Financial Regrets That Slowed My Path to FIRE

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Financial Regrets That Slowed My Path to FIREFinancial 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

Financial Regrets That Slowed My Path to FIRE - Not starting and growing a solid business
The first two of these might be a good representation of my current businesses… I wish they were that third plant! 🙂

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

Financial Regrets That Slowed My Path to FIRE - Buying too much house
Definitely not my house, but this one would reflect even more of the “too much house” factor if it was!

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.

Big mistake.

Financial Regrets That Slowed My Path to FIRE - Bought rental properties after the crash
Wouldn’t that be cool if you bought a rental property and it just started hemorrhaging money like this house is?

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.


Starting late

Financial Regrets That Slowed My Path to FIRE - Starting lateI 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!!

— Jim

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24 thoughts on “Financial Regrets That Slowed My Path to FIRE”

  1. Anyone can go on and on about their successes, but it is those stories about failure that teach the hard lessons in life to the up and coming. Certainly, this is how I learn.

    My failures are no different than anyone else’s in that I “should have” started earlier and taken more risks. At the same time, I could have partied a bit less and focused more on my finances.

  2. Oh man, I’ve done so many of them. Recently I posted as well about one of the mistakes I’ve done. But I try to consider every dumb mistake as a lesson for myself. I try to to learn something from it, and don’t do it ever again.

  3. Hi Jim, thanks for sharing. I think most people can look back and be regretful. In 2010, I had the opportunity to get into a search engine marketing business with an old coworker. Rumor has it he is doing very well. I also have a few other minor regrets. I am greatful, however, for what I do have. I can only try to do my best moving forward and learn from the past.

  4. Like many others, I should have started earlier, I shouldn’t have trusted the financial advisors who sold me a rotten “life insurance”… many things I could have done better if I had found the FIRE community 10 years before I actually did…

  5. Failures or mistakes yes, regrets no. I’m of the firm belief your decisions in the past shape sho you are today. Without my mistakes would I be on the right path now? Who knows. One big one was paying off student loan debt early on at the exclusion of 401k match. Another was not pushing hard enough to get college scholarships. But.. paying off college debt is part of what lead me to my current behavior.

  6. I also wish that I would’ve had a little more hustle during the 2008 crash (e.g. buying some local real estate). Maybe it was a good thing I didn’t b/c I got a divorce a little later, but I could’ve bought some shortly afterwards. It took me another 6 years to buy my first house and just the last two years to max my 401k. Oh how I wish I would’ve been doing it for the past decade. I would be a lot closer to FI.

    1. Thanks for sharing, Jason! Sounds like most of us have made some mistakes in our past that slowed down the pursuit of FI, but as long we learned from them, I think we’ll come out ahead in the long run.

      — Jim

  7. Don’t beat yourself up too much Jim. Hindsight is 20-20. We’ve all made huge mistakes… I made tons on my way to FI.

    Just try to learn from the mistakes…. in fact, the very act of writing this post should help keep you from repeating them. Self reflection is a very important part of learning.

  8. I regret not starting Financial Samurai in 2006 when I first came up with the idea.

    I also bought too much house in 2005, so we ended up renting the garden room downstairs for seven out of the nine years that we lived there. We could’ve bought a duplex and Lived in one very comfortable and since it was just two of us, and rent out the second one. But, I guess it was also nice to live in a nice house from 28 to 37 years old. I just sold it as well, because I couldn’t take being a landlord for that property anymore.

    My biggest finish regrets or trading too much in my stock market account and buying a vacation property in 2007! But things turned out fine, and it’s been quite a ride.

    I think your mistakes are all quite minor and manageable. The irony of having a relatively comfortable job when you first start up is that it doesn’t give you as much motivation to fire. Because my job made me get in by 5:30 AM and leave after 7:30 PM, all I wanted to do was save money and get the hell out of there!

    1. Those are a couple of doozies, but if things work out in the long-run, that’s what really matters.

      I’m with you on the job factor – having some rough hours and a stressful job like you had would definitely be a motivator to get out! 🙂 My job isn’t bad by most standards and that has definitely hindered my urgency on FIRE, but I guess the good news is that it’s really getting to me now and the motivation is higher than it’s ever been!

      — Jim

  9. I truly owe being financially smart to my parents. Even while taking up my first summer job, I had this feeling that they were being rude to me as they didn’t wish to take my responsibilities anymore. But the fact that I started paying for my own insurance helped me a lot when it came to planning my goals in advance.

    1. That’s really awesome! Sometimes parents feel like doing everything for their kids is the right move, but in most cases, it’s the exact opposite. Putting you in the driver’s seat of your expenses can be the best way to learn.

      — Jim

  10. Yes, everyone has the right to learn through mistakes. That’s why it’s all the more important for us to keep an eye on our career growth, right through the beginning of our teenage years. Ever since we land up with our first job, it becomes more important for us to learn about setting aside a portion of our income and put it in some Roth IRA.

    1. I like that AS – I’m hoping to get my daughter on that path by starting her with a Roth IRA in the near future. She’s only 8 right now, but if I have her working for the Route to Retire brand, I can pay her a fair wage and start funding a Roth for her. It probably won’t be a tremendous amount, but it could be a good way to get her on track understanding the path she should be taking as she continues to grow up.

      — Jim

  11. Hey there,
    Thank you for writing about financial growth.
    I don’t regret my financial condition, because I give my best to improve my financial condition.
    I think if you give your 100 % to a work then you don’t need to be regret.

    1. Hi Flora! If you’re doing what you can to improve and optimize your finances, it’s hard to have any regrets there. Even if they aren’t regrets though, I think it’s still good to learn from any money mistakes you might make along the way.

      — Jim

  12. Hi Jim! Would you still recommend Cashflow Quadrant as a helpful read today? I am young now (24) and aiming to purchase my first rental property in 5 years. My year 1 is focused on research so I’m interested to learn if a book published in 2011 is still applicable to FIRE in 2020. Thanks!

    1. Hi Sam – Cashflow Quadrant is an excellent book. But it’s important to know that it’s not a step-by-step guide to real estate. It’s more conceptual in its nature about thinking differently. I still highly recommend it, but it’s not going to teach you how to invest in rental property. For that, I would strongly recommend becoming a part of the Bigger Pockets community. Listen to the podcasts and webinars and dig around in their forums. There is no other place I know like that where you can learn the actual ins and outs of real estate. They do have paid plans, but the free plan will give you access to everything you need right now.

      Good luck!

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