If you pay attention to the careers of the people at the pinnacle of their field, Mark Zuckerberg, Bob Dylan, Oprah Winfrey, they all point to someone who mentored them into and through their success. For Zuckerberg, it was the late Steve Jobs, when Jobs passed away Zuckerberg wrote this on his wall: “Steve, thank you for being a mentor and a friend. Thanks for showing that what you build can change the world. I will miss you.” For Bob Dylan, it was famed songwriter Woody Guthrie, for Oprah, the legendary poet Maya Angelou. In this article, we have mentioned about the power of mentors.
Mentoring and being mentored is frequently talked about and oft-given piece of advice, but how the hell do you actually do it? The world doesn’t seem to be full of Jobs-level people wanting to help out the little guy, so how do we find them? And how do we convince them to help us get better?
Setting out on any great pursuit, whether you’re chasing your first million dollar deal or want to be the next great novelist, is like pushing out into the ocean in a solo sailboat. You can go it totally alone, nothing but your wits and your sense of direction to guide you. Or you can go with the charts and maps and lessons given to you by the world’s best and most knowledgeable people to guide you.
Mentorship, both what I call blood-and-coffee mentors and following the work of the Greats as mentors long after they’ve passed on, is essential to having a full understanding of whatever world you want to conquer. There are lots of people out there ready to share their wisdom and expertise with you, but who should you pick?
First Things First
What area do you want mentorship in? Anyone thing you are interested in, running, day trading, golf, has a whole world of people who have committed to excellence in that field and who you can tap to mentor you.
What are you passionate about? What do you think about in the first ten minutes after you get up every day? Beyond food, perhaps an interest in a few more hours of sleep, what comes up first? Chances are that thing is what you’re after, and that’s the thing you should pursue mentorship in. Mentors offer accountability, momentum, and insight into a world you might just be setting your foot into for the first time.
If you aren’t sure what it is you are passionate about, check out our other content on developing Clarity of Vision or What if You Couldn’t Fail. Another avenue you can take if you don’t have a specific idea in mind yet is to find a mentor who can help you in a more rounded, general way, rather than someone with a specific area of expertise.
A life coach, a pastor, an older friend or relative who you admire, someone who you look up to and want to be like. This isn’t just about material measurements like wealth, attractiveness, or success in a field (though those are things to look for in a mentor as well), what people do you see and think to yourself “wow, I want to be like them.” That’s a good mentor to have, especially if they’ve got training in things like personal development or vision casting.
Whether you’ve got a specific area in mind that you want to improve, or whether you’re lost in the wind and need someone to help you find guidance, mentors can help. Let’s break down the two kinds of mentors, blood-and-coffee and the Greats, and look at what’s great about each option (hint: you can do both).
Blood-And-Coffee: People You Know (or Want to Know)
The first type is what most people assume you mean when you talk about mentorship. A real-life blood-and-guts person who is alive, in the room with you, and talking. A lot of people are mentored by their parents off and on, by their religious leader, teacher, etc., but I’m talking about someone you know who you have asked formally to have a mentor-mentee relationship with you. This is someone who knows what that relationship looks like and is willing to invest in you.
How to Find A Mentor
It is important to be pretty choosy when it comes to deciding who should mentor you. It isn’t about success in measurable terms (more on that later), it is more about someone you want to be like. Jeff Goins puts it this way: “Don’t just find someone who has a job you want or a platform that you covet. Find someone that is like you, someone with a similar set of strengths and skills you want to emulate. Otherwise, you’ll just end up frustrated. Spend some time finding the right person. In fact, have several candidates before committing to a single mentor.”
That last bit is exceptionally important: you need to be intentional about who you select to be your mentor. If your grandfather is a horribly lazy dude, prone to bouts of excessive drinking and long rants, spending an hour with him every week discussing your future is going to be a pretty big waste of time. Not that you shouldn’t spend time with family, but don’t ask someone to mentor you if they don’t clearly have something to offer.
What to Look For
Wealth and fame aren’t actually the best indicators of a good mentor. They’re not an indicator, but you don’t need to find someone who makes millions of dollars a day with 500K followers on whatever platform matters to you. Mentors don’t need to have that level of achievement to be valuable teachers, and frankly, those people with high levels of success might not have time or energy for you until you’ve made more progress in the field. Having said that, if you find someone with that level of success who is willing to invest in you? Jump on it.
Pick someone who you know is a good fit, someone with a similar set of skills and strengths. And, vitally important, someone you think you could get along well with as a person. If someone is a genius woodworker, and you really want to be a good woodworker, but they’re a horrific person and trying to get advice from them will be hell, don’t bother.
One of the first things you should do before you get into a scenario where you ask someone to mentor you is familiarize yourself with their work. This might seem obvious, especially in some fields, but asking someone to mentor you without being familiar with their body of work is at best weird and at worst insulting. If they’re a writer, read what they’ve written. If they have videos, make sure you’ve seen them. If they’re a teacher, engage with their subject and resources and figure out what makes them tick.
Knowing someone’s work before you meet with them gives you a huge advantage in winning them over when you do meet. Speaking of meeting:
How (and When) to Ask:
- Don’t ask for the person to “be your mentor” right off the bat. That’s a big ask. Far too big for the first meeting.
- Rather, ask for an initial meeting — something informal, over coffee maybe. Keep it less than an hour.
- Come with questions that you’re prepared to ask, but let the conversation flow relationally. (Note: the formality really depends on the potential mentor’s communication style — something you should be aware of before the initial meeting.)
The big thing to understand about mentors and this stage of the relationship is that being a mentor is work. It costs them time, energy, and resources. So you have to prove to them that you are someone worth investing in. The way you do that is by first, as Goins says, NOT asking them to mentor you right off the bat. If this is someone you’ve known for a while and have some relationship with already, then sure, go ahead and ask. But if this is someone you’ve primarily had an audience-speaker relationship with, whether that’s on stage or in a classroom or as a fan of their published work, you need to get out of that relational dynamic and into one that is more personal.
This is why this type of mentorship is called blood-and-coffee. You take a real-life person you admire and buy them coffee. Now they might be the kind of person who only drinks tea, or weird mineral water, or beer from a warm keg, so be prepared to pivot and meet them where they are. Remember the mentor should need to do as little bending and working as possible, as you’re asking them to give you something you can’t exactly return in any meaningful way.
Find a natural way to engage with them in a fairly casual setting. Asking an author to discuss one of the ideas in their books over coffee is typically going to be a pretty effective way of going about it. No matter the field, people love talking about what they do. If they’re passionate about it (if they aren’t, why the hell are you bothering?), they’ll enjoy a conversation about it with someone who has done the work to be an interesting dialogue partner.
This is where reading and being familiar with their work gives you a huge edge, as it shows them you’ve committed far more than just lip service to admiring them as an expert, you’ve actually engaged with what they’ve made.
It helps immensely to prepare ahead of time, write down a bunch of questions you have about themselves or their work (don’t get super deep or personal, unless they would prefer something like that), and engage at the level you think they’ll want you to. But don’t ask the questions in a big line like an interview, let the conversation move naturally. Having said that, be prepared to have a follow-up question so things don’t seem like they’re fizzling out. It is a little like dating in that way, you’ve got to be able to demonstrate that you’re someone who is fun to be around. Someone worth talking to.
Making the Ask
Okay so now you’ve arrived at the moment where you think you’re ready to ask them to mentor you. How in the world do you ask? In my experience, the best way to do it is to be direct, honest, and a little bit flattering. Not grovely, just acknowledge their excellence and explain why you think they’d be a great mentor for you.
A lot of people think that asking someone to do something like this is a complicated math problem, but most people prefer direct honesty. “I admire your work, who you are as a person, and I think you’re someone I would like to be more like in five years. Would you mentor me?”
If you’ve handled the previous steps well, they’ll probably say yes. Or they’ll say no, and maybe they’ll offer an alternative, someone with more time perhaps. Be open to their response, they might suggest a specific timeline (“I can give you the next six months but then I’m off to Greece for the year”) or ask for something in return, assistance with a project or something. Consider your options, then get nitty gritty with the details.
How often do you meet, are they going to have you read books on the subject and discuss, etc. Let them set the pace, but always be eager and ready to learn.
Mentored by the Greats: How to Benefit from Old Dead Geniuses
Now you can’t sit down with Dr. Martin Luther King Jr. or Winston Churchill to ask questions about leadership, but you can, thanks to the wealth of information available to us about these figures, read their works and letters. In this way, even the Greats of the past can be our mentors, though this sort of thing is best used as a supplement to blood-and-coffee mentorship.
Engage with their Work
Find someone you admire and engage in their work. Many of the great hitmakers of our world have written about it, about how they got there. Autobiographies can be a fascinating insight into the experiences and psychology of the people who changed history.
For people who’ve written a whole wealth of texts, it is important to engage with more than just their most popular works. Beyond their work you can also find interviews they’ve done in a variety of settings, giving you more insight into their philosophy, their mistakes, their intentions, and mindsets.
Hemingway, for example, wrote a little bit about writing in many of his popular works. But in A Moveable Feast, he writes explicitly about the act of writing, about the day-to-day experience of it and even outlines what his daily practice looked like in that time period. As a young writer, this detailed account offered insights that might have taken years to come to naturally.
Look at the Dark Side
But when studying the Greats, it is just as important to delve into their mistakes as it is to understand their triumphs. What flaws did your greatest hero possess? How did those things get in the way of their success? Recognizing the way our most admired figures were human, fallible people not only helps to shape the expectations we place on ourselves but removes blind spots we might otherwise develop.
Again with the Hemingway example, his stark and romantic view of the world was well received by many, but it did not prevent him from a rampant problem with alcohol. In addition to this, he was described by many of his former partners and children as a terrible person, having multiple affairs and ultimately committing suicide at the age of sixty-one. The discipline of writing that he outlined in his work may have produced a bunch of lauded pieces of literature, but his own inability to manage his vices prevented him from having the lifelong success of someone like Stephen King or Maya Angelou. Every single person that can be studied in this way has made tremendous mistakes, and those can teach just as much.
Both are Best
Studying the work, life, and mistakes of the Greats, of the people who made history in our fields, is wonderful for deepening our knowledge base, helping set a trajectory for our career, and in learning tons of tips and tricks to make progress smoother on the road to success. But this does not replace the value of real-world real-life people with knowledge about this moment.
Finding a mentor is a challenging and rewarding task, and it should be approached carefully and with exuberance. After all, you’re only as good as the people who prepared you.
Who are some Old Dead Geniuses I can study?
It depends on your interest, I suppose. Hemingway, I’ve already talked about above. For writers, I’d also suggest Stephen King (not dead per se but this dude is prolific, unbelievable), who has a whole book about writing that I’d highly recommend. Beyond him, there’s Emily Dickenson, who is sort of a complete 180 on what most of us in the writing world would consider a “successful” career.
Viktor Frankel was a child in the Holocaust and went on to study psychology. He wrote a book called Man’s Search for Meaning that is on the favorites shelf of most brilliant people I’ve ever heard speak on the subject of mental health and suffering.
Honestly just google “100 Best ______ of all time” and fill in whatever subject intrigues you. Then see if they wrote any books or did any interviews. Then find biographies about them. The past is a wealth of genius, and barely anyone looks back into it.
How do I find a mentor in my field?
No matter the field of study, there’s going to be some sort of social infrastructure in place for it. Now there are also guards and meritocracies you have to climb, political games to play, to get to the very top of those ladders (it is pretty hard to find Bill Murray’s phone number, in spite of it being the primary method he uses to find movies to perform in).
But you can leverage these networks to find mentorship, that’s one of the primary goals of organizations like the Writer’s Guild and stuff like that. In your city find performing arts organizations, or religious colleges, or science non-profits and ask around. Finding a good mentor is work, but it pays dividends forever so make the effort.