It should hurt a bit … 

To be set free you have to delegate something substantial. At a minimum, it should:

1. 1. Hurt a bit to give up;
   2. Feel risky to let go;
   3. Be stretching for the delegatee;
   4. Make you all a bit nervous;
   5. Constitute a good chunk of your time (20%, for example).

Can you think of a task, process, or accountability you currently own that fits the bill?

More on this here: https://dsabuilding.co.uk/deep-and-deliberate-delegation/