How to Hand Over and Move On

Thousands of books have been written about how to start projects, but only a handful about how to end them. The advice below is based on my experience of doing that; see this post from Andrey Petrov for some more ideas or this talk for some personal reflections.

  1. Be sure you mean it.
    Letting go will be hard on you, but saying you're going to and not actually doing it will be even harder on your successors.
  2. Do it when other people think you should.
    Just as you are the last person to realize when you're too tired to be coding, you will often be the last person to realize that you ought to be moving on, so ask people and pay attention to what they say.
  3. Be open about what, when, and why.
    Tell people that you're leaving and what the succession plan is as soon as possible, which in practice means as soon as you think you won't have to revise what you have said publicly.
  4. Leave for something.
    People who start things usually aren't good with idleness, and idleness tends not to be good for them, so when you leave, leave for something, even if it's something small.
  5. Don't choose your successor on your own.
    You may have strong opinions about who should succeed you, but you should still check those opinions with someone more objective.
  6. Train your successor.
    Share tasks with your successor for a few days or weeks: they will get to see how things actually work, and you'll discover things you would otherwise forget to tell them. Go on holiday for a week and leave your successor temporarily in charge. You'll discover even more things you would otherwise forget to pass on.
  7. Actually leave.
    It may be tempting to continue to have a role in the organization, but that usually leads to confusion, since people are used to looking to you for answers. It will be easier for your successor, particularly if they weren't a founder as well, but the best thing you can do to help them is to find something else to do for a year.
  8. Learn from your mistakes.
    Whatever you have left will almost certainly not be the last thing you ever do. Take some time to think about what you could have done differently, write it down, and then move on: obsessing over only-ifs and might-have-beens won't help anyone.
  9. Remember that they weren't all mistakes.
    Many people are uncomfortable being praised, but give the organization a chance to celebrate what you accomplished and thank you for it.
  10. Do something fun before you go.
    There will never be a better time to try that wild idea that's been in the back of your mind for ages.