Do you love the game?

Be very careful of apathy, hustle, and the infinite and unexamined loop

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Friends, there’s unlimited content out there focused on “Accelerating your career!”. Unfortunately, there’s not enough around “Is your career worth accelerating?”.

I want to start this piece by asking you to try watching this clip (it’s less than 90 seconds) from Adam Sandler’s ode to Basketball, Hustle, and not feeling something. I am not a sports fan, but I know I can’t.

Hustle is a basketball film, sure, but more so it’s a story about fighting for your dreams, overcoming your past, and putting in the reps to become a true professional. It’s an entertaining reminder that the path to self-actualization is a series of bets we take on ourselves. 

Changing careers or starting a company could be one of those bets. And if you’re going to do that—regardless of what scale you’re hoping for—you need focus, drive, and a lack of excuses.

Like a tripod, you must have all three. That’s nonnegotiable.

And there’s only one sustainable way to get that: You need to love the game you’re playing.

If you don’t, you probably won’t beat the next person who does. Or as Stanley Sugarman (Sandler) says, “If you don’t, don’t even bother.”

But, if you do love the game, then you’ll obsess and live it. And that is the most fundamental trait needed to win.

So, let me ask you….Do you love the game?

…and is your nonrefundable time being well spent playing the right one?

If you stopped reading right now and just really thought about the answer to that question, this would have been a minute of your time well spent.

But if you want to pull the thread a little more, below we’ll chat about:

1. Why do we play games we don’t love?

2. The result of playing these games; and the biggest opporunnity cost 🔒

3. How to change games 🔒

1. Why do we play games we don’t love?

I turned 30 a couple of months ago, and a recurring conversation I’ve been having with friends is about changing games…like switching careers or starting something up in pursuit of finding more meaning in work.

I found it interesting that so many of my closest friends were, all around the same time, thinking about the game they were playing. As I thought about it, my take was two-fold:

1. Less interestingly: Turning 30—like January 1st—is an artificial inflection point or “new leaf” in life that probes us to think about change and how we’re spending our time. (Life hack: Any moment can be an equally compelling inflection…like right now if you wanted it to be.)

2. More interestingly: People often stumble into the first phase of their careers—being pulled into a job by following some initial opportunity or idea. When entering the second phase of their career (perhaps at around 30 y/o… although that’s just made up), they can choose to either keep playing the game they landed up in and double down, or decide to start anew, step into another one, and push themselves into a new and more conscious path.

Just thinking about me, my wife, and my immediate friends, that second point becomes very clear:

• I fell into product management accidentally through starting a company

• A friend fell into tech sales because the first real job offer he got happened to be in sales

• A friend fell into operational finance because he joined a brand new startup and that’s what they needed him to do

• My wife fell into content marketing because she was a writer and her first internship happened to be in marketing

I could go on, but you get the picture. It’s easy just to end up doing something because that’s what happened to us, versus doing something because we knew more than anything that’s how we wanted to spend our time.

When we start our careers, IMO, we loosely follow our skills and interests and tightly latch onto whatever pays us the most the soonest and makes the parents proud. I mean, at 21, the most important thing is just getting a job that helps us pay rent. I wasn’t exactly trying to answer the meaning of my life back then, and I know many face the pressure from family to pursue a "safe" or "respectable" career path.

The question though, as I’ve seen with my friends, eventually becomes Is that a game we actually love to play? Is this how we want to spend our unrefundable time?

And we must ask it. Because life is too damn short, as I’ve unfortunately very recently experienced with the unexpected passing of my mom, to play games we don’t love. Games that don’t fulfill us and give us joy, energy, and meaning.

Of course, there are plenty of people who found the game they love very early on and are lucky because they just get to keep playing it. You could well be one of them. But, there’s also a very big camp of people who keep playing unloved games.

Either they never ask themselves the question and just keep executing an infinite and unexamined loop until retirement—never having taken the time to truly reflect on what drives them—or they do ask it, but keep wasting time by falling victim to routine, not making any decisions, and keep playing out of two very sticky reasons:

1. Apathy

2. Hustle

Apathy 😑

When founders and PMs do competitive landscaping for an idea, they often fail to mention one of their most threatening competitors—people’s apathy to changing how they do things already.

Apathy = lack of care / awareness = lack of change. And that’s a very hard thing to break through because we’re all suckers to habit, inertia, and running on autopilot.

Applied to this concept of the games we play, apathy can reveal itself as a sunk cost (“But I’ve already put so much time in. Stopping would be a waste.”, just plain fear—fear of failing to do something new, fear of the unknown, or the fear of disappointing others—, or most scary, apathy can reveal itself as total lack of awareness to the problem at all.

Tell me…does this sound at all familiar?

Wake up at 7:30am. Roll out of bed, open up your laptop at 8am. Sit around in your sweatpants, make some coffee. Have a shower. Work for thirty minutes, then mindlessly scroll through some app. Play Wordle. Eat some leftovers for lunch. Stare at the computer until 5ish. Head to gym. Come home and shower. Whip up some dinner or order in. Watch a few episodes of whatever show. Scroll social media. Then go to sleep…because it was a long day.

And then you do that over and over and over again.

By the way, there’s nothing wrong with that day. I’m merely calling out how easy it is to slip into weeks and months of rote/passive routine. Day after day we run on autopilot.

You can see how easy is is to not ever wonder whether the game we’re playing…and that game’s rules, norms, and expectations…are worth sticking to and sinking more of our time into.

That's the danger of an apathetic life…time will pass you by before you realize it.

Hustle 😵‍💫

The second big reason we stick to games we don’t love is out of the opposite to apathy…hustle.

Sometimes we find ourselves playing very lucrative games where the prize for winning is clear…money, ego, and social status.

And if we’re good at that game, it’s even harder to want to stop playing because money and future prospects cloud out the feeling of needing to change and spend our time doing something else.

Simply, it’s very compelling to just want to win the game we’re playing and know about vs to stop, learn a new game, and start again.

The thing is…hustle and apathy are two sides of the same coin.

With apathy, you are either too disinterested to pursue what you want out of life…or with hustle, you’re too vain to realize you are pursuing short-lived things.

Reading this and just knowing these two forces are at play gives you more awerness than most.

Unfortunately, the cost of ignoring either can be severe.

The last two sections of this post are for paid HTG members only. Consider upgrading to support my work, invest in yourself, and go deeper on this topic.

2. The result of playing games we don’t love games