Where’s Waldo?

Updated: Apr 18

This article is from Jer McKoy, who is an action officer on the Joint Staff in the Pentagon. His fourteen years of Air Force service focus on analysis and technology, and in his current role he analyzes strategic issues and evaluates future capabilities as a solutions architect and product manager. Here he asks a seemingly obvious, yet not so obvious question about seeking mentorship.


Were a prosecutor to put me on the stand today, I doubt any defense would suffice.


I had every opportunity, she would say, so many moments, an unlimited number of opportunities. Who am I to disagree? There is no defense against this complete oversight on my part, after all, the expectations were clearly communicated and the necessary resources readily available.


Why, then, did I fail so spectacularly?


To understand that I went back to a series of books many read as a kid: Where’s Waldo?, a visual puzzle book that forever imprinted horizontal red-and-white stripes with a stress response.


In this series, the eponymous subject struts his stuff in singular style all around the world, from beaches to carnivals to mundane street scenes. As a reader, perhaps as young as three years old, the challenge is identifying the unique features of Waldo among the many similar and overwhelming aspects of the illustrated scenes.


Why red-and-white stripes are so popular in his life and travels is a question many have asked, but it never helped them solve the puzzle. I still vividly remember checking out a new copy from the local library and launching straight away into the fray, only to expend my youthful attention span on the first, second, and third panels before giving up in frustration to go play make-believe Peter Pan.


There is little chance I would have passed the marshmallow test, which Stanford professor Walter Mischel devised in the 1970s to evaluate the effects of willpower by juxtaposing a small, immediate reward with a far greater treat after a period of waiting. While the original goal of using results as predictive indicators of long-term success has since been debunked, my childhood impatience remains a fact.


This is where we turn to mentorship, because, it turns out, mentors are a little bit like our friend Waldo: you know they are out there, and there are plenty of resources to help you find one, but when you are in the midst of searching there are so many distractions.


Some individuals may seem like obvious examples, say a boss or outstanding performer on the team. They do not always have the bandwidth or interest, and personalities have to match as well if the relationship is going to last. There may be other options as well, like formal mentoring programs or online groups, and these have a lot of potential for good if used well. Even informal social contacts from social media can become mentors, which is where much of the military writing scene has had a tremendous impact.


For my part, I never wanted a mentor in the first place.


Every work instance where the word “mentoring” came to my ears or inbox imbued in me a resistance to the term. Why was my mentor supposed to be my supervisor? They did not think like me or want the same results out of life. And is it really fair for me to have to seek out a mentor just to comply with an institutional requirement that people be mentored? I was skeptical and largely avoided the subject altogether.


My problem of finding Waldo doubled because I chose to fade into the noise as well.


The irony in all of this is that I have a tremendous appetite for personal growth, which would seem to align very well with the idea of mentorship. For someone who reads and tries to learn about ways to improve as a person, it is comical that I ignored one of the most accessible means of receiving feedback and making structured progress.


This brings us back to the courtroom and my indefensible position before the prosecutor.


No, there is no actual court, that was just a hook to get you to read this far, but maybe you are a bit like me and that little voice will pop up in the back of your mind with stinging accusations.


You should have tried harder... You could have done better... You are not enough...


This kind of internal dialog can be crippling if you fail to reign it in, which is something you may have experienced during some sort of teambuilding challenge or assessment process already. If not, may I commend to you the value of experience stress that raises these to the surface, as we all have some version of this prosecutor in our heads.


It was actually in the process of personal development that I finally found my reason for seeking out mentors. I started volunteering with a non-profit whose culture and mission resonated strongly with me. The startup vibe was energizing, and we had major challenges to tackle that seemingly put the whole organization on the line. I had no idea what I was doing and it was amazing.


After a couple of years, though, the energy was different. I was still excited, but also frustrated, and many other people were frustrated with me. I could not figure out what was going on, and a few of my teammates were kind enough to share their thoughts.


Turns out I was turning into a really toxic member of the team.


Even today I am still working through how that change came about, but it immediately struck home that I was ill-prepared to tackle the challenges of the task. None of my books provided the necessary knowledge to surmount the obstacle of myself. No previous experience with a winning matched how this felt.


I needed a mentor, someone who could help me reorient and connect with other resources, like a coach and helpful material to learn and apply new skills.


You may not be in the situation I found myself in. Perhaps you are very willing to find a mentor and just struggle to make the time. Maybe you have some rough edges, but have not been placed under sufficient pressure for them to come out and hurt others in ways that leave you wondering how.


Regardless of your situation, please consider taking a few minutes to connect with someone about this topic. I promise you will not regret the investment, and many others later may benefit from that bold step.


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