How do you figure out what to work on?

This is a question that holds a lot of people back from leaving their jobs. They rightly fear the existential dread that comes with an excess of time and lack of things to do.

This often convinces many that taking a leap into the unknown is not worth it. Others who decide to take a leap fall prey to hustle traps. They get excited about someone else’s goals and don’t realize that all they are doing is trying to calm their own fears.

When I left my job I was so afraid of creating another job for myself that I rejected almost any idea that was structured in a way to trade off time in the present for a payoff in the future. Yet I still had the problem: what do I do with my time?

The good news is that most humans, given enough time, will be naturally drawn to things. For me, it was writing, creating online courses, and podcasting. The issue was that there was not much advice on how to do these things without aiming at traditional goals.

If you’re going to write you should try to get published.

If you’re going to podcast, you should try to perfectly execute your launch.

If you’re going to create an online course, you should run a cohort-based-course.

People pick these goals because they are legible. They are the “smart” thing to do. In other words, most people see these are the things you should aim towards, and thus, why not aim for them?

Because I didn’t want to create a job for myself, however, I’ve had better luck embracing what I’m now calling “ship, quit, and learn.”

Instead of orienting towards specific goals far in the future, I design micro-experiments with only one goal: try stuff and then figure out what to do next.

My approach is probably a bit too risk-averse for some but can be powerful, especially for those who are early on an uncertain path and feel stressed about committing in one direction too early. It’s also more powerful if you are able to do many experiments throughout the year.

Let’s break down the three parts:

#1 Ship – Minimize The Friction To Getting Started

You have something you want to do but have been scared. What’s the minimum action you can take that would still feel like you are pushing yourself out of your comfort zone? Do that.

For example, if you want to launch a podcast, open up your recording app, and record a monologue of why you are launching a podcast.

I’ve helped many people get started on creative projects via a one-week “action challenge” in my reinvent course. You can check out some ideas for inspiration here.

#2 Quit – Design For Walking Away

Design your experiment for quitting. When I started my podcast, I decided that if I didn’t like it that much. Many of us were raised with the idea that you should never quit anything. This is useful for some things but absolutely terrible advice for creative pursuits. Quitting lots of things is probably the best way to find the things you want to commit to. When you design for quitting, you also put less pressure on yourself because it doesn’t make sense to overinvest in time or money.

When I launched my podcast, I had a crappy cover I threw together in PowerPoint in 5 minutes and didn’t spend any money on anything else.

was terrified when I launched my podcast but by lowering the stakes I was able to power through that first phase of discomfort and discover the magic of hosting a podcast and having deep conversations with people I admired.

#3 Learn – What Does The Experience Tell You?

This may sound too obvious or too simple, but the goal of any experiment should really be to figure out what to do next. If this sounds like some sort of infinite game, you’d be right. Almost everything I do is oriented towards finding things worth doing, indefinitely. The spirit of “ship, quit & learn” is openness to experience and being willing to see what emerges when we lean into creativity and spontaneity. Often there are three routes people take: scale-up, continue going, or quit.

After I launched my podcast, I decided that “keep going” was what I wanted to do. I liked being able to keep the show small and not having the pressure to grow or use it to make money. Over time I’ve made incremental improvements and have gotten better at interviewing but the spirit of the podcast is still the same.


Just published! The Pathless Path is Paul's book about walking away from a "perfect" job with a promising future and starting over again. Through painstaking experiments, living in different countries, and a deep dive into the history of our work beliefs, Paul pieces together a set of ideas and principles that guide him from unfulfilled and burned out to what he calls "the pathless path" - a new story for thinking about work in our lives. Learn More & Buy The Book Here



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