I walked away from life-changing money in finance to chase my dream of becoming a writer. I had no experience, clients, or idea where to start.
I moved from Nashville to Hawaii to figure it out.
I graduated with a journalism degree, but my brother worked in finance in Nashville. He told me he could get me an interview at his company. I interviewed, got the job, ditched my dreams, and chased a paycheck for six years.
I started working in 2016 and made about $50,000 as a 22-year-old. I felt rich, and the number kept climbing.
By 2021, I was making nearly $150,000 a year. Halfway through my last year, I was on pace to make $205,000. I was also interviewing for new roles in the $250,000 range.
Every day I worked in finance, I knew it wasn't right for me. I wanted to quit and be a writer, but the money was too good.
Finally, in May 2022, when I was up for a promotion, the dam burst. I remember going home one night after a final interview, and I could feel it in my gut. I knew I didn't want to get the job; it would trap me, and I'd regret pursuing it.
I printed off my two-week notice that night and quit the next day. My boss and coworkers were in disbelief when they found out, but for the most part, I had tremendous support from the people in my life.
I heard about a work-stay program at a coffee farm on the Big Island of Hawaii through my brother and sister-in-law, who had visited Hawaii. You can live on the farm in exchange for 28 hours of work a week. That sounded like a pretty good deal since my income dropped from six figures to $0 overnight.
I put my stuff in storage, packed a carry-on and a backpack, and flew to Hawaii, trading in my Nashville high-rise apartment and rooftop pool parties for a one-floor communal living house with six college kids.
I worked as a tour guide on the farm a few days a week. The rest of the time, I tried to figure out how to make a living as a writer.
Visiting and living in a place are different experiences. Hawaii is a rock in the middle of the ocean — sometimes, it feels like it, but for any of the cons, there are more pros.
It was nice to get a break from city life and a good reminder that the world outside your immediate circle is full of people who live life at a different pace.
I wanted to become a freelance copywriter, but the industry is saturated. Many people are attracted to the opportunity to work for themselves, travel the world, and make money by pressing a few keys on a keyboard.
I spent day after day locked in my bedroom in Hawaii — just me and the geckos — sending cold emails and LinkedIn messages. I got a few nibbles but no bites.
I decided I wanted a car to explore the island. I contacted a local car rental service and noticed the owner's website needed serious copywriting work, so we struck a deal. I'd write his entire website for $500 and an extra month of my rented Dodge Challenger. I had my first client.
I started freelancing with an agency thanks to a cold email I sent. Then, I started posting on LinkedIn and picked a couple of clients up that way. Today, I'm a full-time freelance copywriter and ghostwriter.
While in the work-stay program, I wrote some email copy for the farm. The emails did well, and one day, I sat down with the farm's CEO.
He envisioned writing a book about the history of a local church and using it to raise money to restore some of the murals that had deteriorated over the last 125 years. He asked me if I'd be up for writing the book. I agreed and started splitting my time between leading farm tours and researching for the book.
All roads lead home. I moved to Michigan in March 2023 to be closer to my family.
In my first full year of freelancing, I made $85,500. Through November 2024, I've made $110,000. I'm grateful to be doing as well as I am, but I can't pretend like I don't think about the money I would've made by staying in finance.
Gratitude and perspective are more important than the number on your tax returns, but it's also ignorant to pretend like money doesn't matter. I wonder sometimes if I was dumb for leaving that money behind — it's impossible not to.
But was it worth it? Am I happier? Would I do it again? Yes, 10 times out of 10.
When deciding whether to quit my job to pursue this dream, I heard Tim Ferriss on a podcast recommending playing out the worst-case scenario of a decision in your head. How catastrophic is it? How permanent is the impact? How bad would it really be?
Worst-case scenario 1: If I stay in finance, I'll always regret not discovering what I could've made of myself.
Worst-case scenario 2: I try to write, fail, and get another finance job.
For me, the fear of regret was greater than failure.
Now, I never have to wonder, "What if?" or think about what I could've done with my life. I know the answer.