Over the past year, I set out on a mission: to uncover the habits and decisions of people who managed to retire before age 40. I interviewed 50 people who had escaped the 9-to-5, built wealth, and stepped away from full-time work long before the typical retirement age. These weren’t trust fund babies or crypto lottery winners.
These ordinary people made intentional choices with their money and time. And while their paths varied—some started businesses, others invested wisely, a few lived extremely frugally—they all made one surprising financial decision that set them apart: They stopped chasing status and started optimizing for freedom. Almost every early retiree I spoke with said the same thing: at some point in their 20s or early 30s, they realized that owning nice things didn’t make them feel rich—owning their time did.
One woman who left her marketing job at 33 said, “I used to think I wanted a luxury apartment and designer clothes. Then I realized I wanted to wake up without an alarm clock and spend the day with my kids.”
They flipped the script. Instead of measuring wealth by material possessions, they measured it by how little they needed to live the life they wanted.
This subtle shift had a massive impact on their finances. When most people get a raise, they spend more on a bigger house, a nicer car, and more dinners out. However, these early retirees maintained their lifestyle even when their income grew.
One software engineer told me, “After my first big raise, I didn’t upgrade anything. I still lived with roommates and drove a beat-up Civic. That extra money went straight into investments.
Within five years, I was done.”
They weren’t being cheap—they were being strategic. Every dollar they didn’t spend became a seed for future freedom. Many early retirees built businesses—consulting, freelance writing, niche websites, online courses, digital products, and local services.
But they all had one thing in common: they were scalable without demanding all their time. A 35-year-old who retired from his online bookkeeping business said, “I didn’t need to become a millionaire overnight. I just needed a business that made $5K—$10K a month, didn’t need me 24/7, and let me invest the profits.” They optimized for consistent cash flow and low maintenance.
Once they saved enough and had a portfolio of investments, they let their business fade or kept it as a side hustle. Almost everyone I interviewed saved at least 50% of their income, with some pushing that to 70% or more. For people in high-earning fields—or entrepreneurs with strong cash flow—it’s more about choices than income.
One 38-year-old ex-ad executive said, “When I was 30, I made $180K a year. I lived like I made $50K, saved, and invested the rest. People thought I was weird.
But now I wake up in Spain daily and do whatever I want.”
The key wasn’t just earning more, but not upgrading their life to match their income.
Choosing freedom over status
Few of them picked individual stocks or timed the market.
Almost all of them invested in index funds. After selling his small SaaS business, one man who retired at 39 explained, “I didn’t want to gamble. I wanted predictable long-term returns.
So I dumped everything into VTSAX and forgot about it.”
The strategy was simple: earn more than you spend, invest the difference in low-fee index funds, and let compounding work. One of the most surprising realizations I had was that these early retirees approached their personal finances like entrepreneurs. They tracked every dollar, analyzed return on time, optimized costs, and considered long-term value.
A 36-year-old woman who retired after selling her eCommerce brand said, “I treated my life like a startup. I had KPIs for happiness, freedom, and savings rate. Every decision had to align with my goal: financial independence.” It wasn’t cold or robotic.
It was intentional. They weren’t drifting through life—they were designing it. Perhaps the most powerful trait they shared wasn’t even financial.
It was the independence of mind. These people were willing to walk a different path. They didn’t care what their peers thought.
They didn’t feel the need to keep up. They were willing to say “no” to short-term pleasure in exchange for long-term freedom. This surprising financial decision was at the core of every early retiree’s story: They chose freedom over status.
They stopped trying to look rich and started building real wealth. They lived simply, saved aggressively, invested steadily, and built income streams without a 9-to-5 job. And in doing so, they bought the one thing you can’t get back: time.
You don’t need to live like a monk or become a millionaire overnight. But if you want to retire early or have options, start asking yourself: What do you value? Are you chasing approval or designing freedom?
What’s one small financial choice you can make today that your future self will thank you for? You don’t need to wait until you are 65 to live life on your terms. You need to make that one decision.
Image Credits: Photo by Dino Reichmuth on Unsplash
