The freedom of not chasing - Silicon Canals

"For years I assumed freedom was something I'd eventually arrive at. A few more career rungs climbed, a few more by-30 boxes ticked, and the feeling would land. I'd get to finally relax into being someone who had made it. What I've noticed, in waves rather than all at once, is the opposite. The closest thing to freedom I've found has come not from finally getting more of what I was after, but from gradually losing interest in what I was supposed to be after in the first place."

"Years before any of this, I was in my early-twenties in Ireland, working in finance and watching the people ten and fifteen years ahead of me on the career ladder. I had nothing against them. They were good at the work; many of them were people I liked. But I could see the shape of the next decade clearly, and I didn't want to step into it. So I left."

"The trip I planned to take for a year ended up reshaping a lot of what came after - Vietnam, an ESL classroom, an adult language school I ended up running, a self-taught leather side business, a failed online school, a venture-capital internship in my thirties where I went from manager back to intern, a coffee startup, and eventually writing. Looking back at all of that, what stands out is not the variety. It's how much of it I was still chasing something."

"I'd left the obvious script and walked straight onto another one - the leave-your-job-and-build-something script - without quite realizing I was on it. I was reading Tim Ferriss and the rest of the leave-the-corporate-job canon at the time, and a lot of what I felt was "deciding my own life" was, in fairness, doing what those books were telling me to do. Off one script, onto another."

Freedom is described as something that does not arrive after reaching career milestones. Instead, it appears through a gradual decline in interest in the identity and path one is expected to follow. Early in adulthood in Ireland, a finance career offered a clear view of the next decade, and the desire to avoid that future led to leaving. A planned year-long trip expanded into multiple ventures and experiences, including teaching English, running a language school, starting a leather business, attempting an online school, interning in venture capital, launching a coffee startup, and eventually writing. The variety of activities is less important than the continued pattern of chasing a new version of the same idea of self-making, moving from one “script” to another.

Read at Silicon Canals