Evidently there was some sort of election last night. I’ll check in later to see whether democracy was saved or not.
Forgive me if I don’t get on board with the drama. I spent 20 years in DC, the first five or so in the belly of the beast, or at least a nearby kidney. My impression of the whole system is that it’s a trillion-dollar hustle to keep jobs and hook up.
This isn’t reflexive cynicism. I can assure you that it’s reasoned and considered cynicism.
Anyway…
This question often comes up in one form or another: Should I keep my stable, well-paid day job, or should I go out on my own?
It’s a legitimate question. Here’s the spoiler alert: You have to decide that for yourself.
Overall, I’d say, “Yes! Go for it!” But honestly, it probably depends on your season in life. If you’re a young single man, it’s a no-brainer. Even if you step on rakes for a decade, you can still transition to something more “respectable.” If you’re on the other side of middle age and you’re more or less essential to your employer, and the salary pays the bills, you might just want to get a hobby, especially if you have a wife and kids depending on you.
Here’s what I told a guy who asked this recently: If someone rips the sheet off of a table stacked with cash, and that someone tells you it’s all yours if you just take this one, sensible risk, but your wife is extremely risk-averse, walk away from that table. It is so not worth it.
(On the other hand, can you bear living with yourself, or her, if you know you turned away from such an opportunity? It can make you feel like the Spartan who stayed home to play Xbox. Equivocations abound here.)
However… Entrepreneurship, or even just side-hustling, if-you-please, bestows a kind of creative madness that I highly recommend. I’m tempted to call it a “high.” (Which, yes, is uncomfortably close to “addiction,” but whatever - I’ve got it under control, man.) When all you’ve ever known is trading hours for dollars and the comfort that comes from knowing you’re going to get that paycheck, no matter what, every two weeks, you might not appreciate the possibilities out there. The first time you generate a couple of bucks from the aether, from your skill and your will, it makes you want another hit.
If you manage to do that for years, and you’re able to buy houses and meet all the family’s needs, you’ll feel like a god. That happened to me, with the usual end of would-be self-made deities, and I see it every day at my job - broke-to-successful hustlers whose egos cast shadows over mere wage-slave mortals. Kind of like how the Hindenburg must have cast shadows, but I digress…
My main love of, or bias for, self-made work is not just the potential for financial freedom, but for what it does for one’s soul. Your mileage may vary, but for me, stepping out of the common, the expected, the usual - in other words, “reality” - broke me out of, well, myself. Oh, hell, I’ll just go ahead and say it: it saved me from the Matrix. It red-pilled me in a way that reading about it could never possibly do, that I was capable of doing amazing things - that anyone could. It illuminated the potential we all have.
So, yeah, I have some opinions about it. But does that mean I disparage anyone who is perfectly comfortable working in a sensible, bill-paying job? Heck no, for a couple of reasons:
One, if that’s what makes you tick, that’s what makes you tick. As the foul-mouthed apostle of entrepreneurship, Gary Vee, often says, “Maybe you’re not the best #1 at a company. Maybe your best fit is as the #12, or the #43. Just go all in as that number.”
Second, as someone who toils in the trenches for a long time, you’re probably making more money than most would-be entrepreneurs and business owners. And you probably suffer less from the vicissitudes of pride. Provision and character: definitely worth it.
I keep a picture on my office wall, wherever my office ends up. It’s of my oldest child and first-born son. He was three-years-old in the picture. I snapped it from bed one morning after a late night either moving someone or lining up the next week’s jobs. My little guy had come into our bedroom wearing my oft-worn and threadbare flannel. He topped his head with my new promotional swag hat. He looked at me and said, in his sing-song voice, “Thank you for calling My Truck Buddy! This is Chris!” Wherein he really hit the “Chris!” Because, evidently, that’s how I said it.
He was emulating me. My little guy, whose impending arrival caused me to build the company, was now almost literally walking in his father’s footsteps.
The pic captured the love and admiration in his eyes - eyes that look the same to this day. (“Seeing blobs,” as his siblings call them now.) He has the fire, too. He’s working on his own business right now, right behind me, in our little shared office. That’s legacy. He’s already a free man.
I would never tell anybody that working for oneself is the only way. It’s clearly not. Everyone has to work for someone, and even if you’re the top-dog in your own self-built firm, your customers are your bosses. (To a degree - I have thoughts on that as well). But I think - as Rod Dreher does in is chapter on entrepreneurship in “The Benedict Option,” that those of us of a traditional bent ought to be thinking about independence from the “system.” Even if everything doesn’t go off the rails, leaving non-conformists like us selling beads along the roadside, gypsie-like, I think there’s enormous value to detaching from the increasingly hostile grind of corporate life.
What I will commit to is this: we should all be thinking of this now before it becomes too late. More on that soon.