Derek Sivers

How to ask your mentors for help

2019-10-17

I have three mentors.

When I’m stuck on a problem and need their help, I take the time to write a good description of my dilemma, before reaching out to them. I summarize the context, the problem, my options, and thoughts on each. I make it as succinct as possible so as not to waste their time.

Before sending it, I try to predict what they’ll say. Then I go back and update what I wrote to address these obvious points in advance. Finally, I try again to predict what they’ll say to this, based on what they’ve said in the past and what I know of their philosophy.

Then, after this whole process, I realize I don’t need to bother them because the answer is now clear.

If anything, I might email to thank them for their continued inspiration.

Truth is, I’ve hardly talked with my mentors in years. None of them know they are my mentors. And one doesn’t know I exist.