I’ve been reflecting recently on things I like to do. Of course I like creating things, figuring things out, and so on. But something else I like—that I don’t believe I’ve ever written about before—is mentoring. I’ve been doing it a shockingly long time: my first memories of it date from before I was 10 years old, 50 years ago. Somehow I always ended up being the one giving lots of advice—first to kids my own age, then also to ones somewhat younger, or older, and later to all sorts of people.

I was in England recently, and ran into someone I’d known as a kid nearly 50 years ago—and hadn’t seen since. He’s had a fascinating and successful career, but was kind enough to say that my interactions and advice to him nearly 50 years ago had really been important to him. Of course it’s nice to hear things like that—but as I reflect on it, I realize that mentoring is something I find fulfilling, whether or not I end up knowing that whatever seeds I’ve sown germinate (though, to be clear, I do find it fascinating to see what happens).

Mentoring is not like teaching. It’s something much more individual and personal. It’s about answering the specific “What should I do about X?” questions, and the general “What should I do given who I am?” questions. I’ve always been interested in people—which has been a great asset in identifying and leading people at my company all these years. It’s also what’s gotten me in recent years to write historical biography, and, sadly, to write a rather large number of obituaries.

But there’s something particularly fulfilling to me about mentoring, and about helping and changing outcomes, one person at a time. These days, there are two main populations I end up mentoring: CEOs, and kids. At some level, they’re totally different. But at some level, they’re surprisingly similar.

I like learning things, and I like solving problems. And in the mentoring I do, I’m always doing both these things. I’m hearing—often in quite a lot of detail—about different kinds of situations. And I’m trying to use my skills at problem solving to work out what to do. The constraint is always what is right for this particular person, and what is possible given the world as it is. But it’s so satisfying when one figures it out.

“Have you ever thought of X?” Sometimes, there’ll be an immediate “Oh, that’s a good idea” response. Sometimes one will be told a host of reasons why it can’t work—and then it’s a matter of picking through which objections are real, where all that’s needed is encouragement, and where there are other problems to be solved.

Sometimes my mentoring ends up being about things that have immediate effects on the world, like major strategy decisions for significant companies. Sometimes my mentoring is about things that are—for now—completely invisible to the world, like whether a kid should study this or that.

I tend to find mentoring the most interesting when it’s dealing with things I’ve never dealt with before. Maybe they’re things that are genuinely new in the world—like new situations in the technology industry. Or maybe they’re things that are just new to me, because I’ve never experienced or encountered that particular corner of human experience, or the world.

One thing that’s in common between CEOs and kids is that at some level they tend to be in “anything is possible” situations: they have a wide range of choices they can make about how to lead their companies, or their lives. And they also tend to want to think about the future—and about where they might go.

To be fair, there are both CEOs and kids where I wouldn’t be a particularly useful mentor. And most often that’s when they’re somehow already on some definite track, and where their next several years are largely determined. (Say just following a particular business plan, or a particular educational program.)

In the case of CEO mentoring, there’s a tendency for there to be quite long periods where not much happens, interspersed by the occasional urgent crises—deals to do or not, PR emergencies, personnel meltdowns, etc. (And, yes, those calls can come in at the most awkward times, making me glad that when I’m pushing other things aside, at least I can say to myself that I’m typically an official company advisor too, usually with a little equity in the company.)

With kids, things usually tend to be less urgent, and it’s more a matter of repeated interactions, gradually showing a direction, or working through issues. Sometimes—and this applies to CEOs as well—the issues are exogenous, and relate to situations in the world. Sometimes they’re endogenous, and they’re about how someone is motivated, or thinks about themselves or their place in the world.

I’ve found that the kids I find it most interesting to mentor fall into two categories. The first are the seriously precocious kids who are already starting to launch in high-flying directions. And the second are kids who aren’t connected to the high-flying world, and may be in difficult circumstances, but who somehow have some kind of spark that interactions with me can help nurture.

I’ve done a fair amount of traveling around the world in recent years (often with one or more of my own kids). And I always find it interesting to visit schools. (Research universities tend to seem similar all over the world, but as one gets to high schools and below, there are more and more obvious—and interesting—differences.) Usually I’ll give talks and have discussions with students. And there’s a pattern that’s repeated over and over again. At the end of an event, one or two students will come up to me and start an interesting conversation, and eventually I’ll hand them a business card and say: “If you ever want to chat more, send me mail”.

And, yes, the ones I hear from are a very self-selected set. Typically I’ll do an initial phone call to learn more about them. And if it seems like I can be useful, I’ll say, “Let me put you on my list of people I’ll call when I have time”.

I have a busy life, and I like to be as productive as possible. But there are always scraps of time when I’m not doing what I usually do. Maybe I’ll be driving from here to there at a time when there’s no useful meeting I can do. Maybe I’ll be procrastinating starting something because I’m not quite in the right frame of mind. And at those kinds of times it’s great to do a mentoring phone call. Because even if I’m hearing about all sorts of problems, I always find it energizing.

With CEOs, the problems can be big and sophisticated. With kids one might at first assume they’d be too familiar and low-level to be interesting. But at least for me, that’s not the case. Sometimes it’s that I started my career sufficiently early that I never personally encountered that kind of problem. Sometimes it’s that the problems are ones that newly exist only in recent years.

And particularly for kids in difficult circumstances, it’s often that with my particular trajectory in life I’ve just never been exposed to those kinds of problems. Sometimes I’m quite embarrassed at how clueless I am about some economic or social hardship a kid tells me about. But I’ll ask lots of questions—and often I’m quite proud of the solutions I’ll come up with.

I have to say that in modern times, it’s disappointing how difficult it tends to be for someone like me to reach kids who aren’t already connected to the rather high-flying parts of the world I usually deal with. There’s an example with our (very successful, I might add) Wolfram High School Summer Camp, which we’ve been putting on for the past seven years. We’ve always got great kids at the Summer Camp. But in the first few years, I noticed that almost all of them came from the most elite schools—usually on the East Coast or West Coast of the US, and generally had very sophisticated backgrounds.

I wanted to broaden things out, and so we put effort into advertising the Summer Camp on our Wolfram|Alpha website that (I’m happy to say) a very large number of kids use. The results were good in the sense that we immediately got a much broader geographic distribution, both within the US and outside. But though we advertised that scholarships and financial aid were available, few people applied for those, and in fact the fraction even seems to have recently been going down slightly.

It’s a frustrating situation, and perhaps it’s a reflection of broader societal issues. Of course, the Summer Camp is a somewhat different situation from mentoring, because to be successful at the Summer Camp, kids already have to have (or give themselves) a certain amount of preparation (learn at least the basics of the Wolfram Language, etc.). And in fact, it’s not uncommon for kids I’ve mentored to end up going to the Summer Camp. And from that point on (or, for example, when they go to some good college), they’re often basically “solved problems”, now connected to people and resources that will help take them forward.

When my company was young, I often found myself mentoring employees. But as the company grew, and developed a strong internal culture, that became less and less necessary because in a sense, the whole ambient environment provided mentoring. And, yes, as is typical in companies, my values as founder and CEO are (for better or worse) deeply imprinted on the organization. And part of what that means is that I don’t personally have to communicate them to everyone in the organization.

In a company it clearly makes sense to promote a certain coherent set of goals and values. But what about in the world at large, or, say, in kids one mentors? There’s always a great tendency to promote—often with missionary zeal—the kind of thing one does oneself. “Everyone should want to be a tech entrepreneur!” “Everyone should want to be a professor!” etc. And, yes, there will be people for whom those are terrific directions, and unless someone mentors them in those directions, they’ll never find them. But what about all the others?

I did some surveys of kids a couple of years ago, asking them about their goals. I asked them to say how interested they were in things like having their own reality TV show, making a billion dollars, making a big scientific discovery, having lots of friends, taking a one-way trip to Mars, etc. And, perhaps not surprisingly, there was great diversity in their answers. I asked some adults the same questions, and then asked them how they thought their answers would have been different when they were kids.

And my very anecdotal conclusion was that at least at this coarse level, the things people say they’d like to do or have done change fairly little over the course of their lives—at least after their early teenage years. Of course, an important goal of education should surely be to show people what’s out there in the world, and what it’s possible to do. In practice, though, much of modern formal education is deeply institutionalized in particular tracks that were defined a century ago. But still there are signals to be gleaned.

So you like math in school? The number of people who just do math for a living is pretty small. But what is the essence of what you like about math? Is it the definiteness of it? The problem solving? The abstract aesthetics? The measurable competitiveness? If you’re mentoring a kid you should be able to parse it out—and depending on the answer there’ll be all sorts of different possible directions and opportunities.

And in general, my point of view is that the goal should always be to try to find signals from people, and then to see how to help amplify them, and solve the problem of how to fit them into what’s possible in the world. I like to think that for every person there’s something out there that’s the best fit for what they should be doing. Of course, you may be lucky or unlucky in the time in history in which you live. You want to be an explorer, doing things like searching for the sources of rivers? Sorry, that’s been done. You want to be an asteroid miner or a genetic designer of animals? Sorry, you’re too early.

In a company, I view it as a major role—and responsibility—of management to take the skills and talents of the people one has, and solve the puzzle of fitting them into the projects that the company needs to do. Quite often one ends up suggesting quite new directions to people. (“I had no idea there was a thing like software quality assurance.” “Linguistic curation is something people do?” etc.) And over the years it’s been very satisfying to see how many successful careers I’ve been able to help launch by pointing people to new fields where it turns out their skills and interests are a match.

I don’t claim to be immune to the “encourage people to do what you do” phenomenon. And in a sense that informs the people—CEOs or kids—who I mentor. But I like to think that I’m unprejudiced about subject areas (and the more experience I get in the world, and with different kinds of people, the easier that gets). What does tend to be in common, though, is that I believe in just figuring out what to do, and doing it.

Too few people have had serious experience in going from “nothing to something”: of starting from some idea that just got invented, and then seeing it over the course of time turn into something real—and perhaps even important—in the world. But that’s the kind of thing I’ve spent my life doing, and that I try to do all the time.

And (at least given my worldview) I think it’s something that’s incredibly valuable and educational for people to see, and if possible experience for themselves. When people at the company have been involved in major “nothing-to-something” projects, I think there’s a certain glow of confidence they get that lasts a decade.

I can see that my own children have benefitted from watching so many projects of mine go from nothing to something—and being exposed to the process that’s been involved (and often giving their own input). And when I mentor kids (and often CEOs too) I like to mention projects I’ve got going on, so that over the course of time they too gradually get a sense of at least my version of the “nothing-to-something” process.

For the past several years, I’ve spent a couple of hours most Sundays doing “Computational Adventures” with groups of kids (mostly middle school, with some early high school, and some late elementary school). It’s been fascinating for me, especially as I try to understand more about teaching computational thinking. And of course it’s invigorating for me to be doing something so different from my typical “day job”.

Most of the time what I’ll actually do with the kids is try to figure out or build something with the Wolfram Language. It’s not the same kind of thing as mentoring individual kids, but there’s a little bit of “create something from nothing” when we develop ideas and implement them in the Wolfram Language.

I think to most kids, knowledge is something that just exists, not something that they know people create. And so it’s always fun when the kids bring up a topic, and I’m like “well, it so happens that the world expert on that is a friend of mine”, or, “well, actually, I was the one who discovered this or that!”. Like in mentoring, all this helps communicate the “you can do that too” message. And after a while, it’s something that kids just start to take for granted.

One of the features of having done mentoring for so long is that I’ve been able to see all sorts of long-term outcomes. Sometimes it’s a bit uncanny. I’ll be talking to some kid, and I’ll think to myself: “They’re just like that kid I knew 50 years ago!” And then I’ll start playing out in my mind what I think would naturally happen this time around, decades hence. And it’s the same with CEOs and their issues.

And, yes, it’s useful to have the experience, and to be able to make those predictions. But there’s still the problem solving about the present to do, and the human connection to make. And for me it all adds up to the fascinating and fulfilling experience I’ve had in doing all that mentoring over the past half-century or so.

Often it’s been some random coincidence that’s brought a particular mentoree to me. Sometimes it’s been their initiative in reaching out (or, very occasionally, someone reaching out on their behalf). I’m hoping that in the future (particularly when it comes to kids), it’ll be a still broader cross-section. And that in the years to come I’ll have the pleasure of successfully answering ever more of those “What should I do?” questions—that make me think about something I’ve never thought about before, and help someone follow the path they want.