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How Did I Get Here? What I’ve Learned After 4 Years of Early Retirement

4 years of FIRE

I first connected with the Man Overboard Man Overseas online back in May when I was visiting Costa Rica with my family in May of 2019. It turns out that he and his wife had spent quite a bit of time in the picturesque nation, the site of their 2018 honeymoon, and he and I exchanged a few emails about our travel experiences.

I learned that the couple had actually spent a lot of time in a lot of places, and they’ve been doing the FIRE thing for four years now. As someone who hopes to be overseas for the better part of the next four years, this was exciting to hear!

I had the pleasure of meeting the Man and his lovely wife quite recently at FinCon and I hope our paths cross again in the future. I expect our next rendesvous to be of the virtual kind as he has invited me to join him for a recording of his Man Overseas podcast. We’ll wait until we’re actually overseas and settled in Ecuador to make that happen.

I was interested in learning more about both his pre-FI and post-FI life, and he was generous enough to oblige in the form of a guest post. Take it away, Man!


How Did I Get Here? What I’ve Learned After Four Years of Early Retirement



Today, I am sitting at a cafe in Prague. I woke up a few hours ago without an alarm, grabbed my half-naked wife and kissed her, as I do every morning.

Feeling energized after 8 hours’ sleep, I sat to meditate while coffee brewed.

I usually write in my journal as part of my morning routine. But not today. Not because I was rushed or had more important things to do. In fact, not for any particular reason at all—I just didn’t feel like it. In this way, today’s been like any other—I only do what I feel like doing.

I have gym clothes with me. But if I decide to give my 39-year old body a rest, I’ll take Lady Overseas on a train ride to see a castle, or if it rains, meet her back at our Airbnb for a nap.

This is our fifth consecutive month using Airbnb—it’s a Godsend for slow-travel early-retirees. My wife loves AirBnB because it helps fulfills her dream of living in a different city every month.

So far this year, we’ve “lived” in San Miguel de Allende for its colonial casas, Oaxaca for its mountains & mole, Playa Del Carmen for the white-sand beaches, and Prague because it’s freakin’ Prague. In August, we’ll be in Vienna, before jetting back to the States to meet other FIRE fanatics at FinCon.

By now you might be wondering, How did I get here? 

First, if you’re like me, you’re singing Once in a Lifetime by The Talking Heads. The 80s tune could be my life’s background music. I’ve not only found myself living in another part of the world, but I’ve also found myself with a beautiful wife. 


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What the Hell is Financial Independence?


I can tell you exactly how I got here. In fact, I can pinpoint the day I discovered the concept of financial independence. It was 2003, my first year in the “real world.” I was a real estate salesperson, traveling home from a real estate investing seminar in Dallas with a co-worker.

I admired my colleague because he was only 35, but had ten rental properties in our hometown of Houston. Attending the seminar with him, I thought, would be a great learning opportunity—we’d have many hours to chat driving up I-45.

Not only was he a successful investor, but he’d been to the seminar twice before. Throughout the sessions, I jotted down questions I thought he could answer—I selfishly figured it would give us something to talk about on the drive home.

Despite my fifty questions that day, none proved so valuable as those he asked me—questions which altered the course of my life. As he put the car in park, he turned and said,


“What if you had to be financially independent by the time you were my age [35]? Are there things you could start doing to make sure it happens?”


Four hours in the car—that’s how our conversation ended.

Now sixteen years later, I still don’t know if his questions were rhetorical. I hope so. Because I was thinking, What the hell is financial independence? 

Since it seemed like something I should know, rather than ask (and risk looking like a dummy), I bought a Jim Rohn CD with “financial independence” in the title. A few minutes in, he said, “Financial Independence is the ability to live from the income of your own personal resources.”

I wrote it down on a yellow-sticky note and kept it at my desk until the day I retired at age 34.


How I Achieved FIRE


Admittedly, I didn’t discover the FIRE movement until I was a couple years into early retirement. But I had doggedly pursued the first half of the acronym (FI) since that day in ’03.

Before I tell you how I achieved FIRE, I must acknowledge the role that hard work, luck and being in the right place at the right time plays in anyone’s success, mine included. I don’t know how the percentages play out. No one does. But I’ll share my path and let the tumblers fall.

First, adequately inspired that first year out of college (when my education began), I read a handful of books:

Those books served as kryptonite for lifestyle inflation. Rather than upgrade to a Range Rover, I invested in technology companies with asymmetric upside and paid cash for real estate.



Equally important, I caught a lucky break in 2008-2009. While many salespeople were losing their jobs, I had two: software & real estate sales. At the same time, home prices dropped 50%, and I started snagging them before values skyrocketed.

It was a fast-paced life. Everyone was playing politics and jockeying for status. My goal was to make more and more money every year. In order to achieve that goal, I figured out the price to pay, and I paid it: No vacations, endless meetings and continuous prospecting for new business.

I’d catch early flights to Dallas, New York, Tampa, St. Louis—every half-hour scheduled, week-after-week, quarter-after-quarter—I became addicted to the thrill of the deal.


Post-FIRE Life


Pre-FIRE life feels far away now. To illustrate, when I was in Zambia a few years ago, a kid who reminded me of Akeem from Coming to America, asked if he could…come to America.

I said, “Of course.”

He said, “Great, I will go there! Tell me, for how long will I be on a bus?”

I said, “You can’t get there by bus. We’re 14,000 kilometers away.”

That’s how far away pre-FIRE feels now. We no longer set alarm clocks to catch early flights—nor for any other reason. Forthwith, I propose FIRE folks proudly share the date they last used an alarm clock the way recovering addicts share their sobriety date.


Hi, I’m Man Overseas, a former overachiever who’s found a simpler life. It’s been 1,462 days since I last used an alarm clock. On that day, I declared independence from the shackles of “more,” increasing my personal options instead of possessions. With this in mind, I started traveling the world. I did it for the same reason Thoreau went to the woods “…because I wished to live deliberately … and not, when I came to die, discover that I had not lived.”


Every day the status-seeking circuitry in my brain dies a slow death. My prospecting now is for countries to call home for 30 days—my toughest negotiations, with AirBnB hosts.

I still want more—it’s part of being human. Except I want more of what’s important: creativity, building relationships and providing value to others. FIRE done right is finding meaningful things to do, albeit when you feel like doing them.


Misconceptions of FIRE Life


Life in early retirement isn’t all castles & rainbows. The biggest challenge for me, which I didn’t anticipate, was disentangling my identity from the hundreds of thousands of dollars I used to make every year. In truth, I didn’t realize the attachment I had to my once-precious ego.

Other challenges occur with friends & family. Many of them are convinced we’re draining our bank account. They see us asking for discounts and tracking expenses on an app, unaware that we’re counting costs to ensure work stays optional for the next 65 years.

Still others hear us refer to the budget, and assume we’re poor. They associate “living on a budget” with being newly unemployed or living on Social Security. When we visit my mom, she’ll wait til my wife is out of the room. “Are y’all going to be ok,” she whispers, “with money and everything?”

Others are too busy upgrading their lifestyle or can’t grasp the math of FIRE—the latter I can understand. I, too, struggled to trust the numbers my first year in early retirement, despite having mastery-level knowledge of basic math. That is to say, if there exists a fifth-grader smarter than me, I haven’t met her yet.

We live on rental income from real estate that exceeds our expenses. The best part of retiring with real estate is that you’re not withdrawing 4% from your assets every year. Though I still use The 4% Rule as a guiding principle. I find it helps us to stay focused on net worth, with the aim of continuing to grow along with it.


The Finish Line


“Human beings are works in progress that mistakenly think they’re finished,” – Daniel Gilbert, author of Stumbling on Happiness


Not even early retirement is a finish line—it’s an opportunity to learn more about yourself and the world. What I’ve learned most about myself is that I expected to do it all in early retirement. Perhaps a relic of my hard-charging past, I would get down on myself for foregoing opportunities.

I thought by way of FIRE I’d freed up countless hours to do what I feel like doing. And I have. But opportunity cost still applies whether you’re pre-FIRE or gallivanting the globe. For example, we loved Oaxaca, Mexico—we made great friends and ate good food. Except we’ve now deemed Prague our favorite city, and realize we may never visit Oaxaca again.

A more micro-example would be the opportunity cost of sight-seeing versus writing a blog post. Since the latter comports with my values above—creativity, relationships, value to others—it takes priority.

Never content to let the days go by, tomorrow I’ll wake up (1,463), grab my wife and sit to meditate while coffee brews. Then I’ll prospect for AirBnB’s in Thailand and find hosts willing to negotiate.

Same as it ever was.


[PoF: Be sure out the Man Overseas blog and podcast, and if you’re interested in getting started in real estate investing to become financially independent, check out my pal Coach Carson’s free online course!]

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8 thoughts on “How Did I Get Here? What I’ve Learned After 4 Years of Early Retirement”

  1. Just make sure you have a plan. People retire early all the time, but then they don’t have a purpose in life. Whether it is reading, traveling, etc. Just make sure you stay busy or they may find themselves lonely and bored in retirement. I see it all the time.

  2. Subscribe to get more great content like this, an awesome spreadsheet, and more!
  3. I will know that I have made it when I can throw my alarm clock in the trash can. You and your wife are living the life we want to live. Real estate is on the cards for my family in 2020. Good article. Nothing like reading about freedom as you are working overnight. Very motivating.

    • Throwing the alarm clock away is a glorious feeling.

      If you keep expenses low and reinvest your rental income, early retirement will come faster than you think. Send me a note as your Day 1 approaches so I can virtually welcome you to FIRE.

      Thanks for your comment.

  4. I was wondering if Man Overseas is using a rental-management company to handle his rentals? Seems like that would be necessary, as he’s literally overseas and not around to handle the inevitable needs of a rental – collecting rent, dealing with repair requests, work related to move in/out activity, etc.

    Those things are what keep me from looking into buying rental properties. I really don’t want to be tied down to that work, and I certainly don’t want the conflict that invariably results from having to evict a deadbeat renter.

    • Good question, Lynne. As part of my strategy to have fewer properties owned free & clear, I manage them myself instead of using a management company.

      Rent is deposited in my bank account. I text General Contractors when I need them for repairs. Much of the work to re-list a property when turnover occurs can be done overseas, but I will sometimes pay a colleague for help with pictures and placing sign in yard & lockbox on door. The tenant’s agent does most other work for 50% of one month’s rent.

      I don’t have a lot of turnover. IMO the most important aspect of being a landlord is doing grunt work upfront with prospective tenants. I use a thorough tenant-screening service (applicant cost), and Skype interview finalists as if I’m interviewing them for a job. We usually sign long-term agreements with rent increases built into the Lease.

      Hope this encourages you to get started in real estate investing—I think it’s easy money.

  5. You are correct in predicting that the Talking Heads song started playing in my head as I was reading this 🙂

    You are preaching to the choir about how you view real estate. I too am trying to develop a real estate machine that will meet (and hopefully exceed) my annual expenses from just the positive cash flow. Then I do not have to consume the principal and theoretically can have a self-perpetuating money printing machine.

    As I woke up earlier than I would like getting ready for work I look forward to the day I no longer will have to set an alarm.

    Congrats on making the most of a 4 hr car ride and setting on a path that people often dream of but usually don’t take the steps to achieve it.

    • Thank you. Just played Once in a Lifetime on Youtube. Can’t believe it has almost 20 million views!

      I’m going to steal “self-perpetuating money printing machine.” Love that.

      Look forward to hearing about the day you trash your alarm clock. Thanks for your comment.


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