Open Ambition

In my world as a venture capitalist and a veteran of four fairly successful startup companies, I see and have experienced failure, a lot. My colleagues and I talk about it a great deal, in familiar ways and in ways that assign value to failure that occurred in a meaningful way. With the big ideas and within the teams that build companies around these ideas, modest success is simply not valued as highly as failure that occurs while attempting something bold, new, and ambitious.

Outside of my world, failure is spoken of in ways that make me think the people doing the talking view failure more superficially than we do. It’s a pause on the way to success, something you move on from. It’s as if failure is treated as a currency that gets spent on the way, but it’s a currency that’s been in circulation too long; it’s grimy, and you don’t really want to touch it if you can help it.

In the ”sky’s the limit” world of startup companies it’s all about being in a place where you’re brave enough to go do something new and bold and the only thing you are scared of is not succeeding. My colleagues and I frankly spent less time worrying about the failure side of our businesses than we do understanding what the obstacles to success are. We know failure is going to happen. In those early days of our companies, in fact, one of the few things we know is that the plan will end up being wrong, or at least that the numbers in all those cells will be. But understanding why they are wrong – examining, seeking the knowledge of where we failed – is how we find the path to success.

It’s not that we’re in love with our failures, but we do have meaningful relationships with them.

Meaningful failure. It’s not just where things didn’t work out. It’s failure that happened even when you were really, really motivated for and focused on success. It’s that confluence of ambition and reach, hard work and commitment, preparation and talent; where all of that comes together, and it’s still not enough.

It’s why most of us have an iPod while we also still use Windows computers; Apple sure failed to get the Mac mainstream, but learned from that when they entered the music and phone businesses.

But this is a really big failure. What about the failures we all experience in our jobs and personal lives that happen on a very human scale. You can have ambitions, you can place yourself in uncomfortable and vulnerable positions in order to achieve something of importance to you, and still you can fail. In fact, if you accept, even embrace failure, then about all you can control is how you respond to it when it happens, and what you take with you to as a result of it.

I like the analogy of failure being the lubricant in the engine. Without it, the engine stops. Without the meaning from the failures we create and encounter, the engine of success will stop. Or rather, when success happens it will be a lot smaller. Failure can tell you why what you hoped would happen didn’t but also why something like it, or better, can and will. If you’re not experiencing failure, then, perhaps you’re not hoping with enough ambition. Embracing it, anticipating it, being resiliently open minded, well, that’s just being a good steward of a high performing engine.

That’s why when I describe what it’s like to be in a high octane startup I refer to it being in a place where you remain calmly focused on the very few reasons why you will succeed and not on the seemingly thousands of reasons why you might fail. You’re striving for performance towards the big goal, not results of any specific setback along the way. It places you on the balls of your feet, not your heals. You know failure’s bound to happen, so lean into it.

It’s as simple as shifting your perspective to a “fear of not succeeding,” which is fundamentally, and in a very nuanced way so much different from a “fear of failing.” By focusing on what it takes to succeed, you can embrace the fact that there will and should be many junctures involving failure along the way. It’s the focus on success that enables you to get the big things done in life.

But embracing failure and extracting the data isn’t enough. You need a resilient, open mind to care for and make use of what you learn from your failures. Resiliency is important; it provokes a stretchiness and adaptability of your frame of reference and enables you to let go of that firmly held set of assumptions developed yesterday in order to embrace a better, more informed set today.

I like to think of my life as living in a continuous startup. At some point along the way, I realized that it’s at the moment of failure where the real meaning is, where you can figure out both what you are deep down inside and then how to be a different, more capable you the next time. That in order to be living a life of meaning and value, failure has to be not just acknowledged but embraced as the missing ingredient to success.

When you’re busy being focused on how you’ll succeed and failure occurs, it seems so much simpler to look at what just happened as fodder and information to take another run at finding out how to succeed the next time. It may be that the “next time” is the next iteration of the business you run at your company today or a totally different business at a totally different company. The constant, however, is standing at a juncture of success, open-minded learning, and meaningful failure and being ready to take the next step.