The Way of Work explores stories of where we fit in the world of work. This is part of the series, Not Obvious, exploring why work advice fails us (the intro was last week). Also, check out The Other Side of Enough, exploring what life is like when you have enough to never work again.
Is there any more obvious advice than “you need to work hard to be successful”?
In my estimation, this advice sits atop the The Hierarchy of Obvious. No less than our entire cultural ethos is founded upon this overused cliché. From an early age, we’ll hear:
“You can do anything you want… if you work hard.”
We wake up each day, blasted by the gospel of hard work, but instead of divine wisdom, these messages sound like something you’d find on the back of a tub of protein powder.
If we have a problem, the answer is simple: we’re not working hard enough. Like cause-and-effect, hard work is the way we have control over our lives. As if, despite the mountains of expectations and pressure we put on ourselves, what we really need is more pressure. More expectations.
Before the anti-work crowd thinks I’m starting a rally, put down your posters, because I’m coming for you too.
Our cult-like devotion to work is so ingrained we barely question it. But maybe that’s exactly why we should.
The Hard Work Hype
Let’s get the obvious out of the way: if you want to be the Michael Jordan of your highly-competitive field, then yes, you will need to work very hard. If you have that type of singular, obsessive ambition, say goodbye to balance. We can basically guarantee you aren’t going to have a normal life. You will bleed for your dream, your identity tied to every win or loss.
If you’ve taken VC money, have a high billable hours quota, or racked up massive debt, then buckle up, because you’re locked into an extended level of servitude. I think the technical term is “hosed.”
But if you have a single other goal, that ambition will become diluted. Here’s a simple one: don’t have a heart attack before 40. That’s a nice goal! And in SMART format, too! Unfortunately, there will be a time when you’re forced to trade-off that goal for the other as you reconcile your multiple ambitions.
Here’s another inconvenient truth: you can work yourself into the ground and still get absolutely nowhere. Some grind in circles only to never “make it.” Others stumble into the right room once and walk out rich.
But hey, it could all work out! It did for me, so it’ll definitely work out for you too!
I know hard work — I threw my entire being into my early-to-mid career. And it worked! My workaholism was perfectly timed to my personal situation (young, no kids) and the opportunity (joining the company at the perfect moment). I wrote before:
“The foundations of my career were built on intense, hard work, so it would be insincere to recommend anything else.” - From early startup to $2B public company, what 12 years at Privia Health taught me
But let’s suppose it hadn’t worked out for me. What if luck hadn’t fallen my way? What if that chronic stress killed me a few decades earlier? What if my workaholism had made me miss my kids' childhood or ruined my relationship with my wife?
Let’s suppose you have become successful. Congratulations! But you look back and realize the cost was too high. Whoops, the ROI was negative! Hard work can be a foundation of meaning, but it can also leave us empty when pursued at the cost of everything else.
Suppose you base your work ethic on others around you. Welcome to the hunger games of hustle! Because just when you think you’re the last one standing, there’s always some maniac (like me, when I was younger), who is so foolish and hungry with blind ambition that he’ll go to unspeakable lengths of burnout to fill that void of meaning in his life. Are you sure you want to match that guy?
I could keep going… how we mistakenly define “work,” how less work can make you more productive, how you can work hard on the wrong things, and so on (but this is getting long, so I’m moving on).
Look any closer at the “work hard” virtue, and it becomes a lot less obvious, but a lot more gray.
The Work-Free Fantasy
After burning out on the “work more” hype, we naturally turn to its appealing alternative: “work less.”
I’ve been down this road myself. Heck, I wrote a series about my time away from work: Don’t Work.
Who isn’t tempted by these seductive whispers? Escape the 9-5! Slow down! Don’t be a fool; detach, relax, touch grass.
But “work less” can be just as vague and unhelpful. Again, if you were hoping for me to pick a side, you picked the wrong post.
People seem to buy this advice for the fantasy alone, like the lottery player who knows they’ll never win but enjoys the brief escape of imagining what life would be like if they did.
“Work less” sounds nice. But it also doesn’t sound right.
You can write your polemics about why we shouldn't work so hard or how things weren’t always this way (I wrote one too). But they don’t change the fact that tomorrow, you still need to decide when your work day starts and ends.
For many, “work less” is just a dream they consume in between stress-filled shifts of hard work. Would you tell someone trying to break into an uber-competitive field or living inside a crisis to “work less?”
What “work less” does sound like is the prescription of the privileged. I imagine myself giving a lecture about the perils of overwork… to the construction guys building the house next door in freezing weather. “You should take a sabbatical!” Then, I go back to writing something inconsequential in my home office.
And try NOT working. You might realize that doing nothing is its own kind of existential horror. The early retirees I interviewed still question how to spend their days.
Hustle isn’t always bad. Sometimes you have a spark of inspiration. You’re building momentum on a project or new job. You’re exploiting a rare opportunity. Work gives you structure, community and meaning.
The “work less” crowd doesn’t realize that if you care about what you do, it’s not easy to clock out at 5PM and call it a day. Sometimes, we want to work hard.
The Mirage of Balance
One side says work more. The other says work less. Maybe the answer is somewhere in the middle… I know: BALANCE!
Yup, we just need to find that perfect state of equilibrium. Content, at peace, one with the world…
“Ommmmm…”
And also: not how things actually work.
It’s pleasant sounding, but these ideas fall apart the second you actually try to live them. Think about it. Where is this place called balance? Hour 40?
Even in my most peaceful moments, I’ve never felt balanced for long. Sure, I’ll get a fleeting glimpse, but then I’m off again. Even if I’m exquisitely mindful, I either work a little too much or a little too little. At best, I’m slightly off – too tired or too much left in the tank.
Let’s use a concrete example: tomorrow, should you work one more or one less hour?
Let’s say your employer dictates X hours. Should you work X+1? Just to catch up? To get ahead? To build something on the side? Or should you work X-1? Even just to coast a bit? Run an errand? Get in a workout?
Because plus-or-minus one hour can be life or death for a busy person. Between a thriving career or stalled one. Between health and burnout. Between a great relationship and a nonexistent one. Each day we choose an option from the menu. Only you decide. How’s that for balance?
The problem isn’t that we’re bad at finding balance. It’s that balance, as we imagine it, might not exist at all.
No Answers, Only Choices
The work more/less/balance advice isn’t all wrong, but it misleads us into looking for the “just right” answer: a correct number of hours, a perfect equilibrium, a universally optimal work ethic. An elusive Goldilocks-mode – not too much, not too little – just enough work to complement our ambition.
But when our own messy reality doesn’t match the tidy advice, we assume we’re doing something wrong. What if there is no ideal state, just the ongoing mess of recalibration? After wrestling with this question, here’s my disappointing conclusion: there is no right amount of work.
You’ll never know if you’re working too hard or not enough.
You won’t know if your effort will be worth it (until later).
There’s always more you could have done, in and out of work.
At some point, you’ll probably regret either how much you worked or how little.
At the very least, none of this is obvious.
All we can do is pay attention. To the way we prefer to work inside and the way the world expects us to work outside. Instead of balancing, we’re juggling, continually asking ourselves:
What is my ambition(s)?
Is my work sustainable?
Am I pushing because I want to, have to, or think I should?
How can I shape my circumstances to fit my needs?
And endless more questions…
Each day, we pick a time to start and stop. These become data points to inform the next. Never in complete control, but maybe a bit more than before. Owning, not outsourcing, our choices and their consequences.
We find no perfect answer, only adjustments and iterations, tuning as we go, hoping to one day stumble into something that feels like our own way. Even if it only lasts for a day.
Bonus: Ambiguous Advice
▸ “Work hard, play hard.”
Nothing says balance like blending your burnout with blackout.
▸ “Only work hard on things you won’t regret later.”
As we all know, 20-somethings have always been perfect predictors of their 80-year-old selves.
▸ “Outwork everyone else.”
Let’s lock two schmucks like this in a room together. No exits. Just endless hustle. And see how it turns out.
▸ “No one remembers how hard you worked 20 years ago other than your kids.”
Yeah, but your kids may ALSO caution you against the logical end of this argument… because they ALSO want you to pay the bills.
▸ “Don’t stop working when you’re tired. Stop working when you’re done.”
Okay, then I think I’m done now.
Next up, is exploring the “sacred hows” behind productivity:
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This really makes you think there's no perfect balance between working hard and taking it easy. It's more about adjusting every day based on what matters to you. The part about hustle being exciting when you're inspired vs draining when you're just following pressure stood out. Maybe the key is knowing why you're working in the first place. What do you think?
The value of "hard work" and the advice to "work harder" only makes sense (to the extent that it does at all) when applied to traditional forms of work where results can reasonably be assumed to reflect effort. Much of modern work does not fit that bill.