Tom Dekan

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Combatting perfectionism after selling my business

A technique to reduce perfectionism by using money and loss aversion

Over the past 2 months, I’ve experienced two of my startups ending - one in euthanasia and one in sale. During my startup that we ended, I kept my perfectionism under control by the time pressure of building for our customers. I would ask customers what they wanted; consider what they actually wanted; and then build it quickly.

The problem

Shortly afterwards, I sold my other software business (Redstone HR) to a UK company. Since then, I’ve been building software to accelerate the future businesses that I build.

Perfectionism has been rampant.

My perfectionism has felt like a colony of rabbits alone in a lush woodland. The rabbits spend their days happily increasing in number, without the constraints of hungry predators.

As a side note, I think that the word ‘perfectionism’ is inaccurately self-complimentary.Perfectionism sounds impressive. You care so much about your work that you want every aspect to reach an ideal.

In practice, perfectionism means that you fixate on insignificant details and don’t focus on the most important things. Being a perfectionist is bad thing for achieving your goals. Perfect is the enemy of good.

Use our evolutionary roots to combat perfectionism

Tip: Use loss aversion to combat perfectionism -> Add time constraints with real financial consequences.

  1. Set a deadline with specific targets
  2. Send money to a friend immediately
  3. Tell the friend to dispose of the money if you don’t meet the deadline1

A real financial penalty forces you to focus on the most important things. If you instead focus on trivial details, you’ll increase your chance of not getting your money back.

On point 2, it is important to send the money before beginning. This is because the constraints become real once you send the money from your bank account. Sending the money away makes it real. You’ve suffered financial loss: if you don’t meet the deadline, you don’t get your money back.

Over the past few month of me doing this when perfectionism has peaked (perhaps 6 times), the results have been 100% positive. Throughout each day, I’ve prioritised more significant tasks and minimised my time in a recursive spiral of trivial details.[^examples]. It takes some effort to set up the constraints, but it’s a useful strategy when perfectionism starts to take over.

Try it out. Send your money away for the day.

  1. I recommend that you don’t ask the friend to donate the money to charity. You don’t want to gain any alturistic feeling by failing to hit your target.