Letting Go of Ambition #3

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Hello friends and welcome back Life Reimagined, a weekly elixir designed to make you feel good and live better.

If you’re new here or missed the last newsletter, I’ve been releasing parts of a new essay, Letting Go of Ambition, for the last couple of weeks. This week, I’m excited to share the final part of the essay, which you can find below.

If you want to read the full essay from soup to nuts, you can do so here:

📍Letting Go of Ambition

While it’s not perfect, I think this essay is the closest I’ve come to explaining how I’ve landed at much of my current perspective in life. It details a hard-earned lesson that led to the most enjoyable period of my life so far.

Letting Go of Ambition #3

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

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,

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,

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.

— Cal

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