I quit my full-time job in NYC to freelance… And failed. (Johanna's Agile Life Story, Part One)

Updated: Mar 1

I quit my full-time job in New York City to freelance write, teach literature classes online, and build a coaching business. I thought I was combining the best of both worlds: the productivity of a New Yorker and the freedom of an entrepreneur. The grind of an hour long commute, meaningless work tasks, and endless bureaucracy had worn me out. Location independence was my key to the kingdom: I was about to be my own boss – and travel the world.

That's what was supposed to happen.

My work life balance, which had been strained when I was working full time, completely fell apart. My friends came to visit me wherever I happened to be—Peru, Ecuador, Indonesia—yet I found myself skipping out on ruins to meet writing deadlines. Travelers I met on the road would suggest a boat trip and I would ask, "Will there be Wi-Fi?"

I couldn’t leave the workplace; I was the workplace.

I responded to work emails as I woke up and fell asleep, poured my heart into low-paying projects, and spent half my time between tasks trying to decide what to work on next. It took energy and time to switch between roles: consultant, ghostwriter, entrepreneur, freelancer… Each identity was equally urgent.

And of course, I felt terribly guilty when I wasn't hustling, so I never turned my work brain off. I would think, "Is this a potential client?" when I met new people. Every experience was material for an article. I even thought about inventing a pen I could use while surfing to write down ideas I got in the water.

Being an entrepreneur felt like running towards a finish line that never got any closer: no matter how hard I worked, I was always behind. I started to fantasize about clocking into a mindless day job where I wouldn't have to make decisions alone or work without guarantee of pay.

The irony wasn’t lost on me.

Apparently, I am my own toughest boss. Technically I had freedom, but I spent all sunlight hours inside and ate dinner in bed because my kitchen table was my work desk. I was haunted by a sense of foreboding that I had forgotten a deadline or missed an opportunity.

It wasn't sustainable. Or balanced. Or even financially viable. It felt like there was a magic tool out there that successful entrepreneurs had found—if I could just get the right system or planner or business coach, I could overcome all these challenges.

Finding the ultimate work tool became my new focus; I spent the next months implementing every productivity tool I could get my hands on.

Go straight to Part Two

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