The Best Business Mistakes I’ve Ever Made

Recently, I have been taking stock of my journey as an entrepreneur. I’ve realized that I had learned quite a bit the hard way. Making mistakes and learning from them, as an individual leader or as a team, is enormously beneficial. Now, I’m not advocating for making mistakes to make them, but I am suggesting that we don’t let a good mistake go to waste.

Making mistakes is part of leading. They are part of life. If we fear failure and bash those who make the occasional mistake, we stifle people’s ability to take risks and innovate and may find our competition leaving us in the dust.

In reflection on some of my most colossal blunders over the years, I came up with a list of key learnings that have helped me both professionally and personally.

#1. Bad decisions don’t get better with time. Decisiveness is critical in helping you move faster than the competition, but it also means sometimes having to make decisions without the benefit of reams of data to back them up. We all make poor decisions sometimes. The real shame is when we don’t admit the blunder and try to ride it out in hopes that things will get better. Being able to identify a misstep quickly and being decisive enough to course correct is critical to success.

#2. You’re not always the smartest person in the room. As an entrepreneur and leader of a team, I felt intense pressure to have all the answers. Looking back, I recognize my faulty assumption. I may have started the company, but I’m certainly not the only one with all the answers. We have a smart and creative team that analyzes things in very different ways than I do. This is an enormous source of strength for us as we discuss and debate business topics before making decisions. This diversity of thought helps keep me honest.

#3. Hope is not a plan. We started our business on a hope and a dream. What we quickly realized is that hope is not a plan. As our organization matured and we became more established leaders in our industry, we took tangible steps to be intentional about who we are, where we’re headed, and how we plan on getting there. With the assembly of our Board of Advisors, our market repositioning, our all-hands strategic planning processes and reviews, we developed a planning cadence that focuses our work effort throughout the year.

#4. Don’t be afraid to fail. Starting a new business was a terrifying experience. What I realized quickly, however, is that fully experiencing life is about taking risk. Now, I don’t mean a constant Vegas-style gamble, but I am an advocate for putting yourself out there in an uncomfortable situation where you very well may fail. Assess the situation and mitigate as much risk as possible to stack the deck in your favor, then execute with everything you’ve got and don’t stop until you’ve succeeded in your endeavors.

Theodore Roosevelt made a speech at the Sorbonne, in Paris, France on April 23rd, 1910. I’ve memorized and carried part of this speech with me throughout my business endeavors:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

There is no great effort without some level of error and shortcoming. And when you make a mistake, don’t get so caught up in wringing your hands that you don’t capitalize on the learning opportunity.