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No Matter What They Say, Failure Sucks The pundits say that whoever fails the most wins. The pundits are wrong.

By Steve Tobak Edited by Dan Bova

Opinions expressed by Entrepreneur contributors are their own.


It's said that doing the same thing over and over and expecting different results is the definition of insanity. If that's true, and I think it is, then someone should alert the Centers for Disease Control because there's an insanity epidemic spreading across the business world like wildfire.

Every day I see more and more entrepreneurs and business owners failing over and over and expecting different results. And I bet I know why: all the so-called pundits and thought leaders promoting the loony notion that "whoever fails the most, wins."

What a load of nonsense. Seriously, that is one of the dumbest things I've ever heard in my entire career, and that's saying a lot because I've been around a long time. And I've heard and seen enough B.S. in my lifetime to turn the Himalayas brown.

Maybe it's different in the world these people live in – where it's all about getting wantrepreneurs to click on their posts, buy their books, and attend their seminars – but let me explain how it works in the real world. You know, the one you and I work in.

The goal in business is never, and I mean never, to fail. The goal is to succeed. I don't care what the popular wisdom of the day is. Failure is not good. Failure is bad. The mistake everyone is making is they're confusing risk with failure. They're not the same.

Related: The 7 Rules of Personal Productivity

Risk is good, but even that statement has to be qualified. You only want to take risks that fit your risk profile. And you only want to take smart risks that offer reasonable potential return on investment and, here's the good part, offer the best chance of success … not failure.

I'm not saying you should fear failure. On the contrary, every successful executive and business leader fails along the way. That just comes with the territory. You know, no pain, no gain, that sort of thing. Nothing ever goes straight up like a rocket. Every career, every business, every company has its ups and downs. Everybody knows that.

But if you want your business trajectory to trend upward over the long haul – and that is what you want – here's how successful people accomplish that:

First, they're passionate about developing a product or service that solves a big customer problem. They may have a few mishaps along the way, but ultimately, they prevail. Ultimately, they succeed – meaning their product ultimately beats the competition and wins.

But let's be real. The fewer bumps in the road the better. After all, failure costs time and money and that's never a good thing.

Second, when they do fail, they take it hard. It doesn't defeat them – not by any stretch – but it's sufficiently painful to cause them to take a good hard look in the mirror, determine what went wrong, learn from the experience, and do things differently going forward to avoid a repeat performance. That's the key.

Related: Don't Let Debt Crush Your Financial Dreams

Successful business people are those who recognize that, while failure is a fact of life and a learning opportunity, the result is not pleasant. That doesn't mean they don't take risks; it just means they take smart risks that make good business sense because the goal is to minimize failure.

Since we all love sound bites, let me be crystal clear about this: Whoever fails the most does not win. On the contrary, the very notion that more failure is in any way related to winning is absolutely ludicrous, nonsensical, and grossly irresponsible to suggest.

That said, if you're going to fail, fail fast. If you're going to try something out, you want to know sooner rather than later if you're on the wrong track so you can make adjustments before you run out of runway. Facebook's "The Hacker Way: Move fast and break things" expresses that concept quite well, I think.

Look, markets don't reward failure. They reward those who accomplish what they set out to do and succeed. It's not rocket science.

If you don't believe me, try leading some VCs down a gilded path that doesn't end well a few times. See how many return phone calls you get after that. Oh sure, they'll be polite. They'll say "keep us in the loop on your next gig." Just don't hold your breath waiting for a reply.

Better yet, here's a little thought experiment. Say some guy comes to you with a concept he'd like you to fund. "I have no idea if it's good or bad," he says, "but I read that whoever fails the most wins, and I can keep cranking out ideas as long as you can keep funding them. So what do you say?"

Would you write him a check? If you answer "yes," don't be surprised if the CDC shows up at your door in hazmat suits.

Related: 8 Reasons Why Your Marketing Sucks

If you liked this article, you'll love Steve's new book, Real Leaders Don't Follow: Being Extraordinary in the Age of the Entrepreneur, available everywhere.

Steve Tobak

Author and Managing Partner, Invisor Consulting

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

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