“The secret of happiness is freedom,
and the secret of freedom is courage.”
— Thucydides
As I mentioned in my previous post, I set a financial goal early in adulthood—a specific number that represented freedom to me. I reached that goal by age 35, and almost every decision I made up to that point was focused on getting there. Now that I’ve had some time to reflect on that journey, I want to share the top three choices that made it possible.
1. Prioritized Saving & Investing Early
I’ve always been a saver. There’s always been something more appealing to me about saving than spending—maybe I’m just inclined toward that end of the endowment effect spectrum. If you’re unfamiliar with the endowment effect, it’s that cognitive bias that makes us feel like what we currently have is worth more than what we could get with what we currently have.
So, in my case, the $5 I earned from shoveling the neighbor’s driveway always felt worth more than the couple packs of baseball cards and a bag of M&M’s that I could’ve purchased with that $5 if I rode my bike up to the local Walmart with my friends. And the $50 that I saved after doing a few weeks of those kinds of small jobs felt more valuable than a Gameboy or Nintendo 64 game cartridge. After a full season of odd jobs, I had accumulated $200, and it felt like more than anything I could’ve spent it on—whether it was a new gaming system, a bike, or a Starter jacket, or whatever the cool kids were buying back in those days.
I remember opening up the little red safe that sat on the desk of my childhood bedroom, and realizing that after a few years I had over $700 saved. I talked to my Dad, and he helped me invest that money in an index fund. By the time I turned 18, that money grew into …my first real, noteworthy (i.e., over $1,000) financial accomplishment, which gave me a solid start to continue investing in my young adulthood. But my journey was just beginning.
Throughout high school and college, I worked every summer and throughout many of my semesters in college. By that point I had expenses to take care of, but my attitude towards money remained the same—I wanted to save and grow as much of it that I earned as humanly possible. I didn’t work to be able to afford fun after taking care of my necessities, I worked to be able to start building a future. I carpooled whenever possible, brought in brown bag lunches, or—when the job was close enough to home—I walked home to enjoy a lunch there. Why waste gas driving when you can get some exercise walking in the middle of your day?!
I remember all the other guys on my crews (when I worked one summer for the County Highway Department) or teams (when I picked up a seasonal job as a runner at a local law firm) heading over to the local pub or diner for lunch every day, but I could never understand how they could justify spending 1-2 hours worth of the money that they just earned on lunch. There was no logic in that to me. Sure, sometimes a big burger with a big side of fries and an ice-cold Coke sounded great, but I always felt proud that I knew the small sacrifices I was making that day were taking me closer and closer to a life of freedom one day that not everyone else who was living life day by day was ever going to be able to achieve.
Looking back, I don’t know how much—or how little—I actually managed to accumulate from these early savings habits. I do know that I ended college and started marriage with about $25,000 in a CD, which although a terrible place to have your money at a young age—in retrospect, what was I doing?!—at the time felt like a small fortune.
But more important than the amount of money that I saved was that I had learned how to save when I was earning very little, so that as I started to earn a little bit more year by year, I could save more of what I was earning, rather than simply spending more of it on passing frivolities that would ultimately amount to nothing. And while I initially didn’t know much at all about how to make that money grow—I don’t know what kind of mutual fund my cash went into when I was young, and I certainly would’ve been more aggressively investing when was in college rather than letting money sit in a money market account or CD—I would eventually learn how more about how to make smarter investments, think strategically about using Roth and Traditional accounts for tax efficiency, and really make money work to make more money. But (and this is key and we’ll come back to this below) everyone has to start somewhere!
2. Focused on Building Multiple Income Streams
I’d be lying if I said I started building multiple income streams intentionally, with any real forethought or strategic planning. On the contrary, I stumbled into my first—and most significant—additional income stream the same way many of us stumble into opportunities in life: through a stroke of good fortune.
Growing up, my parents invested in music lessons for me. I eventually earned my undergraduate degree in instrumental performance, with one goal in mind—to perform. Landing a job in a symphony orchestra was the dream during those wide-eyed years of my late teens and early 20—but I never, not even once, imagined I would end up teaching music.
Fast-forward a few years: I was pursuing a graduate degree in something completely unrelated to music, but I kept in touch with friends who were building careers as music educators. One day, one of them reached out. They had too many students, couldn’t take on any more, and asked if I’d be interested in handling some of their overflow. Honestly? I had no idea what I was doing. I had taken exactly one pedagogy class in college—a fancy word for “how to teach”—but I left that class feeling no more prepared than I had entered it. Truth be told, I think the professor wanted to be there even less than the rest of us.
Still, even though I lacked confidence and wasn’t exactly equipped for the challenge, I did something that has served me well over and over again in life: I said, “Yes.”
What started with one student quickly grew to ten. Then it kept growing until I hit a familiar problem that non-scalable business models often face—I ran out of time in my day to sell more of my time. (Later, I would wrestle with the decision of whether to scale the business further, and if so how—but that’s a story for another post.)
This small, unexpected opportunity to try something new turned into a thriving income stream, one that brought with it unexpected benefits—chief among them being the incredible investing power of traditional and Roth i401(k)s. If you’ve never explored how starting a small business on the side can allow you to maximize retirement savings through a self-employed 401(k), I hope this moment plants that seed in your mind. It could be a life-changing strategy.
This first exposure to earning money outside of a traditional job—and the ability to leverage tax-advantaged accounts—opened my eyes to the many ways to pursue financial independence beyond just earning a paycheck. It was the first, but certainly not the last, way I began to accelerate my journey toward financial freedom.
3. Focused on Reducing Expenses Without Sacrificing Quality of Life
Right from the start, I want to acknowledge the elephant in the room: “Quality of life” means something very different to everyone. Some of the things I share doing here—and in future posts—will sound like major sacrifices of quality of life to some of you. I’m quite sure many of you will say, “Nope… saving X amount of dollars just isn’t worth giving up Y to me.”
And you know what? That’s totally fine! We’re all here to build the life that we want for ourselves. What might sound like a hardship to one person could feel totally natural—or even enjoyable—to someone else. For me, the ways I chose to cut expenses and live frugally felt worth it. In fact, I often enjoyed the process. But you’ve got to find what works for you, and you will.
That said, here are some of the practical things I did between ages 18 and 35 to reduce expenses and accelerate my journey to financial independence:
A. I drove old cars.
I know, I know… this isn’t exactly groundbreaking advice. But I can’t overstate how much money I saved driving older vehicles. I think my best purchase ever was a 1999 Honda Civic that I managed to pick up in 2011. It had been garage-kept, and driven only ~65,000 miles in those 12 years. If I could come across that perfect of a car every decade or so, I’d be a made man. That car was a dream for anyone pursuing financial independence: fuel-efficient, reliable, cheap to maintain, low insurance costs, and barely a blip on the property tax radar.
That Civic saved me thousands compared to buying a newer or flashier vehicle—and let’s be honest, almost every car is flashier than a 1999 Honda Civic. Those thousands didn’t just sit idle either; they went straight into investments, where they’ve had the potential to grow into tens—or even hundreds—of thousands over my lifetime.
B. I lived in the most affordable housing I could find.
During college, I quickly learned that dorm life was not for me. So, before the start of my second year, I started looking for the most affordable apartment I could find. Unsurprisingly, the cheapest apartment was on the very outskirts of the college town, but that savings of several hundred dollars a month was well-worth the extra distance to me. And as an added benefit, I stayed in the best shape of my life walking to and from class every day. I was far away from the noise and messy alleyways of the frat houses and on-campus apartment complexes, and instead enjoyed relaxing strolls down brick-paved sidewalks overhung by flowering dogwood trees.
When I moved to the city I’ve now called home for 15 years, I repeated the same strategy: find the most affordable apartment possible. It wasn’t in the best part of town and certainly wasn’t glamorous, but it allowed me to save aggressively and invest consistently. Each month, I funneled those extra savings into my investment accounts, helping me build momentum toward financial independence.
After five years of renting, I finally scraped together a down payment for a home—selling pretty much everything that wasn’t bolted down to make it happen. That house? Again, nothing to write home about. I’ll never forget the realtor saying, “This’ll work for a few years, then you’ll want to upgrade.” Clearly, we didn’t share the same outlook on frugal living or long-term goals.
The house had been owned by a 95-year-old man, and his out-of-state son just wanted it sold. It hadn’t been updated in decades, but with some elbow grease, I made it work—buying it tens of thousands below similar-sized homes. My mortgage ended up being about half the cost of renting a similar place. Lower housing costs also meant lower property taxes and insurance premiums, allowing me well in excess of $1,000 in my pocket every month for years.
Add in the tax benefits of running my small business from home for over 10 years, and that house became the perfect launchpad for building wealth. After 10 years, I sold it for double what I paid, freeing up significant capital to fuel further investments.
Was it the best investment I’ve ever made? Maybe not—my IRAs and solo 401(k) might claim that title—but it was massive in helping me reach my financial independence goals.
C. I budgeted with Financial Independence in mind.
This one is kind of a catch-all category, but I think it’s also an important thing to consider.
Many people budget by saying, “I have X amount of dollars coming in, so I can afford A, B, C, D, E, F, and G, which all adds up to X.” Others budget by saying, “I have Y amount of dollars coming in, I’m going to save 10% of that, and with the remaining 90% I can afford H, I, J, K, L, M, N, O, and P.”
But what would happen if you were to say, “I have Z dollars coming in. How can I cut Q, R, S, T, U, and V down as much as possible so that I can save and invest as much as possible?” This is a radically different approach to budgeting—one that makes your financial independence the top priority, and gives every budget line item, every purchase, and every financial decision you make a definite purpose. How much could you save if you began to look at your finances this way?
Without this mindset, I wouldn’t have pursued used cars or house hacking so relentlessly. It was because I prioritized Financial Independence that I viewed every expense—housing, transportation, and beyond—through the lens of, “How can I minimize this so I can maximize my savings?” Prioritizing financial independence wasn’t just another tactic—it was the engine that drove everything else.
Ready to Change Your Life? Here’s Where to Start
If you’ve made it this far, you might be wondering—how can I start moving toward financial freedom today?
Here’s the truth: You don’t need to nickel and dime every coffee or cancel every streaming service to build real wealth.While small savings can add up, the biggest gains often come from bold moves—reducing your major expenses and building a second (or third!) income stream.
Think about this: What would it look like to cut your two biggest expenses—housing and transportation—by 30%? Or to start earning just $500 a month from a small side hustle that leverages your skills, interests, or experiences?
That could be tens of thousands of dollars saved and earned every year—not by giving up your $5 latte, but by making intentional, strategic choices about the big stuff.
Want to get serious? Here’s where to start:
- Explore one way to earn extra income—maybe freelancing, selling a service, or something small that could grow. What’s something that you’re really gifted at? Maybe something you really enjoy as a hobby, or maybe even a skill you developed as a kid but haven’t ever really used since, but that has the potential to be valuable? What’s a skill you think you could grow and potentially turn into a profitable side hustle? You don’t need a master plan—just a willingness to try.
- Audit your two biggest expenses—could you house hack, downsize, refinance, or drive something more affordable? Every dollar you free up is a dollar you can invest toward your freedom. Do a little bit of math to see what feeding up $100, or $500, or $1,000, or even more would do for you if you not only saved but also immediately invested those savings. What kind of a nest egg could that build you, and what kind of a lifestyle of freedom could that nest egg grant you in the long run?
- Revisit your budget—are you currently comfortable allocating every dollar that you bring in towards one expense category or another. Are you saving some, but not nearly what you could if you started to prioritize your financial independence more highly? Or are you currently looking for every way to live more minimally now so that you can live the life of your dreams in the future?
- Invest in yourself—read, learn, and start taking steps. No one builds wealth by accident. You’re here, which shows you’re not just interested, but you’re also motivated. Make developing this part of yourself that will eventually lead to your financial freedom a top priority. View it as something you get to do and that you’re excited to do—not something you have to do—and you will find the time to make it happen.
Start small if you need to, but start today.
I’ll see you in the next one!
