisions. It can be very helpful, especially if you’re receiving counsel. Just don’t expect other people to give you clarity. There is no substitute for doing your own thinking.

And when making a big change like giving up your corporate gig to write poetry in the woods, you’re the only one who knows if that’s a decision you can live with. Learn to trust yourself.

Life Never Comes Together

Even if you try more stuff, understand tradeoffs, and find good counsel, you will likely never figure out exactly what you want or how to get it. There are at least two reasons for that.

The first reason is that you are an unreliable madman. You are not the rational, grounded character that you want to be. You are wild and dynamic, and so are your desires.

One month, you’ll want to embrace your hedonistic impulses; the next month you’ll want to dedicate your life to helping others. A few years later, you’ll want to build a large company. And after securing a round of funding and hiring ten people, you’ll realize you actually want a relaxed life in the suburbs.

You and your desires will change in unpredictable ways.

The second reason is that dragons await you. Right when you think that everything in your life has finally come together, a ten-headed, fire-breathing dragon will block your path and send you running in another direction.

That dragon may be the unresolved traumas of your childhood, the devastation of unrequited love, or direct confrontation with the fragility of life. These moments will shift your inner world in profound ways.

What you learn from these experiences is that life will never come together in the way you want. It will always be a half-finished puzzle. Knowing this can help you avoid the illusion that some achievement, some amount of money, or some person will finally make your life complete. The puzzle is never complete.

What Should My Friend Do?

Now that we have a better understanding of what figuring out what you want entails, I want to offer some words of advice to my friend who is unfulfilled and thinking about leaving his job. But first, I’ll like to share a story about the first big career change I made.

In 2016, I quit my job as an investment banking analyst after one year to become a marketer at a fully remote startup. Friends and colleagues told me I was making a stupid decision. When I told the head of my team I was leaving, he said, “You’re young and naive. You’re going to regret this decision.”

The rational part of me agreed with the skeptics, but my intuition told me to leave anyway. And I listened to the intuition. I had no idea if I would enjoy or be good at my new job. All I knew is that my year in investment banking taught me that no amount of money is worth spending your life in a cubicle working 100 hours a week. And that was enough to exit the game of finance and look for something else.

That decision ended up being one of the most impactful ones of my life. It sent me on a meandering path as a digital nomad and helped me develop the skills that later inspired me to start writing online. Most importantly, leaving that first job gave me confidence in later years to listen to my intuition when it told me it was time to make a change in my career, romantic life, or how I was living.

Following my intuition has not always led me to good places. I’ve made many mistakes and taken too many wrong turns.

But in learning to take action when the voice inside me says that it’s time to try something new, I’ve avoided the biggest mistake of all: allowing inertia, fear, or social pressure to keep me in a situation that I know is not right.

And over the long run, my refusal to bow down to fear and settle has gotten me closer to designing a life that I’m excited to live.

So…what should my dear friend take from this story?

Should he hear that I listened to my intuition and found a better path and conclude that he should find the courage to quit his job?

Absolutely not. That’s what worked for me, but my friend is a different person.

If there’s anything that he or you should take away from this exploration of figuring out what you want, it’s that you should not listen to me or anyone else about what to do with your life.

Only you can answer that question. And I hope some of what we’ve discussed so far will help you with that challenge.

Before we wrap up, I do want to invite my friend to consider one more thing. When we spoke about his conundrum, two dynamics struck me. The first is that he didn’t know what he wanted. I’ve already addressed my thoughts on how to approach this problem.

The second dynamic is that he seemed to be treating his potential job change as a life-or-death decision. And at least part of his decision paralysis stemmed from this feeling that he was making an irreversible decision that may ruin his life.

My invitation to him is to think about the job change in less grave terms. Job changes are consequential, but they are not life-or-death decisions. Treating them as such impedes clear thinking. If you believe making a change may ruin your life, you will likely stay on the current path to avoid that calamity.

The reality is that every job change comes with some set of tradeoffs. You may make less money, lose prestige, or give up perks you enjoy. But in doing so, you may create space for new paths with more of what you want and value. You won’t know for sure until you get clear on what you want or try something different and see how it goes. Even then, you can never quite predict how the future will unfold.

In the end, the decision is up to my friend. And whatever he decides, my hope is that he doesn’t forget to have some fun along the way. This ride won’t last forever. And for you, dear reader, I wish the same.