5 Not-So-Common Tips on Finding and Cultivating a Mentorship
When pursuing excellence in a particular discipline - athletics, business, academics, music, “life” in general, you name it - finding and procuring a mentor to guide and sharpen you is not a nice-to-have. It’s a must-have.
I’m not going to delve into the why of the matter, however, as I believe you already know the why.
Besides, if the one and only Gandalf had mentors during his time on Middle-earth, then you and I both need them during our time on Regular-earth. The equation is simple.
Now, while the why may be simple, the how is a different matter entirely.
Many individuals recognize the supreme value of mentorship, but often feel stymied in their attempts to actually make it happen. This could be due to a variety of factors: lack of direction (“where do I even begin?”), fear of being turned down, or, quite frankly, laziness.
In my own life, while walking down the path of attempting to identify suitable mentors and enter into fruitful relationships with them, I’ve made no small number of mistakes. Fortunately, these mistakes have birthed many valuable lessons and insights which have enabled me to, eventually, experience some pretty amazing and invaluable mentorships that I am forever grateful for.
Here are a few fundamental principles and essential ground rules that I’ve picked up during my own personal journey.
1. It’s not necessary to find the highest-level expert in the field
Say what?
This statement may catch you by surprise. After all, why wouldn’t you want an unrivaled expert in your field of interest to be the very one who personally teaches you, nurtures you, guides you, challenges you during the process of honing a specific skill set or discipline?
There are many answers to that question, but one of the most important is this: they may not be the best teacher.
[As an aside: while mentor and teacher are not synonymous, all mentors are teachers to some degree, which is why I raise this point.]
The interesting thing about true masters of a specific domain, is that they’ve been so deeply intertwined with the subject for so long that the fundamentals, the critical information that a beginner must learn during the early stages of skill acquisition, have become so deeply internalized that these basic principles are now seamlessly integrated into their actions without even having to think about them.
As Josh Waitzkin aptly put it, the foundational steps are no longer consciously considered, but lived.
“Very strong chess players will rarely speak of the fundamentals, but these beacons are the building blocks of their mastery. Similarly, a great pianist or violinist does not think about individual notes, but hits them all perfectly in a virtuoso performance. In fact, thinking about a “C” while playing Beethoven’s 5th Symphony could be a real hitch because the flow might be lost.”
~Josh Waitzkin (8-time national chess champion and Brazilian Jiu-Jitsu black belt)
What’s the point to all that? Well, this can make it very difficult for a well-seasoned maven to dig back down into the depths of their mind, in order to extricate, section out, and then teach the basal yet essential principles they learned long ago but now employ unconsciously.
It’s not that they can’t teach or mentor a student in the ways of their craft, but they may not be able to do so as well as others in the field. There’s a large difference knowing and teaching. For example, I’m sure many of you can recall a prior physics or math teacher, or sport instructor, who may have been brilliant within their craft but yet you had a difficult time learning while under their tutelage.
This concept even carries over to reading books. As I’ve sought to improve my chess game, I’ve actually found it quite helpful to not exclusively buy books written by Grandmasters (the highest achievable title in chess). You would think that a Grandmaster would be the best person to learn chess from, but, for reasons mentioned above, this isn’t always the case. For example, I have found treasure troves of insight within the works of Jeremy Silman, an International Master (one step below Grandmaster) who has built a strong reputation for his ability to teach beginners, despite the very fact that he is not a Grandmaster. It’s his knowledge of the game, in concert with his gift of teaching, that makes him shine, not the standalone fact that he’s a highly ranked chess player.
Ergo, when you seek mentorship from someone: they don’t have to be the absolute best; in fact, it may very well be optimal if they are not. You don’t need to head straight to the tip-top of the skill pyramid. Often you can find someone who is still extremely proficient (way more so than you), who will be able to instruct you and augment your learning process in a manner much more effective than even the “best” within that discipline.
Find a great teacher. Not necessarily the unparalleled expert.
2. Mentorship doesn’t have to be a formal, official arrangement
Probably one of the worst things you could do upon discovering a prospective mentor is to call them up and ask, “Hey, do you want to mentor me?” This is tantamount to you calling and saying, “Hey, do you want to take on an unpaid, part-time job?”
While I’d be remiss to assert that no successful mentorship has ever been started this way, this doesn’t change the fact that it’s still an odd way of asking. Even if they do say yes, it puts them in the awkward position of feeling like they need to plan out regimented meetings and send out a syllabus or something.
Here’s one of the most important things to know about mentors: a mentor is anyone you can learn from, who can impart wisdom upon you, who can directly or indirectly help to guide the decisions you make and actions you take. He or she can be a family member, a coworker, someone you already interact with quite regularly, or perhaps someone you only speak to on a quarterly basis. It also helps to ensure this individual is not a fool.
Some of my best and most fruitful experiences with mentors have risen out of informal relationships. From time to time, usually without it being planned in advance, they’ll provide me with a gem of seminal insight, or a particularly profound nugget of wisdom, which permanently alters my course for the better.
Should some mentorships be formal? Absolutely. But more often than not - at least during the beginning stages - it’s best to just let mentorship “happen.”
Don’t be the weirdo who comes right out and asks for it. That would be like my clumsy, ill-fated attempts to date a few women I fancied back in high school and college; rather than allowing our relationship to nurture and grow for a bit, and giving them subtle yet clear context clues of my interest, I just came straight out and asked, “Hey, would you like to be my girlfriend?”
Yeah, that rarely ended well.
3. Take a break and do something else together
Talk about things and do random crap that don’t at all pertain to your usual subject of study. Enjoy sarcastic banter and making fun of one another; grab a beer together; play a video game or chess; go on a bike ride; travel or go cliff jumping; play a sport; go see a movie or simply take a walk around town.
This accomplishes a couple things. First, it will help you connect to one another as human beings. It’s not rocket science: the more you get to know them, laugh together, and share a broad spectrum of experiences, the more you’ll be able to dismantle any personal barriers that you - often unintentionally - assemble and put up between you and other people. Within the context of mentorship, these personal barriers serve nothing other than to ultimately impede the learning process that could otherwise flourish unhindered between the two of you.
Second, and I can’t overstate this enough: it will nurture your creative processes in a profound way. Oddly enough, remaining singularly fixated on only the subject of study is not the optimal approach, even if your only goal is to learn that specific subject!
Steve Jobs knew this very fact, and summed it up well in an interview with Wired back in 1996:
“A lot of people in our industry haven’t had very diverse experiences. They don’t have enough dots to connect, and they end up with very linear solutions, without a broad perspective on the problem. The broader one’s understanding of the human experience, the better designs we will have.”
~Steve Jobs
Broaden your experiences, not just as an individual but also with your mentor. It may seem like a waste of time, especially if you’re someone who becomes intensely obsessive with that one thing you’re trying to master or accomplish, but it will be more than worth it.
4. Remember they are not infallible beings
When you highly esteem someone, heavily admire their work, and love receiving advice from them, it can be easy to arrive at the subconscious conclusion that this person is without error or character flaws, to elevate them to something of a deity and hang on every word they speak or write as if it were inerrent ideology.
Then, when they inevitably crack (or shatter) the standard of perfection you’ve set for them - say, by making a mistake, or by slighting you in some way - it’s as if the ground crumbles beneath your very feet as the world comes crashing down around you. You either become pissed off at them and write off anything they ever said as fraudulent and worthless, or stew in despair and disbelief because the person who you believed would never mess up or upset you, just did.
Like anything in this world, when you make a good thing into an ultimate thing, it becomes an idol that will eventually enslave you, let you down, or both.
Nobody is perfect, and the privilege of being mentored by someone you highly respect is always an extremely delicate balance of trusting their wisdom and yet continually remembering they are nothing more than human; at the end of the day, they are prone to the very same pitfalls and character flaws as you. If they screw up, or irritate you in some way, just relax. Take a few deep breaths, forgive them, get over it, and get back on course.
5. Your personal network: don’t ignore the power of it, and don’t neglect to broaden it
While the maxim “it’s not what you know, but who you know” may be a cliche, that doesn’t make it untrue.
Everything from crucial internships, to the job I currently hold and love, to incredible opportunities I’ve experienced, to being connected with some crazy awesome and widely-respected mentors, have all been fruit I was able to pluck and enjoy as a result of seeds planted long ago in the form of interpersonal relationships.
This is one of the many reasons it’s imperative not only to refrain from burning bridges, but also to form as many as possible. You just never know how a friend, a prior coworker, or even an acquaintance, may be able to help connect you with a reputable individual who would otherwise be all but inaccessible. You can never have a network that is broad enough.
In fact - and I’m sure I speak for my fellow introverts when I say this - keeping in mind the above sentence is one of the primary tonics that keeps me going during formal social gatherings and conventions. You know, those dreaded events which require one to endure that insufferable affliction otherwise known as small talk. I would rather swallow a live hand grenade than spend a few hours small talking with strangers who I’ll probably never see again. But again, you really never know what may come as a result of it - they may be able to help you, or you may be able to assist them, in remarkable ways.
While by no means exhaustive, I hope the above points provide a small window of clarity into the often cloudy and undefined realm of mentorships.
Agree? Disagree? I’d be curious to hear anything you’ve found helpful, be it with the actual finding of mentors, or nurturing the relationship once it’s already formed.
