How to Develop a Mentoring Relationship

I’ve always heard people talk about mentors, and how great they are, and how everyone should have mentors, etc. etc. This is particularly prevalent, I’ve found, in the unschooling world. It’s a known fact that having an apprenticeship, internship and mentorship is a really useful tool in learning anything you’re hoping to learn. But I’ve never really truly had a mentor because I didn’t know where to begin in developing that kind of relationship. Now, I feel like I do have a mentor, so I’d like to offer some suggestions for finding one.

  • Find a mentor for a specific interest. I don’t recommend trying to find a “life mentor”. I know some people have great luck with that, but I think, again, it’s hard to know where to start and it’s tough to know exactly what they’ll be helping you with. In my opinion, friends (especially friends who are older than you) make great “life mentors” and most of the time, mentors should be found around something more specific. For instance, I have a tiny house mentor. I’ve been interested in tiny houses for a long time and I’ve done a lot of research about them over the last few years. I finally decided that I wanted to find someone I could talk to about the subject, and then it wasn’t nearly so difficult because I just was looking for someone in my area who had built a tiny house. Which leads me to my next point.
  • Don’t go into the experience necessarily looking for a mentor. Start with just one meeting, or even emailing back and forth. You could even talk over Skype or FaceTime. I started by asking the person I found if she’d be interested in meeting for tea and to talk about her tiny house. It was incredibly nerve-wracking for me to make the plan, but definitely worth it. While we’re on the subject, here are a couple recommendations for a “coffee date” that I found effective:
    • Plan questions before the meeting and then commit them to memory as much as possible. This is because I think it’s better to make it feel more like a conversation than an interview (this will also help in letting the relationship develop into more than just a one-time meeting).
    • Record your conversation. This allows you to listen fully and again, keep it more like a regular conversation. But you’ll still have the conversation so you can take notes later if there are things you want to remember.
    • After you’re finished with your meeting, go home and take notes based on your memory and the recording. In the next few days, send the person an email thanking them, and reminding them of anything they said they would do (maybe they said they’d send you the name of someone to talk to or a link)
  • During your first meeting or discussion, pay attention to opportunities to continue the conversation. This is a good thing to mention in your email. For me, that would look like this, “You mentioned that you’d be willing to look over my plans after I work some more on them. Thank you so much! I’ll be sure to send them along because having the opinion of someone who has experience with this will be so valuable.” This both reminds the person you talked to about what they’ve said and also reiterates the fact that you’re really glad they offered. If while you’re meeting, the person doesn’t offer something like that, feel free to ask them in your email later (something like “Would it be alright if I continue to ask you questions when they come up?” or “Maybe we could meet again in six months or so to touch base on my project?”). It’s really important to advocate for what you want.
  • Make the relationship worth it for your mentor. Is there some way you can help them out in exchange for their time? I wrote a testimonial on my mentor’s website, but there are other ways you could help out. Is there work you can do at their business or house? It’s a fine line to walk between helping them and not making it just feel like a barter. You’d like your potential mentor to want to help you out without the suggestion of help, but it’s also important to not take their time for granted.


I hope these recommendations help you find a mentor for something you’re interested in. Let me know if there is anything I can clarify or if you have more questions.



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