Window Seat

Window Seat

I quit my six-figure job to write about travel: one year in

Everything I earned, learned, and am still figuring out after one year as a travel writer

Tori Simokov's avatar
Tori Simokov
May 20, 2026
∙ Paid

Just recently, I hit one year of doing Window Seat full-time.

A huge milestone, to be sure. I took the biggest leap of faith of my life so far—quitting a cushy six-figure job to bet fully on myself and go all-in on a passion project with potential. Now it’s become something much bigger: a respected outlet with a real audience and influence. But typing that still triggers a flicker of imposter syndrome. Not because it isn’t true, but because I’m still catching up to the reality of my own life.

This month marks one full year of doing Window Seat full-time, which felt like a good excuse to pull back the curtain a bit: the numbers, the opportunities, the identity shifts, the things I still wrestle with, and what happens after you build the life you spent years fantasizing about.

Read on for:

  • Exactly what I earned in my first full year, compared to the year before, broken down by revenue stream

  • Why I turned down free trips to beautiful places, and why I’d do it again

  • How my identity is changing and the aspects I’m still wrestling with

  • Where I’m focusing my energy going forward

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