Bullish: How to Woo a Mentor or Forge Your Way Without One

I’m always reading that people who have mentors are more successful — and it always make me bristle. Yes, it does sound like a good idea to have a more experienced person who likes and helps you. But it also sort of sounds like … cheating. If someone else has been guiding you the entire time, don’t you get less credit? (Yes, I think you do — but you also get to keep all the money you make.)

Discomfort aside, it obviously can be helpful to have a mentor, even just for the connections. And, of course, it’s not really cheating, any more than it’s “cheating” to learn science from a professor rather than, you know, discovering it all yourself.

Let’s talk about how to get a mentor — and what it might mean if you can’t.

How to Get a Mentor

Many resources on mentoring suggest that you ask around and do some research to find your ideal mentor, and then you simply … ask. As in, “I really admire you for X, Y, and Z. Would you mentor me?”

As you will be engaging in something of a courtship process, culminating in a “proposal,” your dating skills can actually come in handy in obtaining a mentor! (Although in this metaphor you’re sort of the dude.) Play up how much the person will enjoy spending time with you. Use flattery liberally, but not sycophantically. Figure out where the person’s going to be and strategically position yourself to run into him or her. Soon, you’ll be naked together — wait, I mean getting mentored.

Some people take a softer approach. Penelope Trunk suggests that you “build a reputation as an overachiever.” In other words, you need to be an attractive mentee.

Why market yourself? Studies show that the main factor motivating people to donate to charity isn’t the poignancy of the cause — it’s the certainty that their money will have an effect. Mentoring is generally unpaid; mentors want to wisely invest their time and emotional involvement by mentoring those most likely to benefit (and possibly become powerful and useful in the future).

There are numerous formal mentoring programs that a person can sign up for, some of which facilitate the mentoring process with suggestions, schedules, and even contracts. I once signed up with SCORE (the Service Corps of Retired Executives) to get some business advice regarding my failing dot-com. I got a guy who wasn’t actually retired, and seemed to be using SCORE for his own networking (does anyone really retire anymore anyway?) I’m actually kind of skeptical of anyone who just wants to mentor in general (unless it’s mentoring underprivileged kids or something). Don’t you want a mentor who has really important things to do, but agrees to mentor you and only you because you are so awesome?

At the opposite end of the spectrum, your mentor doesn’t necessarily have to know that she’s your mentor. Since I function largely outside the strictures and procedures of a corporate environment, I think if someone directly asked me to be her mentor, I’d be hesitant. A written agreement? Holy shit. Um, no. But if someone kept inviting me to lunch and being a normal friendly acquaintance and asking me questions and then actually taking my advice and telling me that things were working out pretty well, and then one time I hook her up with someone who gives her a big project and she sends me flowers, I mean … I’d catch on.

Whether you pursue a formal or informal arrangement, make sure that you are reciprocating in some way, even if only by providing emotional gratification to your mentor. Of course everyone likes to be looked up to, and thanked when appropriate, but young people often underestimate just how much many older people would like some magical protégé (or protégée) to really appreciate their work, in a way their own children (who rebelled and went off and started a bar in New Zealand and never bothered to read their dad’s whitepapers, etc.) almost certainly don’t.

You may also be able to provide at least some token help in a more direct way — maybe by sending along helpful articles from sources you know your mentor doesn’t read, or by offering computer help, or politely letting your mentor know what all the cool college kids are doing these days, if that’s relevant to your mentor’s business. Even if you really can’t think of anything you can offer your mentor, and you’re in a position where you can’t buy lunch (I’ve been there), at least offer an, “If there’s anything I can ever do for you, please let me know!” Who knows? It’s totally possible that the person who’s giving you free advice might need someone to help organize people into a line at her book signing — something any friendly, reciprocally-minded mentee could do. Maybe you’re not even in the same country as whoever’s helping you out. Still, an “If there’s anything I can ever do…” at least holds out the idea that, if you become very successful in the future, your offer will still be good.

Maybe You Really Want a Board of Advisors

Maybe the idea of having a single, sagelike advisor is, well … a little intense. And if you’ve got a lot going on, it may not be practical (see Bullish: How to Do Many Different Things at Once). You can certainly have a panoply of mentors for a panoply of pursuits.

Many discussions of mentoring reference the idea of a “Board of Advisors”. Can you buy lunch? If so, it’s pretty easy to get a Board of Advisors — maybe one related to money, one related to marketing, one related to your actual field, one related to lifestyle design, etc. Send off four or five emails that go something like, “I really admire [your work in my field]/[how you're so successful while having young children]/[your book]/[how you built a company from the ground up]. Would you let me ask you some questions over lunch? I would really love a chance to spend an hour with you in person.”

While some mentoring arrangements involve written contracts and a perhaps uncomfortable level of intimacy, lunch is easy. After a couple of lunches (and assuming, of course, that you’ve read everything your mentors have ever written), you may not even need those advisors in person; instead, you can simply imagine them, calling up a mental roundtable discussion whenever you need counsel.

How to Seriously Piss Off Your Mentor

If you’ve managed to get someone to mentor you, here’s what NOT to do:

  • Be both needy and ungrateful. Once, a young man sent me a flattering email asking for some advice. I gave the advice! He said “Thanks!” Yay, right? So, given that that was successful, you would think that maybe he could ask for some more advice a month or two later, or ask if he could pick my brain over lunch. Instead, he emailed maybe 48 hours later with more questions — really detailed, specific questions. I answered, somewhat more succinctly. There was no “Thank you” this time. Instead, another barrage of questions. When I reached my breakpoint of annoyance, I simply deleted his last email. You think he’d get the hint, right? Nope. Instead, he re-sent the email. As in, “I emailed you last week with fifteen questions and you didn’t reply. Here are the fifteen questions again.” Unless you are TheOnion’s autistic reporter, there’s no excuse.
  • Ignore a mentor’s advice — and expect continued mentoring. I’ve heard plenty of soured mentors complain about this. When you’re giving your time for free, you at least expect that your contributions will be respected. It’s infuriating when someone patently ignores your advice — and then asks for more. It’s one thing to have to report back “I missed the opportunity”, or even “I was too scared to do it”. But “I decided not to — can I have some more advice now?” is just rude. (If you sincerely disagree, maybe it’s worth a discussion, or maybe you need a new mentor. But you can’t let your mentor feel that she’s pouring resources into a black hole.)
  • Ask any version of the question, “How can I have everything you have right now without the hard work you did?” As in, “Dear famous film director, how can my very first film be even better than your very best one? Thank you very much. Sincerely, Random Film Student.” Need I say more?

Having a Mentor Raises the Bar

This is good or bad, depending.

A lot of people who rave about their mentors just don’t seem to be very impressive people. I’m not sure what’s going on there. Maybe it’s just that most people are not hugely impressive, but when someone claims the support and guidance of a mentor, she’s really raised your expectations of her accomplishments. If you’re the owner of PhotosITakeOfYourDogAtYourHouse.com, that’s cool. But if you then tell me how great your mentor is, I kind of wonder what’s wrong with you that you needed a mentor for that. Not that there’s anything wrong with PhotosITakeOfYourDogAtYourHouse.com (now that I’ve written that twice, the name is kind of growing on me), but, you know, being a freelancer offering a service with little overhead just isn’t all that hard. If you have an amazing mentor, I want to see the school you’ve built in Haiti.

So, if a mentor agrees to invest time in you, you’re really going to have to step it up. Plenty of perfectly valid life choices seem a little slack once you’ve had “help.” If raising the bar on yourself seems like a great way to get motivated, well, there you go.

When Your Mentor Doesn’t Exist

This column came about when a friend complained that she couldn’t find anyone to give her advice about something both incredibly impressive and incredibly specific. As in, “I just don’t know the next step in establishing a nonprofit male modeling agency and holding star-studded benefit galas for wealthy, cougaresque Upper West Side women in order to funnel the money to help recovering child soldiers in Liberia, some of whom will then be recruited for my modeling agency.”

I tried to be supportive. “Well,” I said, “You do know a very famous person in the modeling industry who helps you with things.” She nodded. “And you do know several important people in the nonprofit world. And your intern is a former child soldier from Liberia.”

Obviously, I have fictionalized this scenario, but she had to agree. Yet, as we all do, she wanted someone who had specific answers to her very specific problems, delivered with calm certainty and resolve. “No one can do that but you,” I said.

If you have a mentor who has already done everything you want to do, you might just be unimaginative. If you can find someone who’s a perfect match, then you’re doing something that’s been done before. That’s great if your mentor is Stephen Hawking, Joan Didion, or some other luminary whose contributions you can only hope to match. But maybe a “perfect match” isn’t so great if your mentor is just a nice person who’s pretty successful.

Alternately, if you can’t find a mentor and can’t even imagine who that person might be, you’re either doing something very stupid or very awesome. (See Bullish: When to Make Massive and Ballsy Life Changes for Your Career.) Also, some people are too hungry for a mentor because they’re just weak.

I tutor students all the time who “ask too soon” — they read a math problem and immediately ask, “Okay, do I multiply or divide?” (Figuring that out is kind of the point!) After a few sessions, they realize the Socratic force they’re up against: “What are the verbal cues in the problem that tell us which operation to do?” I make them figure it out themselves, of course. (Interestingly, those who “ask too soon” are disproportionately pretty girls, since they are the segment of society least penalized for acting like twits. See Bullish: What to Do About Being [Temporarily] Pretty.) There’s value in figuring it out yourself. Many people “ask too soon.”

My friend most definitely does not have that problem (she’s got huge unicorn balls), but I’m pretty sure that working it all out for herself, messes and all, will make her a far more formidable force five years down the road.

In-person relationships may also simply not be the best way to convey information and guidance, Personally, I’m a tremendous introvert. This doesn’t mean I dislike people; far from it. My life’s work is helping people (or giving whatever I can in the attempt). I like exercising around other exercising people (but not talking to them), or reading a book in a cafe around other people (but only talking to the waiter). To me, outside of a few intimate associates, people are best experienced through their work. Sitting near people in a cafe creates a certain ambiance, but I only have so long to be alive; there’s no time for an awful lot of people’s jabbering when you can instead turn your attention to thoughts that have been winnowed, cultivated, and organized with care.

I think about this every time I see some fabulously unnecessary feature on a building built a hundred years ago. I think, Look at your flair, you crazy architect! Put me in a room with that guy, and it would be awkward; show me a surprising flying buttress, and we have had a sublime human moment.

What I’m getting at is that a lot of people who seem like they might be great mentors (except that they’re inaccessible, or dead) have actually already given you the best of themselves: that’s why they write, or build companies, or make art. The rest is made up of details that may or may not apply to you, irrelevant quirks, and disappointing human foibles.

When I was in high school, I decided I was going to write a book about role models for atheists. Some of these role models would be historical figures, and some would be fictional. One of them would be Jean-Luc Picard of Star Trek: The Next Generation. The book would be called “There’s a Klingon in my Pantheon.” It’s best for all of us that this book was never written.

But back to Captain Picard. I’m not sure a real-life role model could compete; I’ll bet I’m really communing with the very best parts of some idealistic writers, and some excellent parts of actor Patrick Stewart. From Wikipedia:

Depicted as deeply moral, highly logical, and cerebral, Picard is a master of diplomacy and debate who resolves seemingly intractable issues between multiple parties. Though such resolutions are usually peaceful, Picard is also shown using his remarkable tactical skills in situations when it is required. Picard has a fondness for detective stories, Shakespeare, and horseback riding. He is frequently shown drinking “tea, Earl Grey, hot” and issuing his famous taglines “Engage” (when going to warp) and “Make it so” (when giving an order).

What else do you even need to know?! Oh, and “he invented a starship evade & attack tactic that would become known as the Picard Maneuver.” Are you not aroused?

Maybe if you can’t find a mentor — or you feel mentored by ideas, fictional characters, or human culture itself — you’re doing something right.

Engage! (That was cheesy, but seriously, how else could I end this thing? Make it so!)

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    • Pippa

      You already kind of are a mentor with this column, though. Actually, I might as well tell you that taking your advice got me my dream job. I teach ESL in foreign countries and I do this because I’m a language whore, and I found a school that was a full on language school, not just an English school, and I’d have an opportunity to teach languages other than English and thus practice them. I did the whole cover letter and resume and interview thing, but I couldn’t fly in to do an in-person interview. I was going to just cross my fingers and rest on my laurels. After reading a couple of your columns I realized that it was stupid and I should go the extra mile to get what I really wanted, so I sent writing samples and made a youtube channel of me teaching so they could see me, which is what they wanted with the in-person interview anyways. When they hired me they told me those were the exact moves that got me hired. So thanks, online mentor!

      • Jen Dziura

        That is an incredible story! Congratulations! If there’s a Bullish book, I hope to compile a chapter of exactly this sort of story. Well played!

    • Megan

      Please let there be a Bullish book!

    • Renee

      I just spent an hour reading through this column and each post was better than the previous one! This one really struck a chord in me – I’m 30 and still looking for a mentor that probably doesn’t exist. Thank you.