Category Archives: Careers

Alain de Botton is a philosopher and essayist who thinks new and interesting thoughts. While I didn’t love his book on travel, I still find him stimulating and will continue to read him.

Colin Marshall recently interviewed de Botton for his radio program. Here’s the one hour MP3. It’s a great conversation, focused his latest book, The Pleasures and Sorrows of Work. I recommend listening to it on your iPod on your way to…work.

I took some notes while listening. Some are direct quotes from de Botton:

• There’s remarkably little about work and careers in modern literature. This might have to do with the professionalization of writing — writers are somewhat disconnected from the day-to-day office grind most people endure.
• In the last 50 years expectations for both work and marriage have become crazy high. People now expect their work to be interesting (not just put food on the table) and their marriage to be one of everlasting love (not just an institution in which to have children and manage a household).
• The current economic crisis is helping re-adjust work expectations. You are starting to hear things like, “Well, at least I have a job.”
• Often what people think is the most boring part of their job is actually the most gripping. You have to really probe and prod to get people to talk about what they do, hour by hour.
• When little children play grown-up and pretend to be professionals, they love to serve. They like to serve other people (as a doctor, waiter, etc). There might be something telling in this natural tendency.
• Work can serve as an agreeable distraction from thinking about the big questions of life. Sometimes just staring at a blank wall and asking the big questions doesn’t get us anywhere.
• Too much of self-help is relentlessly optimistic. More self-help should paint an accurate picture of the pains and hardships of life, and then reinforce the message that most people need to hear more often: you are not alone.
• The point of reading is to make us feel less alone and less confused.

There’s more, too, including commentary on entrepreneurship and career counselors.

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One of de Botton’s most interesting projects is the School of Life. It’s a handful of courses about big picture life issues — like work and love. The accompanying blog, while not updated in a bit, has some great stuff as well. Here’s a representative post on silence.

The most successful e-marketers sell products about…how to become a successful e-marketer. There's a trend here.

Writers who write books and articles about…how to be a published writer.

Entrepreneurs whose entrepreneurship is about…entrepreneurship.

The networking guru who uses his network to…sell books about how to network.

The personal branding expert whose personal brand is about…personal branding.

These are what I call "meta-careers." Generally, it's best to not seek advice on the topic from people involved in a meta career.

The best advice on networking will come from someone who is not a professional networker. The best advice on entrepreneurship will come someone whose entrepreneurship is not selling books and workshops about entrepreneurship. Writers who write about anything other than writing for a living usually have the best advice on writing.

The term "quarter life crisis" refers to the personal and professional angst of some of today's twenty-somethings.

Last month Eye Weekly published a good overview of the phenomenon and wrote:

Unrelenting indecision, isolation, confusion and anxiety about working, relationships and direction is reported by people in their mid-twenties to early thirties who are usually urban, middle class and well-educated; those who should be able to capitalize on their youth, unparalleled freedom and free-for-all individuation. They can’t make any decisions, because they don’t know what they want, and they don’t know what they want because they don’t know who they are, and they don’t know who they are because they’re allowed to be anyone they want.

In other words, it is a "crisis" that afflicts a privileged slice of the young adult group: the introspective urbanites who have the time and energy to wallow in their introspections and contemplate deeper identity issues; the people who can financially afford to think about what they love to do versus what they have to do. As this older Financial Times piece put it, the quarter life crisis is when highly educated young people are paralyzed not due to "lack of opportunity, as may have been true in the past, but from an excess of possibilities."

With generational proclamations it's important to ask whether a so-called "new" phenomenon is in fact new to the current moment or instead something all people of a particular age have experienced over the years.

I do think today's flavor of youthful existential angst is new. First, the generation in question, Gen Y, might be the most ass-wiped in history. We are called the self-esteem generation because of the way our Baby Boomer parents have coddled us: anything is possible, we are all uniquely gifted individuals, so on and so forth. This can result in expectations out of whack from reality. More young people today than ever before say they expect to be millionaires by age 30, as just one example. What follows monstrously unrealistic expectations? More intensely felt disappointment and confusion.

Second, the idea of an excess of possibilities is true in a real sense — we have grown up in a world of unparalleled peace and prosperity — but also in a newly magnified comparative sense. Today, if you're 24 and online, your sense of what's possible from a how-to-live-life perspective is limited by the bounds of a boundless internet. Sure, when you read newspapers from all over the world or follow blogs from people doing amazing things your arc of vision is broader than whatever is happening on your cul-de-sac. But this also means you can compare yourself, in vivid detail and in real-time, to whomever is at the top of the game you happen to be playing in. Possible consequence: feelings of inferiority, envy, slowness (there's always someone younger who's done more and read more), stupidness, loneliness ("Everyone has it figured out but me").

Neither article offers very good advice for those suffering from quarter life malaise. The FT piece says young people should just grow up. The Eye Weekly piece says, “If you feel you’re in crisis, this is a great opportunity to draft a five-year plan with steady concrete goals to help you get to where you want to be. Anyone can transform their life in just a few years.” Which is delightfully unhelpful advice. It goes on to say, "Growing up may be hard to do, but in the end, the gains outweigh the losses… In other words: it might just be time to grow the fuck up."

Ah, growing the fuck up, a great American pastime. One gets the sense that to grow up for these authors means to relinquish those lofty dreams and accept that you are a selfish piece of shit whose life is going to be unremarkable — which is to say your life is going to be like most people's lives, and to aspire for more is cute in that youthful idealistic borderline-precocious sense but "grown-ups" know it's is just needlessly stress-inducing; grown-ups know the Cold Hard Truth is that the secret to happiness is low expectations. Grown-ups, they would probably say, know that you should not try to find your calling and just find a stable job — that way you'll have a life during the evenings and weekends.

My own highly unqualified musings on careers and life strategy for the twenty-something years have piled up over the past five years: that people should adopt a centenarian life strategy (you're going to live till you're 100); embrace your 20's as the odyssey / wandering years; expose yourself to bulk, positive randomness; travel as much as possible; don't do what you love, do what you are; choose jobs based on the people more than company (reach out to heros); de-emphasize long-term plans or goals; default to 'yes' to avoid later regret; perhaps embrace uncertainty; see virtue in shade over light; work on your ping-pong backhand.

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Here's an old NPR commentary of mine on the weak collective consciousness of Gen Y, and so why we should be careful about generational generalizations.

(thanks to Charlie Hoehn for pointing out the article and Cal Newport for brainstorming parts of this post)

My friend Josh Newman offers a helpful hint for young men:

If you're a student looking for an internship or post-college job, khakis and a medium-blue button-down don't say "professional".

They say "dickbag".

I definitely agree if above referenced fashion sense is combined with the intentional protrusion (don't say it's not intentional) of chest hair just barely popping out of that medium-blue button down.

I'm sure you're proud of that chest hair. You worked hard for it. You drank your 2% instead of 1% milk growing up. You eat well. You exercise.

But please. Spare us. Nothing screams "dickbag wannabe banker" more than the young male who feels a need to wear business casual with the top buttons unbuttoned enough to flaunt the chest hair.

Professions where you are paid by the hour are not scalable. A prostitute who charges $100 an hour only has 24 hours in a day. At some point, she will hit a ceiling on her earnings. Similarly, dentists, lawyers, contractors, bakers, and consultants can see only so many clients at a time.

By contrast, scalable professions allow you to make more money without an equivalent increase in labor / time. An author writes a book one time and his effort is the (basically) the same whether he sells 500 or 500,000 copies. A Hollywood actress need not show up at every screening of her movie to make money off it.

Career experts generally favor scalable professions.

Nassim Taleb, in The Black Swan: The Impact of the Highly Improbable, offers the opposite advice: pick a profession that is not scalable.

A scalable profession is good only if you are successful; they are more competitive, produce monstrous inequalities, and are far more random with huge disparities between efforts and rewards — a few can take a large share of the pie, leaving others out entirely at no fault of their own.

One category of profession is driven by the mediocre, the average, and the middle-of-the-road. In it, the mediocre is collectively consequential. The other has either giants or dwarves — more precisely, a very small number of giants and a huge number of dwarves.

In other words, the scalable professions tend to be winner-take-all-markets. J.K. Rowling makes a ton of money, but most authors make a pittance, whereas almost all dentists can etch out a good living that’s similar to most other dentists.

Put yet another way, scalable careers produce extreme outcomes (fat tails both left and right), whereas non-scalable professions tend to have a higher expected value with lower variance.

Taleb advises non-scalable careers because he attributes so much of one’s success in scalable careers to randomness and luck, much more so than your typical career advisor who will talk endlessly about how hard work and persistence can make any dream come true.

So what’s your risk tolerance? Are you looking for massive professional and financial success or would you be happy with a surer small slice of the total pie? Do you see huge success as significantly dependent on circumstances out of your control?

This is related to my old post on parenting styles. If you want to guarantee your kid is not a fuck up and leads a productive and “successful” life, be totally overbearing and induce lots of stress early on. If you want to give your kid a chance to end up in the history books, give him a long leash and excessive freedom to explore, but be aware that with freedom comes risk — he could more easily get into drugs and alcohol, for example.

Bottom Line: If you swing for the fences, you’ll either hit a home run or strike out. If you swing for a single or double, you’ll probably get there, but no farther.