The Wayless Way: Finding Freedom Beyond Ambition

“The Wayless Way, where the Sons of God lose themselves and, at the same time, find themselves.” — Meister Eckhart

I’m a twenty-nine-year-old banquet server living in Eugene, OR, pursuing my writing dream. There are thousands just like me in Eugene alone. “Yuccies” (Young Urban Creatives) are growing among Millennials and Gen Z. Dropping out of tracked careers to pursue what Paul Millerd calls The Pathless Path.

Common, perhaps, but not easy.

The Cycle of Identity

It took a prolonged dark night of the soul (that still visits time to time) to deconstruct my old identity enough for a new life, relatively unburdened by expectations, to emerge.

When I explain “who I am” to new people, a guttural moan forms in my throat before I catch myself and repeat the practiced (and audience-dependent) 1-2 sentence summary. At work, it’s the odd jobs I’ve held—DoorDasher, freelance writer, marketing manager, hedge fund manager (that’s a fun one), gardener at a Texas commune and (later) Zen monastery, and director of a start-up accelerator.

It’s a long story, one that is laid out in depth in my memoir. But I think its twists and turns are illustrative of a larger cultural trend, an awakening out of the fever dream of chasing money and status. It’s a two-steps-forward, one-step-back kind of deal. And it doesn’t often make sense to me, let alone the friends and family watching it unfold.

Andy Johns illustrates this in his wonderful essay on What happens when you leave your career (and identity) behind: the path from status-obsession to an authentic, vow-driven life is not linear.

It’s more of an orbiting than a straight line. An eyes-closed, heartfelt groping for a gaping void that is as tantalizing as it is terrifying. But on the other side lies a freedom and level of well-being more wonderful than I ever thought possible. I have tasted it, so I know it’s there. And it is a life-long practice to continue feeling into it, even as so much of myself wants to run away screaming.

The First Turning: COVID and the Call to Something More

At the start of COVID, everything changed for me. I was just under two years out of a drug recovery program for cocaine addiction, working as a marketing manager for a cryptocurrency startup. As my sobriety stabilized and my mind cleared, I began to feel into a subtle but growing discontent with my career trajectory. When my company went fully remote, I told my boss I was taking a few days off and disappeared into the southern Rockies for a five-day solo trip. It was there that I first conceived of an alternative, heart-centered vocation: writing.

I quit my job and began a book. It was based on my time at Stanford, where I started a hedge fund out of my dorm before moving to New York City in 2017 to invest in a series of new cryptocurrencies.

But the start mirrored what is generally true in big transitions. One element of my life shifted: what I wanted to focus my time and energy on. But another element did not change: my attitude towards work itself.

I told everyone who would listen that I would finish my book in ninety days! Take out a personal loan if I had to (thankfully, I managed to cut costs enough to avoid this trap). I was going to be a successful writer, ride or die. Status and money were still what really mattered.

This will probably come as a surprise to no one, but the book ended up taking five years (just a hair over my original goal), finally coming out last month.

The Return to “Normal” and the Monastery Interlude

A year and a half ago, I emerged from an intense period of residential training at a Zen monastery, having all but given up on my writing dream. It was a necessary part of my path. Letting go of the ego-driven desire for wealth and fame that had persisted in my transition from crypto-bro to writer.

From late 2023 to the end of 2024, I spent almost three months in silent retreat. Much of which occurred during six months of living at the monastery. It was an experience that radically altered (and at times, seemingly eradicated) my sense of self. The last ten weeks of 2023, I was in almost constant retreat. An intensive period known as “ango,” where the monastery residents wake at 3:50 each morning and pass the day silently working and meditating.

Coming into the monastery, the old patterns reasserted themselves. I was going to get enlightened right away, damnit! Blow away the “competition” and ride off into the sunset with thousands of adoring spiritual followers caravaning behind me.

After a short honeymoon period, reality struck.

I became thoroughly miserable, wondering why I had voluntarily put myself into prison. I had to shut up and sit perfectly still. Check all my ideas, desires, impulses, and give them up to a rigorous schedule not of my making. After waking each morning, we would have about thirty minutes to slug coffee, stretch out, and file into the meditation hall by 4:27 (at the monastery, every minute of free time counts) for two hours of meditation followed by a fifty-minute chanting service.

After a short cleaning period where I could stretch my stiff legs, we would march into the cafeteria for a formal “Orioki” style breakfast. A nearly hour-long, laboriously choreographed dance of painstakingly folded napkins, chanting, and rigid posture that, again, often felt like a kind of prison. The rest of the day would proceed likewise, with a couple of breaks in the afternoon and evening, before finally collapsing into bed at ten each night, only to do it again the next morning.

I would often fantasize about standing up and screaming “FUCK MEDITATION!! FUCK ZEN!! AND MOST OF ALL, FUCK YOU!!!” before storming out of the meditation hall. But something kept me there. For weeks, and then months.

The Paradox of Freedom Within Constraint

In those weeks and months, something started to happen. A freedom of spirit emerged out of the rigid confines of the monastic structure, a structure which I had spent my entire twenties up to that point avoiding as the antithesis of life’s highest end: freedom of action. To be a slave was the worst thing one could be, I reasoned. And therefore, the best thing one could be was the opposite of a slave.

I wanted to be an autonomous entity. Freed from orthodox, inflexible work, from government over-reach, from financial want, and from overly needy romantic partners. Not coincidentally, cryptocurrency espouses a similar aim: freedom from banks and traditional financial structures.

In truth, the freedom I really wanted was the freedom from fear and adversity. Freedom from everyone else, without feeling the agony of their absence. Freedom from loneliness and pain of all kinds.

The monastery is a place of “anti-freedom.” Your every movement is scrutinized, and in the meditation hall, while the round is going, you must stay absolutely still. Even cracking your neck or shifting your aching legs is prohibited, which at times can feel like physical torture. This is the paradox of spiritual work. It requires, especially early on, enormous exertions of will and self-discipline to free yourself from the very thing that is stopping you from being your Self (which is to say, your “self”). A flower grows not by continuously tilling the soil. But, for the most part, by being left the hell alone.

Coming Full Circle: The Corporate Return

After emerging from the monastery (itself, not an easy decision—I understand now why people commit themselves to ten or more years there), I found myself in a state of almost total openness. Like Michael Singer in The Surrender Experiment, I decided to take whatever job or opportunity landed in my lap. And so, when my old boss reached out to me about a fancy new position she was hiring for, I thought what the hell, let’s do it.

I was going to be the director of a new startup accelerator. Building a program to support crypto founders as they scaled their businesses from product-market-fit to the big leagues. I’m going to help people realize their dreams.

The money didn’t sound so bad either. You don’t spend a lot of money while living at a monastery, but you also don’t make a whole lot.

I had spent the previous eighteen months, including my time at the monastery, “drying out.” Becoming spiritually sober, not just physically. Trying out alternative (and even radical) ways of living. Like buying a plot of land in Upstate NY and building an ill-fated cabin with my girlfriend.

I finally felt solid enough in my recovery to face high-pressure work without running to drugs whenever the stress levels got nasty. The refuge of self-pity and despair was no longer my go-to tool in my arsenal. Now I had mindful breathing, gratitude, love-and-kindness. I had practices for generating solidity (sitting like a mountain), and spaciousness (sitting like sky). Perhaps my self-destructive relationship with working in the crypto sector had been a “me” problem after all. I could engage with it as it really was: a job.

My life quickly became like many other six-figure, fully-remote keyboard jockeys. There were endless meetings, conferences to attend, and Very Important People to suck up to. I moved to Eugene with my girlfriend to live a life unburdened by grandiose dreams of writing the next bestseller or making quick millions as a hedge fund manager.

My family was thrilled. “Look at Dean! Over his addiction and finally settling down on the upper-middle-class path.” I could practically feel the air on my neck, as the collective sigh of relief blew past me.

The Inevitable Reckoning

But as I threw myself wholeheartedly into the job (for that was my promise, I would give it my all), I felt myself moving away from a deeper, silent vow which I had not yet fully articulated. A vow to bring forth the deepest, truest aspirations of my soul.

It took only a few months on the job to realize that I was slipping into the mundane psychosis of workaday life. The Amazon packages, the DoorDashed meals, a planned vacation to Europe, and revived dreams of home-ownership were not remuneration enough for this terrible trade-off.

I went back to the monastery for a week-long retreat four months into the new job. I was recovering from an outbreak of hives, which I thought was from work stress. But now I realize it was something deeper. A physical reaction to ignoring my life vow.

On the second full day of the retreat, I went to the teacher interview room. Inside the mission-adobe hut nestled beside a bamboo grove was the wise old teacher, sitting cross-legged with candles flickering around him.

“What is your practice?” he asked when I sat down. I expected the question. But when I went to answer, the words caught in my throat.

“Well…” I began, “The truth is I’m spending most of my time wondering whether I should quit my job.”

He frowned, then spoke sharply.

“To do what? Nothing?”

I blushed. Stammered something about wanting to finish the book I had been fiddling around with for years before he interrupted me (I was babbling, something Zen teachers never indulge).

“My advice,” he broke in, “is to make your decision immediately. Then, spend the rest of the week immersed in your practice so you can enjoy the beautiful spring unfolding around you.”

With that, he rang his handbell, and I rose and walked out, laughing at his directness as I returned to the meditation hall. There was no hedging, no sympathetic mirroring of anxiety, just a no-nonsense directive to “make up your damn mind!”

In my heart of hearts, I knew I wanted out. Not wanted, needed. I had managed to save a decent amount of money. I was financially supporting my girlfriend, but she was starting a new job and could start chipping in for rent. We could move into a cheaper apartment.

The vision came together: The unglamorous but purpose-filled life of the starving artists. She would make her comics, and I would write! It was going to be great.

The Wayless Way

It took me another six-and-a-half months to finally leave. I had made a year-long commitment and wanted to do right by my company. I left in November, just missing out on the juicy Christmas bonus (and boy, could I use that money now).

I DoorDashed nights and threw myself wholeheartedly into finishing the book. The status drop was almost instantaneous. Of course, I harbored the secret self-indulgent notion that I was the next Bukowski, working odd jobs and serving up everything to writing, no matter the cost.

I finished the book in January. And miraculously, found an indie publisher to represent it! It came out in early April, 2025.

After I finished the book I noticed some of the old patterns re-emerging. Wanting to work manically to promote the book, to sell hundreds and then thousands of copies and book speaking gigs and… and… and….

And what?

I took a deep breath and relaxed. To pay the bills (money had gotten tight, which tends to happen when you are an unknown writer), I took a job as a banquet server. It pays well enough to cover my modest living expenses, and I earn my wages with my body instead of my mind, freeing my thoughts to focus on what I truly care about.

But still, questions remain. I have sold less than fifty copies in the first month, and, as the gap in my resume grows, the fear of losing out forever on financial freedom rears its head from time to time. Am I behaving rashly? I wonder, giving up everything for nothing?

But when I quiet my mind and look deeply into what matters, the questions dissolve and the fear dissipates. I have seen it again and again. On the other side of fear and self-doubt is awakening. There are only two things that consistently make my heart sing and my mind clear: meditation and writing. I could not imagine my life without either.

I recall my life before, when every day was a means and not an end.

I did not really taste my food, I imbibed fuel for my ambition.

I did not really have friends, I had potential business partners.

I did not see the sky, just light to guide me towards my goal.

It was a strange, dreamlike existence. A bizarre psychosis more chronic than the drug-induced one that landed me in a psychiatric ward almost a decade ago. But all self-growth happens through misery of a kind. Without suffering, there is no growth, and since I never regret growth, I never regret suffering either.

In the end, it’s amazing what happens when we finally let go of the idea, of all ideas, of who we’re supposed to be. May we all find this freedom.