WHEN GREAT IS THE ENEMY OF GOOD
It’s not like the idea of generalism just occurred to me. It’s something I had to figure out after going a long time in the opposite direction. Like many of us, when I was a kid, I thought I should grow up to be the best at something—and for me that something was the guitar. I wanted to be the fastest and most virtuosic guitarist around, so I could become famous, get tattoos, and do drugs and all that. Obviously, this isn’t how things turned out. Here’s why.
First, I have maintained a healthy paranoia regarding substance abuse, because with a family history of addiction problems, I know very well what I might end up like. I also maintain an unhealthy fear of needles in general and have way too much of an indecision problem to settle on something as permanent as a tattoo. Plus, I don’t care all that much about becoming famous anymore, for reasons we’ll later get into.
Those, ahem, lofty goals aside, I realized about five years into playing guitar that specialization wasn’t getting me to the places I wanted to go. By the time I was in high school, I was (in my opinion) the best guitarist around, but only a few people enjoyed hearing me play, since I only played stuff that other guitarists wanted to listen to, like sweep-picking guitar solos. (For nonmusicians, an example of sweep picking can be heard quite prominently throughout the work of virtuoso guitarists from the 1980s, like Yngwie Malmsteen; check out “Arpeggios from Hell.”) Because—and this is something every specialist eventually realizes—there comes a point in every skill when you become so good you suddenly lose people on a common level and begin appealing only to other specialists, and that’s when you know you’ve gone too far. Most people in my high school didn’t want to hear virtuosic guitar solos; they just wanted to be asked to the prom by some singer-songwriter kid with a Dave Matthews haircut. So it would have been better if I hadn’t spent so much time perfecting sweep picking and instead had gotten just a little better at singing. This was a clear case of where a skill stack (singing and playing the guitar) was more attractive than specialization (being a solo guitarist), because if the goal was to get attention as a person/musician, it was the generalist (in this case, my “friend” Tom) who was doing so, and not the specialist (me), who might every once in a while impress people with a fiery guitar solo but could not write a catchy melody. And since most people are basically philistines when it comes to this stuff—they don’t care for all that technical mumbo jumbo—they just want a tune they can hum along to.
That was lesson number one, in which somebody who was not as good at the guitar as me was getting the thing that I wanted out of being a guitarist, which was having people say how good a guitarist he was, when everybody should have been saying how good a guitar player I was. But how would they know that, since none of them were musicians? As you can imagine, all this made me somewhat displeased.
So specialists mostly appeal to other specialists—I got it then. But this was also not the only case where I was the person who was better at something yet not doing quite as well on the, let’s call it, commercial level. Yes, I was (in my opinion) the best guitarist in my high school, but that hardly says anything, since there were only about ten kids in my high school who even played the guitar to begin with—it’s not like I had all that much competition living in rural Wisconsin. It wasn’t until I began auditioning for college that I realized how ordinary my abilities were, even as a so-called specialist. This was lesson number two: not only had specialization not gotten me to where I wanted to be in life, but even with practicing seven hours a day, I still sucked. I didn’t “suck suck”; I just “sucked” in the sense like, wow, really? All these years and I’m still not even close to being nearly as good as I thought? That’s a bummer. Because there I was, practicing every waking moment on that bastard of an instrument, and I got my ass handed to me by some twelve-year-old Korean kid in an audition for Berklee. That literally happened.
So lesson number three was waking up to the grim reality of diminished returns and how little I got back for every additional hour I dedicated to getting better at the guitar, when I could have gotten so much more in return if I’d merely invested that time in other skills like singing, songwriting, or producing. I still would have gotten shown up on a technical level by that kid at Berklee, but that was going to happen anyway. Even if I’d decided to increase my practice by seven more hours per day, I seriously doubt I would ever have gotten to be as good as he was. Maybe he simply had connections in his brain that never formed for me because he started playing guitar when he was two but I didn’t get started until I was in eighth grade. Or maybe he was just smarter than me. That is also possible.
One problem with specialization is that success is too often dependent on factors beyond your control, like who your parents were, where you were born, how you were raised, what you look like, and so on. The good news is that generalism doesn’t rely on any of that, so it doesn’t matter if your parents were models or meth addicts, and it doesn’t matter if you have any skill at all. You can be a total loser and still succeed. I did.
But if I’m going to impart to you any wisdom at all, it’s probably best to tell you a little bit about my own journey from being a specialist (and not succeeding) to becoming a generalist and doing fairly well for myself, all things considered.
As you probably gathered (and we’ll return to it), I started out wanting to be a guitar player. I practiced my calluses off, striving to become the best guitarist in the world, even though I know now that was never going to happen. But the things I learned by acquiring that skill have been super important and eventually helped me become a writer, business owner, and entrepreneur.
Now, since we’re already such good friends, I’ll let you in on this. Sometime around ninth grade, my buddies asked me to participate in a wet T-shirt contest to see who had bigger man boobs—me or my friend Sean. I’m sorry to have to report this, but it was about the only competition I won in high school, though the upside was that it inspired me to start getting in shape. So after being humiliated in front of everyone whose opinion I cared about, I began reading a bunch of books on dieting and exercise, and eventually I signed up for tae kwon do, where I got into strength training and kettlebells. What are kettlebells? They’re a form of weights that sort of look like cannonballs with a handle on them. Don’t worry about that now. We’ll come back to it.
In the meantime, I experienced a lot of panic attacks and went through a period of agoraphobia when I felt like I couldn’t leave my house without a chaperone and a lucky charm of some kind. I’m not going to sugarcoat this: life pretty much sucked at this point. And that’s probably where I bottomed out. High school is tough for a lot of kids, right?
Through tae kwon do, I learned about meditation and started to get a hold of myself. In 2006 or 2007, while I was still in high school, I decided to start a YouTube channel and a blog to talk about getting in shape, and lifting weights, and meditation, and pretty much everything else I was interested in. I wanted to help others because I was starting to feel a lot of benefits from consistently working out, and my life was changing in some positive ways.
I was thrilled to be accepted into school for music, except my grandmother (isn’t that a grandmother’s job?) talked me into getting a “real degree” in economics and finance. But I continued to blog, and I put up a lot of information about exercise and my personal struggles with weight and anxiety.
People responded to that and saw me as someone to whom they could relate, someone, they said, who is often helpful and sometimes funny. And about my second year in, I realized I could maybe do this for a living—that is, fitness. At first I was doubtful, because I thought back to how I never made it as a guitarist, even though I practiced more than anyone (or so I thought), and I looked at my fitness levels and admitted I was nowhere near the most in-shape person in the world. I realized I was never going to be the strongest or the biggest or the best at anything. But I knew I could become fit in a very general way—lean and strong and muscular and flexible. I could balance on my hands and do muscle-ups and lift heavy things. And that impressed people: they saw that I was good at many things, and they wanted to know how I did it.
Also, because I wasn’t specializing, I didn’t get hurt as much as everyone else—the friends who were bodybuilding or powerlifting and driving themselves to the breaking point in their training would get injured and lose interest.
So there I was, also writing my blog and making videos for YouTube, meditating a lot, and practicing tae kwon do. It was really centering me. People also began complimenting me on my writing, so I took that as an invitation to study writing more deeply and to learn how to be a good communicator and craft prose in a way that is casual and accessible. People were following my blog, they said, not only to learn about generalism and fitness but to enjoy my storytelling and all the outrageous things I had to say. So that was neat.
This was an epiphany of sorts, though a very gradual one, whereby I began to see the value in a skill stack, in which the combination of my fitness abilities and my writing skills—even though I was far from being the best at either—seemed to be intriguing when put together. It was like a sandwich: even if all the ingredients aren’t amazing themselves, they still taste pretty good when mushed together. Eventually I realized that I never needed to specialize. I never needed to be the best piece of pastrami: I just needed to be good enough pastrami and then have some bread and sauerkraut and creamy-enough dressing. I had almost no direct competition because most of the people I was up against in the fitness industry weren’t writers, and most writers weren’t in the fitness industry.
Come my senior year of college, I fell into my first big book deal because one of my followers was looking for someone to write a book about fitness. I got the deal and even did a pretty darned good job with that book (or so the publisher said), so it led to a series. And along the way, I learned a lot about marketing and business and sales. I learned about psychology and philosophy as well, and I studied all of it with furious interest so I could start to make a living based on everything I was doing. Up until that point, I had done a fine job at getting attention but almost nothing to make any money from it. I began to spend a lot of time with business mentors, and I went to conferences to have my mind exploded by people who made more money than I even knew existed. And all of that added to my skill stack, by the way.
So back to my grandmother’s advice—or not, as the case may be. While this was all happening, I was still in school studying economics and finance. I said to my adviser, “Hey listen, so I’ve got these books I have to write, and I’m running a business, and I was just wondering if instead of taking that last free elective, I could have a couple of ‘life credits,’ let’s call them.” Well, long story just a little less long, he had no idea what I was talking about, and I eventually dropped out.
And that, too, became part of my message, because as my business grew, people began asking me where I went to school, assuming I must have degrees in all of this. But I relished showing that college is not necessary to be successful. Education is a good thing. But you can get that from books and coaches and mentors.
The funny thing, however, is that I have been offered the opportunity to go back to school for philosophy (which I’m working on now) because one of my followers happens to be a professor at this most adorable little university, and he’s hoping I’ll have a better experience as a grad student. OK, sure, why not? We’ll see how that goes.
The point of this is that eventually you do indeed become the person you want to be, even if you don’t think it’s in the way that you want. You become somebody who is successful and productive and useful, but not by being the best you hoped to be—in my case, with the guitar. You become a generalist, and that’s how it happens. It’s the accumulation of all these different skills that sets you apart; it’s how you manage to weave them all together in a (at first) haphazard but (eventually) deliberate way that makes your existence enchanted. Lessons you learn in one area apply to what you’re doing in another area, and the other way around, and no skill you ever learn remains completely unused. Everything is connected, and everything comes into play eventually.
So don’t throw anything away, because good things are going to come from everything you’re doing or will be doing. Your skills may all very soon coalesce, and you’ll have money and C-level fame. But here’s the thing I want to leave you with: if you’re not something without the C-level fame, then you’re not something with the C-level fame. No amount of commercial success is ever going to make you happy.
The last set of skills we need to talk about here are character traits. Because self-improvement isn’t about getting things; it’s about becoming someone, and the someone worth becoming is a person who cares about not what they get but rather what they create. The “getting” should be just a by-product of doing decent work. Your concern should be focused on whether you’re putting things into the world that people benefit from and enjoy using, and another concern should be whether people like being around you—so it’s not just about what you create but also about the kind of person you are because of what you create. For now, all I want you to know is that everything works out OK in the end—well, at least it has so far for me. Life is hard. Writing is hard. Everything is hard. But eventually you find meaning in all of what you do because you discover that happiness is found by engaging in good activities, and that’s what being a generalist is—it brought me to where I am today, which is a lot better than where I was a decade ago.
Now you know my little autobiography (though, trust me, you’ll find out a lot more). Let’s talk a bit about freedom.