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.