Failing Doesn’t Mean Failure

A lot of us — probably MOST of us — are afraid to fail. Failure hurts, either physically or mentally, and our brains obviously try to guide us away from pain and unpleasantness. But that also means, in an awful lot of cases, that we also don’t TRY. We anticipate the failure, even though it’s never happened to us, and doing so impedes our ability to grow and succeed.

Despite the popular belief, kids’ minds aren’t really like sponges. That all starts to fade at about age 5, when the prefrontal cortex starts to really develop. What kids lack, and gain only with time, is a fear of failing.

Failing is the very essence of learning. If you do something over and over and over and never fail at it, you’re not actually learning. That is, you’re not necessarily changing the structure of your brain. You’re perhaps reinforcing existing structures (specifically, synaptic connections between neurons), but you’re not creating new ones or changing existing ones. By definition, then, you’re not learning or changing or growing.

Failing does not make YOU a “failure.” That’s a hugely important concept, and this week I’d love it if you did nothing else but think about that a LOT and really embrace it. You can fail all the freakin’ time, and still not be a failure. You’re only a failure if you repeat the exact same failures over and over and over. If you’re not repeating, then you’re learning. You’re growing.

Yes, sometimes failure can hurt. Fail to fill the car with gas and it’s an inconvenience; fail to pick the right stocks and you could go broke. But most of our day-to-day failures aren’t all that bad. They’re not epic decisions that will change your life. So whatever new thing you’ve been thinking about — perhaps something that’s on the road to your success definition — give it a shot. Fail at it. Examine why you failed. Learn from that, and try again.

YOU aren’t a failure. Well, unless you never TRY. Not trying is a big failure.

It’s Never Too Early to Teach

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.

Not Everything is All or Nothing

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.

Mastery: Teaching More than Tasks

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.

Unstructured Apprenticeships

One of the things that I think makes people nervous about “taking on an apprentice” is what they perceive as the up-front work involved. Jeez, they think, I’m going to have to come up with a whole curriculum to teach!

Not so. Sure, an established apprenticeship program — something formal — will have some structure, but even that doesn’t really take the forum of a “curriculum.” The concept of curriculum, I think, just comes to us from that toxic teacher-student relationship that is drummed into us when we’re young, and largely continued throughout our lives. Teaching doesn’t NEED to be fully structured and formal.

Take my apprenticeship as an aircraft mechanic. I spent more than 80% of my time right on the shop floor, putting jets together. There was no “curriculum;” what we had was a simple checklist. There are obviously a huge number of tasks that go into a fighter jet or attack plane, and so the people running my program just wrote down a bunch of the major ones as a checklist. I simply had to work with a journeyman or master mechanic on each one, and as I did them, they “signed off” on my having done so. Anyone, in any situation whatsoever, can do the same thing. Just brainstorm a list of stuff you do, and make sure your apprentice gets to do them all with you. Add to the list as you go — there’s no need to “get it right” up front. Your apprentices don’t even need to become experts in each task, or even be able to complete them on their own after one go-round. Part of being an apprentice is first to simply be exposed to tasks, and, as you repeat them over time, to gradually become proficient.

Think about the tasks you perform at work. Or, forget work — what are some tasks you perform at home, in a hobby you have, or something else? Those are things you can teach — and you just need to find an apprentice willing to run through them with you. That’s it. Even a small list of automotive maintenance tasks can help change someone’s life by making them more confident, more self-reliant, and more capable.

Start making your list. There’s even a place in “The Grind” to start writing them down, but I expect, and hope, that you’ll need lots more space really quickly!

Why I Teach

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?

“Teaching:” a Word to Avoid?

One thing I feel people get wrong about “Be the Master” is around the word teaching.

The word “teaching” gets a bad rap in many organizations, because nearly everyone immediately visualizes a classroom environment. They start to worry about resources, like where they’ll find room for it, and how they’ll set aside time for everyone to basically take off work and go into class. That’s not what teaching should mean, but I get that all of our cultural experiences tell us that’s what it is.

“Mentoring” gets more love in most organizations, but I still dislike it. Mentor was a dude in “The Odyssey,” and his student wasn’t named “Mentee.” And mentoring STILL creates that toxic “teacher-versus-student” vibe, where one person is demonstrably better than the other.

In most true apprenticeships, teaching isn’t a formal thing you set aside time for, go into a different room for, and so on. Teaching isn’t one person being set above another. In a true Master/apprentice relationship, it’s just people working together. One of them likely has more experience than the other, but they can both learn from each other.

When I worked as an aircraft mechanic apprentice, I worked alongside a journeyman or Master mechanic. They taught me a lot, much of which wasn’t in our extensive manuals on how to assemble the aircraft. The “tricks of the trade,” so to speak. Yet even as a first-year apprentice, I could contribute, because I was never made to feel like I was in a traditional classroom environment where my instructor was “superior” to me. A good example: there are a couple of hard-to-reach spots in an F-14, and you have to snake your hand up through machinery to install cotter keys in the end of bolts. It’s hard, because you can’t really get any tools in there, so you have to bend the end of the cotter key by hand. I suggested snaking a piece of safety wire up and round the cotter key, and then yanking down on it to bend the key’s “leg” down. “Huh,” the guy I was working with said. “Let’s try it.” It worked, and it called a couple other mechanics over to show them.

If you read “Timothy the Blacksmith” again in “Be the Master,” you’ll see that Timothy and Edmund learned from each other, and though Timothy was in the “superior” position in the smithy. THAT is what apprenticeship and Mastery is all about. It’s teaching in that it’s knowledge transfer, but it’s not a class, it’s not a “lunch and learn” session, and it’s not “mentoring.” It’s simply working alongside someone, showing them what to do but also letting them actually do it — and paying attention to their observations. Apprentices often bring a fresh, unbiased view to their work, and it’s useful to have them articulate that view. It’s a good way to have “ah-ha!” moments and change your perspective on something that you’ve just gotten in a rut about.

A true Master/apprentice relationship doesn’t require you to take time away from work to teach; you teach AS PART OF that work. Working and teaching as there exact same thing. Sure, it takes a little longer to get things done, because you’re letting your apprentice do some of the work, and they’re just learning how. But it’s nothing like hauling everyone into a classroom and talking at them for a few days, hoping they remember it all, and then tossing them onto the job. Because apprentices get to work right along their Master, and because they get an opportunity to make mistakes (which their Master will catch and correct), they actually learn faster and more thoroughly than the “tried and true” classroom approach.

It’s 30 years later and I can STILL absolutely remember which actuator in an F-14 needs that safety wire trick.

Everyone’s Afraid

Since the late 1990s, I’ve been a fairly regular speaker at technical conferences. I’ll talk to groups of 15, and I’ve spoken to groups of 5,000. I’ve almost always done pretty well, but if you think all that experience makes me any less nervous…

When it comes to serving as a Master to one person or hundreds, we all get afraid.

Back in the late 1990s, I worked for a company called Micro Endeavors, based near Philadelphia. They were well-known in the FoxPro world at the time, and they were growing a name in SQL Server education. They were approached by Shirley Brothers, who now runs the “Intersection” conferences (like Dev Intersection), who wanted to partner with them to launch a FoxPro event and a SQL Server event. Part of the deal was that some of Micro Endeavors’ trainers would get speaking slot at her other dev-content shows until the new ones launched, and I was tagged to be SQL Connections’ first conference chair. So that was my first speaking gig, back in 1996 or 1997 – I think I presented on ActiveX Data Objects (ADO; this was before .NET had launched).

So my entry into the world of conference speaking was a little unusual; honestly, with most conferences these days, it’s easy to submit a session proposal. Most conferences are eager for a diverse variety of speakers and actively solicit submissions. The exceptions are your major first-part vendor shows like Microsoft Ignite; they’re less open to outside speakers (and if they do accept you, can get a little dictatorial about what you present on and what you say, which is why I don’t present there).

Once I got over the basic nervousness of standing up in front of a bunch of people and pretending to know what I was talking about, I’ve really only had a couple of scary presentations.

One was at TechEd… 2007, I think, in the US. This was a few months after Windows PowerShell had launched, and Jeffrey Snover called me and asked if I could give a presentation on it for TechEd. He’d been scheduled to present, but had a schedule conflict and wasn’t going to be able to attend. “SURE!!!!!” I said. Well, TechEd time approaches and the organizers contact me. They tell me that the session is overbooked, and ask if I’d be okay scheduling a repeat the following day. “SURE!!!!” I said. A few weeks later, the repeat was overbooked, and they asked if I’d be okay live-streaming the first session. “SURE!!!” I said. This was in the LiveMeeting days, so I show up and they’ve got the stage bathed in lighting. There are three cameras. I have to present slides from their machine, and if I want to do a demo, I have to make a big deal that I’m about to do a demo so that someone in the back can push the screen share button in Live Meeting. The lights are hot, and I’m sweating bullets. The room has like 5,000 people in it. I was working with SAPIEN Technologies at the time, and my partner, Christopher, was working for them as well. He came up from the expo hall and sat in the front row, right in front of the podium, for moral support. And Jeffrey Snover walks in and sits next to him. “Um, hey, what’re you doing here?” I asked. “Oh, PowerShell is getting an award, so they rearranged my schedule so I could come accept it. Have a great session!” Gulp. So I start. I’m telling my jokes, I’m waving my arms around, and I’m sweating like a whore in church. I do my demos, and I keep seeing Jeffrey leaning over and whispering to Christopher, which makes me even more nervous. I finally get to the end – a perfectly timed session, by the way – and everyone claps. Jeffrey stands up, says, “good session,” and hustles out. Gulp. I answer a few questions for people, and start walking out with Christopher. “What the hell were you guys talking about?” I asked. “The first time, he said, ‘I’m glad he’s up there, because I couldn’t say that but it needs to be said.’ After that, we realized it was making you nervous, so we just kept doing it.”


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Don’t Impress Your Heroes

In fact, don’t even worry about your heroes. Here’s what I mean:

Too many of us too often measure ourselves against our heroes and role models. There’s nothing inherently wrong with that; having something or someone to look up to can not only push us to succeed, it can also give us some clues on how to do so.

But you have to draw a clear line between that and valuing your own worth by comparing yourself to someone else.

“I’m not nearly as smart as [person], so there’s no way I could teach someone the way they do!” is something I hear a lot. And you’re right: you can’t teach the way they do.

But you can teach differently.

And your different might be just what your audience needs. Remember, your “worth” isn’t something you can define for yourself. Your “worth” is defined by the people around you. Are you providing them something they assign value to? Are you making a positive impact on their lives?

If so, then you’re “worthy,” by definition.

So admire your heroes and role models. Just don’t measure yourself against them; don’t try to be someone they’d be impressed by. Instead, be a hero for someone who needs one.