I don’t mind talking about my failures. People who know me know I’m a believer that I’ve learned more over the course of my life from my failures than I have my successes.

Not long ago I saw a piece in the Wall Street Journal talking about how some leading Ivy League schools and others are becoming deliberate in teaching their students it’s OK to fail.

‘Bout time, I say.

I think failure brings success for a couple of reasons. First, the sting of failure is something no one enjoys, and it’s a great motivator to keep us from repeating a fail. I’ve had some doozies in my career. Once, writing a news story about a vintage fighter jet appearing at a local air show I got my numbers wrong and essentially told my readers this 1950s jet could reach altitudes that would let it fly in outer space. My editor at the Oakland Press called me at home to mockingly ask if I wanted to do a follow up story about the miraculous technology that enabled such a feat.  

The editor’s scorn was bad enough, but what really burned was that thousands of people saw my mistake. Lesson learned: check it and check it again.

A few years back we had a chance to go after a nice piece of new business. It was in a market segment we coveted, with a marquee client, and I directed the team to pull out all the stops to win it. We did, and only after the fact did I realize it wasn’t the strategic work we really wanted to do. In my haste to win a marquee client in an attractive market segment, I didn’t take the time to fully understand what we would be asked to do. Lesson learned: don’t read into something what you want it to be. Read what is really there.

Another positive that comes from failure is that we tend to analyze our failures more closely than we do our successes. You get a big win and you think, “I nailed it!” But did you? Maybe a competitor fell on his face. Perhaps there was an “invisible hand” working in your favor you were never made aware of. Chances are you just won’t know it because we don’t examine our successes with the same critical eye we cast upon our failures.

I don’t know who coined the expression “Fortune favors the bold,” but I’ve always believed it true and have often followed it in my decision making. Boldness sometimes leads to failure though, it’s part of the deal. Accepting that, and accepting that in the big picture I’m also going to benefit from those failures has been a big part of what’s worked for me over the past 35 years.

Early in my career my employer entrusted me with a promotion that brought much more responsibility than I’d ever handled before. In giving me the news he said “We know you’re going to make mistakes and that’s fine. Just don’t make stupid mistakes and never make the same mistake twice.”

It was the best advice I ever got on how to learn from failure.

Allison Matz

Matz joins the Boileau team with writing and communication experience from her previous role as Academic Department Coordinator at Grand Valley State University, her alma mater. She earned her degree in English literature and writing and enjoys being able to express creativity and storytelling through her chosen career.

Berkeley Benson

Prior to joining Boileau, Benson worked as a writer and illustrator for both agency and in-house organizations. In 2018, she graduated from Cedarville University with a bachelor’s in professional writing and information design.

About the Author

Randy Boileau
Randy Boileau has decades of journalism, PR and marketing experience with organizations like the Detroit Free Press, Miami Herald, Bank of America, Comerica, Mazda, Donnelly and Varnum LLP. Since founding Boileau Communications (now Boileau & Co.) in 2005, the company has grown from a one-man PR shop to an award-winning PR and marketing communications firm. Randy is also an avid outdoorsman and can be found biking, kayaking or fishing in his free time.
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