Checklist: Should I Stick or Quit?

Should you keep on doing the same or quit and start something else? I read a good answer on Quora to “Should I stick, pivot or quit?”. @jeremysliew writes:

The most valuable resource for an entrepreneur is their time, and if they are wasting it on a quixotic startup, they will never get that time back. But when you’re winning, when you’re REALLY winning, it feels easy. If it feels hard all the time, then you are probably doing something wrong. And when you’re doing something wrong all the time, then you should probably stop.

That’s worth a thought.

As I’ve been on both sides of the table in the past, I’ve engineered my own checklist:

  1. Is this fun? Hard fun and serious fun are both among the valid types of fun. If I’m accomplishing meaningful things with a good team, it’s fun.
  2. Am I learning new stuff?
  3. Does this pay for living? Am I able to support my family? Security is not a fashionable startup concept, but I think security has value when you are responsible for other people.
  4. Is this helping me to fulfil my dreams? Do I have a chance to become financially independent?
  5. Is this the most interesting thing for me to do? If the only chance to do something else, something important is right now, then I’d need to consider the opportunity cost.

Answer “YES” to all five, and the decision is easy. Same goes with 5 × “NO”. In between is where it’s difficult. I’ve seen talented people get stuck to a business that pays for a (good) living. If you are really good at what you do, it’s easy to become a well-paid consultant. But is that enough for a life? Should they quit their comfortable, established business and laboriously start something new? Hint: the above checklist helps to find the right answer.

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