3 Powerful Ways to Make the Most of Past Mistakes

Dwelling on past mistakes doesn’t serve you or anyone else. In sharing the worst financial mistake I ever made, I hope these powerful lessons help you move past your own decisions so you can make smarter ones in the future!
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Joseph and I couldn’t stop grinning at each other over the tops of our ice cream cones.

Were we celebrating an anniversary? A birthday? A book launch?

Nope, none of the above.

Although all those things would warrant a delectable sweet treat, none were the reason for this indulgence. We were about to let go of huge mistake from our past.

Our realtor had just called and told us we would no longer be homeowners in NY. The bank had accepted our short sale and we had a closing date circled on our calendar!

The weight on our shoulders (caused by owning a home we no longer wanted in a state we no longer lived in!) instantly evaporated after that life-changing call.

We rejoiced even more so when, four weeks after that ice cream date, we signed over the documents to the hero we never met—a landlord from NYC.

A Literal Nightmare on Elm Street

Our first house (a duplex) was a literal nightmare on Elm Street. Yes, the house is actually located on Elm Street!

Joseph and I bought this house a few years after we were married with a vision: renting out one side and living in the other, effectively having more than half our monthly mortgage paid for.

We were young and excited about all the possibilities our venture into the real estate market held for us.

Perhaps too excited.

Because we not only paid too much for the home, we also didn’t pay close attention to the location.

Our past mistake: house on Elm Street

Then 2008 happened…

The housing market crashed right along with our dependable renters and their monthly payment.

After two expensive evictions later, and a neighborhood that wasn’t bouncing back (and began attracting drug dealers), we had two choices:

  1. Struggle to find reliable tenants and possibly face yet another eviction.
  2. Give up and stop trying to rent the house, which would mean being saddled with an extra mortgage we couldn’t afford.

After many discussions, tears, and worry over our nearly perfect credit scores, we chose a third option:

A short sale—which would free us from a too-expensive house payment and allow the bank to recuperate at least some of the money lost.

The nightmare was over.

Looking back, I wish we had never seen the open house sign on that Sunday afternoon years ago. I wish we had never stepped foot on that property, or taken a tour, or signed our lives away to a building that would later become the worst financial mistake we ever made.

But we can’t go back and change our past mistakes. And hard years don’t mean ruined years.

We can only change the future based on decisions we’ve made in the past.

Why Learning From Past Mistakes Matters

Maybe you’ve stayed in a toxic relationship for far too long, been a little too carefree with credit cards, or struggled with binge-eating all of your feelings.

But just because you’ve made one decision you’re not proud of doesn’t mean that mistake should define who you are.

And it doesn’t mean you can’t make smart decisions going forward.

Because when you study a bad decision out of curiosity rather than self-inflicted judgement, your future self can actually benefit from the choices you made.

Here’s how:

1. Look for the lesson

Failure is an unexpected teacher.

While I would love to avoid her classroom entirely, it is through failure that we gain wisdom through our experience, learn about ourselves, and figure out what we can do differently in the future.

When I find myself recovering from a past mistake (after wallowing for a little bit, let’s be honest!), I like to ask:

  • Where is the positive in this?
  • What can I take away from this experience that will help me make better decisions going forward?

For example, now I know that my retirement plan probably won’t include rental properties! And I’ll definitely be more aware of the location and price when Joseph and I buy our next home.

This process allows me to “redeem” my mistakes by looking at them in a different light and acknowledging that I did glean wisdom along the way, even if it wasn’t my favorite manner in which to do so.

past mistakes quote

2. Forgive yourself for past mistakes

Most of us are quick to forgive others, but slow to give ourselves the same courtesy.

For some reason, it seems far easier to self-sabotage with negativity and give into the guilt and shame over what happened than to channel our inner Elsa and “let it go”.

(I’ll be the first to raise my hand here!)

But the only thing self-inflicted punishment does is send you down a tunnel of emotional turmoil. Being hard on yourself doesn’t change the outcome. Nor does it make you feel any better.

To keep my past mistakes from haunting my present, I give myself permission to say,

“All right, that wasn’t my best move, but now I know what not to do next time.”

Not only have I identified what happened and my part in it, I also recognize that moving on is the only way to move forward.

bad decisions quote

3. Don’t Let Fear Affect Future Decisions

Naturally, fear about mistakes we’ve made in the past gives us pause when we consider making future decisions.

Will I make the same mistake? What if I screw up again?

Caution can be a good thing! But don’t let your past paralyze you into worrying so much about a particular decision that you do nothing at all. Use the wisdom you gained from past experiences to make more knowledgeable choices in the future.

I recommend you establish a “decision-making process” to make this easier:

  • Gather essential information about the decision, including advice from trusted mentors. (Just be aware of the 70% rule!)
  • Write a pros and cons list (my favorite!) with this handy note pad
  • Pray about the decision
  • Ask yourself which you would regret more—doing it or not doing it?
  • Take action and own your decision once it’s made

Here’s the good news: even if your decision doesn’t pan out the way you hoped, you can always find another character-building lesson in the situation.

don't regret past mistakes quote

What I Never Expected

Even though I’m still waiting to see my 790+ credit score again, it only took a year for it to bounce back to a “normal” level (thankfully!)

And even though we lost money on our NY rental, we were able to learn from that mistake. We later purchased a home in Florida, and when we were ready to move on from there, listed and sold that home for a profit.

That gave us enough money to purchase a truck and Fifth Wheel RV so we could set off on the adventure of a lifetime!

fifth wheel RV

The old me would have preferred to skip over the three years we owned that nightmare rental, but I can honestly say that the new me has learned to be grateful for the experience.

Without it, I would have never understood rental properties very well (or the housing market for that matter). I also had no idea what a short sale even was until that option presented itself to us!

Now I’m able to take that knowledge and experience and apply it to future decisions—like when we decide to quit the RV life and buy a sticks-and-bricks home again.

Let’s hope that is far into the future though. I enjoy the nomad lifestyle too much. 😉

Let’s chat in the comments!

What powerful lessons have you learned from past decisions and how have they shaped you into the person you are today?

Pin this post to reference later:
I've made a lot of mistakes in the past. Thankfully I've been able to use these helpful tips to let go of those mistakes, learn from them, and move forward instead of beating myself up!
I've made a lot of mistakes in the past. Thankfully I've been able to use these helpful tips to let go of those mistakes, learn from them, and move forward instead of beating myself up!
I've made a lot of mistakes in the past. Thankfully I've been able to use these helpful tips to let go of those mistakes, learn from them, and move forward instead of beating myself up!

Disclosure: Some of the links in the post above are affiliate links. This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. Read my full disclosure policy here.

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  1. Kalyn, I applaud your willingness to share these personal lessons. I agree that “failures” should be thought of as “learning moments” and finding a way to create positives out of negative experiences. I did not learn that lesson until later in life, but when I did I was able to look back on things and ask myself ‘what could you have done differently or what can you learn from this?’ I am nearing retirement age and find myself wanting to go back on the open road. Sell my home, buy a RV and just travel without needing to worry about deadlines or anything. I worked as a Travel Nurse for about 7.5 years and worked all over the country. I still have the travelbug in me.

    Enjoy this time on the road,

    1. Aw, thank you Sue! Joseph and I have said we’re going to do this until we’re sick of it…I’m afraid I may need to come up with some other form of metric because I’m not sure the travel bug ever goes away.

  2. I really enjoyed this post! And I love what you said about how we can choose to view our mistakes. Instead of over analyzing them and dwelling on the negative aspects, we can view it as an experience and then figure out what we can learn from them. Glad you are enjoying RV life – it seems to agree with you!

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