Success is a strange reason to stay

This is one of the loneliest positions there is, because it comes with no sympathy. The company works. The career is enviable. Complaining is not socially available to you.

So people don’t complain. They stay, and get slowly worse at the thing, and start describing it in the past tense without noticing.

Two different problems wearing the same coat

One: you still want this, but the job it has become is not the job you wanted. Founders hit this constantly — they built something to make a thing and now they run a management structure. Fixable, usually, by changing the role rather than the company.

Two: you have changed and the work no longer means anything to you. Not fixable by reorganising. That is a leaving question, even if the leaving takes two years.

It is worth knowing which one you have before you make any announcements.

The sunk cost has a face

The hard part is rarely the money. It is the people who joined because of you, and the identity of being the person who built this. Walking away feels like telling everyone it was not worth it.

It was worth it. Things end anyway. Sometimes the hardest part of changing your business is admitting that you have changed.