When I was a teenager, I made a plan to retire young. I wasn’t just daydreaming, I was studying, analyzing, and laying the foundation for financial freedom decades before it would become a reality. While my friends were thinking about cars, concerts, and college parties, I was spending my time at the library, poring over... The post Retired at 42. The Plan, Execution, and Mindset Of An Early Retiree appeared first on Dad is FIRE.
When I was a teenager, I made a plan to retire young. I wasn’t just daydreaming, I was studying, analyzing, and laying the foundation for financial freedom decades before it would become a reality.
While my friends were thinking about cars, concerts, and college parties, I was spending my time at the library, poring over books by Robert Kiyosaki, Warren Buffett, Benjamin Graham, and Carleton Sheets.
I was obsessed with learning how money worked, how investments compounded, and how people built wealth. That obsession turned into a blueprint, and that blueprint became the life I live now.
So how did I retire at 42? Here’s what really worked: the plan I built, how I executed it, and the mindset that kept me on track.
If you’re into this kind of stuff, follow along and let’s build real freedom together!
The Plan: How I Built a Two-Tier Strategy for Early Retirement
The plan I created as a teen was simple but ambitious:
- Get enough money in a taxable account to last from my early 40s to 60.
- Simultaneously, max out tax-deferred accounts to fund life from 60 until death.
That split strategy gave me options. I didn’t have to touch retirement accounts early or worry about penalties. I had real money I could access when I needed it and traditional retirement funds waiting for me later.
It wasn’t complicated. It was intentional. And that made all the difference.
The Foundation: A Relentless Focus on Saving and Learning
I was raised with two core financial lessons: frugality and investment.
My mom was incredibly frugal, and she taught me the value of saving. Money wasn’t something to be wasted, it was something to be protected.
My dad was a businessman, and he taught me the importance of investing. Saving alone wouldn’t be enough, I had to put my money to work.
From a young age, I took these lessons to heart. I worked whatever jobs I could find and saved every dollar I earned.
While most people waste money and time, I hoard money. Always have.
I Retired at 42: How I Think Differently Than People Still Working
The Hustle: Paying My Own Way Through College
When it came time for college, I refused to take on much debt. I worked in a factory to pay my way through school, grinding through shifts while earning not one, but two degrees, by the time I was only 20 years old.
I also flipped products on eBay. For example I would sell DVD players on eBay for $400. Then I would go buy them at Circuit City for $200. I did this with many products. I would just stalk Slickdeals.net, buy stuff, then sell it on eBay. This still works.
The discipline to push through hard things and willingness to hustle became two of my defining traits.
I took out student loans. I paid them back. Quickly. I paid them all off less than a year after graduating college.
The Career: Learning Mortgages Inside and Out
My first job after college was as a technical writer, but my first financial job started when I became a mortgage broker.
At the time, interest rates were in the 7s. The job gave me an inside look at how the mortgage industry worked, how loans were structured, and how people used real estate to build wealth.
I absorbed everything I could. I saw the mistakes people made, the ways they overleveraged, and how banks operated. I also saw 1000s of credit reports, tax returns, W2s, paystubs, etc. I connected all the dots.
All of this knowledge became fuel for my long-term plan.
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My Career: From Mortgage Broker to Financial Services First Vice President
After leaving the mortgage industry, fed up with the nonsense and fraud I saw behind the scenes, I pivoted to financial services.
In Financial Services I could apply my problem-solving skills, analytical mindset, and deep understanding of investment products.
Breaking into the industry wasn’t easy with “worthless Psychology and Philosophy” degrees. The first company I targeted received 40,000 resumes per month, and I didn’t have a finance-related degree. But I did have cleverness.
Instead of following the rules, I found a back door, I contacted the company’s webmaster and asked them to forward my resume to the recruiting department. It worked. I was hired shortly after.
My Career: Climbing the Ranks Without Playing the Game
Over the next 20 years, I worked my way up, holding a variety of diverse and high-impact positions.
My focus was always on efficiencies and investment products, and I became known as a creative problem solver, someone who could tackle the toughest challenges and find ways to improve processes, optimize systems, and enhance investment strategies.
I worked on special projects for the CEO, COO, CRO, and other high-level executives, often being called in to solve complex problems that didn’t fit into traditional roles.
I managed an Investment Risk team that reported to the CRO. I was a SR Manager in The Research and Advice Department. I led the Investment Policy Committee. I had rather senior roles despite my worthless degrees.
I was always the youngest person in the room.
My ability to figure things out, do hard things, and see opportunities others missed made me a valuable asset.
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My Career: Credentials, Discipline, and the Bigger Plan
Throughout my career, I earned multiple professional licenses and became a Chartered Financial Analyst (CFA), widely regarded as the most challenging certification in finance, even more difficult than the CFP or CPA.
I eventually climbed to high-ranking titles like First Vice President, but my financial success wasn’t immediate.
Despite my growing expertise, I didn’t make $50,000 a year until I was in my 30s. The journey wasn’t about chasing a high salary, it was about positioning myself for financial independence.
My career wasn’t just a job. It was part of a larger strategy, to learn everything I could about finance, investing, and efficiencies, while quietly executing my long-term plan for early retirement.
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The Real Estate Play: Building My Taxable Portfolio
At age 21, I bought my first rental house with only $800 out of pocket.
It wasn’t a fluke. I had been stalking for-sale listings and for-rent listings for years, learning the market inside and out. I understood property values, rental demand, and financing strategies before I ever made my first purchase.
Then I did it again.
And again.
Over the next few years, I kept buying houses, all with no money down.
My strategy was simple: let tenants pay off the properties while I held onto them, and then sell them later to fund my early retirement.
Meanwhile, I maxed out my 401(k) every year, building my tax-advantaged savings so I’d have funds waiting for me when I turned 60.
How I Used Real Estate to Retire at 42 (And Believe It Still Works)
The Execution: Sticking With the Plan for 20 Years
For the next 20+ years, I stuck with the plan.
There were challenges, but I never backed down. I had to figure things out, do hard things, and adapt when necessary. But I never lost sight of the goal: complete financial freedom before 45.
And then, at 42 years old, I retired.
The Mindset That Made Early Retirement Possible
Retiring young wasn’t just about numbers. It took discipline to keep going, strategy to make the math work, and a mindset built to stay focused for decades.
Here are the principles and habits that actually made my early retirement possible.
Related Video: 9 Mental Shifts Required for a Successful FIRE Journey
1. Satisficing Over Maximizing
I don’t chase “the best.” I chase “good enough.” I don’t need the best car, the best house, or the best luxury experiences. I focus on what works for my happiness and financial goals.
This is why I was able to save and invest consistently, because I never felt the need to upgrade my lifestyle unnecessarily.
2. Hoarding Money Like It’s an Obsession
I hate spending money. The only time I spend is when it’s something that makes me genuinely happy. I can’t waste money on things that don’t bring real value to my life.
3. Doing Hard Things and Figuring Things Out
I worked in a factory to pay for school, learned the mortgage industry inside and out, had a successful career in Financial Services (despite “worthless Psychology and Philosophy degrees), and managed rental properties on my own.
Whatever the challenge, I figured it out and pushed through.
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4. Being Immune to FOMO
I say it all the time on Twitter when people ask how I retired early: “I’m immune to FOMO.” I don’t chase trends, I don’t care what others are doing, and I never spend to impress.
I stuck to my plan and ignored the noise.
5. Ignoring Bad Advice
I’ve heard a lot of “good advice” that would’ve wrecked my plan. If I listened to all of it, I’d still be working. I got good at spotting what didn’t make sense, and walking away.
If I Listened To “Good Advice,” I Would NOT Have Been A Liquid Millionaire At 38
6. Long-Term Vision and Unbreakable Discipline
Most people want instant gratification. I was playing the long game. I delayed rewards, stayed the course, and trusted my plan even when things got tough.
Life After Retirement: Living the Plan and Paying It Forward
Now that I’ve retired, my focus has shifted to helping others understand money, financial independence, and the realities of early retirement.
I’ve built websites, written extensively about personal finance, and continued to share the lessons I’ve learned. It’s my way of paying it forward.
But I also keep my identity anonymous because this was never about selling courses, building a personal brand, or making money off people’s dreams.
I actually did it.
And now, I’m enjoying life on my own terms, just like I planned.
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The post Retired at 42. The Plan, Execution, and Mindset Of An Early Retiree appeared first on Dad is FIRE.
