<img height="1" width="1" style="display:none;" alt="" src="https://ct.pinterest.com/v3/?tid=2613570466604&pd[em]=&noscript=1" /> Skip to Content

33 Money Mistakes (Examples of Recovering from Financial Mistakes)

33 common money mistakes (including big ones!), as well as several amazing stories of people recovering from financial mistakes to be better off.

Money mistakes are not the enemy. They're actually catalysts for change in your financial life.

woman with hand around mug, looking to left, text overlay "recovering from financial mistakes? Real stories to inspire you to keep going"

Financial problems come and go, and you're always learning about ways to get better at managing your money in the future.

I know I say all of that soooo casually, so you should know that you're talking to a recovering perfectionist who used to fear making mistakes. I'm talking sweat-provoking, sleep-depriving, visceral fear at the thought of it.

In fact, I used to fear I'd commit a money mistake so bad that it would cause a huge money disaster in my life, and I would end up back on my mother's couch.

But now that I've lived through lots of financial mistakes (you can read about my personal ones below), I know there's another side to them. A much more informed, better-off side.

Let me share with you some common money mistakes, some big money mistakes, and then how to turn these suckers into your next opportunity. Did I mention there are examples and stories from real-life people (like Dave Ramsey and Suze Orman) of how they rose from terrible financial mistakes to come out on top?

Stick around.

Common Money Mistakes

There are lots of money mistakes out there, and I'm going to share with you some of the more common ones.

Common, yes, but they can definitely cause financial stress in your life.

  • Overwithdrawing your checking account.
  • Missing the mortgage payment.
  • Forgetting to pay a bill on time.
  • Spending money on a cheaper product and then having to buy it over and over because it wears out much faster than if you had purchased a more expensive product to begin with.
  • Spending too much money on Christmas and the holidays, and having to deal with a January (and February) money hangover.
  • Not setting up automatic withdrawal of your paycheck into your savings account each month.
  • Buying savings bonds and then losing them over the years.
  • Getting a late fee on library books or anything else.
  • Filing your taxes late.
  • Getting locked into a car payment or lease payment for the rest of your life.

We've looked at some common ones…now let's go into the biggest money mistakes you can make.

Pssst: are you dealing with any of these? You'll want to check out how to get your finances in order.

Biggest Money Mistakes

What are the worst money mistakes or the biggest money mistakes you can make?

First off, a disclaimer here (actually, two):

  1. This is my opinion (granted, I have years of experience working with people on these sorts of problems).
  2. You can come back from any financial mistake, no matter how big it is. So don't get disheartened!

Now that I have that out there, I'd like to list out the biggest money mistakes a person can make:

  • Buying too much of a house – in both size, so that the maintenance costs are really high, and taking on too much of a mortgage (so that you are living house-poor).
  • Not creating a will.
  • Not having health insurance.
  • Not having life insurance.
  • Not starting your retirement savings.
  • Not starting your retirement savings early enough.
  • Relying on social security benefits alone to retire.
  • Not confronting your money problems.
  • Hiding your bills in a shoe box and hoping they'll go away.
  • Saving for your child's college education instead of saving towards your retirement.
  • Not sharing finances with your partner.
  • Not caring about finances because your partner is “handling” them.
  • Not submitting your taxes. At all.
  • One of these 12 common budgeting mistakes.

Without Making Mistakes, Your Opportunity to Grow is Much Less

There are two problems with fearing mistakes:

  • The tremendous amount of self-made pressure
  • Developing a fear of trying new things (because *gasp* what if you make financial mistakes?)

From personal experience, I can tell you that being an audience member in a self-created fear factor show is no fun. Not only that, but it can stunt your growth big time. This means you're not finding solutions that work for you and are getting caught up in the muck that doesn't. It's a never-ending loop!

So how do you free yourself from the loop effect? By making some mistakes and learning from them.

Worst Money Mistakes, Turned into Opportunities

You can recover from financial mistakes.

And not in the way that your parents or grandparents did, which didn't seem to turn out so well overall.

I mean, you can be the hero/heroine of your own financial story, and really bounce back.

Let that sink out.

How can you take all the financial stress in your life right now, and all the money mistakes you've made, and use it as motivation to put you + your family in a BETTER position than what you would have been in, had the mistakes never happened to begin with?

I'm going to share some solid examples of this, and I think this will help calm you a bit about your situation.

Dave Ramsey's Financial Mistake: Bankruptcy

Unless you're intimately familiar with Dave Ramsey, you may be surprised to hear that the man declared bankruptcy early on in his career. Roughly 20 years ago, he and his wife filed for bankruptcy and “lost everything”.

At the age of 26, he was a broker with real estate holdings of around $4 million. This portfolio of properties was financed on various short-term loans, all of which came up for renewal at the same time. Lenders called in $1.2 million of his short-term debt (meaning they expected him to pay up because they didn't think they would get paid otherwise), and he couldn't.

He had way over-leveraged himself, and at the same time, was using part of the debt to pay for things like expensive cars and exotic trips. He and his wife took six years to pay off the $500,000 they owed the IRS and various friends and family members.

Rising Phoenix: Since his clash with bankruptcy, Dave has built up quite a career teaching others to unload their debts as quickly as possible (and then to never go back).His reported net worth is $55 million. All because lenders called in roughly $1.2 million in loans and he couldn't pay them back.   

Jean Chatzky's Financial Mistake: 401(k) Cash Out + $7,000 Credit Card Debt

Several weeks ago I was invited as a media guest to Fidelity's conference on the subject of empowering women financially. One of the speakers was Jean Chatzky, who was quick to point out all of her financial mistakes early on in her career.

On her list included:

  • racking up $7,000 of debt while outliving her salary as a business reporter for Working Woman magazine in expensive New York City
  • cashing out a $1,500 401(k) when changing jobs (which would be worth $25,000 today)
  • earning 9% interest on the money while paying out interest of 27% to service her debts

From these experiences, Jean “realized that I needed to understand money so that I could fix what was wrong in my financial life – and by understanding it, and fixing it, I was able to explain what I was doing to anyone who was willing to listen.”

Rising Phoenix: Since these financial mistakes (and while working through them),Jean's been on Oprah, a financial editor of NBC’s Today show, successfully authored books and has a speaking career. All because she decided to let her financial mistakes define her by making her a better person.

Suze Orman's Financial Mistake: $50,000 Loss + $250,000 Credit Card Debt

Suze was a waitress earning $400/month with very loyal customers. Like, very loyal.

Together, they gave her $50,000 in order to open her own restaurant at the age of 30. Unfortunately, she invested the money with a broker at Merrill Lynch and lost it all within three months.

Not only that, but she was $250,000 in credit card debt as well. She gets a seemingly bizarre idea of applying for a position at Merrill Lynch with a social worker degree and seven years of experience as a waitress, and they hire her to satisfy new Affirmative Action regulations.

She successfully sued for her $50,000 back, stayed at Lynch for several years learning about money, and then became vice-president of investments at Prudential Bache Securities

Rising Phoenix: Of her financial mistakes and past, Suze says, “Sometimes poverty is the greatest gift you can ever be given. Sometimes loss is the key that leads you to gain.” She has a reported net worth of $35 million, is a successful author, speaker, and has a successful television show. All because she lost $50,000 to a broker and found herself $250,000 in debt on a $400/month income.

Amanda L. Grossman's Financial Mistake: Unemployment Stints + $36,000 in Student Loan Debt

Depending on how long you've been following me, you may not know why I started my blog. It was 2008, and I was newly laid off a second time from my second post-college job.

Yep, you read that right − exactly two jobs, and two layoffs in less than four years. Instead of wallowing on the couch as I did after my first layoff (albeit while still job searching; I scored my second job within a few months, which is quite necessary for someone who graduated with $36,000 in student loans), I decided to make something great out of the time I was given.

Writing has always been a passion of mine. One I was afraid to claim because of the countless stories of writers never actually making it.

And money?

Well, I just loved the subject and was endlessly fascinated by it since my early teens.

So I went to the library, got out several books about how to write a newspaper column, and spent part of my three months of unemployment writing six columns called Frugal Confessions.

After I finished, I sent them to several newspapers across the country. While none of the newspapers accepted it (I did receive a nice letter from one editor telling me I was close, and to keep going), I was introduced to my friend Helen at my next job, who then introduced me to the idea of opening a blog at the Houston Chronicle.

Rising Phoenix: Over the last several years my dedication is beginning to pay off. I was able to quit my day job in early 2013 and pursue Frugal Confessions fulltime. I've appeared in Woman's Day magazine, Business Insider, lifehacker, US News & World Report, abc 13 and Fox 26 news here in Houston. Better yet, I'm able to continue working at something I'm passionate about while raising our son. Now that's priceless. All because I decided to give this writing thing a try during a stint of unemployment.

Eye-ball-popping amounts of debt. Anemic emergency savings − or none at all − to fall back on. Bad jobs. Low pay. Hitting rock bottom. Living on Mom's couch. You could say that these are reasons why no one should listen to these guys (and myself) ever.

OR, you could see this for what I think it really is: learning from people who have been there, and who have turned their financial mistakes into their greatest financial assets through the School of Hard Knocks.

Money Mistakes We've Personally Made (Money Oopsies)

It's generally not mistakes that hold us back, but the fear of mistakes that holds us back. This plays out big time in finances, because let's face it, financial mistakes can be, well, costly.

And guess what? I am certainly not immune to making financial mistakes, nor am I immune to having financial problems (yes, even though I'm a personal finance blogger! Actually, it's great blog fodder).

Money Oopsies #1: IRS Letter Saying We Erred on our Taxes and Owe $2,315

About a month ago, on a Friday (way to ruin the weekend…) we received a letter in the mail from the IRS. Gulp. And it said we owed them $2,315 from our 2012 tax return. Double gulp.

And guess who does our taxes each year? Me.

After I called our investment people, we figured out that I had made a sale of a stock in 2012 without reporting it. Since I had never done this before, I thought that I would not owe taxes on the gains from this until we actually withdrew the money (which we have yet to do). Wrong.

The IRS had gotten a form saying what the gains were, but because I had not reported what the cost basis was (what it cost us to buy the funds in the first place), they thought we had gained a whole lot more than we did.

We fixed this error by providing the correct forms and an explanation to the IRS. The new estimated amount we owe is just $65. Whew. And since I'll probably be investing for the rest of my life, I now understand much more about tax rules on gains.

Financial problems were averted by confronting the money mistake I had made. Whew!

Money Oopsies #2: Shutting Down a Checking Account with Automatic Deposit Missed

Several years ago when I was moving from Florida to Texas, I shut down my checking account. Unfortunately, I had completely forgotten that an automatic bill pay was still active on the account. So I was dinged with a $39 fee. You can bet I haven't ever done that again! Plus I honed my skills in asking for fee-forgiveness when a mistake is made.

Money Oopsies #3: Missing a Payment when We Changed Money Guards

Remember when Paul and I switched places to heal the money friction in our marriage?

The experiment went well, but there was a missed bill payment during the changing of the money guards (not the mortgage).

Paul caught the mistake several days later, and we were not assessed a late fee.

If we had feared money mistakes and not changed the guards, we would still be on separate pages when it comes to finances. Imagine all the gained ground that would never have happened.

Fortunately, this one didn't cause a financial problem at all.

Money Oopsies #4: Forgetting to Notify Our Bank that We'll be Traveling

Let me set the stage for you. It's day 5 of our incredible 6-day trip. We're tanned (not burned, a true miracle thanks to my overzealous slathering of 50-60 SPF).

We're well-fed.

We've had three awesome adventures already: snorkeling in aquarium-like conditions, biking along the coastline, learning about tequila production, hiking some actual Mayan ruins dedicated to the Goddess of fertility, childbirth, and writing (ummmm….our travel agent really got my number!).

But we're looking for just one more adventure before coming home, something that was on my “would-love-to-do” list: hiking the ancient Tulum Mayan ruins.

On Day 4, someone at the front desk graciously walked us through how to make it to the ruins, located on the Yucatan Peninsula. We would need to take a taxi to the ferry (10 minutes), then a ferry ride to the peninsula (45 minutes), then a bus ride straight to the ruins (1 hour). The total cost would be around $140, round trip, for both of us.

Perfect. Especially since we had spent no money, except for tips, since landing in Cozumel. Splurging on this thing I had wanted to do was a no-brainer.

So the next morning at around 7:30 we got a taxi to take us to an ATM machine (we had to use our bank's debit card to get actual cash, as the bus and taxi would not accept credit cards). The first one is closed because of how early it is. So we go to a second one. Unfortunately, our debit card is declined. Then we go to a third one, and again, the card is declined.

My belly sinks a little because I think I know precisely what has happened: our bank suspects fraud since we never told them we would be in Cozumel, so they are automatically declining our transactions.

Cozumel 4

Call it pregnancy brain, overwhelm (yes, I have found overwhelming to be the only emotion more pronounced for me since becoming pregnant; so far there have been no tissue-wetting sob fests in front of the tube for marginally sentimental commercials to report), or just pre-trip laziness, but I didn't call our bank. Honestly, I thought that traveling with a no-foreign transaction fee credit card, coupled with the fact that our trip was all-inclusive (and it truly was; even the excursions were included) meant that we didn't need to bring much cash at all.

Once we got back to the wifi-wired hotel, having been too late to make the bus times and such, we received text messages and calls from the fraud department asking us to press “1” if we meant to make this transaction, or “2” if this was not us.

Overcoming the Fear of Making Money Mistakes

I'm here to tell you that no matter what money mistakes you make, you will prevail. Things will get better. Need some more reassurances? Check out any of the episodes on Gail Vaz-Oxlade's show ‘Til Debt Do Us Part, or dig into Suze Orman's tragic story of collecting $50,000 to invest at around the age of 30 from her loyal diner customers…only to lose it all because she blindly handed it over to an investor (*spoiler alert* this was the catalyst to her becoming what she is today).

So how can you feel comfortable moving forward with your financial decision-making and test the waters out without suffering from huge financial catastrophes?

Here are a few tips:

  • Test the Waters: Investing for the first time? Don't mortgage the farm (or anything even close to that). If you start out with small denominations of money with whatever you are doing, chances are good that the risk will be less. Yes, the gains may be less as well, but you're testing the waters so that you can make a few mistakes, learn from them, and implement changes for larger future gains.
  • Educate Yourself: Read articles, and books, and do lots of research on what you want to do. Not only will this put you ahead of the curve, but it will also give you a bit more confidence in what you are trying to accomplish.
  • Ask Questions: Ask anyone from my previous job about me and they might say, “Oh yeah, that girl who asked all those questions“. It's true, I ask questions constantly. And you know what? I learn quite quickly this way. Find people who are knowledgeable about what you want to do or who are where you want to be, and ask them questions.

Money mistakes do not have to define you, even though they might feel like they do while you are living them. I've made more mistakes than I care to count. I gave myself some reflection time, made my apologies, and the world did not end. In fact, since I took the time to learn from them, I actually gained even more confidence as well as figured a few things out the second time around. I would not be where I am today without having made these mistakes.

Recovering from Financial Mistakes

Out of financial mistakes, the size of Dolly Parton's…personality (ha!) can come the most wonderful of things. In fact, it's the one thing that unites most of the financial greats.

Dave Ramsey, Jean Chatzky, Suze Orman, and lots of personal finance bloggers (myself included!) all delved deep into finances after finding ourselves in pretty embarrassing financial straits. We really learned how to manage our money from the school of hard knocks.

You see, the dire financial straits are what motivated each of us to learn about money and move on to better versions of ourselves.

It's the proverbial phoenix rising out of the ashes, and none of the best financial gurus are exempt.

Let me show you what I mean.

Living Paycheck to Paycheck

Living paycheck to paycheck is very stressful. It means you are juggling the entire month long, waiting to pay certain bills until you reach payday, timing account transfers and direct deposits, and waiting.

You can’t ever get ahead financially – barring a decent pay raise – because there is no room to save money.

When the occasional emergency pops up, the juggling takes on a whole new level of intensity, and sometimes other bills just don’t get paid.

  • Build Up an Emergency Fund: I know, I know, I already mentioned (and you already know) how difficult it is to save when you are living paycheck to paycheck. But there are some ways to accomplish this that you may not have thought of. Have you had a large tax return in recent years? Check with your HR to see if you can adjust so that your monthly paychecks are larger instead of getting it all at the end of the year. If you are paid every other week, then two months out of the year you will receive three paychecks. Instead of spending the paycheck (or allowing it to magically absorb into thin air), purposefully deposit a chunk or all of it into your savings account.
  • Focus on One Category of Spending and Whittle it Down: It may seem overwhelming trying to figure out where to start when it comes to decreasing your expenses. But if you choose just one category (food or entertainment, or phone/internet/cable) and focus on whittling it down, you will begin to make some headway. Next month, choose a different category. As an example, you can challenge yourself to cut your food bill by 30%. You might not be able to, but by setting such a lofty goal you will be sure to be in a better position than if you had never set the goal at all. Here are some ideas for saving on fixed costs such as your home or rent.
  • Share the Load with Someone Else: You can cut your bills significantly in a short amount of time by taking in a roommate/housemate or carpooling back and forth to work. Yes, this will be a big change for you. However, it will also lead to sizable breathing room in your budget. Plus you never know who you may meet. My Aunt has been renting out rooms in her D.C. home for decades, and every time I visit her I meet someone new and interesting.

Denied a Mortgage Due to a Low Credit Score

If you wish to purchase a home and need to take out a mortgage (like most people do), then you have to care about your credit score. Having a low score means you may be charged a high interest rate – a costly mishap on such a large loan – or be denied altogether.

  • Keep Your Income to Debt Ratio Low: Any debt that you can pay off, even the debt you carry until just before the grace period ends for the sake of rewards, will help your credit score. This is because your debt-to-income ratio will decrease.
  • Check Your Credit Reports and Correct Blemishes: Obtain a free copy of your credit reports (on AnnualCreditReport.com) and look them over. If there are blemishes on your credit report, then you may be able to clear them up by contacting the creditor/lender directly and making a deal. Try to negotiate that upon settling with them, they will report a zero balance to the credit bureaus (and get this in writing).

Stuck In a Payday Loan Cycle

The problem with short-term payday loans is that the interest rates are so exorbitant that they tack on lots to the principal and you end up owing more than you can pay back from your next paycheck. If you are living paycheck to paycheck—likely if you found yourself at a payday lender counter—then you have no additional funds to pay off the interest. And so the loan continues to compound and grow. It is not likely you will be able to break a Payday loan cycle through your paycheck alone.

  • Contact the Payday Loan Lender and Ask for Interest to Cease: Some people have had luck with contacting their lender and coming to an agreement where if they make specified payments on the loan, no additional interest will accrue. It really will depend on the lender and person you speak with, so good luck to you!
  • Make Early Payments: If you can swing it, paying your loan early will decrease the overall amount due (most loan payback amounts are set up assuming that you will pay on the next due date). Even paying a few days early can help cut down on the amount of interest being tacked on.
  • Find a Quick Infusion of Cash: I do not mean taking out another loan, but rather finding a way to earn extra money just long enough to pay off the payday loan and put you on solid footing so that you do not need to take another one out. This could be extra hours/shifts at work, getting a weekend job, posting your services and getting new clients, selling part of your belongings, taking in a roommate, etc. Anything you can do to increase your income will help. While this will help you short term, try to think of ways to continue pulling in extra income so that you don’t start in the cycle again. If nothing else, keep the second source of income long enough to build yourself an emergency fund (aka antidote to payday loans).

One More Solid Piece of Advice about Money Problems

Money problems should not hold you back from living your life now.

Some days are much more harried than others. Some seasons are much more intense than others.

Some seasons are also much more flush than others (you know, in the cash area).

Maybe none of your seasons have felt flush with cash. Maybe you're drowning in debt, drowning in money details, and feeling utterly confused as to how to move forward with your money strategies (heck, you don't even have any money strategies).

You've still got to live your life.

You still need to take the time to breathe. To explore. To connect with others. To do the things that make you, YOU.

Because whether you've got money issues or not, taking an entire season off and waiting in the sidelines to do all those wonderful things that make you feel energized just because you're waiting until all that other stuff is lined up perfectly is foolish with your time + life energy.

And I can say that because I'm right there with you!

“The promises of this gorgeous day are so seductive that it becomes easy to only go through the motions of living in the now without really living.”

I wrote this when I was speaking about how to keep living despite being saddled with debt. But it can really apply to being saddled with anything.

So ask yourself: What are you putting off until your money situation is exactly the way that you want it to be? What are you putting off until you have “enough money” to do so, and what exactly is “enough” anyway?

You might be surprised by your answers.

As for me, I'm off to take that hike. For once, the work can wait a few hours.

What are some of your money mistakes made, and did you learn something from it? Are you holding back from a money decision because you're too afraid of the potential costly mistakes? 

The following two tabs change content below.

Amanda L Grossman

Personal Finance Writer and CEO at Frugal Confessions, LLC
Amanda L. Grossman is a writer and Certified Financial Education Instructor, Plutus Foundation Grant Recipient, and founder of Frugal Confessions. Over the last 13 years, her money work has helped people with how to save money and how to manage money. She's been featured in the Wall Street Journal, Kiplinger, Washington Post, U.S. News & World Report, Business Insider, LifeHacker, Real Simple Magazine, Woman's World, Woman's Day, ABC 13 Houston, Keybank, and more. Read more here or on LinkedIn.

Adriana @MoneyJourney

Wednesday 10th of May 2017

I couldn't agree more. Waiting to actually enjoy life only leads to growing old and regretting everything you didn't do when you had the chance!

I'm a very frugal person (been called stingy at times, but I don't deny it) but when it comes to creating memories or pursuing hobbies I never say no! You can always save more money, but you can't turn back time.

Mike Collins

Thursday 4th of May 2017

This is the best advice I've heard in a long time. Some people take being frugal to an extreme and won't do anything at all if it isn't in their budget and can be paid for in cash. But then something always comes up (the car needs new brakes, the water heater died) and it just gets delayed again and again. I'm not saying we should all go crazy and spend without thinking, but there has to be a balance and you have to enjoy your life while you can.

Amanda L Grossman

Friday 5th of May 2017

Thank you, Mike! I'm glad it struck a chord with you as well.

Peggy@be findawealthmanager.com

Wednesday 18th of May 2016

Loved to read this blog Amanda! Yes, there are lot of things are available here to learn for making investment and taking any financial decision. We can learn lot of positive things from their mistakes and that's why their financial mistakes are the biggest financial asset for us. Thanks a lot for sharing valuable information.


Friday 15th of May 2015

It happens to the most detail-oriented of us sometimes. We have notified them for the last 5 years like perfect traveling angels because at the first Fincon ever, I didn't notify them that I'd be in Illinois while hubby stayed in Texas, and they cancelled like 35 transactions my husband was making on Amazon for his new school library. And he wasn't able to get everything once we cleared up the mistake. Grrr....

Bill in Houston

Thursday 14th of May 2015


Thanks for posting all of that card contact info. It is a smart thing to notify them if you're going to make a trip abroad, or within the US if you don't travel period.

I found out about credit card notification by accident. We were (are) American Express cardholders thanks to Costco. Before our honeymoon in 2006 I thought, "Wouldn't it be nice to have some Mexican currency before we go?" We went to the office, had some dollars exchanged for pesos, and then the lady behind the counter said something akin to, "If you're going abroad I can make note on your account so nothing happens with your card." She explained what you did about fraud and freezing your account. Yikes.

We told her when we'd be gone, and then I also notified Mastercard of the same thing when I got home. We do that every time we go abroad, although I leave AmEx at home. Looks like I don't have to now :)

Hey, our last trip we did the opposite of you. We stayed in Tulum and took the ferry from Playa del Carmen to Cozumel.