Back in… oh, 1996 or so, I was working for Bell Atlantic Network Integration near Philly as their LAN Manager. I was 25, according to my calculator. Boeing, which at the time had a big facility in the Philadelphia area, was going through some major layoffs and looking to re-skill aircraft mechanics. That’s irony, by the way, because I had been an aircraft mechanic who was laid off, before I got into IT.

Anyway, Penn State University wound up with the contract to do night classes, and they were basically just going to run these guys through Microsoft Official Curriculum (MOC) for Windows NT 4.0. Penn State didn’t have enough instructors, so they reached out to Micro Endeavors, a Microsoft training partner who was incidentally supplying contract developers to Bell Atlantic. One thing led to another, and I wound up teaching some of those classes under a moonlighting agreement. Micro Endeavors helped be get my Microsoft Certified Trainer (MCT) credential, which led to me teaching my first formal classes.

Now look, it wasn’t super-easy. I put in a full 8-10 hour day at BANI, drove over to the local Penn State campus, and taught for 2-3 hours. I didn’t feel at all prepared, despite the 2-day “train the trainer” course I’d had to take as part of the MCT requirements at the time. I mean, I knew Windows, and I knew I knew Windows, but teach it? I didn’t know it that much. I mean, I wasn’t an expert.

And I didn’t need to be. I knew more than my students did, and what’s more I knew it from the same real-world perspective they’d eventually experience themselves. We went through the MOC, and along the way I shared some relevant stored from BANI and the previous job I’d had at a consulting company. We did the labs, and I pointed out some alternate situations I’d run into a couple of times to sort of juice things up. This went on for about 6 weeks. 6 weeks of long days 3 days a week, 6 weeks of nervousness (which did get better as time went on), 6 weeks of feeling unprepared. 6 weeks of doing just fine, after all.

10 of my 12 students got jobs in IT; the other 2 were a bit older and opted for an early retirement program. I was hooked.

Less than a month later, I’d tendered my resignation to BANI to start a full-time job as a trainer at Micro Endeavors. A few months later I was developing custom courseware under their tutelage. A few months later I was in charge of their Training & Courseware Group.

See, Micro Endeavors took a chance on me. They funded some of my growth, but I had to do plenty of heavy lifting and give plenty of sacrifice on my own. And it immediately paid off for us all — they kept the Penn State contract, I got a job doing something I loved, and 10 guys got new careers to support their families. My second-in-command at BANI got promoted into my job role. All of that happened, in large part, because I swallowed my nervousness and my feeling of “not being good enough” and just got on with the mission. I could have chickened out at any time and just stayed put in my comfortable corporate position. I’m really glad I didn’t.

I tell this story only in part because I learned that feeling inadequate or nervous is no excuse for not doing something, especially when the potential outcome is helping someone else with something important. I tell it also because after a few months at Micro Endeavors is when I decided I’d been incredibly lucky with what life had handed me to that point, but I needed to start acting a bit more proactively. Luck runs out. It was that summer, in 1997, that I started developing what would eventually become “The Grind,” and it’s where I started understanding that my own success would come primarily through helping others be successful, even if all I could do was help in small ways.

And you can do the same.

I was speaking with some folks this week who said they were having trouble convincing their bosses to allow for “teaching” at work. That struck me as kind of odd — like, who doesn’t want people teaching each other? — so I dug a little deeper.

There’s a cultural thing in the US. Maybe it exists elsewhere, too, but I know for sure it’s a thing in the US. We tend to only look at extremes of thing. Either you can’t drink wine at all, or it’s a health food and you have to drink ALL of it. No coffee or ALL THE COFFEE. We don’t moderate our diets, we “go on diets,” often extreme ones. It seems like everything, with us, is all or nothing.

Apprenticeships certainly don’t need to work that way, nor does Mastery. When you’re pitching the Master/apprentice relationship to anyone, make sure they understand that you’re not asking them to create a new job role in the company that ONLY teaches. You’re not asking to step out of your production role and into a non-production teaching role.

In fact, that very idea misses the point of Mastery entirely.

Masters in a trade actually practice their trade. They have a job. They produce things. They simply do so alongside an apprentice. The apprentice also does work, produces things, and so on — they just do so under the watchful eye of their Master. Mastery is, in many ways, a “part time” thing. Your apprentice might only be with you for an hour a day, or a day a week — that’s fine. Honestly, it’s a better way for people to learn than to just go at it for 40 hours a week (or more); short “learning sprints” give the brain time to process, make neural connections, and actually learn.

So pitch Mastery as something that happens organically as you do your job, not as some separate job. You’re not teaching — you’re coaching. You’re not unproductive; you’re simply being productive while someone else watches.

There’s a soft benefit to the apprentice/Master relationship that I think a lot of people miss out on.

Let’s start by looking at the “soft” side of the traditional classroom experience. Setting aside after-class social time, which is obviously one of the things that comes along with college, class time confers very few benefits beyond what the class alleges to teach. You just kind of sit there and absorb, right? Or, best case, you have some really engaging discussions. Okay, maybe a GREAT class makes you a better person in discussions, or a better person for debates or critical analysis — cool.

Contrast that with a true apprenticeship, which is simply where an experienced person works alongside a less experienced person on some actual tasks. Yes, the apprentice learns to complete those tasks — but they learn SO MUCH MORE.

They learn about cooperation. They learn to work WITH someone. Done well, they learn a lot about the give-and-take and back-and-forth that collaborative work relationships require. They also learn how to work in whatever environment they’re in — how to joke with colleagues, how the ebb and flow of conversation works, and more. True apprenticeships make people so much more confident and self-reliant, you honestly might not believe it unless you’ve been through it.

I’ll return to harping on my own apprenticeship: I started as a very shy 17 year-old who was sensitive to teasing, wasn’t very outgoing, and didn’t quickly volunteer to speak up or make friends. I was dumped onto a shop floor with mostly Navy veterans. I can assure you, they weren’t a shy bunch. I got teased a LOT — but it increased the longer I was there, as they felt me getting more comfortable. I learned to tease back. I learned to speak up. I got into an argument with a senior mechanic over a tail light installation I felt he’d bungled, with the end result being him redoing the work and apologizing to me. That’s a HUGE life skill, and I’d never have learned it all just sitting in a class. Sure, a lot of my issues had to do with my age, but I see similar results in people who apprentice much later in their lives, too.

Today? Well, I strongly feel that without those “soft” experiences as an apprentice, I’d never have become the public speaker I am today. The mechanics I worked under were the first to encourage me to quit that job and “get into computers,” advice I eventually took and never looked back from. They saw something in me that I didn’t see, and helped me start to build the confidence to go after it. I’d never have had that in a classroom, because that’s not the point of a classroom.

When you’re sharing your knowledge with someone in this way, you’re also sharing your broader life experiences. The side conversations that naturally occur when you’re WORKING ALONGSIDE someone are half or more of the value of the apprentice/Master relationship. And again, this isn’t just at your workplace — simply working alongside anyone, in any kind of task, offers the opportunities to share life experiences with each other, get to know one another, and broaden both of your perspectives.

I have had so many people who have taught me so many things over the years. It would be very easy to adopt what I feel is the majority world opinion and think, “well, they were paid to teach me.” And it’s true that many, if not most, were paid to teach me things.

But I feel that information and knowledge are free. “Free as in beer,” meaning available without the exchange of money or value, and also “free as in speech” meaning available without restriction. What we pay for is the TRANSMISSION of knowledge: we pay for the teacher’s time, not what’s in their heads.

And that’s why I teach. Yes, sometimes I get paid for that, but plenty of times I don’t. And it’s fine — if I’m making enough to cover expenses, then I don’t feel I should be hoarding knowledge.

While I feel that most of life is not as binary as it’s sometimes made out to be, I do feel that knowledge is pretty binary: you’re either sharing it, or you’re hoarding it. Maybe you get paid to share it, which is absolutely fine and respectable, especially if knowledge transmission is your full-time job.

But if you already have a full-time job, and if it’s already making ends meet for you, you still need to be transmitting knowledge. You don’t need to change the world. You don’t need to moonlight as an instructor. Share something small, with just one person. Constantly be transmitting knowledge that you have, so that other people have it. The transmission of knowledge, I feel, is what truly sets us apart as a species. Other animals use crude tools; it’s our ability to share what we’ve learned that allows each generation to iterate and improve our tools, our processes, and our collective lives.

So many people have taught you things without being paid to do so, haven’t they? I mean, really think about it — I’m sure you learned something yesterday, or the day before, that didn’t come from a paid teacher in some kind of formal class, right? Well, if that knowledge was transmitted to you free of charge, then you’ve incurred a debt. You can pay it off by transmitting something to someone else, also free of charge.

The success of your life is measured by the lives you’ve helped succeed. And you don’t have to help in some major, earthshaking way. Remember, even horseshoes are powerful.

Wouldn’t you rather live in a world where you helped one person take even one tiny step forward than in one where you didn’t?