5 Highly Successful People Share Their Biggest Financial Regrets

By David S. Chang

Best Financial Advice

Life is full of regrets. One of the most common phrases I hear is “if only” followed by what they wish they did or didn’t do. Most of the time it’s not investing early enough or making a bad investment decision. 

Successful people are no different. They too have made mistakes or decisions when it comes to their finances. Here are the top regrets for five top executives and multimillionaires. Click here to get more tips on making better financial decisions and getting back on track (even if you started late!)

Debbi Fields, founder, Mrs. Fields

Learn to manage the money you have now, no matter how little.

“Looking back now, I know that I would have greatly benefited had I initiated an investment strategy as a young adult. I was so busy trying to save every dollar and living paycheck to paycheck that the idea of wealth creation was never really a consideration.

“Not thinking bigger than my bank account was my error — I could have set up a simulated investment account, joined a club, or learned about the buying and selling of securities.

“The key to managing money and building a nest egg is learning how to manage small amounts and grow them wisely over time. It can start with pocket change and grow beyond anything you imagined! The key word here is ‘imagined’ … You have to add a zero or two to your net worth and direct your attitude and financial strategy toward getting there.”

Jon Stein, founder and CEO of Betterment.

Don’t overthink investing.

“I wasted so much time and money by overthinking investing. Whether it was opening a dozen brokerage accounts, getting too concentrated in individual securities (thanks Enron), and attempting to do overly complicated transactions — it was a waste.

“I should have just taken the index route in my younger years. I’d be in a better place for retirement now, and I would have been able to spend more time with friends and family.

“The money is one thing, but I’ll especially never get back the hundreds of hours I poured into trying to beat the market.”

Alexa von Tobel, founder of LearnVest.com, author of “Financially Fearless”

You need a plan for your money.

“Not having a financial plan is a plan — just a really bad one! Given what I see as a general lack of personal-finance education, it can be all too easy to wing it with your money.

“I was lucky enough to learn this lesson while still in my 20s, so I had time to put a financial plan into place for myself.”

Click here to learn more about getting a financial plan complete!

Mark Cuban, billionaire entrepreneur and owner Dallas Mavericks.

Learn to manage your credit cards.

“[C]redit cards are the worst investment that you can make. That the money I save on interest by not having debt is better than any return I could possibly get by investing that money in the stock market. I thought I would be a stock market genius. Until I wasn’t.

“I should have paid off my cards every 30 days.”

Ken Lin, CEO and founder of Credit Karma

Buying an investment that was a “sure thing.”

“In 2008, I bought shares of WaMu (Washington Mutual) two days before they collapsed. At that time, I thought that it was panicked selling and that a bank like WaMu wouldn’t or couldn’t go under.

“Clearly, I was wrong. It did teach me a valuable lesson about how fast things can change in business.”

David S. Chang

Award-Winning Entrepreneur, Wealth Manager and CEO | Chief Editor, Author, Keynote Speaker, Consultant ArtofThinkingSmart.com | Political Consultant | Army Officer National Guard | Living To Fulfill Needs, Solve Problems, and Live Passionately!


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