Mine hasn’t been your typical success story. You know the type: a journey from Point A to Point B, with a steady climb and tidy profits at the end.
In fact, I’m not even sure this qualifies as a success story. Seems to me like there’s more failure in it than success!
But I get to visit five to ten countries every year, and I’m no longer chained to a desk job. So that counts for something, right?
Like many career stories, it starts with me graduating college (asking “Do I have to leave? Could I pull a Van Wilder?”) and landing face-first in the real world.
In a cubicle.
The time will come, not so many years from now, when we will look back on cubicles the same way we look back at practices like bloodletting with leeches. Symbolic of a less-enlightened era.
Upon graduating college at 22, I went to work for a subprime mortgage lender. Somehow, I ended up with the worst cubicle in the building, too – right outside the corporate president’s office. (I can still see him frowning at me, 15 years later.)
I started darkly joking about “How long until I can retire, again?” The idea of spending the next 40-some years of my life working in an office was enough to cause an acid reflux of cynicism.
Granted, nothing can stay terrible forever. I escaped subprime loans and started doing renovation loans for real estate investors. Mostly flippers, renovating dilapidated homes to turn around and sell, but a few landlords as well, who kept the properties as long-term rental investments.
Related Article: Why Are You Building Wealth?
My First International Trip and Lightbulb Moment 1.0
A year or so into my real-world career, I visited Europe for the first time. My roommate and I took ten days off to go visit my friend (okay, she was my ex-girlfriend, but it’s not as weird as it sounds) in Rome.
As a loan officer paid on commission, I knew I wouldn’t be earning a cent while traveling. I wasn’t happy about it.
I muttered my usual sardonic “When can I retire, again?” routine and then had a sudden mindset shift. Who said I had to wait until my 60s to retire?
I was working with all these real estate investors, some of whom were stacking up rental income with each rental property they bought. Why couldn’t I do the same thing? After all, if I had enough rental income, I wouldn’t need to work! I could travel all I wanted while making just as much money!
The Building Wave… The Crashing Wave…
I spent the next three years in a frenzied buying spree. Buying 13 rental properties, I thought I was just crushing it left and right. I planned to retire by 30. I was a rockstar!
It just so happened those three years were 2006-2008.
But as tempting as it is to blame the subsequent market crash – and believe me, I did at the time – the truth is I didn’t know what I was doing. I didn’t have a mentor, or any coaching. I was just throwing money around, hoping it would get randy and start reproducing.
Disillusioned, I stopped investing in real estate. For that matter, I stopped investing in anything else, too. I felt trapped by my rental properties, because I couldn’t sell them. I had overpaid, the market had crashed, and I hadn’t calculated the properties’ cashflow properly.
It was about this time that I cursed my younger self and my dream of financial independence. How naïve! How greedy! Why couldn’t I just fall into line like all the other worker bees?
So, I took a job working for a company that sold landlord legal forms.
Lightbulb Moment 2.0
Over the next few years a curious thing happened.
As part of my job duties, I was called upon to provide education and tips for landlords. I realized that, after having made every possible mistake in the book as a rental investor and landlord, I had actually received a first class (if expensive) education in rental investing and property management.
In looking around at the so-called gurus and the other landlord educators out there, I realized that I knew as much or more than most of them.
I gradually dawned on me that my dream of passive income and financial independence hadn’t been the problem. Nor was my broad strategy of rental properties the problem.
The problem was that, the first time around, I hadn’t known what I was doing.
I started buying rental properties again, starting with a home for myself to live in… with a housemate to pay most of the mortgage.
Related Article: Tim, Who Lives for Free: A House Hacking Case Study
Moving Abroad, Losing My Job, and What Came Next
My wife Katie could tell that wanderlust was slowly infecting me, between telecommute job and my love for international travel.
She signed up with an international recruiting service for international schools (she’s a school counselor) and told me casually over dinner one night. The next thing I knew, she had job interviews all over the world.
The job offers started fluttering in, and we chose Abu Dhabi. Because, well, why not? And because one nice perk they offered was free housing!
Moving abroad involved some serious work, especially with 15 rental properties. But we did it and had a few short months of saving a lot of money, before my employer and I had one too many headbutts.
What do you do when you lose your job in a foreign country with no contacts, no network, no familiarity with the local economy or job market?
You start a business, of course. I got together with a friend and former colleague, the brilliant Deni Supplee, and we launched an educational service to help people buy their first small multifamily (2-4 unit) rental properties.
The Switch Backed Path to Financial Independence
Spoiler alert: I haven’t reached financial independence yet.
But if there’s one thing that’s clear to me, it’s that the road to FI is a winding, jumbled, crooked mess. Unexpected turns leave you lost and wondering which way to turn. Perhaps not for everyone, or even most people; I suppose most people just take 5-10% of their paycheck and invest in their 401(k).
For anyone who wants to take the path less traveled, to reach financial independence and quit their day job at a youngish age, be prepared for the unexpected.
Of course, you don’t have to make all the mistakes I’ve made. Please, please don’t – whatever strategy you choose to build your passive income, get coaching and help from someone who knows that niche. If dividend stocks are your thing, find dividend income experts and learn every tip and trick you can from them.
I am an entrepreneur in my heart, so I love rental investing, and I love teaching it to others. But the world is full of opportunities for you to create passive income, beyond rental properties or dividend-paying stocks.
If you haven’t yet fallen in love with the dream of financial independence, let me pose a simple question to you.
What would you do with your life, if time and money were no longer constraints?
Because those are the stakes. That’s the reward, once you reach FI. A life that no longer requires you to work a full-time job to pay your bills and pursue your passions.
It’s a beautiful dream. And even though pursuing it has cost me greatly in my life, I don’t regret a moment of the struggle. That struggle has taught me far more than all the happy, cocky, carefree moments of my life combined.
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