Imagine consuming nothing but stale baguettes and water. Fighting for dominance against armies of cockroaches. Living in a tiny, unheated attic in the depths of winter, life-force draining away with every rattling breath.

19th century Parisians have a lot to answer for.

The literary gypsies of the Bohemian movement lived in self-imposed squalor, but the ‘starving artist’ mythology they created somehow made the whole mess seem heroic and très chic.

The thin veneer of romanticism overlaying the starving artist lifestyle is peeling away, laid bare by the humdrum reality of modern-day existence. Creative ghettos have gentrified. Being poor is not sexy.

Everyone knows someone with big dreams. I’m a dreamer! Maybe you are too. Here’s an example of what happens to the dreamers seduced by the starving artist myth:

You move back into your childhood room to save on rent. The racing car bed and N*Sync posters don’t quite create the same atmosphere as the Boulevard Saint-Michel circa 1920, but that’s OK. While your friends accumulate money and careers and other such bourgeois trappings, you await the day you get your big break and everyone finally recognises your brilliance.

And wait…

And wait…

And wait…

…until your brittle bones turn to dust and you’re working shitty odd jobs to make rent and phantasms of forgotten dreams drift through your semi-consciousness and Justin Timberlake’s faded yellow nightmare visage accuses you through those 16-year-old eyes: what the fuck have you done with your life, anyway?

At the risk of sounding like an Infomercial, there has to be a better way.

And there is! If you’re an aspiring artist, an entrepreneur, or a dreamer of any description, what follows should be pretty damn encouraging. It’s time to get strategic.

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Brutalised by Statistics

A ‘normal’ career has one very appealing feature: Your effort is directly proportionate to the reward you receive. If you’re a plumber, the more taps you fix, the more cash in your pocket. No-one’s labouring away unblocking toilets in obscurity, hoping that one day someone will recognise their unparalleled brilliance in U-bend gasket seals.

The flipside is that there’s an upper limit to how much money you can make, because you can only fix so many taps in a day.

This is what risk analyst Nassim Taleb calls a ‘non-scalable’ career. A baker can only bake so many loaves. A lawyer can only represent so many clients. A teacher can only grade so many students.

Artists – which really means anyone from writers to musicians to entrepreneurs – have no such upper bounds. Something idea-based can be sold over and over again with almost no extra time or effort. It’s infinitely scalable. Your debut album might sell 10 copies (three of which your mum bought) or 10 million, but the amount of work that went into recording it was the same.

Of course, there’s a catch.

Scalable careers don’t follow a normal distribution, with a clear relationship between effort and reward. Instead, they produce grotesque inequalities. It doesn’t necessarily matter how good you are, or how hard you work: a select few people capture almost all the rewards, while everyone else gets next to nothing. In statistical parlance, this is called a ‘long tail’ or ‘power law’ distribution.

The publishing industry is a classic example. Every year, a million new books hit the shelves. On average, each title will sell a paltry 250 copies. If you include self-published books, the median (middle number of sales) rapidly approaches zero. Like venture capitalists, publishers rely on diversification: one of the bets they make will succeed in spectacular fashion, more than making up for all the failures. Individual authors don’t have this luxury.

The left-hand side of the graph is dominated by the Dan Browns, Stephanie Meyers and other such literary marvels. The peak of sales almost immediately plummets into a long, tragic tail of aspiring authors stretching to the right (which would be several kilometres long if I had drawn this to scale). There’s not much of a happy middle ground here.

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Introducing the Barbell Strategy

The ‘golden middle’ has thousands of years of tradition in philosophy and aesthetics, but it doesn’t jive with risk management today. Nassim Taleb is best known for his work on ‘Black Swans’ – rare events of enormous magnitude that are impossible to predict. They can be negative – like the global financial crisis, which no-one saw coming – or positive, like an astronomically successful debut book or film.

Taking the middle way is only an illusion of safety. You’re still exposed to potentially ruinous events, with no chance of the unlimited upside that also swirls out of the same chaos.

 

Instead, Taleb suggests targeting the two extremes of the spectrum at once. On one end of the barbell, you play it safe with a secure, staid career. On the other end, you take a lot of highly speculative risks. In the middle, as little as possible.

The perfect Barbell Strategy job has “few intellectual demands and high job security, the kind of low risk job that ceases to exist when you leave the office”. Ideally, it should be something that won’t force you to bastardise your other work; non-political and low-profile. You do your nine to five, and then you check out. All your evenings, weekends and vacation time are free for working on your speculative side-hustles.

As Taleb points out, comfy sinecures have frequently been fertile ground for greatness:

The great French poets Paul Claudel and Saint-John Perse and the novelist Stendhal were diplomats; a large segment of English writers were civil servants, Kafka was employed by an insurance company.

If your big dreams don’t work out, you have a regular income source to keep working towards financial independence. If your side-hustle does start bringing home the bacon in a major way, you can ease out of the day job by reducing your hours, or taking a sabbatical – which brings us to the vertical barbell.

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The Vertical Barbell

Flip the barbell up so it’s balancing on one end. In this model, you spend a chunk of time focused on accumulating wealth and security through a regular job, then the next spell single-mindedly focused on your art.

Again, Taleb points out this has been a pretty successful strategy throughout history.

Many of the ‘doers’ turned ‘thinkers’ like Montaigne have done a serial barbell: pure action, then pure reflection.

It’s also the approach I’ve taken (no comparisons to Montaigne intended). Being a fulltime journalist is not the sort of job where you clock off at 5pm and never give it another moment’s thought.

I worked intensely for almost five years in a fulfilling and rewarding career. Now I’m taking a sabbatical – perhaps for the same length of time – to pursue some creative and entrepreneurial passion projects.

If my speculative gigs don’t pay off, I can fall back into a regular, non-scalable career. It might be that I’ve got all the other stuff out of my system by then. If not, I can always repeat the cycle.

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(Incidentally, it’s a really bad idea to try and jump straight to the high-risk end of the barbell without doing the hard work first. This is a mistake that lots of aspiring entrepreneurs and freelancers make, as I explain in my review of the 4 Hour Work Week.)

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The Starving Artist vs the Barbell Strategy

Let’s recap:

Starving Artist	Barbell Strategy
If you fail, you have no backup plan and no financial security.	If you fail, you’re still working toward financial independence by other means.
Stretches the patience and generosity of friends, family and society to breaking point.	Completely self-reliant.
Requires eating a few shit sandwiches – doing unpleasant things to pay the bills, or compromising on your values.	No need to compromise your integrity or ‘sell out’.
If your identity is solely tied up in your art, your writing, or your amazing business idea, failing will prompt a bone-crunching existential crisis.	Not achieving recognition is upsetting, but you have more than one string to your bow – you’re still an accomplished insurance broker, or whatever it might be.
You have no capital, which is crucial for getting anything entrepreneurial off the ground (all successful artists are entrepreneurs).	You can accumulate capital to give yourself the best shot at making your side-hustle work.

The Barbell Strategy has applications in all sorts of domains which involve managing risk, from health, to finance, to reputation. It’s an intriguing concept which deserves further exploration.

(UPDATE: here’s how it also underpins my investing strategy)

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Art for Art’s Sake

Derek Sivers is a musician, entrepreneur (he sold his CD Baby business for $22 million) former circus clown, and all-round interesting dude. People with high-paying jobs often ask him for advice, because they want to quit to become full-time artists. But full-time artists ask his advice too, because they’re finding it impossible to make money.

Both groups of people get the exact same answer:

1. Have a well-paying job
2. Seriously pursue your art for love, not money

Sivers says this is the lifestyle followed by the happiest people he knows.

How nice to not expect your job to fulfill all your emotional needs. How nice to not taint something you love with the need to make money from it.

This is something incredibly important to me, best explained by a weird analogy about my pants.

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The Breezy Denim Hotpants of Freedom

I used to own a pair of denim cut-off shorts that were objectively hideous – stained, ragged, and holey. As the fabric disintegrated, they got shorter and shorter until public decency was perilously hanging in the balance. Successive girlfriends tried to throw them out, but they never won.

Being told what to do rubs me the wrong way, to the point that I will apparently die in a ditch over the pettiest causes. If the order comes from above, I obey, but it hurts. I’ve had some amazing editors, but each overzealous stroke of the red pen – an obscenity censored, a critical passage defanged – is painful.

I sometimes get offers from companies who want to enter ‘partnerships’ with Deep Dish, which basically means running thinly-veiled ads shilling their products. The legitimate offers I politely decline. If they’re shady, I take great pleasure in casting them into the fiery pit of the spam folder.

If I wasn’t so well-positioned financially, these sort of offers might start to look pretty tempting.

The Barbell Strategy clearly separates bread-and-butter work from creative pursuits. Your identity isn’t solely tied up in one or the other, and you don’t have to bastardise what you do in an attempt to curry commercial favour.

This might be the single biggest advantage to me.

Here on this blog, I can be as vulgar and honest as I want. I don’t have to compromise on anything. Instead of being under pressure to pump out a stream of low-effort dross, I spend a stupid amount of time writing each post. In short, I can hang out in my raggedy-ass Daisy Dukes, a gentle breeze percolating through the many holes, and do my own thing.

Let me tell you…

It’s a hell of a good feeling.

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Further Reading

Note: The public library will loan you these books for free. If you’d rather buy them, use the links below to send a few pennies to support this site, at no extra cost to you (read more here).

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The Black Swan – Nassim Nicholas Taleb

Taleb is a pompous blowhard, a merciless troll, and probably the single most insightful author I’ve ever read. The Black Swan is a good introduction to his oeuvre because it contains one of his most interesting ideas, and isn’t as sprawling as his later works. Once you’ve got his measure, follow up with Antifragile, which is where the barbell strategy comes from, as well as Fooled By Randomness and Skin in the Game.

Anything you Want: 40 Lessons for a New Kind of Entrepreneur- Derek Sivers

By contrast, Sivers is one of the nicest people in the world (but no less insightful). This short but excellent read details his journey to creating and selling CD Baby. Unlike the borderline sociopathy of most business books, he stresses that the goal is always happiness, not money. For a taste of Sivers’ work, check out his essay Balance, which I’ve drawn from in this post. He’s appeared twice on Tim Ferriss’ podcast, and both episodes are well worth listening to.

1000 True Fans – Kevin Kelly

This influential essay has done the rounds of the Internet several times. Wired editor Kevin Kelly argues that creators can find a middle ground between the big winners and the long tail of losers, as they increasingly connect to small groups of highly devoted fans. Selling to these fans directly, rather than through middlemen, can be enough to make a decent living. This is encouraging if true, and would work well in conjunction with a Barbell Strategy approach.