What Nobody Tells You About Finding Mentors

Ryan Holiday
Feb 17, 2018 · 9 min read


Because you were lied to. School is important, don’t get me wrong. But it’s also become a massive shell game. The class of 2013 graduated with an average of $35,000 in student loan debt. And yet…the majority of college graduates have to move back in with their parents. Underemployment for grads is nearly 20%. College grads working minimum wage jobs is up 70% in the last decade. In other words, you paid all that money and now it turns out that you’re not even qualified to start in the field you’re supposedly credentialed for.

  • You think the point of an internship is a few dollars here and there (rather than skills and access). Newsflash: If you’re not learning anything it’s your fault. For instance, three of the interns worked at Gawker — I can think of a million lessons they should have picked up, the most priceless should have been about what kind of person NOT to be and what a miserable job the blogging grind is.


I’m using the word “Mentor” in this article because I am using a general term to describe a flexible and often informal relationship that can vary from person to person and field to field. You, as you are looking for a mentorship, almost never ever use this word.

That is, bring something to the table.


How do you find the right mentor for you?

You’re asking me this question? C’mon man, you have to know who the leaders and innovators and talented people in your chosen field are. If you don’t, then you’re not ready for a mentorship yet. If you don’t know what your chosen field is, you’re not ready yet either.

Don’t be presumptuous.

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. 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.

Take a chance.

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.

Now What

They took a chance on you. So deliver. Have your shit together. Want it badly. Don’t be crazy. Spot new opportunities, never care about credit. All the “Advice to a Young Man” stuff.

Make use of the access and the opportunities.

A good mentor elevates–you get invited to stuff you otherwise wouldn’t have, you meet people who you wouldn’t have otherwise, you get to work on projects that were previously out of your reach. Rack up as much of this as you can. It’s worth more than money, manyfold.

Bring outside information in.

That is, this mentor is not now solely responsible for your education, well-being or success. You better be out there reading, experimenting and connecting with other people–so you can bring that perspective to your mentor and bounce it off them and learn how to make use of it.

What do you want to get out of this?

What’s your grand strategy? If you don’t have the answer to that question, it’s going to be hard to really get the most of this connection you’ve formed. As you’re working for or with someone else, you need to be working towards where you want to go.

Stay in the picture.

You are easily forgotten by busy people, 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. It’s easier to keep something alive than it is to revive the deceased…but it’s on you to keep the blood flowing, not the mentor.

Your personal life is irrelevant.

No one cares what’s going on with you, until they do. But before then, it’s on you to handle that shit by yourself, privately. (“If you need to cry, go outside,” etc. etc.)


When you screw up (and you’re going to screw up a lot), 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.

Pay it forward.

You don’t pay a mentor back by helping them. You pay them back by moving on and being successful (which reflects well on them) and then returning the favor to someone who is in the position you were once in.


I’m sure there are a million more tactics that I’m forgetting. But that’s OK because a large part of this is going to be learning by experience. Sometimes you have to touch the stove to know it’s hot, I get that. The point is to reduce the chance of making fatal mistakes, or of missing out on once in a lifetime opportunities.

Like to Read?

I’ve created a list of 15 books you’ve never heard of that will alter your worldview and help you excel at your career.

Ryan Holiday

Written by

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR

Ryan Holiday

Written by

Bestselling author of ‘Conspiracy,’ ‘Ego is the Enemy’ & ‘The Obstacle Is The Way’ http://amzn.to/24qKRWR

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