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The Search for Mentorship in the Modern Digital Age

What is mentorship, really?

As I’ve matured in my life and career, I’ve come to value mentorship much more highly, both from the perspective of mentor and mentee. Ironically I would say that I’ve had very few mentors in my life, and potentially never what I would define (and may endeavor to define in this post) as a true mentor. But, what exactly is mentorship? If we care at all about dictionary definitions, we can look at Webster.

Mentorship: the influence, guidance, or direction given by a mentor

Mentor: a trusted counselor or guide

Now, we could probably be somewhat pedantic about this definition, but I think it’s a decent start for where I’m heading with this post. For fun though, let’s maybe look a bit at the etymology of those words. There are many different sources of truth for etymology right now, but recently I’ve been enjoying Etymonline. Whether or not it’s accurate is beyond my scope of expertise and is left as an exercise for the reader. Feel free to peruse the entry for Mentor at your leisure: https://www.etymonline.com/word/mentor

Here’s a short excerpt:

mentor(n.) “wise adviser, intimate friend who also is a sage counselor,” especially to one who is young or inexperienced … from Greek Mentor, in the Odyssey, the name of the friend of Odysseus and adviser of Telemachus

True Mentorship

I think the big divide, from my perspective, between a casual mentorship relationship and a meaningful one is really just how engaged the Mentor is with the Mentee. Now, this engagement actually runs both ways. As a mentee I’ve commonly had the feeling that the people mentoring me in various situations don’t really care either way about the outcomes for me. Often then are engaging in a form of corporate masturbation designed to enhance their performance eval with a bullet point showing that they were going above and beyond by offering guidance to those with less experience. I have actually managed to get non-negligible value out of these types of relationships, but I would say this is where my personal experience with mentors tends to end.

On the flipside, I’ve been a direct Mentor to people who just were not engaged enough to realistically take advantage of the benefit. As a Mentor, this can be extremely frustrating. I once had someone I was mentoring to try and teach them how to code, after they had reached out to me to ask how to get into the world of software. Being relatively gracious with my time, I offered not only to give them a list of buzzwords to look up, but to even set aside time to meet with them weekly and talk through things. By our fourth meeting they had been late to one and missed another, and on that fourth day they didn’t show up and didn’t even have the courtesy to reach out. I waited on the call for about 15 minutes before jumping off. Later that day I let them know that I would no longer be engaging with them. Crazily enough, this person was upset and did not seem to understand how I could be so annoyed as to break off the mentorship program entirely.

This wasn’t the only time I was annoyed by a lack of energy coming from my Mentees. What I find is that even someone who is engaged, punctual, and eager, often will not put a meaningful amount of effort into the process outside of the meetings. Whether that be reading, learning, working on projects, or some other form of personal effort. They often wish to depend entirely on the 1:1 meetings to make progress, and rarely, if ever, increase the amount of effort being put in even if I directly tell them that their current pace isn’t making the time worth it for either of us.

For my Mentees I go above and beyond. I know first hand that the worst situation to be in is one where expectations for performance are high but the guidelines for meeting the performance bar are either amorphous or non-existent. I don’t just meet with my Mentees, I help them design an entire program for themselves. We come up with the goals, a list of resources to spend time absorbing, and overall structure things so that they are measurable and reflect that person’s goals directly. This often includes writing or voice recording substantial amounts of information to help them make progress. Meaningful mentorship does not look like handing someone a list of resources and offering them your well wishes. It means engaging with them fully, and caring about their success. If the Mentee undermines that by not caring about their own success, it can make things much more difficult.

As a parent I actually think that the parent child relationship is a perfect reflection of this paradox. The difference is that you have to care and stay engaged even if your child is completely unwilling to. I’ve often encountered this issue with my child. I was always quite strong in mathematics, and I tutored people from middle school all the way through college. I always gave up on the kids who didn’t care enough to really try, mostly because you often have such a volume of potential students that it’s not necessary to waste your time on people unwilling to learn. However, when that student is your own child, you must find a way to break through. What I discovered was that I had to make it interesting for my daughter. I knew early on that the best way to make it interesting and exciting was to help her succeed, because I could see her being drawn to other aspects of her life where success was attractive. It can be difficult early on, since you have to find a way to get over that initial hump and start generating those successful moments, and in many ways you are fighting an inertia that may have been building for years. This actually includes a type of inertia present in my own personal psychology, manifesting in a lack of patience and grace.

I think the child-parent analogy for Mentorship is so clear to me because this was something I was missing in my own life. My father was nothing more than the ghost of past traumas. My mother, while wonderful and supportive in many important ways, was medically and mentally debilitated to the point of being unable to offer me what I needed. I was always pushing forward in my own territory, feeling alienated from others. For the majority of my life up to college, teachers were constantly amazed at my performance and really pushing me to succeed. That was wonderful, to a degree, but it turns out that the value there was more about fueling my own internal desires to succeed, not really offering me something tangible on top of that. Certainly in college I didn’t find anything even approaching real mentorship from any of my professors, and I now look back on some of their approaches to teaching as being almost the antithesis of what I think it means to do the job. If I were a professor now, I would view it as my primary responsibility to the students to get them excited and engaged in the field, and more to help them unlearn things they had already taken for granted. Especially in the modern era where (and I’m paraphrasing Alan Kay here) the world of Computer Science is treated more as a vocational school for Enterprise development (C, Java, etc.) than anything else. It’s incredible to look back at past talks by Alan and see him make these same criticisms of even the mighty Stanford, signaling that this is the state of the world and not just a poor experience that I had at a state school. That said, I would certainly hypothesize that the chance of experience a deep and meaningful mentorship increases drastically at high tier colleges and especially as you become a graduate student. To the point where I still consistently find myself thinking that my own most reasonable path forward in life is to go back to school and find this sort of meaningful mentorship for myself.

Self Mentorship

The parent child relationship is also worth holding onto for another reason. I’d like to reflect briefly on a quote from Seneca:

“Every new thing excites the mind, but a mind that seeks truth turns from the new and seeks the old.”

On the day to day we tend to be swept around by whatever is in front of us. Work, family, hobbies, plans, etc. We have habits, rituals, responsibilities, and these things tend to dictate where we spend our energy. Much like the parent-child dynamic, one (the parent) knows what is best for the child in many ways (or at least thinks they do, which in fact may be even more dangerous than be disengaged entirely). The child, despite consistent reminders and redirection from the adult, will likely ignore what’s “best” for them and still follow the shiny. I think we can find this own relationship in ourselves, and philosophy is often an interesting way to experience this. It’s sort of a common trope in philosophy, although I struggle to find a direct quote that fully encapsulates what I’m trying to say. I’ll paraphrase from a few different sources to give it a shot:

Reading philosophy elevates, the mind, bringing you to a higher level of intelligence momentarily. Resist the urge to bring these thoughts immediately back down to the real world, where you’re more likely to apply them to your worldly problem that mine them for the real insights you are after.

The main idea really is that you can have different modes of thinking. In this analogy the day to day is your “child mind”, where you just follow the shiny thing. The elevated mode of thinking is the “parent mind”, where you can plan and hope and design for your own future. In this elevated mode, you can set forth a path that gets you to wherever you want to go, even if that’s just finding a way to uncover clarity about where it is you want to go. Self discovery can itself be a destination, if you so wish. In fact it might be necessary for those of us who spent their formative years not going deep enough into that world. You still can only increase the probability that your “child mind” will actually follow the path, but if you continually make time your can increase that probability to the point where it begins to “proc”. Eventually habit formation will take over, and ideally both mental states will be doing the “right thing” more often.

The point that I’m making is that you can be your own Mentor. Some of us are blessed with parents or other people in our personal lives that can really fill these gaps for us, or at least offer us the means of finding other role models that can be better Mentors. Others may find a deeper connection in a high school teacher, a college professor, a boss, a coworker, or even a friend. For the rest of us, I don’t think we should stop searching for that, but we can also become what we need the most by figuring out what that path looks like more concretely. My deepest relationships as the Mentor always required that I learn new things to help my Mentee achieve their goals. Through this process I learned a lot about defining goals and figuring out what to learn to have the context necessary to help the student, and how to do so efficiently. By doing this for yourself, you can actually achieve much more clarity than with a student, since students often have no idea what it is they really want, other than a general desire for progress and the feeling of forward momentum. And when you are both Mentor and Mentee, you can be sure that both Mentor and Mentee will be fully engaged.

Mentorship in the Modern Era

Another Seneca quote, which I think cuts to the heart of this:

It is not good for you to wander through many authors; you must linger among a limited number of master-thinkers, and digest their works, if you would derive ideas which shall win firm hold in your mind.

Here Seneca is saying simply, find those authors that resonate with you and really dig into their works to try and get all the value you can. Often someone’s collected worked can be read entirely in just a few months of serious study, and you can benefit from a lifetime’s worth of their perspective. I’ve already mentioned him in this post, but Alan Kay is someone who really sticks out for me here. When I am listening to his talks and reading his old essays, I am often in this elevated mode of thinking which helps me begin to clarify my goals and where I want to go. This has led me to really digging into his work, and also to take seriously his own mentors and recommended readings (e.g. McLuhan).

One of the major issues in the modern era is the sheer amount of information available. For example, I put together a list of computer science authors whose work I really wanted to dig into. This list alone is only maybe 20 names, and it’s worth noting that computer science is just a small subset of the things I’m interested in learning more about right now. And yet, just to read the life’s works of these 20 people is somewhere between 12-21 million words (turns out word counts are non-trivial to track exactly if you don’t already have all the sources on hand digitally). For perspective, this year (2025) has been my most productive year as a reader by far. It’s only August 31st, and I’ve read 42 books amounting to nearly 4.2 million words. That’s great progress and actually probably close to p99 (or even higher), meaning I’ve read more words this year than almost everyone else on the planet. And yet, at this pace it would still take me 3-4 years to get through just this list of 20 authors which comprise a small subset of the things I want to learn. If I wanted to diminish this to say a year, then even by most optimistic estimates it might take me 3.5 hours of average daily reading time to accomplish that. It’s completely untenable, which I hope you agree with.

On one hand, you might say “just read a subset of things written by each author”. Sure, but how do you know what subset to read? You could rely on word of mouth, reviews, etc. But then you are offloading the responsibility of determining the value of a piece of writing to other people. That defeats the point in my opinion. Often well regarded pieces of writing are worth reading, but probably the most important part of reading is finding the ideas that everyone else missed, or didn’t understand. This same problem is present in even the selection of which authors to read. How do you really know that an author is worth reading ahead of time? You kind of don’t, until you’ve done the reading. And the same can be said of any particular book or paper, you really have to read the damn thing before you can make a value judgement. Even worse, you can’t just read one or two things to decide if an author is making your shortlist. The first book I read my Nietzsche (The Birth of Tragedy) would have entirely put me off of the author for life if I had used this strategy. In fact I find this to be the most common strategy employed for filtering out authors as well. As Alan Kay (yes, I’m a big fan) has said on multiple occasions, bad books are often as important as good books.

So what’s the solution here? Well, I honestly don’t know. In some ways I think you really do just need to do the reading. However, I’d just caution you to protect your time. It’s your most important investment, after all, and your most limited resource when weighted by value. If someone has figured out a magical equation to determine the list of authors an individual should be interested in, I would love to know. I don’t think algorithms or ML-based recommendation systems do any good here, since they depend entirely on obvious patterns. If we could depend on obvious patterns being a good heuristic, then we could just read the spark notes (or similar summaries) of all the most popular works and move on.

Conclusion

I have a lot more I want to say on this topic. The main premise comes down to, how do we define and find good mentorship, and how do we filter the massive deluge of information coming in? I think these are still unsolved problems, although getting lucky in college or with your career is often helpful. Ironically one of the easiest places to find these type of “trustworthy” Mentors would be something like Youtube in the current era. However, I’d argue that the attention economy is insidious enough to make me wary of every single platform that depends on attention mechanisms.

This is something I’m thinking about a lot, so please reach out if you have some thoughts to share.

References

General Case Studies

Developmental Cascade Studies

Meta-Analyses

Adult Reading Studies

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