Updated on 08.18.15

10 Money Lessons Learned the Hard Way

man with head in hand

Sometimes the only way to understand the depth of a mistake is to make it yourself. Photo: David Goehring

The Internet offers a treasure trove of practical advice for managing your finances. With the click of a mouse, you can find information any personal finance topic that piques your interest – from budgeting and investing to the big decisions in life, like what to consider when you buy your first car or home.

Beyond the Internet, those of us lucky enough to have money-savvy parents can learn a great deal from their wisdom. And in the absence of a parental figure, many people can turn to other family members, friends, or mentors for financial advice.

But, despite all of this, many of us choose to learn our lessons the hard way. Here’s an example that illustrates exactly what I mean.

When I was 20 years old, I worked in a group home for mentally challenged adults for a little over $8 an hour. Even though I was hardly getting by, I got the itch for a new car, and headed straight to the dealership to take a look – much to the dismay of my protective parents.

After the world’s saddest negotiation effort (I didn’t really know how much I paid or owed until after the fact), I walked out the door with a brand new Mitsubishi Galant – and a $500 monthly payment that was suspended for 12 months due to a “12 months – no payment/0% APR” promotion I had just signed up for.

Sadly, I spent the next four years making a car payment that took up 30%-50% of my income at the time, until one day, it was finally paid off. Years later, I sold the car on Craigslist for around $2,500.

While I regret the purchase wholeheartedly, I did learn a few valuable lessons that you really can’t grasp until you live them yourself – lesson No. 1 being just how much of a burden debt can be.

With that huge car payment always looming behind every corner, I had very few choices in life. When I wanted to move during a break-up, I quickly found that I couldn’t afford to. And I don’t even want to talk about how much more money I could have in retirement savings if I had stuck with the reliable, paid-off car I already had.

Money Lessons Learned the Hard Way

But, you live and you learn, right? It happens to the best of us. And sometimes, the lessons you learn the hard way are the ones that really stick. We asked a number of writers and bloggers in the personal finance community to recall some money lessons they learned through the school of hard knocks — here’s what they said:

Lesson 1: Treat student loans with respect – and remember that it all has to be paid back.

Lance Cothern (Money Manifesto): After accumulating over $80,000 in student loan debt over my wife’s time in college, we learned the hard way that you should only take out the minimal amount of student loan debt that you’ll need to graduate. While you think you need some luxuries while you’re in college, we quickly realized we had to pay all of that money back, plus interest, after she graduated. Luckily, we were able to hustle hard and pay off the more than $80,000 in student loan debt in less than three years. Unfortunately, we had to live a very frugal lifestyle — just like we should have in college — to make it happen.

Chenell Tull (BrightCents.com): The financial mistake I learned the hard way was not planning ahead when it came to taking out student loans. I took the maximum each semester and told myself I would figure it out later, once I had graduated and had a good job with my degree – in geography, might I add. It was quite obvious that I knew nothing about personal finance or the job market during that time (post-recession, 2009). I left college with $72,000 in student loans, and I’m still paying for that mistake years later. But, I’ve learned to have a strategy and put a plan in place BEFORE taking on that kind of burden – although I doubt I’d even take on a car loan after this experience.

Kirsten Whittingham (IndebtedMom.com): During my last year in college, my mother passed away. I inherited enough money to pay off my student loan debt and that of my future husband’s. We were so confident that we could earn enough money to cover our payments that we used the money to buy a new car (my car wasn’t running anymore) and for a house down payment. Those seemed like good investments at the time. After all, a mortgage is “good debt.” Now, we are trying to sell our house (for a loss) and don’t have that “new” vehicle anymore. But we still have $70,000 in student loan debt. Lesson learned: Pay off debt first.

Natalie Bacon (The Finance Girl): The biggest financial mistake I made was financing private undergraduate schooling in addition to law school. This landed me $206,000 of student loan debt. While my debt is down to $130,000 now, it’s a hard battle. I don’t travel much and I don’t own a home. I’ve learned a ton from this experience, but unfortunately, it’s a lesson that will take years to recover from. My advice to anyone considering law school: Don’t do it if you have to finance it! The pay is not worth the debt in today’s economy (see several New York Times articles for more on this). The positive from this experience is now I know more about money than I ever would have known otherwise – and that is turning out to be priceless!

Lesson 2: Obey the power of compound interest, and always arm yourself with information before you invest.

Kate Dore (CashvilleSkyline.com): I stopped investing for an entire year during the financial crisis! I was young, had a very limited understanding of market cycles, and freaked out when my investments lost a chunk of their value. While I was squirreling money into a savings account, I missed out on some seriously good deals. Even worse, I bypassed the chance to earn compounding returns on fresh capital for a whole year! Now, I think long-term and plan to ride out future market corrections by always continuing to invest.

Andrew Schrage (Money Crashers): I learned that waiting even just a few years longer to start saving for retirement can put a huge dent in your final savings numbers due to the power of compound interest. Start early and save as much as possible to really get your financial future on track. Don’t wait and don’t cater to your short-term wants instead, as tempting as that is.

Gary Weiner (SuperSavingTips.com): At age 23, I heard a radio program featuring my former brother-in-law, whom I idolized, seeking investors for his latest venture. I met with him eager to invest, and he tried to talk me out of it before reluctantly selling me half a share (nearly $10,000, decades ago). I went to his office in New York with my check, which he made me re-write as payable to cash before giving me my stock certificate, numbered #0001. He told me I’d receive information in the mail shortly, but when the mailing never arrived, I tried unsuccessfully to get him on the phone. Finally, I went to his office which had mysteriously closed. The next time I saw him was on the evening news being led off to jail for fraud.

Lesson 3: When you make a loan, get all terms and conditions in writing (if you want to be paid back).

Valerie Rind (ValerieRind.com): My husband asked for a loan to cover a cash-flow crunch at his start-up architectural firm. Blindly, I gave him the money even though I didn’t: (a) know much about his financial past; (b) ask about his business plan; (c) get a proper IOU; or (d) follow up to see how the money was spent. One loan became several, and in the end I lost my entire life savings, plus the marriage imploded. On the positive side, I forged new careers in personal finance and writing. A new life, a new life savings!

Lesson 4: Don’t get on the new-car hamster wheel – or buy more can than you can afford.

Kimberly Parr (EyesOntheDollar.com): I think one of my worst financial mistakes was buying a new car shortly after getting my first job, even though my paid-off Honda Accord still ran just fine. After that, my husband and I traded our cars for new models every few years for the next decade, essentially chaining ourselves to two car loans for 10+ years. There’s a good chance that Accord would still be running, and I would have about $100,000 more in net worth instead of the thrill of new car smell and heated leather seats.

Steven D. (EvenStevenMoney.com): One of the biggest mistakes I made right out of college was buying a car that I couldn’t really afford. I bought a nice Mercedes Benz and I financed 100% of the car; add insurance, gas, and maintenance to the mix and I found myself very broke with a nice car. I learned the hard way that buying a nice car that you think you deserve and can afford is the reason most people stay in debt today. My money would have been better off paying off student loans or investing in my 401(k), not making payments to a bank for a car I couldn’t afford. I haven’t owned a car since I sold my Mercedes almost five years ago and I couldn’t be financially happier.

Lesson 5: Don’t forget to shop around… for everything!

David Rubenstein (CreditShout.com): I got a great quote for car insurance right after graduation, so I stayed with that company for over 10 years. Later on I found out that after the third year, they were charging me among the highest rates going. Only after a friend told me to shop around did I realize how much money I wasted over the years. Of course, they tried to win my business back. But it was too late.

Donna Freedman (DonnaFreedman.com): After fleeing an abusive marriage I was so dazed that I signed up with my sister’s car insurance agent. Life got more hectic by the hour so I let “insurance price quote” fall off the radar. Five years later I used an insurance tool to find a better deal and learned I’d been overpaying by almost $700. Did I mention “five years”? What really made me shake my head, though, was that I thought I “didn’t have time” to comparison shop – but I had time to do stuff like walk places to save $1.75 on bus fare, babysit, do online surveys, etc. How many surveys would I have had to do to make $3,500? Pick the lowest-hanging fruit first. Price quotes for insurance, cellphones and cable/Internet provide the most bang for the budget.

Lesson 6: Don’t fall into the easy financing trap.

Grayson Bell (DebtRoundUp.com): I learned not to get sucked into low financing promotional rates, especially when listening to the radio. On a whim (seriously, a whim), after hearing an ad for a Jetski, I bought one. Well, I financed it. They were offering $69/month payments, but what I didn’t catch is it goes up after a year and the finance charges were retroactive to the original loan amount. I didn’t pay it off, ended up breaking down, and I sold it for $800. I lost a ton of money and much of my pride. One of the worst financial mistakes I’ve made to date.

Lesson 7: Don’t buy a house without doing your research.

Daniel Zajac (FinanceandFlipFlops.com): I bought a house in my early 20s because I thought it was cool. I totally underestimated other factors such as location independence (especially as a 20-something), maintenance, and transaction costs of a sale. Renting, in many situations, can be the best bet.

John Schmoll (FrugalRules.com): The biggest financial mistake I’ve made was buying our first, and current, house with no money down. We bought it a little over eight years ago at the height of the bubble. We were about ready to have a child and had the preconceived notion that we had to be in a house. The lesson I learned out of it is to be patient financially and take your time in making a major purchase. I allowed emotion to guide what we did instead of taking a hard look at the numbers to see that it just didn’t make sense for us at the time – rather that we should have waited one to two years to build up a sizable down payment.

J. Money (Budgets are Sexy): My biggest financial mistake was buying our house at the peak of the market with no money down, no budget, and within 48 hours of meaning to look for an apartment to rent. I literally took one wrong turn down a street and became a home owner on a whim (!). Everyone told me it was “the American Dream” so I pulled the trigger without really asking myself if it were *my* dream. A helluva wake up call to have, but one I’m very thankful for as it completely turned around my finances as well as my career :) Can’t say I regret it (though I still hate the thing).

Lesson 8: A life without a budget is a life without a plan.

Zina Kumok (DebtFreeAfterThree.com): I interned in New York City before my senior year in college. I was actually making good money and hoped to save about $4,000 by the end of the summer. But I ate out all the time (sometimes three times a day), used cabs instead of the subway, and shopped frequently. I knew about budgeting, but didn’t attempt to limit my spending. The next summer I had an unpaid internship – so having that $4,000 cushion would have been really nice. I’m still kicking myself for wasting so much money, especially when I knew I’d graduate with $28,000 in student loans.

Michelle Schroeder-Gardner (MakingSenseofCents.com): A financial mistake I learned the hard way was that I worked full-time all throughout college, but spent my money on everything and anything except for my student loans and tuition bills. This led to me racking up much more in student loan debt than I needed to, which I had to pay back later down the line (I am thankfully out of student loan debt now!). I have since learned how to manage my money better, budget more realistically, and I know where my true priorities are. Buying all of those clothes and meals out was a huge waste of money!

Joseph Hogue (Peer Finance 101): I got in on the beginning of the real estate boom in 2002 and made some really good money, a huge start for a 26 year old. Unfortunately, I made the same mistake so many others make when suddenly coming into money. I never had material wealth before and thought happiness could be bought. I paid cash for a new Porsche Boxster, a Rolex, designer clothes, and a house way bigger than I needed. It was fun for a little while but I ultimately wasted a lot of money. I still have a nice nest egg and do well but I wish I had learned the real value of things earlier. 

Jacob Wade (IHeartBudgets.net): I learned that giving a teenager $100,000 to spend however they’d like is NOT a good financial move. I received an inheritance of $25,000 when I turned 18, and at the same time received $70,000 after breaking my neck in a horrific car accident. I (luckily) recovered quickly, but now had about $100,000, no budget, no plans, and lived WAY too close to the mall. I blew through ALL the money in two years. I now know how to handle ANY windfall in the future, and it involves mutual funds, not mall food. 

Marissa Anwar (ThirtySixMonths.com): I was young and naive, and very superficial when it came to my spending. I spent $1,200 on three pairs of jeans (they were really, really nice ones with holes and rips everywhere) and took the tags off to sneak them in the house. My mom, bless her heart, decided that they looked too worn and included them in her Salvation Army roundup a few days later. I still haven’t told her how much those cost.

Lesson 9: Debt can affect your life in more ways than you realize.

Rebecca Stapler (Stapler Confessions): I used to think of student loans as “good debt.” Although I graduated from college without any student loans, I amassed over $100,000 in student loans during law school. Then I married another lawyer and we combined our finances to discover that we were drowning in over $200,000 of student loans. I didn’t realize that being so heavily leveraged would require us to pay $1,300 a month in debt service alone, and impact our choices about what areas of law to practice, how many children we could have, and where we could live. Now that we are living that reality, we have learned to love the frugal life. So, I guess that’s two financial lessons learned the hard way!

John Rampton (Due.com): When I was younger, I would pay the minimum on my credit card every month. I did this for almost two years before I realized that I wasn’t paying off a dime of my debt, I was just paying that $200/month in interest. I then sold my fancy car to pay off the debt. I literally paid of my debt two times over. Since that day I haven’t let something get past one month on my statement without paying it off. Sometimes you just have to pay it to learn. 

Lesson 10: Cash flow trumps assets (and everyone needs an emergency fund).

Kurt Chisholm (InnovativeWealth.com): I was a good saver in college. Since it was in the late 1990s, all my savings went directly into the stock market. How could I lose? The answer came in 2001-2002. I needed to dip into my savings to pay for a large purchase. I had to sell my stocks to make this purchase. This was painful, and it taught me that it is important to have an emergency fund or about six to 12 months of my earnings in cash. Don’t “invest” your emergency savings. Cash is king.

Amanda Abella (AmandaAbella.com): I wasn’t being diligent with saving up an emergency fund and as luck would have it I had an unexpected dental procedure done at the end of last year. It wasn’t covered by insurance (naturally), so I got myself into some debt by putting it on the credit card. It sucked. Now I’m super aggressive about putting money in my emergency fund.

Todd Tressider (FinancialMentor.com): My biggest financial mistake was selling a profitable, stable business for a relatively small multiple of cash flow. By the time I paid taxes on the profit there was no way I could replace the revenue stream by investing what was left. Rather than enjoy the sweet milk of this cash cow business I foolishly slaughtered it for a few pounds of hamburger. The lesson learned was how a perpetual stream of cash flow can actually be far more exciting and valuable than a large, lump sum of cash after paying taxes on the gains.

What money lessons have you learned the hard way? Can you relate to any of these situations?

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