“Dreams come true but not free.”
Stephen Sondheim, Into the Woods
The experts quoted in last week’s post were focused on Millennials, but their advice also applies to people making mid-career/midlife changes. No matter your age, it’s the same dilemma: you’re inspired and ambitious, but the economic realities are unimpressed. What’s a dreamer to do?
The popular mantra [of positive thinking] comes from the actor Will Smith, who said: ‘Being realistic is the most commonly traveled road to mediocrity.’
But ‘mediocrity’ is a loaded term. Who, after all, wants to be ‘mediocre’ or ordinary? And yet, save for a few, aren’t we all? By implying that the only options are superstardom or mediocrity, we ignore where most of us ultimately land – that huge middle ground between anything and nothing much at all.
Mediocre?! Who you calling mediocre?! Well, um… you. Just like the rest of us.
Mediocrity is a hard truth for high achievers to swallow. Will Smith didn’t have mediocre in mind when he said that, neither did Steve Martin when he advised “Be so good they can’t ignore you.” Georgetown professor Cal Newport debunks them both on in So Good They Can’t Ignore You: Why Skills Trump Passion in the Quest for Work You Love.
“Cal Newport [says] that we have got the passion/purpose equation backwards. ‘It misrepresents how people actually end up passionate about their work,’ he says. ‘It assumes that people must have a pre-existing passion, and the only challenge is identifying it and raising the courage to pursue it. But this is nonsense.’
“Passion doesn’t lead to purpose but rather, the other way around. People who get really good at something that’s useful and that the world values become passionate about what they’re doing. Finding a great career is a matter of picking something that feels useful and interesting. Not only will you find great meaning in the honing of the craft itself, but having a hard-won skill puts you in a position to dictate how your professional life unfolds.
Seems reasonable, but not everyone is convinced:
“Newport’s recommendation begs examination of another aspect of the ‘you-can-be-anything’ framework: should we expect to pursue a passion within our career or is it wiser to try to satisfy it outside of one? Sure, it’s convenient (and nice!) to be paid for something we’d love to do anyway. But is it realistic?
“Marty Nemko, a career counsellor in the San Francisco Bay Area and the public radio host of “Work with Marty Nemko,” offers up a resounding ‘no’. He’s all for people pursuing their dreams, as a hobby. ‘Do what you love,’ he says, ‘but don’t expect to get paid for it.’” 
I.e., separate your dreams from the economics and there won’t be a problem. How? Keep your day job. Click below for a six-minute look at someone who followed this advice.
“Didn’t Einstein have to have a job in the post office or something?”
“As any artist knows, for every Banksy or Beyoncé, there are thousands of dreamers whose artistic impulse has to be sustained by paid gigs, which tend to be unglamorous. Such is the life of Robert Friedrich, a New York City-based comic artist who splits his time between creative work and a dull cubicle job he’s held down for more than 20 years. Starting with a love of superheroes, he eventually began mining the minutiae of his daily life to create Failing Fast, a ‘visual diary’ of the modern workforce. Finding a refreshing twist on the often fawning sub-genre of artist profiles, the director Sarah Hanssen makes Working Stiff a broadly relatable take on the creative life, in which passion doesn’t pay the bills and every small success is savoured, if fleeting.”
I confess, I tried, but was never good at keeping my day job. I was too much in tune with the point of view of another cartoonist (click the image below for the full text):
“So, what’s it like in the real world? Well, the food is better, but beyond that, I don’t recommend it.
“Having an enviable career is one thing, and being a happy person is another.
“You’ll be told in a hundred ways, some subtle and some not, to keep climbing, and never be satisfied with where you are, who you are, and what you’re doing. There are a million ways to sell yourself out, and I guarantee you’ll hear about them.
“To invent your own life’s meaning is not easy, but it’s still allowed, and I think you’ll be happier for the trouble.”
Watterson gave that advice in 1990. Economic realities have changed a lot since then, but dreamers still dream. I’d say go ahead — inspiration will make you happy — but then also take Stephen Sondheim’s advice to heart. I sure do these days.
 Op. cit.
 Op. cit.