Don’t Fail for Dumb Reasons (Like I Did)

Failure is a possibility. Just don't let it be self-imposed.

You can’t expect to win unless you know why you lose. – Benjamin Lipson

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One of my startups failed for a dumb reason.

Years ago, I led marketing for a startup that had built a new way for brick-and-mortar businesses to grow through word-of-mouth. We found a niche (gyms) where our solution worked surprisingly well. Growth was solid, and churn was low. But after a couple of years, we saturated our niche and needed to find territory to expand.

But how? We weren’t short on possibilities:

• We could take the same product and apply it to another niche.

• We could move from brick-and-mortar to e-commerce.

• We could stop being a pure B2B company and create a consumer product.

• We could build an API that other software companies could tap into.

• We could have solved more problems for our existing niche.

The issue? We lacked conviction on any of these options. Unsure of where to go, we tried a bit of everything. Our hope was that something would stick and we’d have this “aha!” moment that would show us the path forward.

But you already know how this story played out.

The answer never came. By dabbling in a bunch of strategies at once, we didn’t give any one idea its due. In the end, we couldn’t convince ourselves (or our investors) to commit to any particular path. When we ran out of time, our only option was to sell the business (and not for much, by the way).

I didn’t mind that we failed, but I hated the fact that we failed for a dumb reason. A reason we had only imposed on ourselves.

Dumb Failures Are The Ones That Are Self-Imposed.

Here’s another way to think about it.

When you embark on the next chapter of a business, you must make decisions based on imperfect and incomplete information. This means you are making a bet. You’re saying to yourself, “Look, this is what we believe we need to do to win. We might be right, and we might be wrong. But we have to act.”

If you made the right bet, good for you. But if you made the wrong bet, at least you made a decision and acted on it. Failing in this manner isn’t desirable, but it’s an outcome you were willing to accept. Because that’s what can happen when you play the game of business. At least you can pick yourself up, dust yourself off, and move forward knowing that you gave yourself a shot at winning.

But what you cannot do is fail to play the game in the first place.

If you analyze your options for months but never make a move; if you make a bunch of half-bets instead of committing; if you let the moves of your competitors force you into reacting instead of strategizing; if you see the right strategy but don’t have the courage to step forward; you have no one to blame but yourself.

Doing this is a dumb reason to fail.

That’s what happened to us. We failed to commit to any one play. We never gave ourselves a shot at winning because we never entered the game.

Failing to Play is Just One Dumb Reason to Fail

But failing to play the game is just one way self-imposed failure can come about. Here are some others:

• Changing the game too soon. One startup I encountered had a CEO who changed the strategy every quarter. The board got tired of that and fired him. The team was exhausted from strategic whiplash by the time I started working with them.

• Staying in the game too long. Sorry Kodak, we’re good on film, thank you very much. If you can’t recognize that your category is in decline and act accordingly, then that’s on you.

• Playing someone else’s game. If your category is already mature and has an established leader, trying to overtake them is like trying to win the Tour de France on a tricycle when the whole field is four stages ahead. Your only hope is that the leader messes up.

• Playing a fantasy game. Earlier, I said that business means acting on imperfect information. But it doesn’t mean acting on to little information. If you’re relying on a single data point or something you “just know to be true,” even though you can’t explain why, you’re in fantasy land.

• Copying another player. Best case, this puts you constantly behind; you can only do something until they make a move. More likely? You copy them right into mediocrity.

• Relying on competitors to tell you how to play the game. Some companies let a fixation on competition box them into a corner. They’re always on defense, never on attack.

• Relying on customers to tell you how to play the game. If customer feature requests overly inform your product roadmap, you’re not thinking strategically. Get ready to be leapfrogged by someone who can.

• Mistaking a product or technology for the game itself. I like to pick on the Humane AI pin for this one. It was an amazing device that few people cared about. It’s still unclear what problem this thing was supposed to solve.

Remember: the only reason you end up in any of these scenarios is because you put yourself there. These paths might be easy (because you don’t have to think for yourself), but they’re not safe, they won’t make you look smart, and they won’t help you win.

Dumb Failures Are When You Give Yourself 0% Chance of Success

When you make a bet in business, you don’t find out if it was the right one until after the fact. But self-imposed failure, from the very get-go, puts you on a course where the chance of success is zero.

Self-imposed failure is not only avoidable, it deprives you and your team of the chance to see what you were really made of. Whatever you’re working on, I hope you don’t fail. But if you do, please don’t let it be self-imposed. Good luck.

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Thanks for reading

If we haven’t met, I own a consultancy called Flag & Frontier, where I help my clients define their category strategy, align their executive teams around their strategic narrative, and win their category. If you’d like to meet, you can find a time for us to chat here. You can also say hello on LinkedIn 👋.

Cheers,

John

P.S. I have some changes coming soon to The Narrative Field Guide. You can read about them here. Can’t wait to share what’s next with you.