On Irrational Fear

Yesterday, one of my co-workers asked if we could grab time on our calendars to speak, outside of the context of our normal one-on-one.

All of you well-adjusted people out there are probably thinking, “… so?”

Let me try to explain.


I’ve now spent three years of my life working on Keen. Some moments have been among the best I’ve ever experienced. Some have been, well, the opposite. But three years, while not that long in the grand scheme of things, is still a decent bit. We’ve built this thing up from scratch. Made believers of skeptics. Hundreds of businesses pay us. Almost forty of the best people I know have committed most of their waking hours to co-creating our dream.

You’d think after all this external validation, I’d be confident. And, I suppose, in some ways I am.

But there are times when I’m terrified the rug is just about to get pulled out from under me.

So, back to my co-worker and his request for a meeting. He’s really important to me. He’s had a huge impact on our engineering team, on our product, and I consider him a close friend now.

When he told me he wanted to chat outside of our normal context, my cool brain (a phrase stolen shameless from another one of my favorite people) immediately decided he was preparing to tell me he was quitting.

The thing is I knew it wasn’t going to happen. He’d given me no indication he was unhappy, he’d been planning a bunch of work for the next few weeks for himself, and he’s way too much of a consummate professional to drop that kind of thing on me without lots of advance warnings.

Still, though, I had a relatively anxious night of sleep, woke up earlier than normal, and fretted about it during my shower thinking time.

I doubt I’m alone here. I imagine this is why businesses and their leaders get more conservative as their success grows. When we started Keen, we had nothing to lose. If we failed we’d go back to our high paying tech jobs. Our “failure” would be an acquihire where we’d walk away with high six or low seven figures, each. Nobody could get hurt.

Now, though, it feels like there’s a lot more at stake with every passing day. We have employees with spouses; mortgages; kids! I don’t want to fail them.

How do we not let that pressure affect our decisions? How do we act as impetuously and recklessly as we did when we started the company?

Upon reflection, I think being able to ignore those irrational fears is one of the hallmarks of great leaders. Just look at Elon Musk — there’s a guy who kept betting, kept acting in a way that seemed unreasonable — and now we applaud him for it.

I’m no Elon Musk, but I feel like recognizing this can happen helps me identify when it does happen. That’s a decent enough start for me right now.

What have you been worried about lately? Share with me on twitter: https://twitter.com/dkador

P.S. Oh, and to provide some closure — my co-worker didn’t quit on me. He just wanted to go over some org structure stuff. I think I helped him. ☺

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