Coming to Terms with Letting Others Down Because of My Past Financial Mistakes

It is impossible to look back at the state of my life when I was at my financial low point and not feel some degree of regret.

At that moment in time, Sarah and I were approaching six figures in debt between our student loans, our car loans, and our credit cards.

While our student loans were largely unavoidable, we had been out of college for four years and hadn’t done anything more than make minimum payments on those debts.

The car loans? Far bigger than necessary. We got nice cars, not the kind of older cars we should have bought.

The credit card debts? Completely unnecessary. Almost every purchase made with them was completely forgettable. Those purchases truly didn’t make our lives better in any tangible way.

If we had made responsible choices in those four years after college, we would have had zero credit card debt. We would have had very little left on our car loans, if any. We would have had much smaller student loan debt. We may have even had some savings for a home down payment.

We didn’t make responsible choices. Instead, we dug ourselves a huge hole. We did this on the back of a long string of bad choices, mostly little but some fairly large. We ate at a nonstop string of forgettable expensive restaurants. We bought piles of entertainment. We engaged in expensive hobbies like golfing without the resources to make it a sensible hobby.

We made mistake after mistake after mistake and we ended up in a miserable spot, a spot of our own making.

Since then, Sarah and I have worked incredibly hard to turn that ship around. Today, we’re debt free. We completely own our own home – no mortgage. We’re also currently on a path to be able to retire at least a little early.

I’m extremely proud of that turnaround. It’s the result of a lot of hard work over a lot of years.

But, even with that turnaround, there’s still regret of what might have been.

If Sarah and I had spent those first few years moving our finances in the right direction instead of in the wrong direction, we’d be in far better shape right now.

I don’t know exactly what our lives would be like right now, but I do know this: there would have been many life opportunities open to us that simply aren’t open to us here in the real world right now.

I can’t help but think of those possibilities, either.

Sarah and I would be on the verge of being able to retire right now, shy of our forties. If we lived on about 60% of our income and used the remaining 40% to pay off debts and then invest (which is essentially what we’ve been doing since our turnaround), we would be on the verge of retirement, assuming we did everything else the same.

Sarah could have easily committed to several years as a stay-at-home mother. This was a bridge that we crossed in 2007 and again in 2010. The reason she chose not to cross that bridge was that we were far away from our financial goals and although we could financially handle those years of stay-at-home motherhood, she wasn’t sure what it would be like to return to her career in several years, likely with a smaller salary. With a good financial start, she could have made this leap.

We could be living on our dream property. In 2011, the absolute perfect piece of land for us came up for sale. It was in the country, but our children would have stayed in the same school district. It offered a stream, lots of open grassy areas, some woods to explore, space for a huge garden if we wanted it… it felt like the Shire from the Lord of the Rings novels. We wanted it so badly, but we just could not justify the sticker price at the time. If we had been financially smart from the start, we could have written a check for this land and then written a check to build a house on that land.

Those lost possibilities – and many others – left me feeling incredibly guilty for years. Even though my mind knew that we were actually doing pretty well for our age, my heart kept coming back to what could have been – and it left me feeling miserable, knowing that my own personal stupid decisions left my family without those options. There would be times when I would feel almost as if I were drowning in that guilt, that I completely let my family down and denied them a greater life that they could have and should have had.

I still feel guilty, though perhaps not as sharply as I once did. Rather than just leaving me feel awful, it now feels more like a low level regret that crosses my mind sometimes, like a professional or personal opportunity not taken from many years ago.

How did I manage to tone down that financial guilt? In truth, it came down to several realizations about life, what I can control, and what I can’t control. I hope that these realizations can help you overcome any guilt you might feel from the lasting impact of your own past mistakes.

I Learned Valuable Lessons from My Mistakes That I Would Not Have Otherwise Learned

Right now, I’m in a position to look back and wonder “what might have been” because I learned a great deal from my financial turnaround and from my ensuing years of good choices.

However, there’s no guarantee I would have ever embarked upon this positive financial journey without those mistakes.

You see, when I look back with regret, I’m applying the lessons I learned from making those mistakes to a life where those mistakes haven’t really happened yet or were in the process of happening. There’s no realistic way I could have learned those lessons, at least not in the same way.

Sure, I can dream about how my life would be different if I had learned all of my financial lessons during my childhood so that I never made a big financial mistake in adulthood, but that’s not realistic. I never had the opportunity to learn those financial lessons at any point in my life. I never received any sort of personal finance education, nor did I even really realize that personal finance was a thing.

Feeling regret from my financial mistakes would be like an expert bicyclist feeling regret that he or she fell off his or her bike repeatedly while first learning how to ride. They wouldn’t feel that way – it’s silly. Those early fumbling steps and mistakes taught them the necessary things they needed to know to become an expert bicyclist.

My mistakes taught me things, and without those lessons, I wouldn’t be where I am today.

I Can Only Change Today, Not Yesterday

I might look back at things that happened in my past and wish that I could change them and make them better.

But that’s truly just wishful thinking.

The truth is that I can only change today. I can’t change what I did ten or fifteen years ago. Those things are done. They’re long gone.

All I can do is try to do better today. All I can control is today. No matter how much I wish, no matter how much I pray, no matter how much guilt I feel, I can’t change yesterday. I can only change today.

If I make good choices today, then I put myself and my family in a better position. I deserve to be proud of today.

If I make bad choices today, then I put myself and my family in a worse position. I deserve to feel bad about today.

That’s my choice. That’s what I can control. Feeling guilty about choices I made fifteen years ago doesn’t make any sense whatsoever, because there’s nothing I can do today to control it or change it. All I can do is make my life better going forward from here.

I’m Moving Forward with Good Choices

If I can only control my choices today (and not the past) and those choices shape my future (as my guilt about my past mistakes reveals to me), then it makes sense to recognize that when I make a bunch of good choices today, I’m going to move forward to a better future.

For me, that puts the crux of my financial future on today. Today is the only day in which I have the power to actually control my choices. Yesterday? I can’t change it. Tomorrow hasn’t happened yet. Today is what I can control.

So, the thing I should actually feel guilty – or not guilty – about is the choices I make today. Do I make good choices? Or do I make poor choices?

Those mistakes from the past are actually useful. They inform my choices today. I know quite well what the long term result of making money mistakes is. I know that if I spend my money frivolously today, I end up closing the door to options down the road.

So, each day, I try to turn the lemons of my past into the lemonade of tomorrow. I take what I learned from those mistakes of the past to make good decisions in the present which will ideally lead to good things in the future.

I Made – and Still Make – Good Choices in Other Life Areas

When I look back over my life, I recognize that I made both good and bad decisions in virtually every area of life: personal, professional, spiritual, social, financial, physical, mental, and so on.

I tend to sometimes dwell on the financial because, perhaps more than any area of my life, I can see the huge mistakes I made in the past. Like anyone else, I want to have a good life in every aspect of life, so when I can so obviously see areas where I made bad choices.

It’s like seeing a car accident on the interstate. We might have seen hundreds of miles of perfect accident-free driving on the interstate, but we scarcely notice it. When there’s an accident – a mistake of some kind – we can’t help but gawk at it.

My life is like that interstate. In most other areas of my life, I’m like those many miles of interstate with good traffic. Sure, it might be slower in some areas and faster than others, but overall the traffic flows along and it’s scarcely noticed.

My finances, though… that’s the accident. That’s the five car pile-up that I can’t help but gawk at.

What I need to do sometimes is step back and not just look at that accident, but at the interstate as a whole. Sure, there’s an accident, but most of the things are moving along quite well. Goals are getting completed. I’m making good choices. Things are chugging along as they should be.

Rather than just dwelling on that one imperfect area of my life, I need to step back and look at the many good choices and good outcomes in the many other parts of my life.

My Wife and Kids Love Me for the Man I Am Today, Thus Forgiving Yesterday’s Mistakes

I have a great relationship with my wife and with each of my children. They are relationships built on love and respect and trust. We love each other for the totality of who each of us are.

Each one of us is a flawed person. Each one of us has made mistakes – and still does make mistakes.

On the whole, though, each one of us is a good person, a wonderful person that we all enjoy being around.

My wife isn’t perfect, but she’s always there for me when I need her. She’s smart, beautiful, funny, and caring.

My oldest son isn’t perfect, but he’s a charming and quick-witted boy with an adventurous nature and a kind heart.

My daughter isn’t perfect, but she’s a hilarious, imaginative, and creative free spirit who often sweeps us all along in her joyous adventures.

My youngest son isn’t perfect, but he’s loving and loyal and has this perfect sense of when to be serious and when a moment needs a bit of an icebreaker or a laugh.

I see that my loved ones aren’t perfect, but I also see that they’re made up of tons of good traits that make them into wonderful people that I want in my life. Based on how they act toward me, I believe that they feel much the same way about me.

I may have made big mistakes with my finances, but on the whole I am a good person. The people who spend the most time with me see this and love me because of it. No person is perfect – it’s who you are in the whole that really counts. The people around me tell me every day, in countless indirect (and occasionally direct) ways, that I am a good person that they love and value even through the mistakes I’ve made.

I Have Used My Mistakes to Help Others

As I began to grasp how I had really damaged my financial life and I began to walk through the steps I needed to take to right that ship, I also began to see how a lot of people my age – and people older than me and people younger than me – were struggling with many of the same issues.

They were trying to overcome debts. They were trying to figure out how to have the “American dream.” They were trying to secure a stable future for themselves. They were trying to balance a load of personal desires with smart financial choices.

And many of them were struggling with all of that, just as I was.

As I began to have some insights about how to cut through all of these issues and build a better future for myself, I couldn’t help but think that I wish I had known those things earlier. I wanted to tell all my friends about what I was figuring out, but I also didn’t want to be preachy.

Thus, I started The Simple Dollar. It turned out to be a way for me to take what I was learning from my own mistakes and turn it into a non-preachy way to help others using the skills that I had available to me (the ability to write quickly and in an earnest and friendly tone).

I turned my own mistakes into an opportunity to help others avoid similar mistakes. While it doesn’t really do anything to directly improve my life (other than the fact that it is my primary employment… but it was just one job opportunity among many), it does give me the opportunity to help others. Perhaps, in a wider sense – a national or global sense – I’ve actually helped to reduce the overall financial pain that people have felt.

I Caught My Errors Before Even Worse Things Could Happen

During our lowest financial point, Sarah and I didn’t have enough money in our checking account to pay our bills. We sat there facing a debt mountain that was bigger than our combined salaries without a home loan.

That was not a good situation. But it could have been far worse.

We were never late on a bill – or at least not late enough to negatively impact our credit. We both put aside money into our retirement plans. We had our careers in positions of very good standing with stable future employment ahead of us.

Our positions could have been far worse, in other words.

We could have destroyed our credit. We could have not funded our retirement plans. We could have been in less stable careers with lower income levels.

Things may not have been the best, but we certainly could have done worse. The fact that we did not is something of a saving grace, a nice silver lining around the cloud.

“What If” Scenarios Make Little Sense When You Look Closely

Remember at the start of this article, when I listed a sequence of these beautiful glowing “what if” scenarios that might have occurred if I had followed better financial practices from the day I graduated from college? Those scenarios seem beautiful and amazing… but they’re also not realistic.

Each of those scenarios rely on a lot of assumptions. They assume that those financial changes come with no other negative ramifications in our life.

For example, if we had purchased that dream parcel of land, we would have struggled with property taxes. We also would have different social relationships; two of our closest friends are our neighbors and that relationship would definitely wither.

If Sarah had become a stay-at-home mother, we very likely might have strained our marriage, since I have worked from home for many years. Would our relationship still be great if we were largely together at home every day for years and years and years through the stressful years of parenthood? I honestly don’t know.

What about that early retirement dream? Would I actually be happy with any form of “retirement” right now? I like having something to wrap my hands around and work on. I like to keep busy. I like to feel like I’m working for something and toward something. I wonder if I would lose that.

Those dreams seem wonderful and perfect because, well, they’re dreams. They’re not real. Real life has warts and flaws. Real life isn’t the “highlight reel” that is Facebook. Real life can hurt. It involves lost friendships and strained relationships and things you can’t possibly foresee.

The truth is that I like my life as it is right now and that I wouldn’t be here if it wasn’t for the mistakes. So, no matter how good the scenarios seem, the truth is that I likely wouldn’t be significantly happier or have a truly better life even with those scenarios.

Final Thoughts

It is very tempting at times to let our guilt from the mistakes of the past become a very big driving force in our lives. However, that guilt is often purely self-imposed and entirely based on poor reasoning.

If you feel guilt because of the financial mistakes in your past – or any other mistakes in your past – think about the things in this article and really give yourself time to process them. Not all of them will be true for you, but many of them will.

Let those true points guide you and bring you to a better life, one where you don’t feel guilt for the mistakes of the past, but joy for the opportunities of the present and the possibilities of the future.

Good luck.

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