The biggest money mistake I thought I’d ever make didn’t turn out to be a mistake at all

Courtesy of Caroline Lupini

I studied engineering because it was something I was good at and would offer me a stable job.
But I didn’t love it. It wasn’t my passion and I especially didn’t want to work long hours for the rest of my life.
So I quit. It could have been the biggest financial mistake I ever made, but it wasn’t.
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Picture this: It’s the late 2000s. You’re a high school student, eager to graduate early in the smoldering aftermath of the Great Recession and you’ve got a plan. You’re going to combat the recent financial insanity (that you don’t really understand — did anyone?) by heading to a major university, picking up an engineering degree, and landing a stable job in engineering because that’s what you’re good at, that’s what you like, and that seems like the most responsible thing to do.

Hi, it’s me. Teen Caroline.

And unlike many of my teen cohorts who graduated high school during the Great Recession, I was actually able to do what I’d planned. I did go to a major state school and I did graduate with an engineering degree, and I had landed that engineering job that I’d planned to get. It was all working out.

But in the midst of all the ways by which I’d engineered my life (pun intended) I eventually got to that point every 20-something generally understands; this fundamental, foundational shift in the "plan" and the "agenda" and the skills I chose to leave off of my resume.

I was good at other things, and the problem was, I really liked those other things.

Everyone was skeptical when I changed careers

So I made what I considered (and what was generally considered) to be a huge, quarter-life-crisis level mistake. Financially, it was unstable. Culturally, it was unacceptable, but personally, it was so necessary. I wasn’t happy, which for me can simply stem from the fact that I wasn’t sleeping enough and I had very little of a life outside of my job. It’s an age-old story, but I was suffocating and when I found a way out, I took it.

My way out was that magical unicorn you all see on Instagram and perhaps even wish you had: the freelance writer’s life. Only let’s be real — that wasn’t really the plan when I quit my engineering job, but it ended up offering me the freedom and flexibility I wanted with my life.

But the No. 1 mistake I see people make when they get a glimpse of my life is to assume that it was an easy switch, and that it all happened overnight. Not in the least; in fact, I had to take on quite a bit of debt to sustain the idea that I could eventually sustain myself.

Now, several years later I have an MBA (the MBA was my insurance policy in case my freelance career didn’t work out) and I’ve found a way to sustain myself fully on freelance work.

Writing about credit cards and travel became the career I never expected

Up until now, this article probably reads like an Instagram caption; you know, one of those "I did it and so can you! There’s nothing different about our lives and privileges!" influencer flexes that at best induce an eye-roll and at worst catch an audience member who actually believes them. I get it. It’s annoying and utterly unhelpful, not to mention problematic.

So, here’s the why and the how and the facts for your enjoyment.

My decision to start freelancing began with my love for travel and my aptitude for writing (and a really bad breakup), but perhaps more importantly, it has a lot to do with my travel-hacking prowess.

I’ve spent the past eight years researching and staying up to date on the ins and outs of the foundations of our credit-based economy in the US and learning how to do exactly what banks hate: understand how to use rewards credit cards responsibly and beneficially. It’s pretty much the result of my data-hungry engineering brain applied to basic, everyday economics.

Once I began to understand how to leverage my debt and liabilities in a way that would eventually benefit me, I started stockpiling points and miles currencies and earning in every way I could. That meant paying attention to bonus points categories, learning how to pay bills with credit cards (and paying them off as soon as possible), and leveraging my bigger bills to meet minimum spending requirements for huge sign-up bonuses. Reading the fine print and squeezing the most out of the benefits is the most important thing to do when opening a new rewards card.

When travel then became even more accessible to me, I started collecting as many experiences as I could to provide fodder for my life and work. Writing about points and miles cards became second to breathing, and telling stories about my travels became a fundamental joy. My wide skill set has helped me successfully pitch to a wide variety of clients, which meant that I was finally seeing a glimmer of the sustainability I’d been trying to build since leaving my job in engineering.

With freelance writing, it’s unlikely that I’ll lose my entire client base at once if something happens. This means that I’m always stockpiled with work in one way or another, and things have leveled out over the past couple of years into a sustainable routine.

While travel writing does not mean that I’m on vacation all the time, it just means that I work (a lot) to pay rent in a lot of different places instead of just one. And sometimes, taking a financial risk can really work out.

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