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?


25 thoughts on “Philip Roth and Elizabeth Gilbert on Self-Employment (Sort of)”

  1. As with all things in life, there are trade-offs. Self employment is hard and easy at the same time. Writing is the easiest profession in the world and the most soul-wrenching all at the same time.
    As for clubs and membership, I like Woody Allen’s quote, which is his own take on an old Groucho Marks saying: “I’d never join a club that would allow a person like me to become a member.”

    1. @ethanwaldman I also think there are parallels to how society perceives writing/self-employment. For the longest time it was simply a given that you’d be poor, miserable, struggling, unless you were very, very lucky. Now with the advent of the internet and the democratization and ability to scale that that brings, suddenly the refrain is becoming “Of *course* you can write! Of *course* you can start a business!” 😀

    2. @ethanwaldman You going to share some of that “writing is the easiest profession in the world” mojo with me sometime? Because I normally skip that and go right to the soul-wrenching part. Like the four hours I spent this morning writing a sales page for my upcoming product launch. And I’m not anywhere close to being done. Ughhh.
       @Shanna Mann I love the excerpt from Avi Steinberg and it’s a story I know well. Growing up in a very Jewish household, going to a Jewish grade school where our second language choices were Hebrew or Hebrew, and going to a Jewish day camp in the summer (when I couldn’t do other Jewish things) was rough. I gave up on Judaism – and all organized religion for that matter – but I now find myself an aspiring writer. I guess if I could hack it in the Jewish club for decades then I can probably hack it in the writer’s club for a few years. Fingers crossed at least.
      P.S. If my self-employment didn’t involve so much writing (and typing), I’d think this was a lot easier. It ain’t easy…yet.

  2. What a great comparison!
    So far I’m finding self employment to be more on the hard side than the easy side. There’s more to learn than I’d ever anticipated, and the amount of stuff not obviously related to business that needs to be dealt with (like all those personal issues that end up affecting an tiny business!) continues to surprise me. But the learning and the working on myself are also some of the most interesting and rewarding parts. It’s tough to stagnate as a solopreneur.
    To me it’s like…I don’t know, joining a really tough, elite gym. The workouts may totally kick your butt, but the camaraderie and discipline and physical fitness that you get in exchange make it worth it.

    1. @remadebyhand Great point about the learning and growth that comes with self-employment. I feel like in full time jobs they talk about your “growth and development” but it’s more of a hint of flavor on top of your main meal of 40/hr per week BS. With self employment you’re either growing/learning or not moving forward.

  3. If I have to choose between answering “easy” or “hard’ and not choose some in between answer, then I have to pick hard. 
    Because being employed is easy in that someone is doing a lot of the thinking, planning, deciding for you. Even if you’re in management.  
    You’re also working for the development of a company instead of yourself. Self-work is always harder. It’s more rewarding, imo. I think in the long run self-employment becomes easier over time, though.

    1. @deniseurena I think it becomes easier over time, too. Like Joel’s comparison of it being like a cooking a great meal– there’s a lot of moving parts, it takes some effort to learn the skills and coordinate them, but once you get the hang of it all, you forget how hard it was to get where you are.

  4. Self-employed for years, 10 books under my belt and 2 active projects in the works (not to mention 5 new songs this month, for a total of, er, 100+.)
    Writing is hard. Self-employment is hard.
    Just like being in love is hard. And travel is hard. And cooking a great meal is hard.
    They’re also, if you have that particular spark, unavoidable.

      1. @Shanna Mann Ambivalent about that. Sometimes, letting folks see the dirt under my fingernails is important. They need to know, whether they’re clients or aspiring entrepreneurs, that I’m not in an ivory tower in my Aeron chair directing the troops.
        Other times, though, the aspiring entrepreneur needs to know that they CAN succeed, and success IS sweet. Sometimes the client needs to see elegance and grace, not grit and grime.
        Y’know how we’ve discussed “smart isn’t the right metric” ? I think easy and hard are the wrong metric here.
        How about “happy” and “unhappy” ? (What do you know about Herzberg’s Motivation/Hygiene Theory, his expansion of Maslow’s Hierarchy?)

  5. It seems like a lot of writing on self-employment and writing is focused on how anyone can do it, no matter what. It’s refreshing to hear that people would make others consider the entry requirements more strongly.

  6. Running your own business is worth it – in the hard and easy parts.  When I get to make my own schedule, create my own plans, and still have time to exercise, I say it’s totally worth it.  When I was teaching in a public school, I was running around like a chicken with my head cut off for 60+ hours per week on someone else’s schedule.  Much of it was a living hell, but if you asked me then I would have said, “I like my job.”  A bad case of Denial mixed with People-Pleasing – a horrible condition. 
    I wouldn’t trade it for anything.  Thanks for reminding me of that, Shanna!

    1. @tammyrenzi The chicken with the head-cut off- I had jobs like that, and I would have said I liked them too. Really, I think I just liked the adrenaline rush of rising to the occasion.

  7. This reminds me of when I was in theatre; People in the biz tell people who want to get into the biz that they should only do it if they can’t imagine doing anything else…. 
    I still am not sure I totally understand the whole, “Self employment is terrifying” piece of the equation. Having one single income source is much more terrifying for me. But then, I had the realization a while back that I have an entrepreneurial family so maybe I’m just wired for business ownership. 🙂

    1. @sarahemily If you see the danger of a single source as greater than the fear of risk and uncertainty, yes indeedy you’re wired for entrepreneurship.
      Most folks don’t look deep enough to see that putting all the control in someone else’s hands is the biggest risk you can take with your life. (I wrote a whole book on the subject, so I get all excited when someone gets it.)

  8. I don’t mind working hard at all as long as it is meaningful to me.  Tammy and I have to hustle to keep customers and composing classical guitar music is hard.  But not as hard as the stultifying and mind-numbing work I did as a music teacher, social worker, and bagel maker, just to name a few.
    BTW: I love Roth. American Pastoral is beautiful, but The Human Stain stole my heart.

  9. Now that I’m finally catching up on my Google Reader posts (sad to see it go!), this is perfectly timed. Earlier today, I was journaling to process this transition from employee to solopreneur, and what exactly I’ve taken on. It got me thinking about trade-offs, different types of difficulty, and how well-trained we are to take orders, not think things through. THis could be affected by my reading of Seth Godin’s Icarus book as well…

  10. michaelwroberts  
    Whether a particular “*anyone* can do it” or not also depends on what their  personal goals are, and where they prefer to spend their brain-power and development time and energy… 
    It’s can feel easier to see the progress you make in an external situation (a “real” job) than doing your own thang, because the metrics are pre-set. Ya don’t have to do *that* work, before you can do *the* work… Does that scan, even if it’s not what you would choose?

  11. cjrenzi  
    I guess I’ve been pretty lucky, in that most of the “real jobs” I’ve had over the years have been fairly meaningful for me, in one way or another.

    1. Karen J I Wow!  I mean WOW.  I never had a job that meant squat until 2005 when I became self-employed.  At least that is how I feel.  I am a picky one though, to say the least;)

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