Least favorite hats

My second least favorite hat to wear as a startup cofounder? Nag.

I’m constantly having to ping and re-ping people about this, that, and the other thing.  I find myself expending a fair amount of creativity coming up with “reasons” to ping.  A tiny piece of new information or an inconsequential question that’s tangentially related to the thing I’m actually pinging about.  It would technically be more honest to just say one of the following:

  • Dude, I think you forgot the thing.  Please don’t forget the thing!
  • I know the thing seems small to you, but to me it’s critical for {planning, marketing, customer support, etc}.  We needs our precious now!
  • You keep saying you’ll have this thing ready for me “tomorrow” or “soon”, but you are clearly the worst at estimates.  Just give me an accurate estimate and I’ll let you be until that date rolls around.
  • Please stop avoiding me and just finish the thing!!  I’ll get off your back when it’s done.  Pinky swear.

Yes, that would be more honest.  But not only does coming up with tiny excuses for the nudge make me feel less dismal, it makes the people I’m talking to feel less dismal.  And that makes both of us more likely to muddle through and lead a cooperative existence.  Which in many cases leads to less need to nag.

My least favorite hat is still CFO.  As soon as that starts to take up more than a couple hours a week I’m hiring someone to do it for me.  It’s not difficult.  I just get incredibly impatient and tense that I’m not getting anything done.  Which I am.  But I feel like I’m not.  It’s weird.  Totally worth paying someone else to take those feelings off my hands.

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