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Failure is Inevitable; Make the Most of It

Some of the best leaders in history became that way because they made mistakes.

I love failure.

That doesn’t mean I sign up for it. Doesn’t mean I’m looking for it. Doesn’t mean I’m excited or purposely head towards it.

I try and avoid it like the plague. Who doesn’t? But still, it comes. Just like winter follows fall follows summer follows spring; failure will inevitably be part of your process and — dare I say — your success.

If you haven’t had a reasonable amount of failure, you haven’t learned well enough, and you run the risk of starting to believe your own press release releases. (Basically all that does is make you obnoxious to be around, or set you up for an even bigger failure going forward.)

Life’s great lessons are learned at the lash, or to employ another analogy: life’s great lessons are learned in battle. You win most (hopefully), and you lose some. But those that you lose are the ones that enable you to do better than you ever would have the next time around.

When I’m hiring, I look for successes but I also look for failures.

I look for what people have learned from their failures. I look for how they’ve taken that trial and (to use an old metaphor) girded their loins and gone forward with increased vigor, increased resolve, and increased passion to get this thing right. Did they take those painful lessons, the tuition paid, and leverage them for future success?

Two of the great stories that I love to rehearse are those of Henry Knox and Nathaniel Greene. Most people have no idea who they are, although they are familiar with a certain fort named after Henry Knox. To make a long story short, Henry Knox and Nathaniel Greene rose up through the ranks during the American Revolutionary War from being a grocer in one case, and a bookkeeper keeper in another, to being George Washington’s number two and number three officers. One focused on logistics; the other focused on strategy.

It wasn’t easy. They learned a whole bunch of bad, negative, hard, mistake-ridden lessons early in the war. The fact that they could go from humble beginnings, completely unqualified, unable to do what they were asked to do, and rise to that level of prominence speaks to the fact that mistakes have value if you take them, leverage them and use them to your advantage going forward.

Yes, take a day or two to commiserate, cry a little bit, hug a few people and sit in the corner, rocking back and forth, whatever your process is… At the same time, use that space to refocus yourself on what you’re going to do next.

Back to Henry Knox and Nathaniel Greene.

Not as many people know their names as they do George Washington, but that doesn’t make their sacrifices, their trials and successes any less impressive or incredible. It doesn’t matter what the world thinks of you, not all of us are going to have our face on our money. Henry and Nathaniel became who they were because they failed and then tried harder the next time, and Washington recognized that determination and resilience.

He knew they couldn’t win without it. It didn’t matter their technical skills. What matters is doing great things and knowing in and of yourself that, notwithstanding your failures, and your lack of initial success, you can get where you need to go if you focus on the whole.

Yes, George Washington was the number one. Yes, he had the better press agent. Yes, he was the leader. Yes, he was the face of that conflict and the face of that success. But that was all made possible by a number two and number three. They started that conflict not having any idea what they were doing, rose from every setback and therefore rose through the ranks.

In George Washington’s own words, he could not have done what he did without the knowledge and the support and the skills learned at the lash of Nathaniel Greene and Henry Knox.

Failure is inevitable.

You’re going to come up against it unless you are very (un)lucky.

Don’t go looking for it. Don’t be stupid and cut corners. Yet take it when it comes. Take your mishaps, go through your mourning process, and then use that experience to make you better, faster, and stronger as you go forward.

Aaron Webber is a serial entrepreneur and CEO of Webber Investments LLC, as well as a Managing Partner at Madison Wall Agencies.

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Aaron Webber

Aaron Webber


Chairman and CEO, Webber Investments. Partner at Idea Booth/BGO.