Why You Should Be Trying to Fail, Not Trying to Be Perfect


At OpenView, we make it pretty clear that our firm’s aspirations — a collective term that encapsulates our mission, vision, core values, and purpose — drive everything we do. In fact, you might say we’re a bit obsessed with them.

But there’s a simple reason for that obsession: Our aspirations keep us focused on the things that matter to us — our stakeholders and our portfolio — limiting the possibility that we’ll get distracted by all of the peripheral noise that often sends companies, or VC firms, swirling down the toilet.

That’s not to say that we’re perfect or that everything we do turns up roses. In fact, we’ve fallen on our faces once or twice. And some of our grandiose ideas haven’t exactly turned out the way we thought they would.

But here’s the thing: We embrace failure. Hell, we almost encourage and reward it.

Now, before you start to think that we’re the Pittsburgh Pirates or Charlotte Bobcats of the venture capital world, let me put that last statement into context. We embrace failure when it happens as the result of trying something worthwhile. In other words, if we feel like the things we’re doing align with our goals and capabilities, and that they have the potential to make a massive impact (either for our firm or our portfolio), then failure is an acceptable outcome.

The reason is simple: The acts of experimenting, strategizing, executing, and hypothesizing are impactful, even if they lead to a dead end.

The bottom line is that whether the things we thought would make an impact go down in flames or uncover a groundbreaking new idea that propels us forward, both scenarios ultimately teach us something that make us better going forward.

Unfortunately, too many businesses don’t see it that way. They prefer predictability and perfection and status quo. I’ve got bad news for those businesses: Predictability will do nothing to help you grow into a great, big business, and perfection doesn’t exist.

So, why are you limiting your business by focusing on either outcome?

As Jonathan Fields wrote in a great post on his blog, you’re better off building bad stuff quickly than building the same, average stuff slowly. In fact, Fields phrases his opinion a bit more bluntly:

There’s no greater accelerant along the path to genius than a flaming trail of crap.”

The key is to make sure that everything you do revolves around the tenants of your aspirations. That way (provided those activities and initiatives are geared toward making a massive impact), whether you succeed or fail is somewhat irrelevant.

Ultimately, that means focusing on:

  • Goal orientation (rather than activity or time orientation)
  • Exceeding expectations against tough goals
  • Creating optimal pressure, which leads to feelings of challenge and pride of achievement
  • Checking and discovering flaws in approach and results
  • Encouraging detail orientation, transparency, and high quality standards
  • Discipline to spend time on activities that drive results

To sum everything I’ve talked about in this post up, I’ll defer to OpenView founder Scott Maxwell, who’s made it clear in his blog that he thinks businesses should try to fail more. You might think he’s crazy, but I encourage you to digest this paragraph before you blindly disagree with that sentiment:

One of the points that I make over and over and over is that our culture is stuck with the notion that we must plan and then act and, if there is a failure, then it was either a failure in planning or execution. Most situations and all new situations are unpredictable, so the best approach is to get to a quick implementation, identify the issues and opportunities, and then iterate again. Follow this iterative approach a few times, and you will eventually find almost all the issues and be able to perform at the best level possible. I call this success, but you could also call it failing multiple times.”

With that, I think I’ve beaten the false pretense of business perfection into the ground (see my previous posts on the topic here, here, and here if you missed them). Hopefully you took something away from this series. Or, maybe you’re still not convinced. Either way, I’d love to hear your thoughts and feedback. Do you think perfection is attainable in business? If so, what have you done to achieve it?