Eddying out

“Eddy out!” Greenwood yelled. “On the right!”. Four large yellow rafts, each carrying 3 people and weighing approximately 2500 pounds, followed behind him, cutting their way through a quick moving tendon of water to reach a small calm pool — an eddy — on the other side.

I gazed out of the boat. This was my 20th straight day rafting the Colorado River through the Grand Canyon. Experiencing the canyon in this way had always been a dream. And two days after I decided to leave my job as a data science leader at a high growth startup, I got a phone call inviting me to fill a last minute vacancy on an upcoming expedition.

The evening before we set out on the river, our group learned what it meant to eddy out. Eddying out, in river speak, is to row out of the fast-moving current in the middle of the river into a calm pool of water that’s usually caused by a rock, branch, or unconformity along the river’s banks. This slow pool creates temporary protection from the river’s movement, and allows a boat to sit calmly outside of the unrelenting forward progress of water, giving the people it carries a moment to plan, reflect, snack, or simply sit and look at the red canyon walls above.

— — —

As I write this reflection, I’m finishing up my 6th month of intentional unemployment—of life in an eddy. After leaving my job, I spent one month in the Grand Canyon, five weeks surfing and trekking in Peru, one month connecting with family and friends in California, and then two months traveling across 14 cities in Europe and the Middle East. I intentionally eddied out completely from Data Science: I didn’t pursue any personal projects, I didn’t write a single line of code, and outside of a few dozen hours mentoring within the industry, I didn’t engage with it.

Eddying out was a particularly unusual thing for me to do because I have always been someone whose identity is closely tied to their work. I believe the phrase most of my friends and family would use is “obsessed”. I am that person who sees their performance review as a reflection of their self and their work success as an indicator of their actual value as a human. Apparently?this is quite American of me, based on our current cultural values. But this philosophy also can be harmful, especially in a tech climate where employment relationships can end with short notice, destroying a foundation for identity.

Before leaving my job, my biggest fear was of this unmooring from my identity. If I had one primary intention with eddying out, beyond having wild adventures, it was to restructure this relationship between my Self and work. This motivation was not due to seeking some elusive “balance” with work or heal any burnout—I didn’t feel burned out —but rather to improve my own ability to detangle the part of my life that is work from the rest of my life in a healthy way.

When I shared this plan with others, it was surprising how binary the reactions were: either a “good for you!” or a “Wow I could?never?do?that.” Their trepidation wasn’t about a tether to responsibility, nor was it financial. People were telling me something about their relationship to work. Eddying out requires trust that on the other side of work, there’s a life experience worth the opportunity cost of not working. It requires facing personal fears of feeling listless or bored and owning up to the possibility that you will fall behind in your career and not be able to reenter gracefully.

The skeptics were right in some ways. Not working thrust me into a more judgmental headspace about my own choice than I had expected. On a Monday morning at 9am, I was hard pressed to figure out what value I was getting out of driving the Pan American highway in rural Peru versus what I could be getting drafting analyses or coaching teammates or debating business strategy.

Countless nights I went to sleep ruminating on the usefulness of the eddy —what am I doing? Am I even contributing to the world? Isn’t this the most selfish possible use of my time? If it is, isn’t that a bad and immoral decision to be making? Wouldn’t this time be at least better spent volunteering at a food bank or joining the Peace Corps or something? Aren’t I going to miss out on all the data science advances and new frameworks and AI models that are happening right now while I’m sitting at a cafe in Berlin reading novels?

It took a few months for this endless second guessing to quiet down, and for me to spend less time in the eddy looking at the rushing water thinking about all the progress I should be making and more time?in the actual eddy, doing the things that one does: Stopping. Breathing. Refueling. Tying up the boat to go on a hike to a completely different part of the canyon. Connecting with other people that happen to find themselves in the eddy at that moment.

Outside of existential questioning, there are also risks to eddying out. The obvious one is the opportunity cost of the job-specific learning, progress, and earnings you miss out on while out of work. It can be personally and financially burdensome, if not completely unfeasible, to be unemployed for months at a time.

It’s also risky to confront the allure of not working. I worried: what if I love it so much in the eddy that I never want to work a “normal job” again? That felt like a very valid fear until I was asked by a friend —“so what if you do feel that way?” –and faced the answer to that question, realizing that most of that fear was simply the fear of losing the personal prestige that our culture ascribes to traditional employment.

I also foolishly attempted to use the eddy to timebox personal advancement —as if I could compartmentalize “figuring out my life’s purpose” (whatever that means), processing seven years of work at a high-growth startup, and improving my habits and knowledge into a neatly-packaged 6-month box with a certificate of achievement at the end.

In spite of these challenges, the rewards were high. Yes, there were the beautiful experiences from chasing wild adventures across a dozen countries, but there was also the personal reward of the progress I made decoupling self worth from work. Time was the primary factor here: I spent enough months not working to finally accept that in each of those months I was just as valid a person as I was when I had a high-powered job. But role models were also helpful: I spent most of the past 6 months around people who have drastically different relationships to their work than I do. These include new parents who see work as a transactional relationship that lets them put more time into their family, older couples who have retired and spent their careers in many different industries across many decades, and friends whose personal projects are more a source of pride than what they get paid for.

While pursuing my?ikigai, which for the better part of the last decade has been my focus, I’d neglected the fact that it’s completely valid and useful to focus on any one part of that Venn diagram, as many of these role models do. Being able to call your work your passion is a worthy pursuit but also a double-edged sword—it can create the tangled identity that I was now struggling to untangle.

When I did finally feel ready for something resembling a job (and what “ready” means could be a whole separate essay), my love for my work came back to me like I was remembering a dream. As much as I enjoyed adventure in the eddy, I was reminded that I have a deep reverence for the hard work and struggle of being part of a growing company. I would finish an interview with hurried excitement and share with my partner, “you won’t believe it! This huge company with one of the best data teams in the industry has the?same?problems as this start up I just talked to yesterday! How wild is that?!” I knew I was ready to reenter the river because it felt as if I were peeking over the eddy fence and seeing boats rush by and thinking, “oh they’re about to go down a really gnarly rapid and I want to be a part of it.” I don’t know if this natural enthusiasm would have been as clear to me as if I had still been working, where often the day-to-day problems of company building felt crushingly hard.

In the end, what I found I gained most from the eddy was a more honest assessment of the river itself. Before I rowed the 277 miles of the Grand Canyon, I thought the river was simple: flowing water, tall canyon walls, beachy banks on which to camp, and that’s about it. But after weeks on the river, its complexity revealed itself to me. It is immensely vast and multifaceted, and I had underestimated its depth.

Life in the jobless eddy let me see that we tend to have a shallow view of our careers. We’re on this career ladder, we’re in that job function, we’re in a startup, then it grows, then we get a promotion and go to a bigger and better company, etc. And if we don’t traverse that path linearly, we’ve failed. In reality we have incredible choices in the path we choose to row, how often we stop to explore side canyons, whom we row next to, and what we hold up as examples of successful navigation of the river. The culture of tech exacerbates this single-minded career anxiety that’s already endemic in America: we are always playing catch up and never grinding hard enough, so taking a break just makes that worse. I’ve emerged from my time off with the opposite conclusion: if you’ve spent months developing clarity on what you want to be giving to and getting from work, it makes the whole adventure much more grand.