I Quit My Job
These days, “I Quit My Job” blog posts are a dime a dozen.
Many such posts follow a similar pattern: whiz-bang coder quits high profile job and trades a hefty paycheck to pursue the dream of being self-employed.
My story is a little different. It doesn’t have lots of zeros or a buzz-worthy company name. I didn’t make 6 figures. I didn’t work at a Big 4 tech company in the Bay.
On the contrary: I was making ~90k, 3 years into a career in reinsurance, living on a 21-mile-long island in the middle of the Atlantic.
Does that make my story less click-baity? Probably. But I still hope, if you’ve made it this far, that it’s a story that you can relate to.
The beginning: freelancing
I’m from Bermuda, born and raised. Bermuda, if you don’t know, is one of the world’s biggest reinsurance hubs (reinsurance is insurance for insurance companies – yes, such a thing exists).
Unlike the majority of my Bermudian peers, I didn’t immediately enter the reinsurance industry after college. I was too busy going to Burning Man and road-tripping in my red pickup truck. Out of necessity, I found a way to work while on the road and, without realizing it, fell into freelancing.
Imposter syndrome was so bad for the first year that I didn’t accept that I was actually freelancing until a client referred to me as a “freelancer”. 🤦♀️
Long story short, I did web and graphic design for 3 years and then started to feel…pressure. The bad kind. The kind that settles at the pit of your stomach and makes you feel ill.
A question grew inside me: could I ever really be “successful” if I never held a “real job”?
Jumping ship…to reinsurance
With seeds of doubt sown and my confidence crippled, it’s not surprising that I jumped at the first “real job” opportunity that crossed my path. An advert in the paper (Bermuda is old school) for a Catastrophe Modeling Analyst at a reinsurance company sounded exciting. It had “catastrophe” in the name! It must be interesting!
I went into the job interview knowing less than nothing about reinsurance. In fact, I remember googling “what is reinsurance”, just in case I was asked to explain.
Fast forward a few weeks and I’d accepted an offer. Just like that. A sudden end to 3 years of being my own boss.
Looking back, there were 3 reasons why I took the job:
- A steady paycheck
- The promise of interesting work
- External validation
The job advert dropped in my lap at a time when I was questioning myself as a freelancer and as a human. My lack of confidence in my unconventional career path made me even more susceptible to the societal pull of a “real job”.
Unfortunately, I didn’t have a network of people who believed in taking the path less traveled. There wasn’t a culture of online builders and creators that I could fall back on for support. In my eyes, I was the only person I knew doing something different. And it made me feel like an imposter and a failure.
Round peg, square hole
I threw myself into the Catastrophe Modeling Analyst job. I figured, hey, what I lack in experience, I’ll make up for in effort. Let’s go all in.
At first, that was enough. There was plenty to do and I seemed to be good at it. All was fine until, 3 months in, I came up for a breather. I looked around and started to wonder, what exactly am I doing here?
It wasn’t just the work that was a bad fit. It was working in an office. Being abruptly dropped into a corporate environment with all of its unspoken rules and rituals. Being bombarded by stimuli in Open Floor Plan Hell.
I felt like a character in the Sims as I danced around the kitchen filled with morning chit-chat.
And at home, when I’d finally strip off my office clothes and re-bandage the blisters on my heels, I’d sit down in front my computer and – nothing. No spark. No excitement to build or create.
I started drinking more. And I sank into a very dark, repetitive rut.
Hope?
I’m a stubborn creature. I viewed my situation as something I could “beat”. If I tried hard enough, and put in enough hours, I could make myself into a model reinsurance professional. Out of stubbornness, I buried my head in my work and tried to forget that I felt totally out of place.
A year passed in the blink of an eye and an opportunity presented itself for me to veer off in a different direction: underwriting (yep, I had to google that one too). Perhaps, I thought, this would be the path for me.
At that moment, I had what many people always wish for: a comfortable job, a steady paycheck, a path to progression up the corporate ladder. The only thing I had to do was stay.
Round 2
Underwriting, as you’ve probably guessed, was also not for me.
But unlike the first go around, I filled my free time with learning, not drinking. I took online coding courses and earned my IBM Data Science Professional Certificate. I finished the #100daysofcode challenge on Twitter and engaged with the online developer community. I fell back in love with technology.
Finally, I had something outside of work that excited me. Ignoring how I felt from 9-5, I settled into a comfortable equilibrium. I was coasting.
And the scary part is that I think I could have coasted through the rest of my life.
But something special happened at the beginning of 2020: I started building again. Not building as in course projects that never see the light of day. Building for real people.
Just like that, the spark was reignited.
COVID-19, an awakening
2020 has been a roller coaster. The year started off with a bang as I found my co-founder, applied to Y Combinator and then immediately went into COVID-19 lockdown. Funnily, had it not been for this last part – getting shut in the house for months on end – I doubt I would be writing this post today.
As it did for many people, COVID-19 broke me out of a rut. And in its wake, a new routine emerged: pair-programming. A lot. Every Sunday, for hours on end, I worked with my co-founder on our new side project, PeerWyse.
It was fun. I was learning a lot. Our sessions started to stretch longer and longer. We started to fit in a few hours here and there before work.
Soon, we were coding together every day.
COVID-19 shook me out of my habits and forced me to realize that I was strapped onto a ride heading towards creativity oblivion. My mind, released from the burden of constant office bombardment, started to wonder – what if I made building my job again?
The leap
As you can imagine, I thought about this a lot. I was a mess. For months, I struggled with guilt over not being happy with the opportunities given to me. My stomach tied in knots at the thought of telling my boss.
It bubbled within me until I couldn’t take it any more.
Finally, I quit my job.
You might be asking, why make the leap? Couldn’t you have continued building on the side while earning a steady paycheck?
And the answer is yes. If you’re reading this post, having similar thoughts, keeping a full-time job is probably the route you should go.
But for me, it just wasn’t enough. Every day, I resented the eye strain of endless spreadsheet work, my contacts feeling like sandpaper in my eyes. Repetitive meetings and administrative tasks gnawed away at my focus. In my mind, I designed an alternative path. And I knew I had to take it.
My only regret is not taking it sooner.
What’s next?
There are really two reasons why I’m sharing my story: to inspire and to scratch an itch.
Inspire, because the responses from friends and colleagues have made me realize that I’m living out many people’s dream: quitting a corporate job to become my own boss. Trading admin for creativity. Being in control.
Scratching an itch because I’m sure this all sounds crazy. And who doesn’t like to watch someone make questionable life decisions? 😂
Regardless of which reason resonates with you, I hope you’ll join me on this adventure.
Taking inspiration from Pieter Level’s 12 Startups in 12 Months, the crux of my plan is to:
- Launch products, as many as possible
- Iterate on PeerWyse, the project that led me down this exciting path
- Network with other founders, bootstrappers and indie hackers who are on this journey too
In a way, I’m back where I started. My imperative is, once again, to create.
But in many ways, this place looks very different. This time, I have enough resources to support myself comfortably for quite some time. I have a supportive family, who is seeing me happier than I’ve been in 3 years. And, I have found a network of people like me who are also trying to create something out of nothing and share it with the world.
Come say hi
If I learned anything over the last year it’s that you can’t be successful in a silo. So, I will be building and documenting my progress in public. If you’re on Twitter, LinkedIn or Indie Hackers, please come say hi. 👋
You can also subscribe to my blog if you’re curious to know what the hell I’m up to. 😉
Many thanks for reading and I hope to see you around.
(Interested in working together? Let’s chat: amy@amypeniston.com)