Always Be Experimenting

Each of us has several paths to fulfillment. In life and in work, the best way to find joy is to craft experiments that allow you to learn and evolve.

Here are three things I believe:

1. All of us can thrive in our work and lives;

2. We are expansive enough to have multiple ways we could thrive;

3. The best way to discover what works for you today is to test and learn.

I had a narrow view of career possibilities growing up. The adults I knew or looked up to were teachers, doctors, politicians, policy leaders, or lawyers. It took until my late 20s to imagine a future for myself where I wasn’t one of these things. But then what?

I started with the traditional approach of staring at my navel, thinking deeply about what I’m are good at, deciding on the color of my parachute, and then making a plan. This didn’t work for me, and rarely works for others because: 1) the options we considered are limited to the jobs we can imagine ourselves in today; 2) we don’t know/aren’t honest with ourselves about what we’re good at and like to do; and 3) planning works in a static environment, and we don’t live in that kind of world.

Start by Knowing Thyselves Today

Is there a better way? I think so. The most compelling book I’ve read on the topic is Working Identity by Herminia Ibarra. I read it while working with a career coach during my post-Amazon work sabbatical. The book opens:

We like to think that the key to a successful career change is knowing what we want to do next and then using that knowledge to guide our actions. But change usually happens the other way around: Doing comes first, knowing second. Why? Because changing careers means redefining out working identity—how we see ourselves in our professional roles, what we convey about ourselves to others, and ultimately, how we live our working lives.

Ibarra goes on to argue that we have many working identities that often change as we grow. Knowing that I don’t need to find “the job” was such a relief; in reality, there are lots of perfect fits for each of us. The key to discovering such a fit is brave enough to step outside your comfort zone if you find your work lacking.

The faster and cheaper you can test new working identifies, the better. For example, my wife and I started and quickly shuttered a toy rentals business as a side-hustle right before the pandemic (when you have two small children and toys everywhere, most of which are ignored, the logic of a toy rentals business is overwhelming). Here’s a partial list of what I learned:

• Operations is not my thing — and rentals businesses are ops businesses.

• My skillset overlaps too much with my wife’s to make us good co-founders.

• Inventory is expensive; ideas and strategies (my strength) are valuable, but inexpensive to create. Just give me paper, a pencil, and a glass of wine.

This experience allowed me to cross several working identities I’d pictured while at Amazon off my list (most everyone at Amazon is a start-up founder-to-be).

So ask yourself: what are you testing at work and in your life right now? If you aren’t testing anything, I challenge you to design an experiment and see where it leads you. Here are some of the experiments I’m running right now to help get you started:

Personal Experiments

• Reading Differently: for years, I only read dense non-fiction. If it wasn’t on a college syllabus, I wasn’t interested. I added business books for balance a few years ago. This January, I picked up a book of poetry, The Wasteland, for the first time and it was a holy shit moment. The language, the pacing, the pathos. All of it. I was in. Since then, I’ve started reading more poetry and even writing the occasional verse. More on how thats impacted me to come in a future post.

• Meditating: I’m trying to develop a daily meditation practice. My wife meditates twice a day and I can see the positive impact its had on her. This is very much a work in progress, but I’m actively trying to make it stick.

Work Experiments

• Self as Writer: I’ve always loved to write and gravitated to jobs that required me to write. But writing as part of your job is way different than putting your work into the world on your own and under your own name. I’ve committed to writing this newsletter each week for a year (at least) to test if I like — and am good at — being a writer. So far, I’m having a blast.

• The Content I Write About: essays about the climate, innovation, and strategy are my safe space. Writing about myself and finding joy in ones work and life comes less naturally. This post is a test to see how I do at this; and to see if my readers like this kind of work (please leave a comment and let me know).

• Company Size: After 7+ years at Amazon, I was ready to try a smaller company to see if it’d be a better fit. When Higg closed its Series B last summer, it gave me the unexpected opportunity to learn what it’s like to work at a venture-backed growth company. It’s fascinating and way different than I’d expected.

• Type of Role: Individual Contributor, Consultant, Leader, Manager, Strategic Advisor, Mentor, Writer. Many of these blur together in a single job, but nonetheless I’m constantly evaluating which of these hats I like wearing the most.

Conclusion

Knowing that I don’t need to have a “thing” that defines me professionally or personally was such a relief. We are all complex and have so many known and latent talents that are just waiting to be discovered or expressed.

Thinking of work and life as a set of experiments with unexpected discoveries around each corner has kept me curious, humble, and open to surprising myself — and what could be better than that?