Finding a mentor

April 22, 2007 — 10 Comments

Get Rich Slowly was one of the sites someone suggested to me after my plea for new reading a few weeks ago, and now it’s my turn to pass it along. It’s a fantastic site about the conservative approach to investing. Anyone who only follows the advice of Jim Cramer or Warren Buffet is an idiot. (I’ve made plenty from both) Their strategies although totally different have made a ton of money which means they’ve both done a ton right. Buffet clearly made a bit more and that’s the side that Get Rich Slowly comes down on.

Anyways, GRS has a great post out on Finding a Mentor

Mentors come in many forms. The key is identifying those people from whom you can learn, and to ask them to share their wisdom with you. Do you work in a large firm? Would you like to pick the brain of the CEO? Form some questions and call her. Are you an aspiring writer? Drop your favorite author a line and ask him for advice. Don’t fawn. Don’t gush. If you are polite, and if you are sincere, most people will be pleased to respond. They were young once, too. They know what it’s like to be starting out.

As someone who has learned almost everything they know from a series of mentors–with the latest one being a rather infamous internet star, I think I’m qualified to weigh in on this.

The costs of emailing or contacting someone you want to learn from are about as close to zero as they’ll ever be. Honestly, what’s the worst that can happen? You come off as someone eager to learn. If they ignore you, you know it’s because they’re too busy doing to talk about. If they’re a dick, then you’ve already learned a valuable lesson.

What many of you don’t understand is just how willing most of these people are to lend a hand. They know what it’s like to be where you are. That you’ve even taken the step of contacting them puts you levels above most of the population. That you could cough out a coherent email without patronizing them or treating them like they weren’t human is often enough to get you in the door.

The point is this: You’ll learn more from a mentor directly than you ever will from books. So make a list of the people you’d like to learn from a give it a shot. But an idiot about this. Think about how you’d like to be contacted if you were in their shoes. Would you even respond to an email that literally said “I’d like you to be my mentor?” If you have an intelligent question, ask them–and if it’s appropriate, describe your situation. But never, and I repeat never, act like they’re obligated to do anything; because they’re not. Always remember that there is a reason they’ve had the success they’ve had and you haven’t, and let that dictate the terms. The other caveat is to realize that not all mentors are famous and not all of them are writers. You can find one anywhere, and often times they ones that no one has heard of will give you the best advice on life.

Here are a few don’ts and a few dos.

1) Don’t be presumptuous. I can’t tell you how often I am literally appalled at the balls on some people. Whatever you’re asking for, it’s probably too much, so scale it back. If it’s a question they’ll answer it. If it’s “Will you sit and listen to my life story?” you’ve crossed the line. Obviously the relationship is centered around getting something from them, but you need to space that out over time. Perception changes everything, so consider that asking for everything up front as opposed to a little advice every couple weeks could mark the difference between learning a lot or nothing at all.

2) Don’t compliment yourself. Don’t insult yourself. Both extremes are equally detrimental. They are the ultimate distraction from the issue at hand. The former, they have to (if anything at all) take you down a notch. The latter, they have to waste their precious time reassuring a complete stranger. Either option leaves you spending capital that is already in short supply. Once you’ve finished writing your email, scroll through and find out all the affirmative claims you make about yourself and delete them. Remember what Ralph Ellison said about power–that it was “confident, self-assuring, self-starting, and self-stopping, self warming and self-justifying.” It does not need to make claims, they are implied. That the issue is even being addressed says the opposite about you. And on the other end, if you’re lacking the confidence to get it done, why should someone bother putting any energy into you?

3) Don’t be obsequious. Compliments are one thing, being full of shit is another. A person worthy of mentoring you is going to be self-aware enough to realize the majority of their flaws and faults. For you to come in and pretend those don’t exist shows that you either are too oblivious to accurately judge situations or dangerous brown-noser. They want to relate to you on a real level, and that’s impossible if you approach them as something other than a real person. So it is imperative that you let them know why you respect them, but they are not the second coming of Christ–and they know it.

4) Whatever you do, do not insult them or what they stand for. I got an email a little while back where someone pretty ruthlessly insulted Tucker, and then the guy wanted something from me. Now aside from the fact that I would consider TM a friend and someone who has helped me enormously, how does it benefit anyone to insult my boss (and indirectly me for working for him)? Understand that people hold certain things to be sacred. You need to find out what those are and treat them with the reverence they deserve. Let me say this again, being brutally honest doesn’t make you stand out, it makes you a dick. If that’s the route you want to take, go for it, but people don’t often mentor dicks.

5) Stay in the picture. You are easily forgotten, remember that. The key then is to find ways to stay relevant and fresh. Drop emails and questions at an interval that straddles the fine line between bothersome and buzzworthy. Even if they don’t respond, that they saw your name again means a little. If they forget your name or what you offer them then the relationship is pretty much dead. And it’s easier to keep something alive than it is to revive the deceased. I get an email from one kid every couple weeks and it’s perfect, they are always short little emails and I almost always see through them–but at the same time, I respect the ingenuity.

6) Bring something to the table. Anything. Quid pro quo. Even if it’s just energy. Even if it’s just thanks. You cannot ask and ask and not expect to give anything in return. The bigger the payoff you can offer, the longer they’ll take you under their wing. Figure out what you can offer and actually give it. Here’s a freebie: Find articles and books that relate to their field and pass on a recommendation and then they won’t have to waste their time searching.

7) Apologize. When you screw up, more likely than not, you’ll realize you did it immediately after saying or emailing it. Don’t wait for their reprisal, or the token period of silence. They’ll forgive your errors (within reason) if you indicate a propensity for identifying them. I know when I’ve crossed the line and you probably too. Reproach can be softened by mutual understanding.

Note: If any of these things reference something you think you might have emailed me, chances are it’s not. They’ve all happened multiple times–and some of them are ones I’ve made myself.

Ryan Holiday

I'm a strategist for bestselling authors and billion dollar brands like American Apparel, Tucker Max and Robert Greene. My work has been used as case studies by Twitter, YouTube and Google and has been written about in AdAge, the New York Times, Gawker and Fast Company.

10 responses to Finding a mentor

  1. One post of Drex’s (I think):

    “There is always someone who has gone through what you have before you, and with 10,000 years of recorded history, chances are they wrote it down.”

    At least, thats roughly what it said. But obviously with new tech all the time a mentor would be better than a book about computers even 5 years old.

    I find the best way to do a menial job (landscaping etc.) is to watch the oldest person at the job do it a few times. Kind of like a mentor except more basic.

  2. Exactly. Books are fantastic, but mentors can look at you and see you’re personally doing wrong and correct it.

  3. Refer to this entry to see what I’m talking about:

    Now, the guy I talk about emailing in there I never would have thought to contact, or at least hope for something back, without the things Ryan’s said in here about sincere emailing, etc for networking. Just by emailing the person I mentioned, I eventually got a list of programs he used to do what I want to do and, by posting about it, I was connected with at least two other people who already want to do it too.

    This stuff works. Don’t ever be flustered or afraid to do it.

    This reminds me vaguely of the website About a year ago I came across that website and made it a point to read one letter’s worth of FAQs each day (A one day, B the next, etc), until I had read them all. You won’t believe the kind of “things you always wanted to know, but didn’t” or even “things you didn’t even know you wanted to know” articles you can find there that lay it all out for you.

  4. A great post to revisit. Hard to believe that this was almost two years ago. Thanks, Ryan.

  5. I love the internet. You wrote this almost 10 years ago and today I get to read and learn from it. Great article, Ryan.

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