The Struggle to Find Mentors

Looking back, I can find a dozen or so moments where I made a choice that took my career, my life, and my happiness in a slightly wrong direction. Yet, when I look back at those moments, I can confidently say that the decisions I made were the best, given the information I knew at that time.

The problem with wrong decisions is that you can only retrospectively see it as a mistake. We never purposefully make a decision that is wrong, but we discover it’s wrong when we zoom out a little and understand the greater context of the situation. I don’t think wrong decisions are about a lack of good judgement, but rather a lack of awareness of this greater context.

I am young, optimistic, and trying to move at a million miles per hour. I make decisions every day regarding my future, but am I best equipped to do so? Each year I strive to be wiser and understand more of the world, but I only have 24 hours in day, and maybe 85 years on this earth (though maybe I’ll have longer?). Trying to not repeat the mistakes of those who came before me seems to be a pretty futile task.

For us to be wiser and move society forward, a solo pursuit of exploration and knowledge isn’t enough; we must learn from those who have come before us in order to better understand the context of the world to make better decisions for ourselves and our communities.

If I want to make an outstanding impact on the world, relying solely on my own observations over my lifetime isn’t enough. Instead, I have to seek the wisdom of generations before and combine it with my own vision of the future.

Mentors are like a wide-angled lens for your life, helping you see what’s just outside of the frame.


Podcasts suck for life-guidance. I listen to probably 10 hours of podcasts a week, seeking out the secret silver bullets, the shortcuts in life. Yet, only a sliver of the advice seem to directly apply to me in that moment. These TED talks are sometimes useful, but the information they supply is designed to apply to as many people as possible. The lessons are meant to be universal, so that everyone can resonate with the message. Still, it often feels as though the majority of the lessons, I have to file away for the future ‘just-in-case’ information. Over the past couple of years, I’ve realized that the thing I need is a strong mentor. A mentor will understand the unique challenges that I face, and tailor advice to particularly suit what I need. Instead of seeking a one-size-fits-all approach to advice, I need nuance.


For a long time, I’ve understood the importance of having a mentor, without really doing anything about it. I saw it as one of those ‘nice-to-haves’ rather than essential. More and more, I’m starting to understand the urgency of having one.

With the doors a mentor can open for you, the guidance that they can give you, while it’s a ‘nice-to-have’ its one of the first you should focus on. A mentor is kind of like automating your savings. You don’t have to do it, but putting in the effort early will set up compounding wealth in the long term.

The late and great Warren Bennis, a former professor of mine and role model, knew about the power of mentorship. A generous mentor himself, he believed that a mentor has a great responsibility. When a mentor vouches for you, s/he is giving you a piece of their reputation to uphold. A mentor/mentee relationship is one fundamentally where trust has to be a strong bind between the two.

I used to be a big believer that the best experience is one in which you learn your own lesson. I think that every situation is unique. Every past situation has led to a particularly unique problem that only you are suited to solve. However, as I get older and see more of the world, I’m learning that these problems are the same, fundamentally, but perhaps with a slightly different shade. Time is short, and instead of reinventing the wheel, it’d be smart for me to get the perspective of someone that has seen this before. If I look at all the major mistakes in my young career thus far, I think I may have made other decisions if I had a strong mentor to help me see a broader context of the decision.

I’m a little embarrased, frankly, that it took me this long to realize that I needed one. For someone that is as passionately focused on my personal growth, I neglected this clear step in my development.

Digging deeper, I think it took this long for a couple reasons.

  1. I have an ego

Whenever an issue comes up, I think that it is unique to me. I’m a unique snowflake so any advice I might get from a mentor is likely not going to be as good as my own judgment.

2. I have a weird insecurity with interacting with people that are much smarter/powerful than me.

Perhaps I can blame it on some ingrained Japanese mindset of deferring and honoring your elders, but I often catch myself thinking that smart/powerful people would be too busy to help me, and I shouldn’t bother them.

So why look for a mentor now?

Part of it was reading Lessons From My 20's, by Ryan Allis, a massive 1286 slide presentation, with a great portion on creating your inner circle and mentors. As I started a new job, and took the time to redefine my life and scope out how I wanted it to be, I realized that I needed to prioritize mentors.

I knew that the first step, was to understand what I was looking for.


I think it’s helpful to distinguish between a mentor, and an admired peer. There are many people in my life that I admire that are probably 5–7 years older than me. It’s easier to find those people — you’re from the same generation, and it’s easier to relate because you often are in similar stages in life.

I think it’s valuable to have a set of admired peers, those anywhere from 3–7 years older than you, so you can have a clear idea of what the next step is in your life. However, I think it’s also important to have mentors in your life that are closer to 10–15 years older than you. It’s not only important to see what the next stepping stone is for your life, it’s also important to see what’s two jumps ahead.

I’m looking for one or two people that are about 10–15 years ahead of me in my life, willing to meet with me at least once a month to talk about my life and career, and provide some advice and guidance.

These mentors should essentially be who I might want to be in 10–15 years.

While I’m still flexible and open to meeting many different types of people, I think it’s important that this mentor must be like the following:

  • Brilliant and caring
  • Balancing family and friends with work
  • Giving back to the community through some non-profit work
  • Entrepreneurial
  • Values lifelong learning and development

I know that there are several people out there that fit this image, but the next step is finding one. Easier said than done. This is my game plan.

  1. Create an easy way to keep a list of people to research more. I use Asana for everything — including important notes. When I read about someone that I think might meet the above criteria, I’ll add their name to do more research on later.
  2. Expand the communities that I’m a part of. By participating in organizations that attract the kind of mentors that I’m interested in, I’m more likely to find a mentor that would make sense for me.
  3. Write a blog post. To help clarify my thoughts, and to leave a vehicle for mentors to find me.

Sweet. Already 1/3rd of the way done with finding a mentor.


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