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 Your Job Doesn’t Require a Vest or Apron: Is there anything sadder than the old guy in the vest who greets you at the Home Depot or Wal-Mart? That seventy-eight-year-old guy who’s making minimum wage to hand you the flyer of what’s on sale that week?

I want you, So

The close cousin to this guy, except stationed at the exit instead of the entrance, is the receipt checker/security guy. I’ll head over to the Home Depot and buy 129 finish washers, thirty-seven joist hangers, fifty-one TICO clips. Inevitably, the receipt will be twenty feet long, and the guy with the GED and the lazy eye will give it a glance and a cursory marking up with a highlighter, then send me on my way. His job is to make you pause for a moment and if you don’t start sweating or make a run for it, he’ll let you pass. These guys aren’t security. They’re always overweight, wearing ill-fitting clothes, and missed three out of five of their belt loops. The only weapon they’re carrying are way too many keys. This is just the corporation saying to the insurance company, “But we had security posted at the door” when something does go wrong. This guy is the human equivalent of the plastic owl on top of the seafood restaurant. And as intelligent.

All right, kiddies, tally up your score: How did you do? If you fall on the successful side of things, well good for you. Just prepare to get sued.

As a guy who has had multiple jobs and multiple careers, please let me pass down a little fatherly advice in this arena. Having multiple gigs is a good thing. There is a certain kind of math that goes into this approach. One job is what most people have and that can either be all you need or not nearly enough. Having three jobs usually means they all pay shit. But when you cross over to a place where you have four jobs, chances are you are a rich person. No one can put in the time to work four minimum-wage jobs to make ends meet. But they might be able to pull off three. So four or more jobs means you’re the entrepreneur/businessman/real-estate mogul/celebrity. You’re serving on the boards of several companies.

As far as the multiple gigs, to me it’s about even numbers. One job, even if it does pay well, can be mind numbing. This is the kind of job where you work at a postal sorting facility from age twenty-one to forty-three and then kill yourself and/or several coworkers. Three is just too much for too little return. Go with two so you have variety and aren’t bored, or go with four so that you have so many plates spi

But take heed: Real entrepreneurs don’t call themselves entrepreneurs. I’ve met several super rich guys, the true one-percenters, at some of my vintage race events and when you ask them what they do they all say “a little of this, a little of that” or “I had a company and I sold it.” Those vague answers mean the little of this and little of that is done from a helipad on their yacht. It sounds a little defensive to constantly call yourself an “entrepreneur.” That’s a little like “right now.” It means you haven’t had a salary in years. Every time you say “entrepreneur,” you lop twenty thousand off your pull for the year. I’ve met several self-proclaimed entrepreneurs who want advice from me on starting a business, since I’ve started several. But once I start digging into their schemes, I come to realize they’re selling candles or e-cigarettes on Craigslist from their parents’ basement.

So I’m not going to tell you to “follow your bliss.” Yes, it worked out for Daddy, career-wise. I knew I was fu