Good Work : Reclaiming Your Inner Ambition

After that, I implemented several “gating” criteria to determine if the work I am considering is right for me. One of my favorite filters is “How much would I pay to work on this?” It flips the frame from working for money to paying for the right to work. When I ask this question, very little work other than writing passes the test.

work worth doing. I didn’t want to escape work; I just craved work I cared about.

Looking back, what chunks of time feel satisfying and seem to be more important as time progresses? What am I drawn to do, right now? What am I doing already that feels good? At the end of my life, what will I definitely not regret having done?

Most people have an acute sense of the challenges that lay ahead. They can predict the criticism they’ll face and the insecurity they’ll feel. This is why many, including me, refuse the “call to adventure” as long as possible. Before quitting my job, I spent several years critiquing the corporate world from within, convinced I could help “fix” it.

Angie and I joked that in just a few months, we had already spent more time together than career-focused couples do in a whole year. This felt important: she took quality time seriously and was willing to sacrifice things like money in return for connection, adventure, and love.

This is why freelancing is often a useful, but temporary, first stop for people on unconventional paths. It involves work you are good at and perhaps even enjoy somewhat, but if you try to turn this work into a business or your new identity, you end up creating a job for yourself that includes everything you wanted to escape in the first place.

“People view me as a writer and I am a writer, I'm a productive writer, but I don't start writing until the afternoon. The whole morning is devoted to listening to music and reading and mostly reading books.” What jumped out to me was a comment that signaled how seriously he took this good work: "I did not do this as a career strategy. I didn'

You just need to sit down and write. If you struggle, just notice what is coming up. Don’t tell yourself you should be better at this. Ask yourself questions instead. Get curious about it. Try again the next day. Don’t take it so seriously.

out how to escape the nonsense, exploit the system, or extract as much money from the company as possible.

I’ve had to mourn the loss of parts of myself that once served me, while also reconnecting with other parts of myself that I had suppressed.