Where are the mentors?
You probably can't be a full-time apprentice, but here's how people find mentors
On a Friday morning in September, I rang the doorbell at Orbit Media Studios and announced that I was ready for Andy’s office hours. An impressively bearded fellow asked “is he expecting you,” and that’s when I realized I’d made a mistake.
Here I was, 22 years old in my first job out of college. I’d recently attended Andy Crestodina’s conference Content Jam, and wanted to learn more. In Andy’s session, he shared that he held office hours every Friday at 8:30am, and I — again, fresh out of college — thought that meant that if you showed up, Andy would talk to you.
Was Andy expecting me? Of course not. But I couldn’t say that, so I said “umm...I’m not sure,” and sat with my notebook in the waiting area, to be shown back to the office.
Andy very graciously agreed to speak with me. I pulled out my list of questions. I can’t remember all of them now, but I know the first one was related to the emerging trend of “shows” vs SEO in content marketing. After about 15 minutes, Andy’s actual appointment arrived, but he showed me where to book his office hours online (so he could, ya know, expect me), and told me about a monthly meetup he ran at The Long Room, a bar down the street.
That was five years ago. Andy has since given me wonderful feedback on writing and side projects, made several introductions, and connected me to the first person I spoke with at my current company. I went to Long Room meetups every month for two years, and even after that would show up when the stars aligned. A couple of years ago I wrote an SEO-themed Shakespearean sonnet for his birthday.
Andy has shifted away from office hours, but when they were available I recommended them on many occasions. It always amazed me how few people jumped at the opportunity — 30 free minutes with a 20-year content marketing veteran.
I think it’s because a lot of people have strange ideas about mentorship.
The word “mentor” has come into vogue recently. I hear people reference “conversations with my mentor,” or ask about how to find a mentor, and I’m struck by how little those conversations resemble my experience and the other relationships I’ve observed.
Andy has undoubtedly been one of my mentors, and I’m sure he’s a mentor to many others. But the mentor-mentee relationship doesn’t have much in common with the image I had in my head coming out of college.
Mentorships aren’t like old master-apprentice relationships. So what is a mentor?
Recently I got tagged in a Facebook post on my college’s alumni networking page. Someone was looking for expertise in “content marketing, digital marketing, SEO, PPC, social media, and email marketing,” and a friend tagged me as a person who might be able to answer questions.
I always have time for fellow alumni, so I invited the person to DM me and was ready to schedule a conversation.
A quick look at their profile showed that they were one of those “oh yeah I think that they look familiar” types. We’d graduated the same year, but had never spoken much (which is saying something in a graduating class of ~400). Editor’s note that makes this point: I’m editing this draft, which is from 34 days ago, before publishing, and have realized that I don’t remember the person’s name.
The DM came a week later. In a podcast interview I did with Jimmy Daly, I share the story of my career, and I like to send it over before informational interviews because it answers the most common questions before we get on the phone. With the link came an invitation to set up time to chat.
A few days later I got this message:
“Hey! I found a mentor who lives in my area, but I’d love to reach out to you in the future if I have a specific problem.”
Cool, sounds good. I save 30 minutes. But thinking about this message is the inspiration for what you’re reading right now. The idea underlying this note is “I found a mentor already, so I don’t need you to be my mentor anymore.”
And I don’t think that’s how mentorship works.
1. Before I had mentors, I imagined that mentorship was like the master-apprentice relationship you see in movies. Everything you do is supervised by someone, and you have to blacksmith these 5,000 iron nails before you graduate to journeyman and work on 5,000 wagon wheels. Hmm, maybe wagon wheels is a wainwright? Whatever, swords then. I don’t know anything about blacksmithing.
In an office job, you aren’t likely to have that structured of a relationship. Even if your mentor is your boss, or someone else at the company, you may not interact with them everyday, and it’s likely that you have quite a bit of freedom.
2. Also, you can have more than one mentor. I’ve had many people I’d consider mentors, of various degrees of involvement, and I’ve learned from each of them. Especially as my career has advanced and the work I do daily has changed, the type of mentorship I need has changed too.
3. A mentor is not your therapist. There are some mentors you’ll wind up close to, and they’ll learn more about your life over time — eventually they can ask how your brother is doing or if your cat did anything funny over the weekend, but the relationship (like most relationships) doesn’t start there. In the early days, a mentor doesn’t need to know all the details; just the info that’s relevant to your questions.
Shoutout to my friends Bridget and Sara, who talked about this in an episode of their podcast Self Control & Cheese.
For most people, mentors are their managers or former managers. For some, mentors are experts who noticed their work, or influencers they reached out to, or friends who aren’t really much farther ahead in their careers but see the world in a different way.
Mentors (I’m typing this word so much that every time it almost comes out “mentos”) change over time. If you want to be an executive, it’s good to have executive mentors — but you might need to have manager-level mentors first, because they’ll be closer to what you experience day to day.
If you are a “well-mentored” person, it means that you always have someone to ask your questions — even if you have different people you go to for different types of questions. It also means you have people who can point out what you should be doing, and who answers the questions that you didn’t know to ask. Probably you still spend most of your time not interacting with your mentors.
How do you find those people?
Before you find a mentor, what can a mentor give you?
Today, Dave Chappelle is a comedy giant who many consider the greatest of all time. But in 1993 he had just earned his first-ever movie role, in the Mel Brooks film Robin Hood Men In Tights.
Here’s how Dave Chappelle describes working with Mel Brooks.
“He used to have me come sit next to him when he was directing sometimes. And kinda show me what he was doing, what kind of decisions he had to make. What shots he liked and why. Invaluable information. It’s like you get a glimpse in the mind of genius. You’re 19 years old man, how many kids in college who go to film school can say they learned directly from Mel Brooks.”
Sounds like mentorship, right?
The interesting part of Dave’s quote is what he chooses to highlight. “What decisions he had to make. What shots he liked and why.”
This is what mentors give you that’s hard to learn anywhere else.
Especially in the Information Age, you can learn pretty much anything. Courses, books, articles, documentaries, podcasts, webinars, newsletters, Substacks; there’s more information than ever. And when it comes to the nuts and bolts of hard skills, self-study or schooling is the most efficient way to get it done.
What’s difficult to learn is the decision-making that only experts make — because many decisions are choices that only experts can see.
Every so often I’ll bring a situation to my CMO at ActiveCampaign, Maria Pergolino. And she’ll say “wait, why aren’t you looking at [insert option I’d never consider in a thousand years but is obviously right].”
And I’ll say “ugh I hate you, why are you always right.”
The decision researcher Gary Klein has studied how experts choose a course of action in high pressure situations, sometimes diagnosing, deciding, and acting in under a minute. You may know his research from the “escape fire” story in Malcolm Gladwell’s Blink, where an experienced wildfire fighter escaped a blaze by lighting the grass around him with a match, so that the wildfire had nothing to burn and simply passed over.
For Klein (more research in his books Sources of Power and Seeing What Others Don’t), this is expertise. Expertise isn’t the ability to make the best decision between multiple courses of action — it’s the ability to recognize what’s important in a situation and “see” the solution. Klein’s research, which created a model he calls Recognition-Primed Decision Making (RPD), shows that experts don’t consider multiple paths at all. In fact, that’s what novices do. An expert quickly latches on to a reasonable course of action; a novice has trouble identifying what’s important, so they deliberate (and don’t reach better outcomes).
When Dave Chappelle watches Mel Brooks make decisions or I say “ugh I hate you” to my CMO, we are learning to see.
Mentors can teach you some skills that are hard to find elsewhere, and may be able to make introductions that help you build the right network.
But decision-making is the key value of a mentor. A mentor is someone who can teach you to see your field better, because they can already recognize the patterns you’re missing. When you look for a mentor, this is what you want to find.
Alright alright alright, so how do I find one of these mentor things?
Two ways to find a mentor:
Work with them directly (at your job or side projects)
Do great work and then put yourself in front of them
One way to not find a mentor:
Ask “will you be my mentor”
The best way to be mentored is to work with someone on a daily basis. Look for a job with a boss (or boss’ boss) who really, really gets it.
If you can’t get that, volunteer at non-profits, help an influencer’s side project — get yourself in the proximity of people who can mentor you. If your work is good enough to be noticed, they’ll start to comment on it. And that’s how you’ll learn.
How do I know if my new boss gets it? How do I find these side projects and opportunities? Those are topics for another time, but the people most likely to get mentors find some way to figure that out — even if their methods take them off the beaten path.
The alternative to working with someone every day is to do incredible work and make sure it gets in front of important people.
Remember Mel Brooks? He may have mentored Dave Chappelle, but before that he was mentored by none other than Alfred Hitchcock (!).
When Mel Brooks set out to parody Hitchcock films in High Anxiety, he met with Alfred Hitchcock himself (“Al”) every Friday. Hitchcock would chime in, suggested jokes, and ultimately sent Mel a $25,000 bottle of wine after seeing the film.
There are a few interviews of Mel Brooks talking about Hitchcock, including this one with an entertaining dinner story.
Did watching this clip while editing send me down a rabbit hole of hilarious Mel Brooks interviews when I should really be going to bed? Yeah, of course it did.
In one interview that I can’t seem to track down (but will let you know if I find it), Mel talks about when they first met. How nervous he was. How intimidated to be facing someone he viewed as the greatest filmmaker of all time. All full of nerves, until Hitchcock set him at ease by saying “At the end of Blazing Saddles you had a horde of cowboys break through a soundstage into a dance rehearsal, then run down the street to watch their own movie. That’s when I knew I had to meet you.”
We can’t all be Mel Brooks, but the lesson is clear. If you’re looking for mentorship, start nearby, at work. Do all the networking that people recommend, reach out, follow-up, take the calls.
But great mentors want to mentor great mentees. The work is important. Before you reach out, make Hedy Lamarr storm through a set with some rampaging cowboys, and then Alfred Hitchcock will want to meet you.
Oh, oops. It’s Hedley.
It's awesome to read- just loved it