I recently spoke at Yale University, where it was icy and Gothic, everyone was very nice and very smart, and I was reminded of what it was like to be 21 and not know how to order a cocktail yet. I was also reminded of what it was like to be able to say, “I study literature” (or philosophy, or economics) and have that mean basically full-time: I LIVE THE LIFE OF THE MIND. Oh, college!
Specifically, I was the guest at a Master’s Tea, wherein the master of one of Yale’s residential colleges chats with a guest about some interesting topic. We drank Earl Grey. It was very civilized. Although the posters for my talk said nothing gender-specific, almost everyone who showed up was female. I just have that vibe, I guess.
Master (and Dr.) Paul Hudak of Saybrook College provided a kind introduction about my many careers, and I told the tale of majoring in philosophy, starting a company as an undergraduate, having my company fail five years later, moving to NYC with $400, getting my car stolen immediately, getting hired for a job when the company doesn’t want to commit, developing expertise, and starting more businesses. I gave a list of Bullish bullet points — here are the notes I spoke from:
What people call a “scattered” career or life, I prefer to think of as a “richness of experience.” And it’s worked. Very well. Every weird thing I’ve ever done has come back and helped me somehow. I’ve written about bodybuilding; I’m starting a luxury cat-services company. Standup comedy isn’t a great way to make money, but it’s a huge selling point for other things I’ve wanted to do (everyone wants education products written and produced by funny people). “Focus” is overrated. In 10 years, many of us will be working in professions that do not yet exist. You want to diversify your experience. Even in traditional fields — say you want to go into medical research and try to find a cure for Alzheimer’s — there’s value in getting ideas from unusual places. “Scattered” is an outmoded insult.
Failing early inoculates you against the impact of future failure. My company failed when I was 23. I don’t mean that my home business wasn’t getting any orders so I had to get a job. I mean that the sheriff padlocked the door to my office and legally prohibited me from entering it, and then the landlord sued me and I declared bankruptcy. I didn’t have anyone to help me. I went to court without a lawyer. (I told this story in Bullish: Actually, We’re All Kind of the 1%.) Having failed young gave me a sangfroid worth two masters degrees, at least. My fiance is pretty worried about wedding planning. I sleep like a baby. (See Bullish: To Give Up or Not to Give Up? A Column About Bankruptcy.)
Working at home: I believe in it. Or at least I believe in working on your own schedule. I think best in the morning. Why waste that on the performance of womanhood, and commuting? I refuse to spend my best thinking hours making my hair look pretty. Also, I work within eight feet of an espresso machine, a bathroom, a pullup bar, and a kitchen. Am I really going to be more productive drinking worse coffee, getting less exercise, eating takeout, and wondering which coworker always pees on the seat? My assistant, similarly, makes things happen on the Internet, and I have no idea where she does that from. Do I really need to waste her time making her wonder if I’ll object to her ripped neon Pegasus tights? (I think that’s what the cool kids are wearing these days, right?)
It’s always a good time to be an entrepreneur. Economy sucks? Cool, sell an affordable alternative to something expensive. Labor is expensive? Start an Internet business that doesn’t require employees, or go into headhunting. Labor is cheap? (It’s very cheap right now.) That means you can hire talented people at bargain rates.