Letting Go of Ambition #1

In pursuit of the white whale

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

I’m trying something new and CRAZY this week 🤪. I’ve been working on an essay that is somehow getting longer and longer (usually it’s the opposite). Apparently, I have a lot to say about the topic and don’t want to rush it by glossing over some of the details that make the story tick.

Instead of releasing the growing beast all at once, I’ve decided to share it as a series of posts over the next few weeks. Think of it like a Netflix show that airs every Sunday, instead of all at once.

I may also update each part of the series as the full piece comes together. So if you have anything that you really like, find boring, or are confused by, just reply to this email and let me know :).

OK that’s enough jabbering for now.

You can find the first part of Letting Go of Ambition below.

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.

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. All my optimism, excitement, and confidence 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.

That's all for now. Don’t forget to tune in for Part 2 next Sunday!

— Cal

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