If you looked at my business a few years into my REI journey, you’d think I’d “MADE IT”…
But first, let me give you some context and rewind to the beginning. I was 34 and had just hit rock bottom. After a failed non-profit startup had left me with $7,000 in the bank and no retirement savings, I was faced with two choices: 1) Return to a cubicle and the type of engineering job I had a decade ago, or 2) Give it one more go in an entrepreneurial venture.
If I was in the movie The Matrix, this was a blue pill vs red pill moment. I decided to go red pill and choose the entrepreneurial path.
My chosen strategy was to go full-time into real estate investing - specifically fix-and-flips in Baltimore City. Go big or go home, right? The plan was to give it everything I had for a year. And then, if I didn’t succeed, I’d admit defeat and go back to life as an electrical engineer. Granted, I had to get my wife’s permission first, because she was supporting us on what amounted to a school teacher’s salary at the time. (And remember, I had just used up our retirement funds).
To my great surprise, things actually went according to plan. The first year I flipped 2 houses, the second year I flipped 5, and the third year 6. So by year 3, I was making hundreds of thousands of dollars a year in profit, was working for myself, and had even used saved-up cash to buy a rental house. All while only working 40 hours a week.
According to my original goals… I had “arrived.” I’d accomplished the dream in the books I’d read, the YouTube videos I’d watched, and the REIA meetings I’d attended.
I mean, this WAS supposed to be the dream, right? When I started out, I figured if I achieved all these goals, then surely my days would be filled with perpetual happiness, confidence, and success. I’d be triumphantly gliding through the work week - proud of all I’ve done, and excited for what lay ahead. “Arriving” was supposed to feel so good.
So… why didn’t it feel good?
In all honesty, though, if you peeled back the curtain, I struggled far more than I’d like to admit…
And the struggles were numerous.
Yes, I had achieved career success, but I also constantly wrestled with disappointment and discouragement. I’d think, “You should be so much farther along by now, Matt. The guests on Bigger Pockets would have scaled to twice your size by now.”
And yes, the number of renovations my company did each year kept increasing, but so too had the number of frustrations and headaches. The thoughts went, “All I face every day are problems, problems, and more problems. Nothing ever seems to go right and all I do is clean up messes, fix problems, and jump from one fire to the next.”
Annnnd yes, I was knocking out tasks left and right each week, but I continually felt stressed and overwhelmed with all the piled-up tasks yet to be done. “You’ve got too much to do. You’ll never catch up! You’re falling even farther behind!”
Unfortunately (for me) the list went on… I felt lonely and isolated. I felt guilty at the end of each day that I hadn’t been more productive. I compared myself to other RE investors on Bigger Pockets podcasts who always seemed to have more success than me with much less headaches.
And to top it all off, I wrestled with the constant, giant worry that something bad would happen. The ever-present anxiety that things would go wrong and I’d go out of business. I was flooded with thoughts of “You won’t be able to keep this up Matt. Either the market is going to crash, or you won’t be able to find any more deals, or your contractors will take the money and run. Brace yourself, because things are eventually going to fall apart. It’s inevitable.”
This was the day-to-day reality I experienced. Not fun. Even though on the outside I had all the success I’d hoped for, on the inside there was a constant negative battle raging in my my mind. And it was wearing me down.
Yeah, yeah I know. Cry me a river, right?
Believe me, I’m aware of how this can come across. I can see the satirical headline now: “Another upper-middle-class white guy complains about his problems. Poor him.”
I get it. This is the very reason I rarely shared these struggles with others. Nobody wants to hear about a guy who makes more than them complain about their career.
I was fully aware of how grateful I should be, so why couldn’t I get myself to consistently feel that way? I mean, look at the starving kids in Africa. Heck, just look at the struggling single parents in Baltimore City who live paycheck to paycheck. Who was I to feel bad and have struggles? (And, yes, this guilt made me feel even worse.)
So, what was the problem? Maybe there was an better business strategy that wasn’t so hard? Maybe something existed like all those Youtube advertisements promised - easy, passive, real estate success. I doubted that. Maybe I was just going through a rough patch? Maybe these were growing pains?
More likely, my thought is that I was the problem. Maybe I just wasn’t cut out for the entrepreneurial life. The recent Taylor Swift song with the ultra-catchy chorus comes to mind… “It’s me. Hi, I’m the problem it’s me.”
It wasn’t until I joined a mastermind of other RE investors that I realized I wasn’t alone.
Personally, I have a healthy skepticism of real estate gurus. Ok, it’s more than that, I have a downright aversion to them. As a result, I’d spent zero dollars on courses, boot camps, and masterminds for the first several years of my RE journey. But, finally, I was making so much money I figured I’d give it a shot. So I paid over $10,000 to be part of a RE Investor mastermind.
We’d go on 3 retreats a year together, get personal coaching, do monthly and weekly phone calls, and share strategies. But, I discovered, that more important than anything else, we’d get real and authentic with each other.
Up until then, when it came to my mental battles, I thought I was an outlier. To put it less kindly, I thought I was uniquely defective. I thought maybe, MAYBE, 1 in 50 real estate investors that had the kind of success I had struggled with the kinds of internal battles I did.
I mean, c’mon… when you’re successful on the outside it’s supposed to automatically make you happy, confident, and stress-free on the inside, right? That was the immutable formula of the American Dream. Up until then, just because the formula wasn’t working in my particular case, I didn’t think it could mean the formula was actually wrong. Instead, it must mean something was wrong with me.
This mastermind group showed me differently. It turns out, when we as 25 real estate investors got away for a retreat, gathered around a table, and dropped all pretense, over a third of them could relate with what I was feeling. Maybe over half. Granted, I may have been a more extreme case than the others, but this showed me I definitely wasn’t alone. And it was a comforting revelation.
Many of us face this “Battle of the Mind”
This new knowledge spurred me to do some research on the subject, and this led to even more revelations. It turns out if you’re a high achieving business owner or entrepreneur, you’re much more likely than the average person to face this “Battle of the Mind.” A Business Insider article reported that while only 7% of the general population report suffering from depression, 30% of founders deal with it’s effects. And over 50% of those get to burnout.
Here’s some more recent stats…
75% of small business owners are concerned about their mental health and 56% have actually been diagnosed with anxiety, depression, or stress-related problems (Inc.com, 2023)
25% of entrepreneurs experienced depression for the firs time, 20% anxiety for first time, and 18% chronic stress for the first time. (Global News Wire, 2021)
42% small business owners experienced burnout in past month (Forbes, 2022)
Wow. So there are a lot of people like me.
I guess it makes sense. Owning or founding a business exposes people to certain stresses, worries, and obstacles that the average worker doesn’t face. It’s a pressure cooker for negative thinking, and makes you more prone to overwhelm, anxiety, discouragement, isolation, and depression.
My million dollar question
So, here was my million dollar question. Can I get better? And if getting better is possible, how do I practically go about doing it?