Facing decisions that may work or not

Many times we know the answers to our problems. We just need to untangle our thoughts. And we need to face the fear of embracing a decision that may or may not work.

Derek Sivers describes his approach to mentoring. When he has a dilemma in his life, he writes a really good description of his dilemma before reaching out to his mentor. He doesn't want to waste his or her time, so he writes a very good description of the problem and then summarizes both the context and the problem in half a page.

Before he sends it to his mentor, he simulates a conversation with his mentor. He tries to predict what his mentor would say. Not to waste his mentor's time, he addresses in advance each of these points. Then, again, he tries to predict what the mentor would say one last time. Finally, he includes all of this in his initial summary of the situation.

After going through this process, the answer to his dilemma is clear. He doesn't need to bother any of his three mentors.

After I’ve done that whole process, I don’t need to bother anymore because the answer is now clear. Because I’ve just done the work of summarizing everything and imagining what they would say.

So the punchline is, the truth is, I haven’t talked to my mentors in years. And one of them doesn’t even know I exist.