Finding a mentor

People tend to look for mentors who are too far afield. A mentor who’s 20 or 30 years on in their career. I think this is misguided.

I think most are far better off seeking mentorship from someone who’s just a little bit ahead of them. Someone who’s a year or so in front. Someone who just went through what you’re going through, not someone who went through it a decade ago.

So if you’re starting a brand new business, talk to someone who started theirs a year ago. Or if you’re about to sign your first office lease, talk to someone who just signed theirs. Or if you’re about to hire your first employee, get advice from someone with a two-person company, not 200. I think there’s a good chance the advice will be more helpful.

That’s not to say you can’t learn from an expert in their field, or that you shouldn’t trust anyone who’s been there done that years ago, but that I believe most of your advice should be relevant advice. And relevancy benefits from recency. Memories fade and myths form over time – the closer someone is to the actual events you’re asking them about, the more relevant the advice has a chance to be.

Yes, history has much to teach us, but history also has much to trick us. Last week is a better predictor of this week than last decade would be.

9 thoughts on “Finding a mentor

  1. Absolutely agreed Jason. I also believe that people don’t understand that anyone can be a mentor. It’s like coaches I had throughout the years, different coaches can help at different stages. I was a competitive bowler and the coach that initially taught me the basics of timing in the approach and throwing the ball, was a lot different than the coach that I had once reaching the highest levels. The elite coach had won a major championship in the Professional Bowlers Associations, and knew everything about bowling. However, he would have been a waste to start with, all the coaches in between were highly valuable at their time in my development.

    I tried to follow the same idea this year by starting a daily blog targeted at young engineers and developing people skills at

  2. Great insights Jason. I have struggled with this in the past. Not only in professional but also personal mentors. So, in those times of struggle to find relevant mentors, I have looked into other ways to be mentored.

    Maybe to compliment this idea of mentors that have been down the path you’re about to embark on, is finding someone who is also not in your particular field. I’m a developer, but a lot of the people I surround myself with are artists, musicians and other disciplines. It helps me bounce ideas and get different perspectives on things, so I don’t get into a rut and not explore outside the box of development (or whatever else I’m tackling at the time).

    Thanks Jason!

  3. Don’t really agree Jason. I think age is just a number – I find it more helpful to distinguish between good advice and bad advice, regardless of age. What I do find more useful is paying more attention to actual practitioners than theorists.

    1. Not sure that he is talking about age as much as he is talking about where they are in the journey. He is advocating talking to someone that is a few steps ahead in the journey not 20 steps ahead. Also did they take those steps recently or has it been long enough that the landscape has changed?

      I think this is a huge point and one to use as you filter the advice that you get. Not only finding someone that has recently walked the path you desire to take but has a similar outlook/end goal in mind.

    2. This isn’t about age, it’s about situation. To hammer that home, if a 60 year old just started a business last year, I’d encourage a 20 year old who’s starting a business today to speak with that 60 year old. And vice versa. Don’t care about age, I care about situational relevancy.

  4. Agreed. The internet is flooded with “How to Find a Mentor” guides as if it is a job. Finding a mentor should be natural and relevant to your business focus.

  5. I agree, and disagree. Jason’s points are helpful and valid, so there I agree. I have also discovered, however, that sometimes the lessons to be learned, the true “big picture,” doesn’t become clear until years, or decades, down the road, and only then can the “aha” be uttered, and that lesson be conveyed to one being mentored. Having multiple mentors is a good idea.

    1. Dan, I disagree with this:

      >>> “the true ‘big picture’ doesn’t become clear until years, or decades, down the road and only then can the “aha” be uttered, and that lesson be conveyed to one being mentored.”

      Oh sure, it can be uttered then. But it’ll usually be a waste of time.

      For everyone.

      If you were to receive that “big picture” too early in your journey, you wouldn’t be at a place to fully understand or use that knowledge. That big “aha” usually only makes sense in context of the stack of experiences that led up to it.

      Phil Jackson teaching the Triangle Offense to a jr. high school basketball team would just confuse the kids and be a waste of everyone’s time. They don’t have enough experience or skill to put it to use.

      Likewise… asking Mark Cuban to teach you how to scale a multi-million dollar company before you’ve even grown your business large enough to quit your day job and hire employee #1 would just confuse you and waste everyone’s time.

      In jazz music, you gotta learn your scales and chords before you can truly master improvisation. Beginners should find a teacher to help them learn their scales and other fundamentals before trying to study at the knee of one of the masters.

      (Yes, obviously, those are straw man arguments. Hear me out…)

      There is a benefit of listening to the wisdom of those who are many, many paces ahead of you in the journey…

      There would be a benefit for an amazing coach like a Phil Jackson to come and give a masterclass to the local jr high school squad…

      There is a benefit to attending a masterclass by a successful entrepreneur of a huge, well-respected enterprise, even if you’re a beginner…

      There is a benefit to listening to amazing jazz greats even though you’re just learning your instrument…

      Studying the greats in your field does this one important thing for helping you advance in your journey…

      You are forced to raise your gaze.

      You are compelled to realize that there’s something beyond the hill you’re climbing. Beyond this summit, is another, and another, and still another.

      You’re forced to make a choice of whether or not that destination even looks desirable or not.

      The person you’re taking advice from: are they where you’d like to someday be?

      But, don’t be confused: that’s not mentorship.

      That’s just picking your heroes.

      If a beginning trumpet student listens to Miles Davis, Chet Baker or Bud Herseth, they’re not looking for tactics to make learning scales easier. They’re learning a sense of taste. They’re developing a sense of who they’d like to be.

      If a jr high school kid sees Phil Jackson diagram a complex offensive play on a whiteboard, it raises their gaze. They’re forced to decide right then and there if they’d like to, someday, be able to understand and execute a sophisticated play like that. They now know what all those dribbling drills are about, what the layup drills are for. They have a better picture of how it all fits together. They can decide if that looks like a good fit for them.

      If you hear Mark Cuban give a talk or hear him share a story on a podcast about a business situation—even if you’re not in a place in your business to use it—you’re picking up more than just that lesson, more than that tactic. You’re picking up on how he goes about thinking through a hurdle, how he sets goals and motivates his team. You see glimpses of where he is, so you can decide if that’s a path you’d like to be on. If not, you can rethink things, because you’re still early and there’s still time to change.

      Life is too short to mimic the journey of someone who got themselves to a place you’d rather not arrive.

      But, don’t be confused, those aren’t mentors. And the tactics they’re using today won’t be of use to you unless you’re nearly at their level. Any knowledge they can impart upon you is too advanced, or too dated.

      Is there value in aspirational, taste-building, and trajectory-affirming advice from a hero?


      But, for tactics: I agree with Jason. We’re probably better served finding mentors that are closer to where we are in our journey.

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