The Happy Workaholic

Calling bullshit on balance when life gives you a winning hand

A common cautionary tale is the workaholic who finally loses it. Burning the midnight oil and the candle at both ends, they’ve bitten off more than they can chew, spread themselves too thin, taken no prisoners, and worked themselves into the ground. Eventually and inevitably they crack up and go belly up, fall to pieces, go down in flames, crash and burn.

The antidote is living a more balanced life. Since disaster is deterministic, Type A people are advised to proactively chill the fuck out. Work, they are counseled, is but a means to an end, rather than an end in itself. By focusing more on the end game rather than the game, tension is removed, and life is improved. The Road to Hell is paved by obsessive intentions.

Burn out is def a thing. The tendency to double-down when faced by an uncomfortable or misaligned situation is tempting. An effective solution is instead to fail as fast as possible, stop playing a game that can never be won. Such is the case when work masks deep personality disorders, as for Bobby Fischer — or when working the wrong job sends us off the deep end.

What about the opposite scenario? When an ostensibly “balanced life” sends people down the Road to Ruin? How often have we heard the converse cautionary tale, that of a consummate #winner who has checked all of life’s boxes, only to discover they are a character in a Talking Heads song, wondering how they got there, trapped in a dead end, no way out?

So let’s throw caution and moderation to the wind, and argue that for the very reasons that life is risky and random, we should perhaps follow a proven poker strategy: When you get a strong hand, go all-in. Yes, bet your stack after waiting patiently for this moment when the various factors driving your success, whatever they happen to be, have converged.

The classic poker scenario is high trips on the flop — at a crowded table your immediate goal isn’t to win outright, but force others to fold. Since Texas Hold ’em is a drawing game with a majority of the cards shared, your advantageous situation progressively diminishes with every additional round. The clock ticking, this special moment fleeting, make your move.

By analogy, when the stars finally align on your studies, your business, your relationship, your creativity, your whatever — hit the gas, hard. We are different people at different times of life, and within these select phases are given narrow windows of opportunity. When that light shines, we should give everything we’ve got, because like poker, our advantage rapidly fades.

Andy Warhol famously never said “everyone is famous for fifteen minutes” — meaning we each get these rare moments to shine. What differentiates those who succeed from those who don’t isn’t getting that fleeting few minutes in the spotlight, but what we are then able to do with it. A break triggers a career if you can convert your Warhol Fifteen into a life time.

Most people scoff, dismiss life as unfair, and give up. The trick is to not take rejection and failure personally. Fits and false starts are attributable more to mathematics than the miserliness of the Universe, there simply being insufficient golden opportunities to go around. Soon as you open that envelope and find a Wonka Golden Ticket, you better stake your claim.

Back to our conception of the workaholic, by definition a person suffering from workaholism. Analogous to alcoholism, the workaholic is addicted to working, having succumbed to the mental illness and compulsive behavior resulting from dependency on work. Although not a clinical condition found in the latest DSM-5, we consider it unhealthy.

When the term is used to describe a family member, friend, or colleague, the subtext is that they lead an imbalanced, unhappy existence. “Joe is a workaholic,” means poor Joe has no life, and is fleeing from broken relationships, hidden traumas, intractable challenges, or who knows what else by working all the time. In other words, Joe is focused, but fucked up.

The fundamental problem with this common conclusion is few if any people ever ask Joe how he feels about his obsession. The emotions of those shunned are certainly valid in their own right, but the baseline assumption that a “balanced life” is de facto the happiest life remains questionable. Sure, Joe might have unresolved issues and deep traumas — but don’t we all?

Self help gurus and life coaches from Sam Harris to clueless fraudsters love to talk about the healing powers of meditation, and they’re right. Total immersion channels our otherwise scattered and chaotic energies, similar to the filtering and focusing of diffuse light into a coherent laser beam, creating a state of deep relaxation and mindfulness within each moment.

Work, when fully immersive, is akin to meditation. Some people hate their jobs, arguably most do — while alcoholics like to drink, and workaholics like to work. Although you might believe Joe is avoiding you and all of his other problems, he could instead actually be living the life he loves. Relentlessly sustained over years, such focus is debilitating. But who’s keeping score?

Attention a zero sum game, we can’t have it all. Most choose the lowest common denominator, ground state for flying under the radar. Based on our societal roles, we’re told what to do and how, but rarely why. Just STFU and do it. Workaholics fundamentally question the basics. How much of what we do is obligatory? Who has written our rules of social engagement?

Mortal beings, our energy, time, and resources are woefully finite. “Only so many hours in a day” is either an excuse, or a rallying cry. Fans gape in awe at the vast oeuvres of Pablo Picasso, Frank Zappa, James Cameron — they and other artists who were, by any stretch of their imagination or ours — workaholics. We love what they did, because they did what they loved.

“If you’re going to be wrong,” somebody wrote on an IT message board, “be wrong with conviction.” Let me tweak that by suggesting, based on the best poker strategies and the worst workaholic habits, that if you’re going to lose, lose with gusto — and do it without remorse, eager to buy back into the game. What’s in pocket? What’s on the board? Trips come up? Go all-in.

“Bad beats” are frequent in poker, even the greatest players losing with what seems like the best hand. Yet the greatest players are great not only despite these bad beats, but because of them: big pots can only be won by taking big risks, folding without resignation, and winning without hubris. When the Muse finally puts out, indulge her without reservation. She’s a fickle bitch.