One thing that's hard to ignore in my recent bout of extreme introspection is that I've gotten pretty skilled over the years at hiding a pretty simple fact: my own personal glass ceiling maxes out somewhere around "high average".
That cuts both ways. On the one hand, I pick up things pretty damn quickly and am wired to throw myself headlong into whatever it is I'm pursuing. Ramp up time for any given pursuit is pretty minimal, and lo and behold, pit me against 75% of the general population in any given activity (investing, poker, chess, making money, darts, search engine optimization, juggling, affiliate marketing, and on and on and on) and I'll come out ahead.
I absolutely hate being bad at anything, especially publicly, and will go to insane lengths to not look stupid in front of people. Insane lengths.
But I'm not really good at anything. And never have been. And therein lies an odd rub, one that I think leads to rising water levels in the sea of malaise.
(And yes, I'm mainly going to babble about the dollars and cents aspect of all this, but I'm not necessarily ignoring the personal edification and enjoyment angle of it, either. Most of my recent tussle with malaise centers around the issue of money and how my time is spent in pursuit of it, so that's pretty front and center in my brain at the moment.)
We're somewhat conditioned to heap praise on the jack-of-all-trades Renaissance Person types, but lately I wonder about that. Sure, in theory its great to be well-rounded, to have a diverse and eclectic skill set, to be open-minded and driven enough to accumulate skill and knowledge in a vast array of fields. But really, in the end, what the hell is that actually worth?
I've played many thousands of games of chess. Odds are if we sit down and play, I'll win. Okay, great. While the ego boost is slightly nice, if I could somehow get all those hours I'd dedicated to chess in the past back, I'd do it in a heartbeat. Offer me $20 to eradicate all knowledge of what en passant or fianchetto means and I'd take it in a heartbeat.
And I can repeat the above exercise for many, many things. By and large, they're all activities that I got no immense pleasure from, even at the time, but pursuits that I continued to tilt at, bang my head on, until I got fairly proficient.
So, umm, why? Boil everything else away and odds are great that much of that loops back to a fear of failing, or, more accurately, of being seen as a failure. Which I can own up to pretty easily. Okay. Fear of failure? Check. Tendency to stubbornly persist in endeavors until proficiency is achieved? Check. Frustration and self-loathing based on pervasive feeling of malaise at realization that much of my time is spent in endeavors that have no greater good or promise of larger greatness? Check.
Speaking from a strictly financial perspective, most successful business types make the vast majority of their money (well, at least initially) from something they're really good at. It might be computer programming, trading soy futures, surfboard manufacturing, corporate raiding, selling copious amounts of weed, or building eco-friendly homes. Typically it's something they enjoy doing, aside from any financial gain, which makes it all the easier to amass great piles o' money.
Much of my frustration and malaise of late is that while I've been generally successful in making a goodly amount of money the last five years from widely disparate sources (day job, real estate, equity investments, affiliate marketing, freelance SEO jobs), I've been nowhere near the big score. I'm pretty good at drag bunts, stealing bases, and pushing runs across the plate with sac flies (with an occasional opposite field home run thrown in here and there), but the walk-off home run is still a faraway dream.
To be fair, there's a lot to be said for playing small ball. It's safe and predictable, once you get the hang of it. You're never risking very much at any given point in time. My wife and I are very comfortable right now. We've got basically zero debt other than mortgage debt, have a heap of money in savings, own investment property, and pour money into 401(k)s and IRAs each month. All of which I'm very grateful for, and much of that comes from all of my far-flung schemings and money-making endeavors. But it's not close to being a life-altering sort of thing, as the contraption in its current configuration (day job, business on the side, freelance gigs where I can find them) would need to continue to revolve for quite a few more years before any stopping point was reached.
Despite many small successes, I'd be lying if I said I wasn't disappointed in myself, in many ways. Better than average success isn't a bad thing, by any stretch of the imagination. I'm truly grateful for it. But part of me can't help but wonder what I might be capable of if I stopped flitting around from thing to thing, if I put it all out there and for once in my life focused on one single, solitary thing, with enough potential reward (and risk of ruin) involved that the stakes would be more than meaningful.