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my biggest money mistakes and how I recovered

My 3 Biggest Money Mistakes

Made some money mistakes and want to feel better about your own? Clo Bare shares her biggest money mistakes, how she bounced back and is still on track to retire with millions in the bank.

This was originally published in CNBC + Acorns.

Before I finished college, I dreamed of getting a big job and salary, and taking  luxurious Instagram-worthy vacations with my somehow unlimited paid time off.


But instead, I graduated into an economy recovering from the Great Recession, with an English degree and about $80,000 in debt. 


It was a wake up call to say the least, and I remember job searching at the time feeling like I was digging through the garbage, looking for the least rotten thing.

Eventually, I got into corporate America, and as the years went on, my $700 a month student loan payment became only one part of my financial struggles.


Well into my twenties, I lived beyond  my means, bought a car worth half my salary, engaged in risky investing, and had a diet of take out and $13 cocktails. 


I know that my experience isn’t unique. So many of us never get a formalized  education about our finances. When mistakes do happen, there is often so  much shame around them. But there doesn’t need to be. 


My mistakes were costly in the moment, and there are times I wish that I used that money for other things, like investing. But those setbacks did not define my financial future.


Today I’m still on track to have millions in the bank by the  time I retire at 65, even if I don’t invest another dollar between now and then.


Here are some of my biggest mistakes, and how I turned them around to  become confident about, and successful with, my money. 

1. I bought a new car worth half my salary at the time.

When I moved to Chicago in my early twenties, I was making $42,000 a year, more money than I had ever before, but the bulk of it was eaten away by my student loans, rent, and unsustainable spending habits.


Case in point, my decision to get a new car. 


In the winter of 2015, after a few months of a two hour round trip commute, I  decided my Chevy Lumina wasn’t going to cut it anymore. It was old, ugly, the  windows wouldn’t all roll down, and the AC was broken.


At the time, I was home for the holidays and on December 23, 2015 with less than $1,000 in my bank account, I turned to my parents and said, “I’m going to go buy a car today.” 


Off to the Toyota Dealership


Off I went to the Toyota dealership, where I had the choice between a used 2013 Prius C for $13,000 or a new 2015 Prius C for $20,000. Even in my limited understanding of what a financially responsible person did with their money, I knew the used car was the smarter choice. 


But when I went over financing options at the dealership, I learned that if I bought the new one, I would be paying about $30 more a month on a car loan. So, with all the confidence of a 24 year old with $1,000 to her name, I said, “Why not?” 


Regret & The Impacts of Buying Too Much Car


Which I quickly regretted. Ultimately, this car ate up so much of my monthly income that I wasn’t able to save much– in fact, I went about $200 in the hole each month so I took on side hustles to make up the difference.


Because of those expenses, I went for nearly a decade without an emergency fund. Throughout my twenties, even a $100 expense could throw me into a panic, and I never felt like I could catch up, especially when I was also trying to get rid of my debt. 


If I had bought the used car and invested the $7,000 difference, the money could be worth nearly $12,000 now, and $12k in 30 years could be worth $120k with an 8% average annual return.

2. I thought I needed to pay off debt before I started building wealth.

In October 2018, I got a job that gave me a $20,000 pay bump, and with my new salary I wanted to pay my student loans off as quickly as possible. I thought doing this, even if I had to scrape by and sacrifice some of the things that brought me joy temporarily, it would help me create that happy and  nomadic life I had once pictured. 


So I refinanced my student loans down to 3.54% and started dedicating about  $2,000 a month to my debt.


During this time, I was reading all I could about  personal finance, and came across the FIRE movement. That completely changed my perspective. I realized that I didn’t have to wait to pay off all my  debt before I started building wealth through investing. 


Learn more about my money journey here.


During the nearly two years I focused only on debt freedom, from October 2018 to January 2020, I paid off $40,000 of low-interest debt, and saved about $5,000 in interest.


When Debt Freedom Becomes a Mistake


However, if I had invested that $40,000 instead, I’d have  over $278,000 invested right now instead of $228,000. 


With an average annual return of 10%, that $228,000 I currently have invested  could turn into $3.9 million in thirty years, but $278,000 could turn into almost  $4.9 million.


That’s a million dollar difference.


Seeing those numbers laid out like that was one of the things that helped me start focusing on investing. But it did take some time to get over fears I had about it.  

3. I didn’t understand my risk tolerance and made some very risky investments.

One of my most embarrassing money mistakes happened long before I knew  anything about investing. In 2018, I was 27 and had just started my debt-free  journey.


I had also saved a small $5,000 emergency fund, which was more  money than I’d ever had in my bank account at one time. 


Enter: The Ex


I had an ex who flipped houses in the Chicago area. His investors boasted 20% returns on every project, and while we were dating, I’d seen him  somewhat successfully flip a home a few times.


So, of course, I decided to  invest my entire life savings, at the time, in his business. 


It started with my $5,000 emergency fund, and then I saved up another $5,000 to give him, and eventually, I had about $25,000-$30,000 of my own money invested with his company.


Losing Nearly $60k


For a while, things went well. He’d use my money to invest in a new flip property and when it was over, I’d receive the principal and interest on my loan, with an option to reinvest. I kept reinvesting until he owed me about $58,000.


Then 2020 hit, and payments fell behind. At this point, I’ve been told that the  payments will be coming next month for about two years now, and he recently filed for bankruptcy.


Right now, despite claims I’ll get paid, I’ve mentally written the money off as a loss. 


Don’t Invest in Risky Businesses Unless You’re Willing to Lose


One of the biggest things I learned from this experience is don’t invest in things you don’t understand. And with riskier investments, only put in what you’re willing to lose.


Overall, this mistake taught me how to gauge my risk tolerance so that I can  understand how an investment option fits into my overall portfolio for the long  term. This is key for any investor, no matter what you’re investing in.

I learned that my mistakes don’t define me.

In 2018, I was financially lost. I had about $10,000 in my 401(k), almost no cash on hand, zero emergency fund, and nearly $70,000 of combined debt from my car loan and my remaining student loans.


But as lost as I felt, I realized in the fall of that year, that I didn’t want to beat myself up any more and only focus on the mistakes I had made. So I started making some changes.


2019: Debt Freedom


By April of 2019, I had paid off the car, but it was costing me nearly $4,000 a year with fees, parking, and insurance. Four thousand dollars a year for a car I rarely used just didn’t make sense. In December 2019, I sold it for $10,000 and invested that money instead of buying another car.


In 2020, when I turned 29, I decided to stop working solely on debt freedom and instead focused on wealth building through investing. At this point, my student loans were down to less than $50,000 with low-interest, so I decided to stop the extra payments and pay the minimums.


2020: The Switch to Investing


That year, 2020, I understood for the first time what my 401(k) was, and what it was invested in. I began putting the remaining $1,600 a month I had been throwing at my debt into my investments, increasing my contributions, and maxing out those retirement accounts for the first time.


In that first year of consciously investing, I invested almost $26,000. Prior to that, had only invested about $15,000 TOTAL through a 401(k) match from 2015 to 2020. In 2021, I maxed out my 401(k), IRA, HSA, and contributed to a Solo 401(k) and have continued this approach into 2022 and 2023.

Now and Beyond

I currently have over $200,000 invested. If I get an average annual return of  8% for the next 30 years, I’ll have more than $2 million waiting for me in  retirement, even if I never contribute another dollar. With a 9% average annual return, it’ll be closer to $3 million.


After a few years of focusing on increasing my income, decreasing my spending, and investing the rest, today I have a multi-six figure net worth, a year’s worth of expenses in my emergency fund, and a thriving business teaching other people how to feel in control and confident about their money. 


None of this would have been possible without forgiving myself for my mistakes and deciding to take ownership of my future.

Start Your Own Money Journey

Reading this and realizing you’re ready to get your own money in order?

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Grab my free Get Your Money Right Guide here, or if you’re ready to start investing? See you in my free investing class.

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my biggest money mistakes and how I recovered

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