Reflecting on Financial Mistakes

I hate to make mistakes. I mean undeniably and unequivocally hate it. Rather than moving past the errors, I flip them over and over in my mind. Of course, I don’t like to make mistakes, but financial ones are the absolute worst for me. When I make a financial mistake, I struggle to move past it.

I’ve never made a significant financial mistake, but the little ones still bother me immensely. I can spend days feeling bad because I forgot to use a coupon, left money on the counter, or didn’t buy an item when it was on sale.

I’m over forty now and tired of feeling this way. My scarcity mindset has kept me trapped in this negative spiral for way too long.

It’s time to make a change. I want to stop obsessing over every lost penny. I’ve been working to change my money mindset, and I’ve tried a few things to clear my mind more easily.

Forgive Myself for Making Financial Mistakes

The other day my husband picked up takeout and accidentally left a $50 gift card on the counter. I called the store, found out the cashier put the card aside, and drove up to the restaurant to get it.

I was annoyed at the idea of driving late at night in the cold, but I immediately forgave him for the error. It was an oversight and nothing more.

Would I feel the same way if I left the gift card behind? Nope. I would have been angry that I wasn’t paying attention to what I was doing. I would replay the moments that led up that moment, rather than just letting it go.

But, what good does it do to stay mad for making mistakes? Why don’t I forgive myself like I forgave my husband? We all make mistakes, so why should I feel so guilty and remorseful about mine?

It makes me feel bad, but it doesn’t serve any other purpose, so I’m tossing that behavior out the window. I’m trying my best to view my actions from an outsider’s point of view. If I can forgive my husband, I should be able to forgive myself too.

Learning From My Financial Mistakes

I’m tired of kicking myself for financial mistakes. From now on, I’m taking a new approach to them. From this point forward, I am writing them down in an effort to move past them.

Journaling my mistakes helps me get them out of my head. It prevents the never-ending loop of thinking about something that I cannot change. After writing them down, I ask myself what I can learn from them.

Then, and most importantly, I forgive myself. Mistakes are not intentional or purposeful. I remind myself that I am careful with my money, and I don’t want these tiny financial mistakes to plague me unnecessarily.

This Year’s Financial Mistakes

This has been the year of financial mistakes. I haven’t made too many giant errors, but I’ve made plenty of small ones. By writing these down, I hope to prevent myself from making similar ones in the future. When I make new mistakes, which I will inevitably do, I will forgive myself again.

Here are my top four money mistakes of the year:

Failing to Insure a Package Shipped Through the Post Office

In preparation for homeschool, I bought a bunch of curriculums for my kids. I signed them up for the online version, then went out and bought the paper version too.

After a few weeks of using the online materials, I decided to return the physical books. I found a big cardboard box and sent my husband off to the post office to return them.

I packed over $200 worth of books into that box, and wouldn’t you know the package went missing a day after he shipped them. For two weeks straight I clicked refresh on that tracking link, but the status never changed.

Finally, I scurried over to the Internet in search of answers. I typed, “the post office lost my package,” and a post of mine from 2007 popped up. It seems I did not learn my lesson from thirteen years ago.

I filed all of the appropriate forms, but the post office never found my package ā€”a total loss of over $200.

Money mistake: Not paying for shipping insurance.

Solution: From now on I am paying for shipping! It only costs a few dollars.

Failing to Return Items Before It’s Too Late

Speaking of homeschool, I bought too many curriculums in September. I considered sending one set of books back to the company where I bought them, but I wavered a little too long and missed the shipping timeline. To make up for the loss, I tried to sell them on eBay, but no one bid on them.

“Maybe, we are too far into the school year,” I thought. “I’ll list them in August and recoup some of the money.” Ha, ha, ha. Today the company announced a new line of books that will cost half as much as the books I purchased!

That makes my set completely obsolete. Worse yet, the latest version will cost half of what I paid for the current ones, so I can’t list them on eBay and recoup anything close to what I paid for them. That’s another $150.00 down the drain.

To add salt to my wounds, the company marked down its current inventory by 75%. The books I paid $100, for now, are selling for less than $25 each.

Money mistake: Not returning items in time.

Solution: Don’t waver. If I don’t think I’m going to use an item, I will return it. I can always purchase it again.

Failing to Use Gift Cards

This one stings more than my first financial mistakes.

Every birthday for about five years, my parents bought me gift certificates for the Red Door Spa. Every so often, I would schedule a facial, massage, and pedicure all on the same day. It was a once a year pampering treat that I thoroughly enjoyed.

After my kids were born, I never found the time to spend hours at the spa. I breastfed both of my kids, which means I couldn’t be more than a few hours away from them. The nearest Red Door was about an hour away with traffic, which didn’t leave much time for relaxation.

For years I stared at those gift cards but never made my way to the spa. My kids eventually got older, but I found other things to do in my free time. I went to the gym, ran errands, or wrote in this blog.

From time to time, I considered selling those gift cards, but I never did. I wanted to experience a luxurious day, but I never made time for it. There was always something more pressing I needed to do instead.

I wasn’t too worried about those gift cards. Red Door has been around for ages. Then, in July of 2019, the company changed its name to Mynd. My heart palpitated. Could I still use my gift cards?

It turns out I could. Mynd would accept all Red Door gift cards without exception. I breathed a big sigh of relief and left them in the safe again, fully intending to use them. Of course, I never did. As usual, I found other ways to spend my time.

My relief was short-lived. Mynd filed for bankruptcy this March, making my stash of gift cards completely worthless. I wasted over $500.

Money mistake: Not using gift cards.

Solution: Use them, sell them, or give them away, but no more holding on to them!

Using the Wrong Credit Card

My husband and I use Chase reward cards for all of our expenses. When our grill died a few weeks ago, we decided to buy a new one. As luck would have it, Chase had an offer that would save us an extra money on a purchase from Lowe’s.

That was perfect, because our grill cost $800! We logged in to Lowe’s and placed our order, but in the process, we used the wrong credit card. The offer was only valid on one of our cards, and it wasn’t the one we chose.

Money mistake: Not checking our credit card offers before making a large purchase.

Solution: Double check Chase offers.

Looking Past My Financial Mistakes

In the past, these mistakes would have broken me. I would have pined over them for days, weeks, and possibly months. I would have weighed the mistakes and kicked myself for making them.

None of these financial mistakes will break us. Thankfully, they won’t result in us forgoing anything we need. I need to reflect on them, learn my lessons, and move on.

It’s as simple as that. There is no need to dwell on things that I cannot change. I can only move forward in smarter ways from this point forward.

Have you made any money mistakes this year? What were they? What lessons did you learn? Have you forgiven yourself for making them?

12 thoughts on “Reflecting on Financial Mistakes”

  1. This is definitely me! I made a big money mistake this year and I’m still upset at myself for it.

    We did a 1031 exchange on a rental property that’s far away from us. The idea was to get a property close to us that’s easier to manage. To try to make our finances easier, we put the rental properties in an LLC. It seemed like a great way to separate accounting.

    When financing the new property, the bank would only allow us to work with their commercial lending area (because of the LLC). The loans on those aren’t 15-year fixed at 2.5%, but they are 5-year readjusting at 4% (and likely to go higher). We had a much better mortgage with the old property.

    I’ve been fortunate not to make too many of the small money mistakes. In fact, it’s almost been crazy how lucky I’ve been to have the timing on many financial things work out.

    I finally got over the new mortgage mistake by telling myself that we’ll pay it off before it readjusts, and that it won’t be too much in extra interest. Because we’re starting the financing all over, the payments are low which gives us a lot of flexibility. That’s valuable to us.

    I guess the moral there is try to find a silver lining when possible. It’s hard if it is a total loss, though.

    • Money mistakes can really make you second guess your decisions can’t they? The higher interest rate isn’t so bad, (especially if you can pay it off in 5 years), but the fact that it adjusts could be. The low monthly payment is great. My husband and I put ourselves into a bad situation with two mortgages with 10 year terms. I would never do that again and I am so happy they are now paid off! I hope to never have a mortgage again, but if I did I would choose a lower payback plan and just throw extra at it so we don’t feel so strapped for cash.

  2. The last year I worked I had stock options worth $60,000 I could have cashed in December but I reasoned the smarter move was to execute them in January because as a mostly retired person then I would be in a lower tax bracket that year. It wasn’t necessarily a dumb mistake, the odds were good that the stock would hold stable and it would save me $10,000 in taxes. But the stock crashed and I couldn’t cash it out, even worse since I was no longer an employee it only had a 90 day window before the options expired. It stayed under water the whole 90 days. Instead of $60K I got zero, nada, zilch! That qualified as my biggest money screw up. But I don’t feel bad about it now. It literally was a planned move, they just don’t always work out. You are a very smart money person, it is obvious from your many excellent posts. Besides we learn a lot from our mistakes, its just not a fun way to learn.

    • Hi Steveark, Your comment reminded me of my worst money mistake. Just before the Great Recession my CEO held a forum for all employees. He calmed our fears and told us the news of mortgage failures and banking problems were unfounded and that our company was rock solid. My husband and I doubled our efforts and bought extra company stock. It tumbled and became absolutely worthless just after that. Our CEO was a liar and we paid the penalty for believing him. My options also became worthless at the same time and my retirement fund went from over $30,000 down to zero. So, yup, I feel you on this one!!!

  3. I used to be terribly hard on myself about financial mistakes, and even worse, because as a financial professional I should have known better. Our net worth has gotten large enough now that I just don’t worry about it that much anymore. I make fun of myself now when I catch myself doing a cost/benefit analysis over the purchase of a toothbrush.

    And re: post office insurance, I sold some things on EBAY a while back, and I vowed never to buy insurance again. They have so many restrictions on the insurance that it’s nearly impossible to collect it. They’re happy to take the insurance fee, but in order to collect it you have to prove the worth of the contents, receipts for whatever you shipped etc.

    • I’m hoping that writing down my mistakes will help me purge them from my mind and move past them. I find it difficult to change my money mindset after 40 years of thinking this way. The impact to my finances is certainly not significant, but I’d like to make the mistake, think about it for a brief moment, learn from it and move on. So far, I still let the thoughts linger in the back of my mind.

      I just sent a package to USPS a week or two ago that appears to be lost. If it doesn’t turn up it looks like I’ll have to undergo the nightmare insurance claim filing process. I’m crossing my fingers it just gets to where it needs to be!

    • Thank you for your comment. I completely agree. My biggest mistakes in life have certainly provided the most profound lessons!

  4. It is very tough to forgive oneself for making mistakes. Also it is nice to see someone put out their mistakes for the world to see. Too often we hear only of other people’s success stories and not really find out about all the failures they endured to get their. Therefore we are hard on ourselves even more when we fail because we are comparing ourselves to something that doesn’t exist, financial perfection.

    When I started blogging I decided to start out with a series of all the financial mistakes I made in my life. It ended up being a 5 part series and along the way I kept total of the estimated hit to my financial net worth. It was shocking but when I totaled it up I came up with close to $2 million dollar financial hit. But those mistakes shaped me in to the person today and I am happy to say I more than recouped that loss several fold over and became financially independent before my 50th birthday.

    Am I perfect now? No. I still make mistakes. Most recent one was selling my tesla stock way too early (took a $7k profit when I sold in 2019 but if I held on to it would have had over a $160k profit. It stings but not the end of the world.

    • Thank you for your comment Xrayvsn. A $2 million dollar financial hit is a big one! I’ve made minor money mistakes and some medium sized ones, but not too many giant ones that were out of my control. Honestly, all of them hurt about the same for me. The big ones stung just as much as the little ones, but you are right I learned a whole lot about myself and how to mitigate risks moving forward. Thank you for sharing your story and congratulations on reaching FI by age 50!

      As a side note, I’m actually a long time reader of your blog, but I’m not sure if I’ve ever left a comment! šŸ˜‰

  5. It’s funny how hard we are on ourselves. I’m getting better at this. I accidentally left the cast iron pan on a hot stove on overnight. the old me would’ve beat myself up for days. This time I was able to move through the emotions within a day.


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