Failure is Okay

This article is the 10th of a 14-part series that explores the core tenets of Get Rich Slowly.

Yesterday, for the first time in my 40-1/2 years on this earth, I went ice skating. Initially, I was scared to try, but I eventually gave in to the taunts from my eight- and ten-year-old friends.

I love roller skating and I’m not too bad at it, but the ice skating…well, it sucked. It took me eight minutes to make it around the rink for the first time, clinging to the wall, my shins in pain. It took me five minutes to make it around a second time. Four minutes for round three.

My first half hour on the ice was an exercise in frustration. I couldn’t make it more than a few feet without falling or lunging for the wall. Worst of all, I had to swallow my pride and accept advice from Tristan, Emma, and Harrison, my grade-school guides. (Emma, especially, was keen to skate around with me saying, “You’re doing great, J.D.! Good, good.”)

This isn’t me, but I’m very familiar with that pose…


By the end of afternoon, I could make it around the rink on my own. My steps were shaky and uncertain, but ultimately my personal best was 2-1/2 laps before falling or grabbing the wall. I’ll never be an Elvis Stojko (nor even a Tonya Harding), but now I can say I’ve been ice skating. I could have let my early failures and frustrations get me down. I could have left the ice and said, “I’m not doing this anymore.” Instead, I stuck with it. I’m glad I did.

The ability to keep going in the face of failure is critical to success when learning to skate — and when learning to manage your money. Nobody’s perfect. We all make mistakes with money every day. I’ve made tons in the past, and I continue to make them. Here are just a few examples:

  • I managed to take on over $35,000 in consumer debt before turning things around.
  • I tried (and failed) to repay my debt several times before stumbling on the debt snowball method, which worked for me.
  • Before I embraced the idea of index funds, I repeatedly poured money into stocks that tanked.
  • When I bought my used Mini Cooper last spring, I let emotion override my better judgment, and ended up paying more for the car (and getting less for my trade-in) than I should have.

I could name dozens of other examples big and small. But the key is every time I realize I’ve made a financial mistake, I try to learn from it so I don’t repeat it in the future. Sometimes I do repeat my mistakes, but I try not to. Instead, I try to fail forward.

Building success from the ashes of failure

In Failing Forward, John C. Maxwell writes that there are seven key abilities that allow successful people to overcome failure instead of taking each setback personally. Successful people:

Reject rejection

Successful people don’t blame themselves when they fail. They take responsibility for each setback, but they don’t take the failure personally.

View failure as temporary

“People who personalize failure see a problem as a hole they’re permanently stuck in,” writes Maxwell. “But achievers see any predicament as temporary.”

View each failure as an isolated incident

Successful people don’t define themselves by individual failures. They recognize that each setback is a small part of the whole.

Have realistic expectations

This one is huge. Too many people start big projects — such as paying off their debt — with the unrealistic expectation that they’ll see immediate results. Success takes time. When you pursue anything worthwhile, there are going to be bumps along the way. And remember: The perfect is the enemy of the good.

Focus on strengths

This was one of the biggest lessons I took away from Tim Ferriss’ The 4-Hour Workweek. When I interviewed Ferriss last year, I asked him to expand on this idea. He told me: “Focus on leveraging and amplifying your strengths, which allows you to multiply your results. Fix any fatal weaknesses to the extent that they prevent you from reaching your goals, but perfection isn’t the path to your objectives; finding ways to cater to your strengths is.”

Vary approaches

“Achievers are willing to vary their approaches to problems,” Maxwell writes. “That’s important in every walk of life, not just business.” If one approach doesn’t work for you, if it brings repeated failure, then try something else. Maxwell is saying that to fail forward, you must do what works for you, not necessarily what works for other people.

Bounce back

Finally, successful people are resilient. They don’t let one error keep them down. They learn from their mistakes and move on.

These seven points form a firm foundation for dealing with failure in all parts of life, including personal finance. As you pay off your debt, as you learn to invest, as you cut your spending, accept that some failure is inevitable. But you are not your mistakes. Own them, learn from them, and move on. (And remember: Good habits keep small mistakes manageable.)

It’s never too late to change direction, to start making smart choices. If you’re 40 and don’t have retirement savings, you can start saving tomorrow. If you’re 30 and staggering under the weight of credit card debt, you can cut up your cards and make a commitment to change direction. The wonder of the future is that it can be built upon the ashes of the past.

At 40, I can look at who I am and can connect the dots back through my life. Though I regret not saving for retirement when I was younger, though I regret accumulating massive credit card debt, though I regret living a consumerist lifestyle, I see now that these experiences made me the man I am today. Without them, I wouldn’t be motivated to help others make smart money decisions. (And let’s be clear: I am not advocating that others repeat the mistakes I’ve made.)

Failure is okay

Every day I write this blog, I’m afraid I’ll fail. (At my personal site, I recently said I’ve experienced “1000 days of doubt” at Get Rich Slowly.) Whenever I do my weekly podcast, I’m afraid I’ll fail. And as I’ve written my book over the past nine weeks, I’ve been afraid of failure every single day. But I do these things anyhow. I know that if I don’t try the things I’m scared of — if I don’t risk failure — I’ll never succeed.

I wrote about my fear of failure back in June of 2007. I described how I’d spent much of my adult life shackled by fear. But by saying “yes” to the things I’m afraid of, my life has become amazing.

If you’ve made poor financial choices, don’t let them get you down. Don’t let them make you afraid to try again. Draw from your experience. Fall down seven times, get up eight.


This is the 10th of a 14-part series that explores my financial philosophy. These are the core tenets of Get Rich Slowly. Other parts include:

Look for a new installment in this series every Monday through the end of the year.

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