Should anyone ask, if I did this again

This is a post for future-Simon.

Background: Admin kills me. It absolutely hammers me into the ground. I hate it, I don’t value it and it torments me until I find a way to get it done. So much hate. Server admin - love. ActualReality™ - not so much love.

Running your own company ramps up the admin immensely. Accounts, paying people (love that I can, hate the process), taxes, random paperwork. It’s horrible. 

This morning while cycling to work conversation went something like this: “Do you think $hero has to do this?” 

Answer: “No he has someone do it for him”.

Wow. I like that.

This is a note to future-Simon:

  • You don’t have to be good at this.
  • You can outsource it easily.
  • Outsourcing looks like “Make a checklist. Pay someone to work through the checklist once a month with you”
  • When $item arrives, put it on the stack and forget about it.
  • Hold the stack until the 3rd or 4th of the month (sometime not too early to miss end-of-month invoices, but early enough to make sure you get everyone paid nicely on time)
  • Have them work through the list with you.
  • Put this as a monthly, repeating calendar appointment so it just happens. 


  • Worry less about the things you don’t enjoy
  • Become better at asking for help
  • “Some people actually enjoy this stuff”
  • Live longer with less stress

That sounds pretty good to me.


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