For the first 32 years of my life, I completely misunderstood ambition. I thought it was about achieving the things that most people around me saw as impressive. The formula was simple: all I had to do was shape myself into the kind of person that could keep achieving impressive things.
I never stopped to question any of this until I walked away and quit my job at 32 years old. It was only then that I found a path to being ambitious without trying.
That might sound crazy, and to my past self, I would have called bullshit. But it’s something I’ve experienced, and I’m going to walk you through exactly how I shifted from someone aiming at a never-arriving future, constantly frustrated and filled with discontent, to someone who feels far more ambitious but is able to exist in the present, content and satisfied, despite having far less of a plan.
The Vicious Cycle of “Success”
My story starts in 2017 when I quit my job. I was a bit naive; I didn’t really understand what was about to unfold in my life. I was about to undergo a dramatic shift, but at the time, I didn’t have the language to really understand what was happening. That is, until I stumbled upon the work of coach Joe Hudson and his “Art of Accomplishment.”
Joe’s work really resonates with me because he’s kind of like me. He spent years trying to find a path to success. For him, instead of the business world, he was trying to find that success on a spiritual path. In an experience on a meditation retreat, he found himself in a state where he was filled with bliss and contentment. After the experience, he was determined. As he described it, “I’m going to use meditation to control my experience.”
This rhymes with my own journey. My tool, instead of meditation, was decoding the corporate world. I was convinced that by being more prepared, being better at doing things like resumés and interviewing, I could achieve some form of freedom. But I didn’t fully understand the freedom I was trying to chase. It was a surface-level game, and I was really oblivious to the fact that all I was trying to do was find freedom from my damn emotions.
Before I quit my job, this game kept me locked into a vicious cycle for more than 10 years. Here’s how it worked:
- Feel unsettled.
- Because I didn’t want to feel that way, I’d obsess about my next steps. I’d generate sexy future options, apply for tons of jobs, network with people, and talk to people in new industries.
- Eventually, I’d find a new job, and a huge sense of relief would wash over me.
I did this over and over again. But this same approach turned into proof of success in the world. I landed great jobs, kept making more money, got accepted into a top business school, and I had the appearances of everything working out. People praised me; they thought I had it all figured out.
But I was locked in something Joe calls the “golden algorithm.”
The Golden Algorithm: A Trap of Our Own Making
Here’s how the golden algorithm works:
- Have an emotion you want to avoid.
- Do anything in your power to avoid feeling those emotions.
- Accidentally recreate the emotion you’re trying to avoid.
I love this because it really points out the silly behaviors that humans get locked in over and over again. I was locked in this golden algorithm for nearly 10 years. So, every time I found a new job, I’d find temporary relief. I’d stop feeling unsettled, dissatisfied, and the anxiety of not really knowing what I wanted. But within three to six months, those feelings would show up without fail.
This was really hard for me to notice. It’s so obvious looking back, but at the time, my avoidance strategy was kind of fun. I actually really like looking for new jobs, as crazy as that sounds. So much so that I would help friends do it. I spent a lot of time thinking about how to apply for jobs. Before quitting my job, I even published something called “The Career Transition Playbook.”
Little did I know, this was just so much effort into trying to avoid my emotions.
After 10 years of deploying this strategy, I ran out of moves. I was literally getting rejected from companies, with them telling me, “Paul, you’re clearly a job hopper. This is not going to work.” And they knew more than I did. I really was just trying to jump from job to job. And so, I think deep down, I knew that the strategy wasn’t working anymore. I decided to walk away from that impressive career without a plan.
I blew up my life.
But little did I know at the time that I would stumble upon the actual solution to that vicious cycle I had been locked in for so many years.
Facing the Damn Emotions
The problem? The solution sucked.
It involved having to face those damn emotions I was trying to avoid.
I didn’t anticipate this when I quit my job. Maybe knowing this, I would have waited longer. Having the feelings of not being good enough, the fear of the unknown, being seen as a failure—those feelings washed over me, and I wanted to run. I wanted to escape. I wanted to hide from the emotions again.
But I had this voice inside of me, channeling Robert Frost, saying, “The only way forward is through.” It was an inner call to myself to grow up, face myself, and stop running away. But again, like I said, it sucked. I was transported back to my high school self, the one that hit puberty later than friends, the one that felt really insecure around women, and that felt like I needed to prove myself to the world.
Unfortunately, I was still that young boy.
I realized I probably could have gone many more decades of my life running from those insecurities that have been there so long because the cover story of a successful career gives you this halo of having things figured out. But now I knew the truth: that I had used my career as a protective shield to hide myself from my own inner world.
Eventually, I accepted the call. I went inward. I had to sit with the feelings of not knowing, the fear of not being seen as successful, and the reality of potentially not having as much money as I might need in the future. It was hard, and at many points, I wanted to make the discomfort go away. I had voices in my head that were telling me how to make money, how to turn things I was working on into legible activities. Maybe I could get funded, maybe I could start a startup. I knew I could listen to those voices and I could reactivate my previous life strategies, but I knew I didn’t want to go back.
Instead, I just started to accept that on this new path, I wouldn’t always be comfortable, and that was okay.
And what happened next, over the coming years, surprised me.
The Opposite of Trying
I started to feel okay.
About nine months after I quit my full-time job, I had made some money from freelancing, and some of my fears of going broke diminished. I also, at that point, had almost a year’s worth of evidence without a plan that I was still walking on this planet and was more or less okay. I had also, at the same time, been experiencing this explosion of intrinsic motivation coming online again, pulling me toward things I like doing, like writing, teaching, and podcasting. I was doing them without a plan, letting this inner energy guide me. It was such a contrast to the work I had done in the past.
I asked myself, “What if I follow this way of showing up in the world?” At the time, though, that was a crazy notion. It meant I’d stop looking for work for money. It was against everything I trained myself to do in the first 30 years of my life. But that’s what I did. And for the next year, I only worked on things that felt right. I said no to easy projects that would have made me feel better money-wise. I tried to spend most days waking up and just noticing what I was called to do.
Through this time, though, I often felt sluggish. Some days I didn’t do much. Often, I felt as if I were crazy. It was hard being in the US. I constantly felt this tension: “I’m not successful. All the people around me are pushing so hard in their careers.” I felt like I wasn’t doing enough. But I knew I wanted to keep going on my path. There was no going back.
I needed more time, and so my solution at the time is I ran away. In some sense, I was trying to escape, but by doing this, I really gave myself more time to sit with those scary emotions. I ended my lease in Boston, sold all my stuff, packed my bags, and booked a one-way flight to Taiwan.
Committing To This New Way in Taipei
In Taiwan, I settled into my tiny bed in a small Airbnb. With a lower cost of living, under $1,000 a month, I finally felt more free. But I still felt uncertainty. There was no plan, but there was no going back. So I kept going. Each morning, I’d wake up and do what feels right. After a few weeks, I found myself at a small table in that Airbnb, and I noticed, “Huh, this is interesting. Every day I’m waking up filled with energy, and I’m writing. Maybe this is what I’m meant to be doing.”
In Taipei, I decided I vowed to myself to stay true to this connection, and that meant fully embracing all the weird emotions. This set me on a path where there was no choice but to embrace everything I was feeling. This meant I had to face my fears; I couldn’t hide. Despite this, I started to find wisdom in the scary emotions of life. I accepted that uncertainty is an unavoidable companion on a pathless path.
Over time, I developed the capacity to make decisions not as a reaction to certain emotions, trying to make them go away, but instead to make decisions together with my emotions, understanding that they would always be with me on my journey.
This shift was so powerful. I realized that if uncertainty can never be solved, I had way more freedom in terms of how I chose to spend my time and which risks I could take. I also understood that if insecurity is always present, why not go after the work that I really care about?
But doing this in practice is still hard. And so, I played with many different strategies, including trying to have fun with it. Sometimes when I didn’t feel good, I’d look to my shoulder and say, “Oh, it’s you, the doubt monster. Nice to see you again.”
I found such power in this reframe. In these months, I vowed that I’d stop doing things in order to avoid not feeling good enough and trust what already feels good right now. I came up with a mantra for myself: “Coming alive over get ahead.”
The best description of what I started to experience is something Joe calls “the opposite of trying.” If you think about “trying,” and you put your hands together and you try to move your fingers apart, and you move them apart, then you haven’t tried; that’s doing. Trying is like attempting to but not doing it. I love this example because if you try it, you realize the state of trying is one where you are clenching, you’re tight, you’re constricted, and you can go through life in this state for a long time. I certainly did. But as Joe says, this is a state where you are literally at war against yourself. You are denying what might emerge if you softened into a more natural state.
This is what good work is all about. It is a place to get lost and completely absorbed in the moment.
Embracing Emotional Fluidity
But how do you actually make this transition? Is there a playbook? I’m not sure there is, but something good to aim at is something else Joe talks about: “emotional fluidity.”
And this, to me, has emerged as the secret of thriving on a pathless path. Because no matter what, taking a pathless path is a forcing function for facing your emotions. And this is one of those things that only seems like a benefit once you’re actually on a path like this.
Over the past seven and a half years of being on this path, I’ve had to sit with my uncertainty. I’ve had to let myself be afraid. I’ve had to feel the shame of not always feeling good enough. I’ve had to feel the sadness of letting others down. But I’m no longer activating the golden algorithm, trying to make these go away. I’m dancing with these emotions, trying to fully feel them, even if it sucks.
Some strategies I’ve developed to integrate this into my life are as follows:
- I’m skeptical of, and try to avoid, trading off feeling good in the present for a payoff in the future as much as possible. This could involve taking a consulting project that I know is not going to be a good situation but might give me a bunch of cash. I try to avoid that.
- I try to focus my energy on what feels good right now. What are the things I actually want to do and that I feel I could do for a long period of time?
- I do a lot of work as experiments. I design them to quit. I call my approach “ship, quit, and learn,” and the whole goal is just to learn about my relationship with the work and decide if I want to keep going.
- I try to create slack in my life, keeping space and time open such that I actually can reflect and let the emotions flow. This stuff takes time.
A New Kind of Ambition
Through all this, I’ve experienced a much different kind of ambition. I like to call this “inner ambition.” Here’s how I write about this in my book Good Work:
I’ve come to understand that one of the most ambitious things we can do, following our own true path, does not feel like we might expect ambition to feel. It does not come with pain, or contraction, or endless suffering. Instead, it feels light. It feels natural, as if everything you are meant to be doing is obvious. And all you need to do to “be ambitious” is simply to follow this feeling and stay connected to it.
Our culture will attempt to steal your inner ambition and convince you to use it to do what organizations, your parents, or your manager might want. But this is not your ambition. Your ambition desires more than a job title, a salary, or a brand-name company. It is a fire that burns inside of you—not for a bigger paycheck, but for a bigger life.
Your mission is to make sure that this flame never dies.
We can reclaim this kind of ambition. Thhe one that demands a bigger life, the one that points us toward a path where we can grow and evolve as humans.
Unfortunately, this kind of ambition can involve a devastating release to our own truth. Sometimes, when we point in a direction that will not enable us to be our most outwardly successful self, it means we have to mourn the loss of that person that could potentially achieve those things, a person who you thought you might have become.
We do desire to be seen, and sometimes the hardest thing about this is that we stop being seen by the people we love. We do desire to be seen as successful and ambitious by those around us. But in my experience, when you lean into this raw kind of ambition, you start to attract the attention of others who get this too, those who are already on this journey.
These days, when I work, I feel good. I do the work I’m called to do. I want to keep going, even if it’s challenging and brings up uncomfortable emotions. And the crazy thing? It doesn’t feel like I’m even trying.
