[How-to] Find a Mentor


Through a relatively unplanned series of events, I once found myself on the island of Zanzibar, just off the coast of Tanzania, with nothing to do for an entire week.

Zanzibar, like most tropical islands, is a tourist haunt.  And the tourists all do one thing: lay out on the beach.  But I have a fair Irish complexion (read: ghastly– people regularly mistake my taking my shirt off for the sun getting in their eyes) and attempting to tan myself is like roasting marshmallows with C-4, except boring.  And that’s no good.

Fortunately/accidentally, I found a mentor– a wizened old shopkeeper named Rashid who sold wooden masks to tourists in a small store along one of Stonetown’s hundreds of narrow streets.  Within five minutes of me striking up a conversation, he was lecturing me on the value of hard work.  And when a foreign old man starts talking to you about the value of hard work, you only have choice: you listen.

Rashid in his shop

He gave good advice.  But his views on thriftiness were the first droplets of the monsoon.  It turns out that Rashid had a lot of admonitions.  For instance:

  • Put your faith in God
  • You are young– have sex with many girls
  • [censored]
  • How much did you pay for that!?  Seriously!?  You are getting ripped off!

For the next six days, Rashid had my back.  He found me better-priced guides to go fishing with.  A cheaper hostel.  He brought me to the town square and gave me and my friends coffee and African pastries and introduced us to everyone who passed by who he knew (which was, more or less, everyone who passed by).  Most generous of all, of course, he gave me more advice than I have either the intention or the moral flexibility to put to use.

And all he ever asked in return was my American opinion on whether pro wrestling was staged or not.

Rashid was not who you might think of when you decide you want a mentor, but he had all the same qualities.  He knew the landscape, he had some time on his hands, and he had the good heart to help me out.  Do you have someone like that?

I spend a lot of time on this blog asking you: What do you want to do before you die?  Mentoring is an important aspect of that: who could you talk to that would make that easier for you?  Can you think of a specific person whose advice and blessing you want?  Maybe you just a general persona in mind.  This post is about finding that person, getting in contact with them, and getting them to mentor you.

No one is too cool for you

Honeychild, let me tell you a thing:  There is no one on this earth that you should feel ashamed to try to get to teach you something.  No one is too cool to respond to your email.

This means you need to ask.  Gather the pieces of your ego into a ball, swallow it, and know that without self-pity and guilt, you can ask for help from anyone.

Also, remember that many people want to mentor you.  Why?

  • Asking someone for their advice is a huge compliment
  • They want to pass on their knowledge and opinions
  • They’ve spent so much time “making it” and living for themselves that they want to think about others and help others
  • They believe you’re going to make it big– and they want to help you get there
  • They didn’t have a mentor and wished they had
  • They had a mentor and know how game-changing it is

Good heavens, is that enough reasons for you?  If the problem is self-esteem, leave a comment and we’ll go over it further.

Make like a boy scout and Be Prepared

For now, let’s move on to the part where you’re actually asking.  Even if you’re totally resigned to your hero/role-model/etc. saying no to your request for mentoring, you’ve got to take the chance.

The question here is: “How do I ask so that he or she is most likely to say yes?”.  Again, put yourself in their shoes.  You’re numba one stunna and some kid comes up to you after your big talk and wants your advice.  What!  Who’s this punk?  Do you have time for this?

Probably not.  Little twerp.  You tell him no.  Scram.

But let’s imagine again.  Let’s imagine he got you to say yes.  Something he said tore at your heartstrings and you had to take a chance and proffer him your time and advice.  What would make you pause for a second and listen to him?  Think about it.

In least to greatest importance:

  • He guarantees me it’s a low commitment
  • He tells me a compelling story (that I want to be part of)
  • He’s persistent and bold without being annoying
  • And the absolutely number 1 most important reason: he’s done a bunch of work beforehand and is clearly serious about this

Since the last bit is the most important, let’s delve into that a bit more.

Save for newborns and fuzzy animals, human beings are not hard-wired for mercy.  Hearing a humble plea like “Oh please I look up to your work so much and I would love it if I could have a chance with to speak with you and you have no idea how much I would appreciate it and can we meet weekly?” is far more of a warning sign than a warm welcome.

Why’s it a warning sign?  One of the reasons this person is so scary is because it could be anyone!  They’ve clearly done no work whatsoever before talking to you.  If it’s just some rando fan off the street, how do you know they will make good use of your advice?  How do you know they will respect your time?  How do you know they don’t have hundreds of pictures of you on their hard drive that they peruse every night before falling asleep?

You don’t.

So when you talk to your would-be mentor, try and convey those sorts of qualities: respectfulness, preparedness, and remarkability.  “Hey, I really loved your talk, and I noticed that your thesis applies to these five other case studies, and I’ve written why here in this report.  I think you’ll find it interesting– if you like it, drop me a line.  Thank you.”

Does that sound freakish?  It is kind of freakish.  But it will also be remembered– because who writes case study reports for some speaker they here!?  Oh, that’s right, the type of people who take that speaker super seriously, respect his time, want to make a good impression, and are headed for remarkable greatness.

That brings me to my next point.

How can you ever repay your mentor?

Easy.  Succeed, preferably using their advice.

That brings me to my next point.

How to find a mentor

The single-most useful medium I’ve found for meeting interesting people is meetup.com.  Meetup.com is basically the online yellow pages of fringe interest groups that want to meet in real life.  This runs the gamut from the outdoors enthusiasts of Seattle to vampires of greater Chicagoland (I kid you not).

Whether you’re looking for some dude to teach you the ins and outs of beekeeping or a personal professor of project management, chances are Meetup.com has a ridiculously applicable group that meets within spitting distance of you– at least if you’re in an urban area.

That’s about the only non-obvious specific place I can say to look for a mentor.  Church, school, work, etc.– I’ll let someone else cover those.

Let me just say something about mindset as you track down the perfect mentor.  Keep in mind the principles from above.  Be amazingly prepared.  Always be giving.

Frankly, you should be adding value to your network like generosity is going out of style.  Be a ferrier of information– or better yet, introductions and opportunities.  “Hey man, I thought you’d like to see this… Maybe it will help with your project!”  “I work out Tuesdays and Thursdays with a professor from the U– she would have a lot to say about your non-profit.  Let me ask her about meeting up!”

If you took the time to make one such connection a day instead of reading some dumb article online, you’d go twice as far.

So you tried someone as a mentor and it’s not working out?

Maybe they’re giving you bad advice, maybe they never have time to meet with you, who knows!  You tried to meet with them, and it’s going nowhere.

First of all, recognize that they probably know this too– and they probably feel awful about it.  Here they said they were going to meet with you monthly and help you with your stuff and now they’ve given you crap advice while half-distracted and way less frequently than either of you expected.

That’s OK.  Most people have never taught others before, and they don’t have any idea just how mind-blowingly difficult it can be to teach well.  Forgive and move on.

But, but, but— stay on good terms.  Here’s a question for you: who is more likely to know someone who might be a good mentor for you?  Who’s more likely to help you get set up with that person?  Is it a.) a random person at the cocktail bar of a networking event, or b.) someone who knows what you want to know and who you want to know and would have been an awesome mentor themselves except for some small detail and also now feels really bad that they ditched you and may want to help you further just to ease their aching conscience?

Oh baby, is it ever (B)!  Now I’m no utilitarian, but intelligence demands you don’t lose track of the people who are most able to help you simply because your first stab at mentoring didn’t go as planned.

This is what all of networking boils down to, as far as I’m concerned: be a good person and just keep adding value to the lives of people you come in contact with– and not just the richest and most famous ones, because a.) that’s not being a good person and b.) you never know how life will help you.

Oh, yes–

Be open to the randomness of our strange and wonderful universe

I owe roughly 50% of my success in life to a chain of opportunities I got starting from two middle-school crushes– one on a girl, the other on an eighteenth century Italian composer.  The other 50% of my success I owe to my parents.

Notice a theme here?  Very little of this is my own doing.  The most important opportunities I’ve had in life are neither predictable nor repeatable, and I don’t figure that’s about to stop.

So if I wanted to try to repeat them, the best I could do is keep myself open to luck.  Oh, that sounds familiar.

It’s the same with mentoring.  I stumbled across perhaps the most fortuitous mentor I could imagine (I had dissected his work in job interviews, and regularly return to it in running this blog) at a meetup.com group on something completely different (which I decided to present at and whipped up a presentation for on a plane ride earlier that day).  How does one get more random than that?  Ain’t possible.

So that means my best advice is this: know that good things will be random, so instead of trying to make specific good events happen, live your life so as many random good events happen as possible.  Things will never go quite how you expect.

The randomness includes the fact that I’m not always right.  In fact, while I have a great mentor, I certainly wasn’t freakishly prepared in meeting him, and although I might have added some minimal value in some book recommendations or suggestions I gave him, 80% of him mentoring me is that I showed up at the right time with the right interests and I was probably the first person to ask.

Ramit Sethi calls this the “Craigslist Penis Effect” (yes, this link is actually safe for work)– if you’re trying to find a date on Craigslist (God help you), you’re competing against a pool of diagnosable perverts who augment their typo-laden messages with pictures of their own junk.  If you can write just a sane, normal message and refrain from crotch cam, you’re doing better than 90% of the people out there!

And that’s how the mentoring market is.  Even if you’re not freakishly prepared and adding unfathomable amounts of value to every person’s life who you meet, if you do your homework, take advantage of randomness, and ask the people you want to mentor you, you’ll be way ahead of the curve.

The rules.

  1. Know that no one is too cool to receive your email
  2. Be freakishly prepared and always add value
  3. Repay your mentor by succeeding, preferably using their advice
  4. Be open to randomness

P.S. The /mentoring movement

You know how every single blog and personal website you’ve ever been to has an About section that you can go to by going the URL then adding /about?

Well, one day there’s going to be a /mentoring page for all of those sites too.

/mentoring is where you write what you’re itching to learn and what you’re itching to teach.  Here’s my /mentoring page.  Here’s where it all started.

If you have a personal website or blog, do the world a favor and help this spread.  Much love.

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