Your 20s can feel like an either-or proposition: You either buckle down and be responsible, or you embrace your fleeting youth and enjoy every day while you still can. Today is the very last day of my 20s, and when I look back, I feel like I got the best of both worlds.

Photo at blink-182 concert

Even though I view my 20s as a success, I also can’t honestly say these years have gone “according to plan.” While I put thought into my decisions along the way, some of them panned out better than I expected for reasons I really didn’t anticipate at all — I got lucky more than once.

But a lot of what I stumbled into by chance, you might be able to orchestrate deliberately, especially if you’re reading this earlier on in your own 20s. So…here’s all the sage wisdom I have to offer at the venerable old age of 29.99.

One-Track Mind

I stepped foot on University of Florida campus as a physics major, with certain knowledge of what my future held: I would graduate college by 22, spend 5-6 years earning a Ph.D. in physics, spend another few years in a (low-paying) postdoctoral research position, and then I’d start my “real career” at 30.

But then a 17,000-mile cross-country road trip following college graduation sowed a few seeds of doubt in my mind without me even realizing it. While on the road for 45 days, I learned what complete freedom felt like. Nevertheless, I headed straight to graduate school in California to proceed with the original plan.

Photo of UC Irvine student ID
Both my shortest-lived and my favorite student ID of all time.

Burnout quickly set in as I found myself enjoying the outdoors more than I enjoyed my classes, and I liked my minor role as a teaching assistant better than my primary coursework or research opportunities. After 9 months, I quit the program entirely.

This was the first big accidental success of my 20s. The idea that I might have lived on a meager grad school stipend for the majority of the past decade just to launch my real career around age 30 is now unfathomable. Why would I have ever worked so hard to start a career by 30 when I could have saved enough money to end my career in the same timeframe?

I could say that was exactly what was on my mind then, but that would only be a half-truth. I quit my Ph.D. mostly because I wasn’t having any fun, not because I had a fully-formed plan for early retirement. If I had known then what I know now, I would have made the same decision a lot more confidently.

Between Two Worlds

Lauren and I moved back to Florida (now engaged!), and I enrolled in a 15-month program that would let me earn a master’s degree for $0 if I agreed to work full-time as a public school teacher in a STEM field while doing it. So I did.

Being cast as an authority figure to a bunch of 16- to 19-year-olds when I had just turned 23 myself was a surreal experience. At first, I was treated like an unrelatable geezer, just because that’s what happens when the job title “teacher” is slapped on anyone.

One day (for my own amusement), I had my class try to rank me by age among a bunch of celebrities like Drake and Taylor Swift. I was younger than every single one of them, but of course, my students consistently guessed I was one of the oldest people on the board. No joke, some kids even ranked me as older than Snoop Dogg and Eminem. It was weird.

Photo of Steven with students
Spot the teacher.

On the other hand, the median age of my colleagues was probably closer to 40, so I felt like an outsider on both ends of the spectrum. Actually, in my first year I was routinely stopped by assistant principals and other teachers to be sternly asked for my hall pass. (Fun tip for any high school students reading this: If you just act offended and claim to be a teacher, apparently they just believe you and apologize).

Over time though, I learned that age is a lot less important than it’s made out to be (which is comforting now, on the eve of my 30th birthday). I actually had a ton in common with both my students and my coworkers, and I look back on those years very fondly.

During this short time period with very mediocre salaries, Lauren and I saved an obscene amount of money by first-year teacher standards. While that was very deliberate, it was also heavily assisted by another happy accident: moving to low-cost central Florida from high-cost coastal California.

Again, if I’m being honest, we moved mostly because of the free master’s degree program, not because we were being super smart about choosing an area with a low cost of living. But in retrospect, that’s something we should have cared deeply about and chosen more deliberately — it was life-changing.

Breaking Free

After a couple years of working full-time every day, Lauren and I found ourselves reminiscing about that post-college road trip more and more. With the excuse of calling it our “honeymoon,” we quit our jobs and spent six months in Hawaii.

Photo of Hapuna Beach in Hawaii
Hapuna Beach, Hawaii.

Here we were, a responsible couple, diligently saving money in professional careers, and we just scooped it all up and jetted off to be bums on an island for half a year. That’s an apt example of the dichotomy of my 20s — responsibility and rebellion at the same time.

In keeping with that, we didn’t blow the $100k we’d just saved on fancy island living. We worked part-time in Hawaii — just enough to pay the bills without tapping our savings. I did freelance work like photography and tutoring, and Lauren did a little paperwork and marketing for her previous employer. Thanks to some frugal habits, we ended up coming back to Florida with the same amount of money we set out with — enough to pay cash for a condo in a very low-cost area (selected on purpose this time).

@tripofalifestyle Freedom or luxury: which do you choose? — #philosophy #vanlife #camping #luxury #travel #couples #nature #money ♬ original sound – Trip Of A Lifestyle

Oops, More Money?

Once settled back in Florida, we knew we needed to get to work again. Living in a college town, I figured I could do private tutoring for cash and turn it into a full-time business. That worked out pretty well at first. Then, something strange happened: A competing local tutoring company called me out of the blue and offered me a job.

I didn’t really need or want an employer, but I went in for the interviews anyway. When salary negotiations started to happen, I threw out a number that I thought was ridiculous at the time, since I really had no interest in giving up my tutoring business. To my surprise, they accepted it. Meanwhile, Lauren found a job that paid considerably better than her last, and suddenly, we were saving more money than ever before.

As much as I’d love to take credit for this as part of a master plan, taking a 6-month break in Hawaii was never intended as a career advancement move. Actually, people told us that a 6-month resume gap would kill our chances of finding decent jobs when we returned — and we did it anyway. Dumb, right?

The magic we didn’t understand at the time was that when you gain experience, education, and skills, you are worth more money. But you will likely never realize those gains unless you leave your first job and shop around for a big pay bump. The Hawaii trip forced us to do that. I’m not saying that moving magically lets you increase your salary every time, but neglecting to explore other options ensures you never will.

We also didn’t realize it explicitly at the time, but our large buffer of savings made us feel invincible in salary negotiations, because we were never hard-up for cash. Lauren outright rejected initial offers that weren’t a big step up from her previous position — something she never would have done if we weren’t already financially secure.

If we hadn’t wantonly quit our jobs for a totally unnecessary vacation, we never would have discovered any of that. In retrospect, it would have been stupid to stay at our first jobs after having leveled up our skillset. These are things you just don’t know when you enter your 20s. We’re very lucky to have learned them by accident.

A Universe of Options

Back in high school, my dad gave me some advice while I was registering for classes, and it’s stuck with me since then. He said that when you’re not sure what your future holds, you should always take the hardest path available. Even though you don’t know exactly why you’re doing it, it will leave you with the most knowledge, skills, and options in the end.

“If you’re debating between regular World History and AP World History, just take the AP class,” he said. “You’ll learn more, and it’ll look better on your transcript. Even if you were to never go to college, at least you gave yourself the option to get into a good one by taking the harder class.”

My dad didn’t really spin it this way, but throughout my 20s, I always thought about that advice in the context of money. The more I saved, the more choices I had going forward. When I needed another break, I could take that next break without having to ask anyone’s permission.

For me, this is one of the core principles of financial independence: You save and invest to give yourself limitless options — not necessarily because you have one very specific goal in mind.

Today, as I enter my next decade of life, I have a lot of those options, and none of them involve worrying too much about money any more. That’s pretty cool.

I honestly have no clue what’s next — travel adventures, artistic endeavors, child rearing, or all of the above. Haven’t decided yet. But I’d like to think I’m as well-prepared for any of it as I could reasonably hope to be. And I thoroughly enjoyed the experience of getting here. So, I guess I’m pretty happy with how I spent my 20s.

— Steven

If you want to level up financially without sacrificing the best years of your life, check out our Financial Roadmap. It’s a guide that can take you from broke college student (or wherever you are in life) to worry-free early retiree in under 10 years — with an unusually large dose of travel and fun along the way.

Share this and start a conversation: