Change Catalyst with Shanna Mann: Strategy & Support for Sane Self-Employment

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Philip Roth and Elizabeth Gilbert on Self-Employment (Sort of)

Not too long ago, there was a bit of a hubbub in literary circles.

When asked for his advice, Philip Roth told an aspiring writer:

“I would quit while you’re ahead. Really, it’s an awful field. Just torture. Awful. You write and write, and you have to throw almost all of it away because it’s not any good. I would say just stop now. You don’t want to do this to yourself. That’s my advice to you.”

Elizabeth Gilbert, getting wind of this, wrote in response:

“Seriously–is writing really all that difficult? Yes, of course, it is; I know this personally–but is it that much more difficult than other things? Is it more difficult than working in a steel mill, or raising a child alone, or commuting three hours a day to a deeply unsatisfying cubicle job, or doing laundry in a nursing home, or running a hospital ward, or being a luggage handler, or digging septic systems, or waiting tables at a delicatessen, or–for that matter–pretty much anything else that people do?”

The New Yorker’s Avi Steinburg also weighed in, giving what I think was the most measured opinion.

“Roth’s cranky advice for the young writer is an old Jewish chestnut. The sages of the Talmud offered the same piece of advice to anyone who wanted to join the faith: don’t do it, it’s seriously not worth it, it’s just an objectively bad idea.

The ancient rabbis suggest that you ask a potential convert, “Are you not aware that today the people of Israel are wretched, driven about, exiled and in constant suffering?” It’s a rhetorical question. But if the person replies that he or she indeed embraces wretchedness and constant suffering, you explain to him or her how taxing it is to practice the religion. You mention the gruesome punishments for breaking the Sabbath and other laws. You try very hard to dissuade any would-be applicants. You mess with them—and that is how you welcome them. Joining, in other words, happens through a process of opposition, irony, and dissent. If you’re going to join a messed-up club, you have to pass the messed-up entrance exam. You enter into the sect only when you push back, when you finally say, Listen, I don’t care what you tell me. I know it’s a bad idea, but I’m determined to do it, and I will do it.

That’s the kind of a person it takes to be a writer: someone who’s zealous and ready to argue, someone who has Philip Roth tell him, “It’s torture, don’t do it,” and replies, “You had me at ‘torture.’ ” You don’t enter into it because it’s a great lifestyle decision—it isn’t—you do it because, for whatever reason, you believe in it, and you believe in it because, for whatever reason, you need to believe in it…
My guess is that Tepper was heartened to discover that even the great Roth, it turns out, hates his life. For struggling writers, wretches that they are, that is inspiring.”

Welcome to the Club. Get outta here.

I see this dynamic with business owners as well. “Oy, this is terrible. You work 14 hours a day, 7 days a week, you pay half your income in taxes, and no one believes you have a real job. There’s no security, no health insurance. At the end of the day, you just want to pull the covers over your head.”

Sure, that’s that truth. At least, some of the time. That’s what Philip Roth was referring to.

But what about Elizabeth Gilbert’s point? You get to work for yourself. You call the shots– Control is one of the main indices of happiness. ‘Purpose’ and ‘Mastery‘ are the other two– both things which solopreneurs tend to have well in hand.

But, like Steinburg points out, I think the truth is somewhere in the middle. The cool thing (and also the terrifying thing) about being self-employed is that you’re not buffered from the consequences of your actions. On the con side, that means when you screw up, you can screw up your whole life.

But on the plus side, that positive feedback loop you get into from experiencing the rewards of your efforts is seriously addicting! I’m convinced that’s why entrepreneurs are always like “I hate it, it’s hard, it’s scary — but I couldn’t do anything else” We’re all addicted to the rush of making small bets (whenever we make a decision) and winning. We get better results directly proportionate to the effort we put into things (even more so when we work smarter). And most importantly, we get to do things that we’re good at, for reasons that matter.

What do you think? Is self-employment easy or hard? Or both?