People you can reach out to:
- People you know who have achieved a similar goal
- People you know who know others who have achieved a similar goal (you can speak with them or ask them to introduce you)
- Search for people online who have achieved a similar goal, and reach out to them or see if they have any writing online that is relevant
- People who have achieved a goal that is different, but in some meaningful way associated or relevant to yours
- People who are generally good at strategizing
Prepare some specific questions of areas you’re uncertain about. Being asked for generic help tends to produce mediocre advice. But you can use specific queries that are still general, eg:
- “What were some things you wish you’d known when you were at my stage?”
- “Have you known people who failed at this? Why did they fail?”
- “What’s something that you’re really glad that you did?”
The AskAManger blog has more suggestions for “informational interviews” with people in the field you’re interested in.