47 Financial Experts Share Their Biggest Financial Mistakes

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There’s one thing we can all agree on in the finance world.  That is, we’ve all made mistakes.  The beauty of a mistake is the opportunity they provide.  An opportunity to learn.  We owe a lot of what we know to mistakes.  Perhaps the biggest mistake would be to not learn from our mistakes.

Today I want to explore mistakes and not just any mistakes, but the mistakes of finance experts.  People that make finance their passion.

I’m going to make it easy on you, kind of cheat if you will.  I wrote the top finance enthusiasts and asked the following question, “What’s your biggest financial mistake?”  I got back over 45 answers, and today I’m going to share those with you.

We can all learn from these mistakes and hopefully not make the same mistake.  Or perhaps you’ve made a similar mistake and this will just reinforce that improved behavior.  Either way I promise there are some great take-home lessons from some of the top financial enthusiasts. 

Michelle, Making Sense of Cents

“The biggest financial mistake I have made is not making sure that my income is in line with my expenses. Not too long ago, I was living paycheck to paycheck and never tried to change that. If only I realized that I could’ve been making extra money all along. Thankfully, I started reading personal finance blogs and took part in probably 5-10 different side hustles, haha. It completely changed my life!”


J. Money, BudgetsAreSexy.com

“The biggest mistake I made was buying a house at the peak of the market, with no money down and no plan or even budget… All because everyone else around me was doing the same thing. It eventually ended up changing my life and career for the better (I became a self-employed blogger due to it), but never again will I listen to others over myself and my own dreams/goals/desires.”

Home ownership is great for some people, but not for everyone whether you can afford to own or not. There’s nothing wrong with renting if it suits your personality/goals more!! There are plenty of other ways to invest your money!” 

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    Holly, Club Thrifty

    “Our biggest financial mistake was waiting to invest for retirement until we were in our mid to late 20’s. I wish I had opened some sort of retirement account sooner than that because my money would have had significantly more time to compound, even if I couldn’t save very much at first.” 

    Fortunately, we have more than made up for our late retirement start by now. We’re currently on track to retire in our late 40’s. ——

    Sam,  Financial Samurai 

    “My biggest mistake was being overconfident about my career and income generating powers. In 2007, I felt like I just couldn’t lose after being promoted to Vice President in 2006. I bought San Francisco property in 2003 and 2005, and that wasn’t enough! So I bought a vacation property in Lake Tahoe in 2007 because it was selling for 10% less than it sold in 2006 when it was first released.”

    The financial crisis hit big time in 2008 and my Lake Tahoe property proceeded to lose another 40% – 50% of its value in the next three years. Lesson learned: don’t think the good times will last forever.

    It was tempting to welch on my mortgage when the property was so under water, but the good news is that despite the bad timing, I still own the Lake Tahoe property all these years later. Its value might have just got back to even. But that’s OK because my dream since first purchasing was to be able to bring my family up to play in the snow one day. That day has finally arrived given we now have an 18 month old boy.

    I still own the 2003 SF property, which is now paid off. In 2017, I sold my 2005 SF property because it was too much of a PITA to manage. As you get older, all you want to do is spend time with your family and simplify life.

    Jacob Lumby, Ph.D., Cash Cow Couple

    “Like most people, I’ve made many money mistakes. One example was my decision to attend an expensive liberal arts college after graduating high school. I graduated valedictorian of my high school class and had several academic scholarship offers.

    Instead of taking the full scholarship to my local State University, I decided to attend a small liberal arts college that was much more expensive. When visiting, I bought the whole sales pitch and was convinced that this college was “better” than my other choices. I quickly learned otherwise and transferred from the small college to the State University after just one semester. Even then, my initial decision was quite costly. I spent more than $5,000 in that initial semester.”

    Grant,  Millennial Money 

    Author of Financial Freedom  

    “My biggest financial mistake was falling victim to lifestyle inflation after becoming financially independent. I went from spending $50,000 per year to $200,000 in just one year and significantly reduced the amount of money I was investing. I spent money on an expensive wedding and many other things I didn’t need.

    If I would have continued on that trend I would have been broke again in 6 years! But I was able to trust it around and control my spending. Initially, I found it tough to spend less money as you make more, but now just having the ability to buy things is enough. I don’t actually need to buy them!”    


    Aaron, Personal Finance For Beginners 

    “My current car is my biggest financial mistake… If only I’d discovered my interest in personal finance a year or two earlier!

    I rolled negative equity from my first car into the new loan and then stretched it across a six-year term to get the monthly payment I wanted. I was still a college student at the time, and I’m still not sure how I got approved for the loan I did – the principal of the loan was equal to my previous year’s annual income!

    Next time I need to purchase a vehicle, I’ll make sure I follow the 20/4/10 rule: at least 20% down, no longer than a four-year loan, and no more than 10% of my income on auto expenses!”

    Alexis, Fitnancials

    “Not having an emergency fund. Back when I was 21, I went through a medical emergency and eventually had a bill in the thousands. I couldn’t pay for it and it was a stressful few months. Luckily, I was able to get everything waived because I didn’t make enough money at the time.

    Note, I did have health insurance but my deductible was out of this world. However, it taught me that accidents and unpredictable things are bound to happen throughout life, and I should be prepared so I don’t break down in stress from not having money.”


    Allan, The Practical Saver

    “My biggest financial mistake was not closing my retail business soon enough. It was bleeding money for a year or two. I tried my very best and exhausted all financial options including using my credit cards in an attempt to revive my failing business. Unfortunately, I ended up losing $40,000 in the process.” 

    How I wish I closed my business sooner. If I had done that, my loss would have been minimal.

    I did learn a great lesson with this experience, that is, I am the type of person who would go farther than I thought I could to make things better. I have become more resilient and smart on how I spend my money, where I spend money, and how long I spend my money on something. This lesson has affected me positively not only when it comes to business, but also when it comes to personal life.” 

    Andrew, Family Money Plan

    “The biggest financial mistake I ever made was trying to trade options in the 2009 crash. I found out very quickly that you could make a lot of money fast when stocks went down. But you could also lose a lot of money if you were on the wrong side of the trade. By trying to time the market in short intervals, I ended up losing a lot of money, over $20,000, that was a great learning lesson on investing. Luckily I have turned that around but it made me a long-term investor, not someone who is trying to jump on a quick trend. But it was a hard mistake to make and learn from initially.”

    Arlene, From Pennies to Plenty

    “The biggest financial mistake I’ve made is keeping too much money in my checking account for far too long. When I got my first job out of college, I started saving my money because I knew I wanted to go to graduate school. My paychecks were deposited directly into my checking account, which I thought was great because I was saving. I even had a bank teller telling me I should do something with the money and I said, “No thanks, I’m saving it for graduate school.

    Little did I know I should have been putting it into a 529 plan or some sort of investment vehicle so that my money could earn interest and actually work for me.”

    Ashli, The Million Dollar Mama

    The biggest financial mistake that I’ve made was waiting so long to grow my money. I’ve always been a good saver, but it took me quite a bit longer to get into the investing game. Now that I understand the power of compound interest, I wish I would’ve started sooner.”

    Brian, My Millennial Guide

    My biggest financial mistake was selling an investment too soon. As a newbie investor in college, I usually took profits when I had them. Can’t go broke by taking profits, I thought to myself. However, if I held onto some of those stocks I purchased back then, I would have made a generous return today. Hindsight is 20/20.

    With the rush of investment apps on the market currently, I’m actively doing research on which stocks are undervalued and would yield positive returns for the long haul. So a few years or decades from now, the power of compounding interest will be on my side.”

    Brian, Bucks and Cents

    “The biggest financial mistake I made was sacrificing future financial security for a Jones lifestyle.   
    Fifteen years ago, I was featured in a local newspaper for a money makeover.  At that time I was 26.  I had a consultation done with a local area financial planner and a news reporter featured me in a major metropolitan newspaper.  The financial planner basically said that if I contributed the max to my retirement accounts, I could conceivably retire with $23.0 million dollars at age 85 (it was only a measly $5.6 million at age 65).  I wound up on the front page of the newspaper.  No Joke.  

    But, life is not constant. I ended up starting a family and bought a house in one of the most affluent neighborhoods in the area complete with a pond and blue heron in the backyard.  I bought into a Jones’ lifestyle  Living a Jones lifestyle is expensive; house maintenance, taxes, it all adds up. Even fertilizer and weed control can average $75 a month.  

    Then my family was faced with medical issues; everyone in my family but me.  I ended up getting a second job to cover my expenses to cover my Jones lifestyle and also family medical expenses.  After much thought, I decided to get a real estate license and sell real estate.  This was really hard to do while working full time and taking care of my family.  But, it was one of the best flexible jobs available and I had to try and take control of my debt.

    I ended up selling real estate to pay my massive property tax bills for a couple houses since the housing market crashed for a decade and I could not sell my first house.  So I also became a landlord during this time. 

    My life got to a point that I could no longer function on 5 hours of sleep a night and juggle all the bills.  I lived like this for a decade and a half with this kind of financial stress and it is one of the worst feelings ever.  Your life keeps going on like this and it becomes this circle, or merry-go-round, where you have to keep doing what you are doing to try and keep up with all of your expenses. 

    Then I came across the newspaper article in my basement.  It was the catalyst I needed to change my mind and it was at that point I decided to change my mindset.  What I realized about the last 15 years was that I was not happy.   The sacrifices I made were not bringing me happiness, just a bunch of debt and expensive bills.  I sacrificed my financial future to pay for things like a McMansion, social obligations, cars, and other expenses.

    So, I sold my Jones lifestyle and got back on track with saving money for retirement.  I now save $30,000 towards my retirement (you can read how I am now saving $30,000 per year towards retirement) and now have financial freedom in my life.  

    I did a complete redirect of my life.  Not many people can do this, but my worst financial mistake turned out to be one of the best things that finally made me wake up and realize there are other important things in life other than big houses and fancy cars.  My mind has changed for the better, and I now see the world and my life with so much clarity.  And to me, personally, that lesson is worth so much more than the $30,000 a year.


    Carl, Money Mow

    “My biggest financial mistake was deciding not to become a home-owner after the last financial crisis because I was too afraid. In Denmark, the housing prices have increased with +100% since 2008 and real estate gains are tax-free!”

    Cody, Fly to FI

    “My biggest financial mistake was the purchase of my sports car at age 16. I spent every penny of my savings in order to buy the coolest car I could afford. Now I just look back and think about all of the compound interest I missed out on!”

    Daniella, I Like To Dabble

    “The biggest financial mistake of my life was when I was in college I didn’t care much about my finances or the things I had. I took horrible care of my car and went out drinking all the time, blowing my money like it was going out of style.

    I had a $15,000 student loan that I didn’t care much about paying back when I graduated. I kept the payments ridiculously low and never got anywhere with paying them back until recently.

    I regret not caring more about myself, my finances and my future back then because it would have helped me out now more than ever. I wish I would have learned about my finances and realized how important they were at a much younger age. But either way, I learned. So I guess it isn’t a mistake or regret if I eventually learned.

    Now that loan is almost paid off and my credit score is better than ever. So sometimes, you should thank your regrets because they can be the fire under your butt to get things done.”


    David, Finance Superhero

    “My biggest financial mistake was a $650 Burger King meal in Europe. Yes, that’s right: Six hundred fifty dollars.

    As a college freshman, I was fortunate to travel to Germany, Austria, and Hungary with my university concert band. It was a great experience, but it ended up far more costly than I ever could have imagined.

    On my last afternoon of the tour, while waiting for my return flight to Chicago, I made an innocent yet costly financial mistake: I purchased dinner at the airport Burger King using my debit card.

    Fast forward two months later. I got home after working a long shift at the local movie theater back home in Michigan when I realized I had not received a checking statement in the mail in quite some time. (Keep in mind, internet banking was in its infancy at this time, so I had not yet enrolled with my bank.) After a filling out a few online forms, I registered my account online and logged in.

    When I clicked on my account details, I was horrified to discover that my account was overdrawn by nearly $1,000! As you can imagine, I frantically called my bank to find out how this could be possible, as I hadn’t used my debit card since my dinner at the airport Burger King! I was a working-poor college student, but I prided myself on always maintaining a small buffer in my checking account.

    It turns out international transaction fees caused my account to be overdrawn by a little more than a dollar, and the overdraft fees had snowballed for weeks. I was able to negotiate several of the penalties with my bank, but that fateful Whopper remains my biggest financial mistake to this day.”

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    Emma,  Tuppennys Fireplace

    “Financial mistakes? I’ve made a few! In fact, I think I’ve made more than my fair share! Despite this, we are on track to retire 17 years early so making mistakes doesn’t mean you can’t end up being financially sorted.

    Of all the financial mistakes I have made I think not investing regularly in the stock market until I was 40 is the biggest. I dipped my toe in at 33 and promptly left our money invested in funds that turned into dog funds – yikes! I finally got my act together and started investing monthly in 2008. I knew about stocks and shares and I regret analysis paralysis getting the better of me.

    Now, I encourage everyone to think about investing some savings in the stock market as long as they understand it’s for the long term and to choose investments that they understand.”

    FC, Millennial Revolution

    “I’d say our biggest financial mistake was getting out of the stock market in 2009 and waiting on the sidelines until 2012 because we planned to use the money to buy a house. This caused us to miss 3 years of a bull market run up! Fortunately, we still made it to FI because our savings rate was 60%-70%.”

    Gemma, Seaside Sundays

    “Leasing a car in 2012. My car was getting old and my father-in-law recommended that I lease a car as there is a tax write-off if you use the car for work. He likes a new car every few years so leasing is his thing.

    At the time I was working in sales and on the road most weeks so I needed a reliable car to get around, especially in the winter. However, about 4 months later, I switched jobs to a fully work-from-home job that didn’t allow me to deduct any car expenses. Not only that, the amount you can deduct is actually a lot smaller than people realize and it still makes more sense to buy a car than lease, even with the tax benefits.

    The other issue is that while I owned the car it got a small chip in the windshield and a scratch on the side (never lease a black car, it wouldn’t have shown on a white car!)

    When I handed the car in after 3 years, the dealership charged me over $1000 for wear and tear even though I had purchased a special protection plan for $600. Spending over $14,000 in 3 years on a car that I didn’t even get to keep just makes me so mad at myself. What a colossal waste of money.”

    Gwen, Fiery Millennials 

    “My biggest financial mistake was buying a rental property in a not so great area of town. I wish I had focused a little less on the numbers and a little more on who were the kind of people that lived in that neighborhood, as the tenants I got were less than spectacular. Fortunately, I was able to escape the property with money in my pocket and my credit intact!

    Jackie, Jackie Beck

    “I’ve made plenty of them, but probably the one with the biggest long-term impact is withdrawing money from my 401k when I left a job. I could have easily rolled it over to an IRA, but since it wasn’t much I decided to just spend it instead. Looking back on those years of lost growth over time makes me feel a little sick. That little bit could have been a small fortune by now!”


    Jaime, Eventual Millionaire

    “When I was younger, I thought that I should have all of the things (house, cars etc) that my parents had. Even though I was 20. I bought my first house, two brand new cars, and had the illusion of success at a very young age. Instead, I was in over $70,000 in debt.

    Yes the stuff was kinda fun, but not worth the years at a job I hated because it paid the bills. Thankfully I created a budget and worked my butt off to pay off all of that debt, so I could start a business that I adore.

    So if you are young, don’t do what I did! And if you find yourself stuck in a ton of debt now, KNOW that you can get out of it and live the life you always WANTED but wasn’t sure it was possible.”

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      Jeff, Dollar Sprout

      “Back when I was first learning how to invest, I made the same mistake so many other over-confident investors make: I put too much money into one particular stock.

      I put several thousand dollars into a small pharmaceutical stock that was trying to get a new medical device approved by the FDA. I thought for sure approval was going to be a “slam dunk” and that I would make all sorts of money from the breakthrough, except there was one problem… they got rejected. Overnight, the value of my investment plummeted 50%+ and I was left with just a few hundred dollars in my account.

      At the time, I was crushed. But going through this taught me a really valuable lesson: no matter how much you research an opportunity, never put all of your eggs in one basket or invest more than you can afford to lose!”

      John, Frugal Rules

      “The biggest financial mistake I’ve ever made was during college. My first day on campus I was approached by different sales reps wanting me to sign up for their credit cards. I knew very little about credit cards, only that you could use them to buy things you want. I signed up for two cards because they offered me a free gift. I soon started using these cards to buy things I wanted, but could not afford.

      Fast forward another six to nine months and I signed up for two more cards. After two years of living this lifestyle I found myself with $25,000 in debt. To make matters worse, I followed the same philosophy with my student loans. This resulted in $50,000 total debt when I graduated from college – this took me to the brink of bankruptcy and took five years to pay off.

      As bad as the debt was, the mistake was not educating myself on how to manage my finances. The lessons I learned through paying off debt changed my life forever, in many ways.”

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      Jojo Bobo, Corporate Monkey, CPA

      “I’ve been highly fortunate to have made very few financial mistakes in my life. Sure, I’ve wasted my share of cash on crappy Chinese gadgets that fall apart after a few weeks, but overall, I’ve had pretty good spending habits. Of course, when it comes to spending, you can be careless on small things, and it won’t move the financial needle much at all. It’s the big ticket items that can really do damage.

      Every time I’ve bought a car in my life, it was a used car that I could afford. I pay only in cash, no loans. Then, I drive that car for a decade before I get my next used car. Doing this generally costs me less than $2,000 per year all-in, for gas, insurance, maintenance, and depreciation. That’s been my method every time I’ve bought a car… with one exception.

      My single biggest financial mistake was buying a new electric vehicle in 2011. It was the only time I’ve ever bought a new car. I was excited by the idea of an EV, and I wanted to be an early adopter.  Used EVs weren’t available at the time, so I bought a brand new Nissan Leaf right off the lot.

      We’ve all heard that new cars lose something like 10% of their value the second you drive it off the lot, and another 10% in the first year.  Well, it turns out that EVs are much, much worse than conventional cars when it comes to depreciation. I rode the depreciation down on that EV in six quick years all the way from $30,000 to $2,000. I sold it for pennies in 2017 because we were moving and we couldn’t take it with us. So the depreciation alone cost me nearly $5,000 per year – more than double what a conventional used car would have cost me all-in.  That’s a stiff price to pay just to drive an EV.

      The lesson I learned is to be cautious when it comes to big ticket purchases. It’s great to be an early adopter, but do it with cheap electronic gadgets, not big-ticket items like a car.  You can read all about my total costs of owning an EV here.”

      Jonathan, My Money Blog

      “I would say that my biggest financial mistake is not to invest in myself more.   I wish I had taken more risk early on and devoted more time and money towards learning helpful business and career skills.    It can be scary as you don’t know for sure if it will pay off, but that was probably my biggest mistake in retrospect.”

      Justin, Root Of Good

      “When I first started investing, I didn’t know about low-cost index funds. You know, the kind you can get from Vanguard. So I chose the default path – do what my parents did. I signed up with their full cost broker at Edward Jones and started dumping my investments into high cost fully loaded mutual funds.

      After a year or two of paying too much, I started asking the broker how I could get access to these “new” Vanguard funds I was hearing so much about. The broker told me I could buy a Vanguard index fund ETF through him for “only” a $100 commission. When I asked why it cost so much through him when I could buy it at Vanguard for free, I didn’t hear a great response.

      That prompted me to research investing costs. I eventually switched to Vanguard and managed to save and invest quite a bit over the next ten years. By the time I retired at 33, I had over $1.2 million in investments!

      In dollar terms, I “lost” several thousand dollars in unnecessary fees and expenses before I switched to Vanguard, but I learned a great lesson about knowing what you’re buying and focusing on the costs of investing.


      Kelan, The Savvy Couple

      “Our biggest financial mistake was purchasing our house at such a young age. We were 22 years old, only one of us had a job, and we only had enough for 10% down which forced us into wasting money on PMI (private mortgage insurance) each month.

      It’s kind of scary looking back that our mortgage company pre-approved us with only an intent to hire letter. Purchasing our house at such a young age limited our ability to move around and find the careers that we really wanted, especially me. I was stuck for more than a year desperately wanting to leave my job as a Jail Deputy.

      Luckily Brittany finally landed a teaching job in the very competitive NYS marketplace and I was able to leave. Not only did we limit our mobility to test out different jobs when we were young we also ended up wasting over $4,000 on PMI which we just got taken off our house five years later.”

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      Kris, Chronicles Of A Father With Cents

      “I have so many that it’s tough to pick one but here it goes:  “Paying the minimum payments on my credit card when I was in debt.” I took my finances for granted in my 20s and making the minimum payments was a reflection of that.  If I had to do it all over again, I would have more responsible and pay it off every month.”

      Kristin, Believe In A Budget

      “When I was younger, I really didn’t understand how credit cards worked and got into credit card debt. I was making the minimum payment and not making any progress. One day I finally had enough and knew I needed to make a change!

      Fortunately, I was able to educate myself and created a plan on how to pay them off. I side hustled and used all my extra income towards credit card debt. Today I’m much more comfortable using a credit card to earn rewards and cash back, and make sure to always pay the balance off each month.” 

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      Len, Len Penzo

      “My biggest money mistake was the $1000 hope chest I bought for an old girlfriend. Note to self: Never buy your girlfriend or wife an expensive birthday present if you have any inkling that she is going to dump you one month later!”

      Lisa, Mad Money Monster

      “The biggest financial mistake I ever made happened when I left an 8-year relationship in my early 30s. At the time, I had a rental property that my parents were renting from me. It’s also important to note that they were only able to afford to pay me a few hundred dollars each month toward the mortgage, insurance, and taxes. That meant I was subsidizing their living expenses to the tune of about $800 every month. When I was in the relationship, it wasn’t a smart money move, but it wasn’t financially devastating either. When I left the longterm relationship, that $800 every month was catastrophic to my bottom line.

      The logical move would’ve been for me to move into MY rental house and live with my parents. However, as life goes, logic often does not win when you’re in an emotionally-compromised position. So, I decided to continue to subsidize my parents’ living expenses and stop all savings and retirement contributions so that I could afford (and I use that term loosely) an apartment and live on my own. Why? Because moving back in with my parents – even though it was MY house – would’ve made me feel terrible about myself and like my life was moving in the absolute wrong direction. Picture it. There I was in my early 30s, at a time when my peers were getting married and starting families, I was leaving my fiance and starting over with nothing more than 4 lawn chairs and 2 cats to my name.

      In retrospect, I should’ve moved into the house I already purchased and learned to live with my parents again in order to avoid a decade of financial disaster. Not only did I stop savings and retirement contributions, but I also spent way too much money on things I didn’t need and I missed out on some of the BEST compounding years of my life.

      Thankfully, I started saving and investing early and didn’t liquidate the entirety of those assets when the relationship fell apart. I was able to get things back on track in the last few years and now my family is charting a course toward FIOR (Financial Independence/Optional Retirement) with extreme intensity and a lot of excitement!”

      Liv, Funding Cloud Nine

      “My biggest financial mistake is that I did not start aggressively paying off my student loan debt until several years after graduating college. I just paid the minimum payments because…I thought that’s just what you do with bills. You pay them. About four years after graduation, I had barely made a dent in my six figures of debt and I was getting scared about my financial future. I did a ton of research on how to pay off debt, decided to use the Debt Snowball Method (after trying a few other methods), and now I am happy to say I’m debt-free. I still cringe at those wasted years of paying minimum payments though…”

      Maureen, A Debt Free Stress Free Life 

      “The biggest financial mistake I made was believing in the hype of consumerism and the idea that all these things advertisers put in front of us were things that I NEEDED.

      As I moved through the process of paying off debt and I stopped spending money recklessly it allowed me to look at all the ways in which I was being tricked into this belief system and how I was using money in a way that was detrimental to my financial health.

      Today I have a very different relationship with money and refuse to buy into the hype.  I make conscious spending choices that are in alignment with my personal values and goals. As a result, I no longer use money as a tool to make me happy. Instead, I find contentment and happiness in relationships and experiences.”

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      Miss T, Prairie EcoThrifter 

      “Buying and selling our primary residence too often which has cost us a lot of net worth due to real estate agent commissions, increased mortgage duration which means more interest paid over time and of course land transfer taxes and legal fees.”


      Physician on FIRE,  Physician On FIRE

      “When I had my first full-time job as an anesthesiologist, it was time to settle down in one place, and we decided to build our dream house on the water without knowing enough about the hospital’s financial situation. Four years later, the hospital would go bankrupt, and I’d be left with one of the nicest homes in town and few viable buyers. When it eventually sold, I lost nearly a quarter million dollars on that house; I should have taken the advice to start with a starter home.”  

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      RJ, The Ways To Wealth 

      “My biggest financial mistake was not selling a stock that was gifted to me. It was a banking stock that was gifted to me around 2006. I didn’t know a thing about the company but trusted that it would work out well. After 2008, the stock dropped by about 90% in price. Lesson learned.”

      Richmond, PF Geeks

      “The biggest mistake my wife and I have made with our finances is taking too long to get on the same team with money. We spent the first year of our marriage bickering over our spending, struggling to save, and not having shared goals. Once we were on the same team, we started making much more progress!

      We’ve been able to double our net worth two years in a row and we’re on pace for a third. The best tip we can give people is to identify the weak points in your budget and work together on them. For us, we were spending more on food than we were on rent, so we started meal prepping to save money”.

      Stefanie, Stefanie O’Connell

      “My biggest money mistake wasn’t a major loss, fail or rejection. It was doing nothing. It’s so easy to procrastinate money management – whether it’s investing or optimizing our financial plans. I just got into the habit of saying ‘I’ll get to it tomorrow, or next month or when I have more time or more money, etc.’ And then I turned around and realized that I was almost 30 and had nothing together.  If I had had that moment right when I was getting out of school, how much better off would I be?”

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      Steve, My Wife Quit Her Job

      “The greatest financial mistake that I made was speculating on stocks during the dot com boom.  Because everything I purchased kept going up, I got really cocky and continued to purchase stocks as they were falling during the bust.  The final outcome was that I lost pretty much all of my gains during that period and learned my lesson to never trade based on emotion again🙂  Today, I focus on maintaining a balanced portfolio of funds and my day trading days are over.”

      Steve, Think Save Retire

      “My biggest financial mistake was a super costly one. I was in too much of a hurry to buy a house after I got my first “real” job out of college. I bought in February of 2007, the exact wrong time to invest in real estate. I lost over $100,000 on that stupid house that I never should have bought in the first place. It was my own impatience that caused that poor decision.”

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        Tanja, Our Next Life

        “I’d say my biggest mistake is focusing too much on money and overdoing the savings, rather than focusing on what we want out of life and then building our money around that. Fortunately, we eventually learned our lesson! ;-)”

        Tia, Financially Fit And Fab

        “The biggest financial mistake that I have made was not rolling over my 401k when I switched employers from my first job.  Although the balance was relatively small (a few thousand dollars), I decided to cash out the balance and put the money in my savings account.  Not only did I miss out on time in the market but I also suffered tax penalties. Now I know much better and hope others do not make the same mistake.”

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        Tiffany, The Success Mountain

        “I’d say my biggest financial mistake has been taking out a large amount of student loans to finish flight school. The reason being even though student loans can masquerade as being beneficial, it’s best to try and pay cash as much as you can. Things can change, and often, students don’t end up doing the job they intended to when they signed up for those loans. Be wary!

        I don’t, however, regret the decision to do the flight school itself and further my education, which just goes to show that even financial mistakes can be beneficial, as long as you are learning from them as you move forward!”

        Tracie, Penny Pinchin Mom

        I declared bankruptcy.  When I was struggling to make ends meet I thought it was the only answer.  And that time, it made sense to me. The biggest problem with me doing this was not what it did to my financial credit and history it was that I did not take the time to figure out why I was in this situation.  

        Bankruptcy was a bandaid on an open wound. Several years later I began making the same mistakes again and I had to figure out why I was spending the way I was. Once I did that, I was able to change the way I looked at and managed my money and I’ve never been down that same path again.”

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        Tyler, I Am The Future Me

        “The biggest financial mistake I have made is spending on my credit card until it declined. The limit was “low” only $500 so I didn’t think it would be a problem but that $500 became $1,000 then $2,000 than $15,000 but that habit of spending until it declined didn’t change.”

        Final Thoughts

        There you have it!  Some of the savviest financial gurus dishing out their biggest financial mistakes.  I hope that through their mistakes you have learned a little something and you can avoid making the same mistakes they did.

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        biggest financial mistakes




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