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The Secret to 10X Your Career (Find your Mentor)

Deep down we all want a mentor in life.

Frodo had Gandalf. Luke had Obi-Wan. Rey had Luke.

Similarly, we crave the person who can show us the way. The one who will hire us for the job. Make the introduction. Invite us to the table.

Apprenticing ourselves to a master of the craft we’re pursuing is a tradition as old as the written word itself. A few weeks ago, we talked about how to engage informational mentors. I heard from several of you who wanted a deeper dive into the relational side.

Your wish is my command. Let’s go!

Idea - Choose Informational or Relational

Ok. Let’s start by defining what type of mentorship we’re after.

There are two types of mentors: informational and relational.

Informational Mentors

Informational mentors are those who we learn from but are not tied to in an authentic way. Informational mentors are very helpful to our career growth.

These are the mentors we study. Perhaps an author or podcaster. Someone we learn from by watching at a distance as opposed to engaging directly.

Ryan Holiday is an informational mentor of mine.

I’ve read all of Ryan’s books. I’ve learned more than I can recount. I even exchanged emails with him from time to time, but we don’t have a real relationship. He doesn’t know the details of my life and career. He can’t have the context required to speak directly into the situations I’m walking through.

His mentorship to me is exclusively informational.

Relational Mentors

Compare this to a mentor that is forged through a relationship.

Relational mentors are individuals with whom we are engaged in a direct and mutually acknowledged relationship.

Where informational mentors are very helpful; relational mentors are critical to our career growth. 

Gene De Libero is my favorite example of a relational mentor. I’ll get more into this later, but Gene and I have had weekly calls for a decade. He’s well acquainted with my life, career, business, family, etc. He has the context and the relational capital to speak directly into the decisions I’m making, and he’s chosen to invest the time in cultivating a relationship with me.

We have a genuine relationship that is built on trust and mutual admiration. He is a relational mentor.

Strategy - Cultivate Relationships, Not Mentors

Here’s the tricky part about cultivating relational mentors:

You can’t.

At least not in the way you may think. Any mentor worth having is likely approached by many people who are interested in farming their wisdom, talent, and connections to further the interests of the mentee.

As a result, these people will often be wary of over-eager apprentices who want to use to earn certain outcomes. Again, there is almost always a specific reason you are looking for a mentor.

You need the intro. The job. The invite, the money, or whatever.

Mentors can sense this a mile away.

So, you can’t go looking for a relational mentor with the sole purpose of gleaning something. Save that for the informational mentor.

The relational mentor must be built on a genuine relationship.

The key is to find a worthy mentor in a context where you have a genuine access point. This may come in the form of a job, a shared workspace, a neighborhood, a club, or something else entirely.

Once you’ve established some starting point with the mentor, resist every urge you have to extract value. Instead, take a page from Dale Carnegie’s How to Win Friends and Influence People (or at least read a good summary of the book).

Here are the 6 ways to make mentors like you, according to Dale:

3 and 4 are key. Encourage others to talk about themselves. Talk in terms of their interests.

Let me show you how I did it.

Example - My Mentor Gene

I already told you about Gene.

He has been an incredible mentor to me and I value his wisdom and his friendship deeply.

But I didn’t tell you how I came to know him, or any of the benefits he has brought me past his wisdom and friendship. Here’s what happened:

I met Gene when he hired me to work at an agency as a strategist. The first day I walked into the agency, I saw how he interacted with the employees and how people respected him and immediately thought, “This is my guy. I gotta find a way to get close to him.”

So, I did. We went to a couple of meals together where I asked probing questions about his life, career, and family. I asked him all about his various work histories and all of the projects he had built over the years. We began to get close.

Then, he left.

Just a few weeks after we had begun working together. He was gone.

But, I doubled down.

I began calling and checking in with him. Most everyone else at the agency moved on, but I continued to follow up and stay in touch. I offered to help him move. I visited him in person before he left town. We kept talking semi-frequently.

As fate would have it, he hired me again a few years later (that’s two 6-figure jobs for those keeping track at home).

Once again, I pestered him with questions on how he built what he did, his interests outside of work, and the values that drove him to work like he did.

We grew closer.

This time I was the one to leave the agency for greener pastures. Still, I pursued my mentor.

We began monthly calls. They eventually became weekly.

He offered me an opportunity to be a guest speaker at NYU. He offered me freelance writing gigs. He introduced me to job opportunities over the years and encouraged me to explore them even though I never took them.

He poured time, energy, and real value into my life with no clear return to himself. Of course, most of this is purely because he is an excellent human being with a heart to serve others.

But here’s the crazy part: I never asked him to do any of these things.

I never asked for the jobs. I didn’t ask for the intros. I didn’t mention wanting to speak at NYU or to write for one of the publications he managed.

I didn’t have to.

I had spent the time and WORK (as Gene says) on building the relationship to the point where he knew and trusted me. He knows that I would tell him if I wasn’t a good fit for an opportunity he presented (and I have done this - this year in fact!). He knows I value the relationship I have with him well above any short-term return I could get from a job or gig.

That level of mutual trust has been built over the course of a decade on the back of real interest in who he is, what he values, and how I can help him get the things he wants in life.

In return, he’s done the same for me. Without either of us ever having to ask the other even once. THAT is relational mentorship.

Rare? No doubt.
Hard? Certainly.
Worth it? Absolutely.

If you don’t have a relational mentor, I can’t encourage you enough to begin the process of looking for one. It’s a lifelong pursuit that can alter the course of your career and your life. I’m so grateful I found mine.