The Hardest Thing
On failure and truth-seeking:
We talk so much about how success happens in Silicon Valley. We don't talk nearly enough about how failure happens. Silicon Valley is a place of extreme abundance. Success is everywhere. But failure is everywhere too. Most startups fail. Most ideas don't work out. Most VCs end up with mediocre track records. While the feedback loop of success is obvious, the feedback loop of failure? Ugh... it's full of noise, its very difficult to get to the signal of: what to change?
The hardest thing in business (and in life) is to be constantly truth-seeking and then actually making the changes needed in yourself, your product, your org to deserve the success you want.
Why is truth seeking hard? Because everyone wants to feel good about themselves. Even in failure, one reaches for the most forgivable explanation. "The market wasn't ready." "If it hadn't been for this one mistake, we would have been fine." But more often than not, the real reason is something deeper. Maybe you chose the wrong co-founder. Maybe you didn't hold the bar high enough on execution. Maybe you weren't intellectually sophisticated enough for the problem you chose. Maybe the people around you weren't the right people, and you knew it but didn't act on it. Your well wishers, your friends don't want to be harsh so nobody sits you down and walks you through what they might see. You have to go and find the reasons yourself.
Finding the real issues requires you to challenge the story you tell yourself about who you are. It requires sitting with the possibility that the gap between where you are and where you want to be isn't a gap of circumstance. It's a gap of you. I've had to confront this myself, more than once.
But truth-seeking is only half the battle. The equally hard, maybe even slightly harder part is actually making the changes needed. It's one thing to honestly say: "I made that hire because I wanted to move fast, not because the person was right." It's a completely different thing to then change how you hire. It's one thing to acknowledge your execution bar has been slipping. It's a completely different thing to raise it, have the hard conversations, and hold yourself to a standard that's uncomfortable.
Changing yourself is hard. Changing your org is hard. Changing your product ideology when you've been emotionally invested in a direction is hard. Seeing the truth is step one. Doing something about it is where most people fall short.
There's a famous Churchill quote: "Success is not final, failure is not fatal: it is the courage to continue that counts." I'd add that the courage to continue includes looking inside and saying: I'm going to change this deep rooted thing in myself to deserve the success that I want, and then actually doing it. That's the hardest thing.
