Letting people down

Lately, I've been letting people down.

And I'm absolutely loving it.

In my last email, I talked about The Courage To Be Disliked. The idea that if you try to please everyone, you'll live an inauthentic and miserable life.

I realized that, in an effort to not upset people, I have a habit of overcommitting. I say yes to too many things months out, then wake up and groan when I look at my calendar and realize that I have to spend my day doing things I don't want to do.

One of the worst things I do is commit to trips I end up not wanting to go on.

You know how it goes: you hear about a conference. It's in six months. Your friend is going. It sounds kind of interesting.

You say yes without really thinking of it.

But then, the week before you have to go to the conference you're dealing with a big project at work. Your kid is sick. You just got back from a weekend away somewhere else.

You don't want to go. But you have sunk cost fallacy—you made the commitment and you think of yourself as someone who does what you say.

Your past self wrote a check, and now your future self has to cash it.

My new solution is this: whenever someone asks me for a commitment, I give them a maybe.

I tell them no worries if this doesn't work for them, but if they'd like me to come speak at their conference or something, I'll let them know 2 days before the event. So have a backup plan and count on me not being there.

I think this bothers some people. I get it. It's frustrating to be juggling a million details and have someone no-show. But I've realized that this is the only way I can enjoy this stuff.

No more bad checks that my future self has to cash.

The same goes for email. Every time someone sends you an email or text message, it's a tacit deadline.

Respond within 1-3 days or you're an asshole.

I do it myself. When I send an email and someone doesn't respond, I often build a narrative in my head.

"I bet they hated my email and that's why they aren't responding"

or

"They're probably ignoring me"

I get the feeling, so I project it onto every message I receive. The problem is, I get too many messages to ever respond to all of them let alone do so in a timely manner.

So now, I've set the expectation that you can't depend on an email response from me. I set up an auto responder that says I don't monitor my email and recommend different people to contact for various problems. My assistant combs through and points stuff out to me—somebody reads them—but the default expectation is no response.

Same for text messages. I let them sit. Sometimes for weeks. I'm always friendly in my responses, and I usually do respond eventually, but I've set the expectation that I don't respond quickly.

I'm sure that this has negative consequences, but this too has made me so much happier.

Who knew letting people down was the secret to happiness?

Originally published in the How I succeed by starting companies that (mostly) fail issue of Never Enough.