Top Financial Regrets

🔍 Deep Dive: What 150 People Wish They’d Known About Money

1️⃣ Missed Investment Opportunities (27% of regrets)

The most common regret by far was failing to invest in opportunities that later skyrocketed. For example, “not investing in my 20s” or “not investing in Bitcoin”.

The lesson here isn’t about Bitcoin or any specific investment, it’s about starting early and maintaining consistency.

Time in the market almost always beats timing the market.

How to avoid this regret:

• Start investing now, even if it’s only $50 a month.

• Focus on broad market index funds like VTI or VOO, rather than trying to pick winning stocks.

• Automate your investments to remove emotion from the equation.

2️⃣ Retirement Planning Failures (13% of regrets)

The pain of delayed retirement savings was clear:

• “I didn’t start saving money until I was 65. That’s why I’m still working 🫤”

• “I wish I had saved up for retirement a lot earlier.”

The power of compound interest makes early retirement contributions dramatically more valuable than later in life.

How to avoid this regret:

• Contribute enough to get full employer matching in your 401(k).

• Increase retirement contributions with each raise before lifestyle inflation sets in.

• Consider a Roth IRA for tax diversification in retirement.

• Review your retirement progress annually and adjust as needed.

3️⃣ Education Decisions (10% of regrets)

College regrets centered on ROI, not education itself:

• “Most expensive and useless mistake ever.”

• “College. $180k of debt. And I make $14 an hour.”

• “Going to a private college instead of a state school.”

How to avoid this regret:

• Research potential earnings in your field before committing to an expensive education.

• Consider community college for general education requirements.

• Look beyond four year degrees to certificates and technical training.

4️⃣ Vehicle Purchasing Mistakes (8% of regrets)

Car purchase regrets were surprisingly consistent:

• “Buying a $31k car when I only made $27k/yr”

• “Financing a $30k car on a $45k/year salary”

• “Agreeing to pay $500+ a month for a 2017 car when I can barely afford it”

Cars are depreciating assets—meaning the value declines the longer you own it. In fact, cars lose around 10% of their value the minute you drive it off the dealer’s lot.

This is what can happen:

1. You finance the car.

2. The monthly payment makes your budget tight.

3. Now you want to trade it in for something cheaper.

4. But, the car has depreciated in value and your loan is upside down.

5. You can trade the car in, but you’re still left with some of the loan amount to repay—and then you have no car.

How to avoid this regret:

• Limit total vehicle costs (payment, insurance, gas, maintenance) to 15% of your monthly income.

• Research vehicle reliability heavily before making your purchase.

• Run the numbers on the down payment + loan amount + interest to understand the true cost of the vehicle before purchasing.

5️⃣ Financial Impact of Marriage and Divorce (8% of regrets)

Who you marry is one of the most important financial decisions you’ll ever make. The reality is that love and money are deeply intertwined, for better or worse.

The financial toll of relationships surprised a lot of people:

• “I’m so upset I have to split $150k in equity with her.”

• “I let him have the house [in the divorce]”

• “Married the wrong person. Divorce is so expensive.”

How to avoid this regret:

• Have honest financial discussions before marriage.

• Consider a prenuptial agreement, especially for second marriages.

• Maintain some financial independence even in marriage.

Other Significant Regrets

Here are the final few regrets that are much less common, but can still teach us a lesson:

6️⃣ Housing Decisions (7% of regrets)

Some people said they regret not buying a house sooner, or purchasing a home before they were ready.

7️⃣ Impulse Purchases (7% of regrets)

Sure—if you’re earning more, you should spend some of it on things you enjoy. But it’s important to take care of your needs first.

Several people regretted spending on luxury items, not thinking through purchases enough, or making costly purchases prematurely.

8️⃣ Credit Card & Debt Mismanagement (7% of regrets)

One person put it this way: “Getting too comfortable with debt.”

It isn’t healthy to let debt keep you up at night. Worrying doesn’t help you pay it off faster.

But it is important to not get too comfortable with it.

Another person said they lived by the approach, “Get in debt. Next month we’ll figure out how to pay it.”

And that’s what being too comfortable with debt looks like 👀.

9️⃣ Failed Business Ventures (5% of regrets)

Several people expressed regrets related to failed businesses:

• “Wasted so much money trying to build up a business that amounted to nothing.”

• “Opened a store 10 years ago. Spent about $80k to get enough product in and the store in shape. No one came.”

This one’s tricky.

Building a business often takes an initial investment. And there’s no real way to know whether it’ll work out until you do it.

But you can be strategic about how much time and money you choose to invest, and limit your risk.

🔟 Lack of Financial Education (5% of regrets)

A general thread through all of these regrets was a lack of financial education.

Some people regretted not enrolling in their school’s financial literacy related courses, so if you have the opportunity—then it can’t hurt.

Put It Into Practice

Take 30 minutes this week to review your finances and ask yourself:

• How much debt you have?

• Do you feel good about your investment strategy?

If there’s something you’re not feeling great about, create a plan to address it.

For example:

→ Plan a time to chat with your partner 🫰 about your finances.

→ Book a session with a flat-fee financial advisor 🤓 to review your investment strategy.

→ Run the numbers on any large planned purchases 🏠 (e.g. a new home, vehicle, etc) to be sure you understand the impact on your money.

👉 Remember: Many of these regrets were about inaction, e.g. not having conversations before marriage, not investing, not learning more, etc.

Spending a few more minutes to plan before you take action can make all the difference.

💵 Budget Breakdown: Buying a Car as a 24-Year Old

Today we’re taking a look at a video from Alexis on TikTok, a 24-year old who just purchased a new car (congrats Alexis 🚗).

The situation: Her Ford Escape died in a parking lot, and she had no choice but to purchase a new vehicle.

The decision: After looking around, she chose a used 2022 Mazda CX5. It had 25,000 miles on it at the time of purchase, and after negotiating she paid $26,000.

How she paid: She got a cashier’s check for $5,000, so we’re going to assume that’s her down payment. She also said she got a 6.01% on the car loan (assuming a $21,000 loan amount).

Here’s what this means for her monthly payment:

A few additional notes—36 months is the ideal maximum loan term for a used car, and 60 months for a new car. However, Alexis didn’t share how long her loan term is.

Here’s what I like about this purchase:

• Alexis put more than 20% down, instead of financing as much as possible.

• She purchased a Mazda, and Consumer Reports ranked Mazda as the 6th most reliable car brand (out of 22 brands).

• She negotiated the purchase price with the car salesman (you should always negotiate).

• She got a 6.01% interest rate. In Q4 2024, the average car loan interest rate on used cars, for buyers with 781+ credit scores, was 7.67%.

• She had to make this purchase on short notice, but still thought it through. She knew how much she could put down, researched car brands, and purchased something reliable that fit her budget.

Final thoughts:

With a 36-month loan, the car payment is higher than average ($525 for used cars). We don’t know what her full budget looks like, but this might be a little high. The only thing she could’ve done to avoid this is purchase a cheaper car.

But, overall I think she got a good deal and made a smart purchase.

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