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Financial regrets, I’ve had a few…
As I guy in my early forties, I sometimes take a moment here and there to reflect on how my path in life has gone. I don’t dwell – I just try to look back at my mistakes and learn from them to make for a better future.
And maybe the “regrets” part of “financial regrets” is a little excessive. If you’re a regular follower of my blog, you know that we’ve recently surpassed the million-dollar net worth mark.
We’re in good financial shape right now and now we’re just continuing down the path we’ve been going to expedite our mission and reach financial independence as soon as possible.
However, there are some things that, if done differently, could have put us further ahead than we are today.
So let’s talk about some of the financial regrets I’ve made in my past and maybe there might be something helpful for you as well…
Not starting and growing a solid business
Right now, we have a few small businesses that we own – a publishing company, the Route to Retire brand, and our real estate company.
Of those, the real estate company is the only one generating some good income for us (for now) and it’s still not enough to live off yet.
Looking back to my younger days, I think about how far ahead we could be if I had started growing a business decades ago.
Don’t let this fool you into wondering if I’m naive enough to think that building a business would have been easy because that’s certainly not the case.
I’ve watched for almost two decades as my boss has grown and molded the company I work at. I’ve seen the hard struggles and the long hours he’s put into it over the years.
But I also see the rewards it’s provided over the long haul.
I threw around the idea of starting my own IT company years ago, but I just never made it happen… mostly out of the fear of the unknown. Coincidentally, that’s the same fear that keeps most of us shackled as employees for our entire lives.
If I had taken that chance though, I may have failed, but there’s also a chance I could have built something great.
Buying too much house
Mrs. R2R and I lived in a small house for a few years when we first got together. I bought it with the intent of fixing it up and renting it out.
Along the way, we had some stumbling blocks, but we made it happen and got it rented out.
We then moved into an apartment for a year or so and then took our time shopping around for a new place to live. We hit the market at a pretty good time – then end of 2008.
Our agent is great (I still use him for shopping for rental properties) and he ended up leading us to a nice house in a great neighborhood.
We couldn’t believe how big the house was and the asking price was also in our price range. I was ready to roll forward, but the market was in our favor and winter was approaching (when nobody buys houses in Ohio!).
My wife pushed for us to make a low-ball offer. I was a little nervous about the idea, but I figured let’s give it a shot.
I told our agent to tell the owners that if they accepted, we’d close on it by the end of the year. This was important because a company was making the mortgage payments on it after they paid to have the former owner relocated for employment.
They bit and we got the house for a steal.
We love the house and the area, we have great neighbors, and we’ve lived there close to a decade now.
But here’s the thing – it’s too much house for us. It’s a 4-bedroom, 2½-bath house with a finished basement. All of which is great, but there are only three of us living there.
We don’t need all the space and the bigger the house, the more you have to clean and spend on maintenance and repairs… mo’ money, mo’ problems, right?
We’re now discussing the idea of downsizing or moving to Panama, but if we had just bought the right size house to begin with, we would’ve already paid it off. And that would have saved us a couple grand every month that could be going toward financial independence and early retirement.
Bought rental properties after the crash
We bought that first rental house I was talking about in 2003.
Even though things worked out, we had some problems along the way and I wasn’t eager to jump back on the horse so soon after we started renting it out in early 2008.
Yes, hindsight is 20/20, but if I wasn’t so hesitant, I could have picked up at least two or three houses for pennies on the dollar after the real estate market crash… ouch!! 🙂
Instead, I got rolling later and bought a duplex to rent out in 2015. We did get a great deal and it’s cash flowing nicely.
But now I’m ready to get another and the market’s making the mission a real struggle – prices are too high and sellers are actually taking bids on properties. On top of that, the properties are selling in just days or weeks.
We’re still keeping our eyes peeled for a deal, but if only we had bought when prices were at rock bottom. We could be set right now if we had the foresight when it mattered.
This might be one of my biggest financial regrets.
I bought that first rental property just under 15 years ago when I was around 27 years old, but then we sat there and coasted until the past few years.
I should have been hustling more when I was younger, taking more risks, and taking advantage of some great opportunities as they came along.
Robert Kiyosaki inspired me to buy my first rental property after reading his books, including my favorite, Cashflow Quadrant. I was motivated, pumped, and ready to go. But I wanted to talk about this revelation with others and no one seemed to care.
I couldn’t believe there wasn’t anyone out there who thought that maybe it was possible to reach financial independence and retire before the “normal” retirement age. I was beaten down back into a false reality that you’re just supposed to keep working until you’re old and gray… depressing.
But then, years later, I got motivated again and decided to launch the Route to Retire blog in early 2015. That turned out to be a fantastic idea – not because it’s churning out money left and right – it’s not… yet.
However, it helped me to find the Financial Independence / Retiring Early (FIRE) community. I couldn’t believe the number of great people out there with a similar vision as mine. In fact, that’s one of the main reasons I’ll be attending FinCon for the first time in the fall – just to meet and talk to folks in the community and get rejuvenated about FIRE even more.
My regret is that I didn’t find the FIRE movement and these great people earlier. The excitement of everyone is inspiring and makes me push harder every day to hold myself accountable and to reach our goals as efficiently as possible.
So there you have it – some of my financial regrets. We’re still well ahead of most folks our age and looking to be done with the 9-5 no later than our late forties at most, so there’s not anything to really regret so much, but rather to learn from.
And, if you’re one of my younger readers out there, maybe something I’ve said may help you in your own journey.
Have you had any financial regrets in your life?
Thanks for reading!!