Letting Go of Ambition

At 28 years old, I was terrified that I would never become a real writer.

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.