Entrepreneurs: pick your battles.

Is that the hill you want to die on?

I think we all have territory, spaces and ideas where we’re ready to make a pitched battle, make our last stand. For some reason, we’ve decided that we will draw the line there, and we won’t shift. There could be any number of factors that make that happen. It could come from personal experience, our comfort zones, or the way we were raised.

It might be a developer who hates Ruby on Rails, and refuses to learn it, refuses to join a team that believes in it, refuses to accept that it could be the right methodology for a project. She’s chosen Ruby on Rails to be where she’ll fight. She’s chosen Ruby on Rails to be the hill she’s ready to die on.

It might be an entrepreneur who refuses to admit that her product is not the right fit for the only market, the only audience, and the only demographic who are prepared to listen to her. She’s chosen that product, and her belief in it, to be the hill she’s ready to die on.

When you make that choice, you might choose some other ways to phrase it, other ways that sound a little more flattering, and a little less like a blaze of flawed glory. You might tell people that you’re “bullish” on it, or that you’re just “sticking to your guns” or that you’re “standing up for yourself.”

Nine times out of ten, that’s just a delusion. If you were asked to explain your reasons, it wouldn’t take long for the Why to be answered by a short, sharp, Because. You’ve become so firmly set on that hill, on that battle, that the reasoning behind it no longer matters. The chances are, you have stepped away from any kind of reasonable discussion or argument, and all you want to do is fix bayonets and get down and dirty.

When this happens in business, a company stagnates. A company focuses on an area, or a product, or an approach, and they won’t back down. We’ve seen this in technology companies, time and time again. They pitch a battle, and they fight it. When it happens in creative circles, it’s the same thing. You know why bands and artists fail? It’s because they try to fight a battle against all odds rather than attempting to respond in a different way.

That’s how we ended up with Chinese fucking Democracy, a staggeringly unpolished shitpile of a record that Axl Rose had to make because he had to be right about the direction of the band, no matter what and who he lost along the way.


I find people to be incredibly stubborn. It’s the default human reaction to change, to feedback, to criticism and to new ideas. Humans don’t want to adjust their way of thinking, or admit a shortcoming, because it means giving up an inch of their land. Just one inch. And just one inch seems like an inch too far.

I had an interaction with a CEO recently, of a technology company overseas. He and his team designed some pretty fantastic IT processes and concepts in the mid 2000’s that were innovative, and they were able to gain a few consulting contracts that sustained the business.

Unfortunately, it had been around a year since they’d closed any new deals, and business development opportunities were running out, because their ideas were years behind the time. The CEO was a firm believer in those ideas, and to him — they were his crowning achievement, his best moves, his masterstroke.

He was pitching a battle, himself and his company and his ideas against the shifting landscape of technology. It was a battle he couldn’t hope to win, but he’d reached a point where his inability to give ground, or to shift his strategy was going to lead him into a war of attrition that he couldn’t win.

Do you know what a war of attrition is?

Attrition warfare is a military strategy in which a belligerent attempts to win a war by wearing down the enemy to the point of collapse through continuous losses in personnel and material. The war will usually be won by the side with greater such resources.

World War One was probably the most famous war of attrition. And we learned some pretty valuable lessons…like the fact that even if you do win, you’re so emotionally, economically, socially, morally and industrially crippled that it’s barely worth it.

When you pick a hill to die on, when you pick one issue or obstacle or argument that you are going to fight tooth and nail over, you’re entering a war of attrition. You’re committing to slogging away at the other side, refusing to give ground and wiping yourself and them out in an attempt to be the last one standing after 10 rounds.

That technology CEO was so adamantly against the idea of giving his ground, that he was prepared to destroy his own company in a fight against time, change, and progress.

He’d sought me out to find a way to win the battle, and when I told him that the only outcome was destruction, he was pretty pissed at me. It took several months of discussion, brainstorming and strategy before he started to come around to my way of thinking, and shift his approach from a war of attrition to something a little more strategically acceptable.

We eventually decided to begin winding up the contracts he had that functioned on the old processes and ideas, while developing new ones. To cut down on the overheads, the infrastructure and the expenditure that made his old ideas so necessary, in favour of a leaner approach that was open to new concepts.

I firmly believe that if we hadn’t done that, if he hadn’t walked away from that hill, his company would have died on it.


Photo credit: Maragda Farràs — https://unsplash.com/@maragda11

The chances are, no matter how open minded you believe yourself to be, there’s a hill you’re ready to die on. It might not be as major as that CEO’s, and your business might not depend on it, but it’s there. For me, that used to be the idea that I had to found a huge tech startup, the next Google, in order to validate myself as an entrepreneur.

For some people, it’s the idea that being a cutting edge artist like Beyoncé is the only acceptable career artist, and being Nickelback is worthless. For some entrepreneurs, it’s the idea that a $100,000,000 company is the only worthwhile goal, and a $5,000,000 company isn’t worth their time. When these people reach a point where they have to settle those fights, and meet those challenges, they aren’t going to look for the outcome that is best for them. They’re going to look for the outcome that lets them win, by the sheer metric of ground lost or retained.

When it comes to that challenge, even if they win, they’ve already lost.

I want to challenge you to a different way of thinking. In business, as in creativity, as in war, you have to examine every single battle and ask what you want to gain from it. Because the reality is, that gaining a little ground every time, or draining the resources of your opponent, or doing the most damage aren’t the only objectives. Sometimes, surviving and learning are just as good.


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Jon Westenberg has appeared and published in Business Insider, Inc.com, TIME and dozens of other publications, talking about startup entrepreneurship, writing and innovation. Jon has helped hundreds of businesses worldwide grow their audience and take control of their future. Jon is an investor, an entrepreneur and a dreamer.