If It Doesn’t Hurt You’re Not Doing It Right

personal stories, random thoughts, relationships

The other day, I went to a lawyer networking dinner in Pasadena with my girlfriend, Amy. She asked me to be her date: to rub elbows and drink blended margaritas with too much ice and not enough tequila.

She asked… expecting me to decline.

Because most of the time, that’s what I do.

Amy knows me better than I know myself.

She knows what it means when I get quiet… or talk too loudly… she knows EXACTLY what I’m thinking when someone starts talking about what “they deserve” (e.g, a good job, a good salary) after earning a piece of paper after four years of delaying the real world.

So she knows when she asks if I want to go do something (drink blended margaritas, go to the beach, eat froyo) I’ll act like I’m considering it… but what I’m really doing is opportunity cost calculus.

Here’s what that calculus looked like when she asked me to this dinner:

  • “Well, I’ll take an hour train ride into downtown Los Angeles where she’ll pick me up

  • Then it’ll be a half-hour drive to Pasadena

  • We’ll be meeting these people who aren’t in my industry, so it’s unlikely any long-term relationships will come out of it

  • (plus they’ll probably be way older than us)

  • We’ll eat food, make small talk, listen to some speeches for two hours

  • Then get in the car and drive 30 minutes back home

  • At which point it’s 9 p.m., and I know I can’t work after 8…”

“So going to this event = an opportunity cost of 4 hours of work.”

Then I think: “Well, shit, 4 hours is lot, to hang out with a bunch of people I’m never going to see again…”

This happens in the pause after Amy finishes her sentence.

She catches it (and I catch her catching it). It happens in a blink but it’s still noticeable, like flicking on-and-off a light switch.

Opportunity cost calculus is something I do several times a day. It is, without a doubt, the thing I hate the most about myself.

What I Hate Most About Myself

I hate the idea that I’m calculating. I hate that I’m a schemer, a Scrooge that clutches his seconds and minutes with shriveled hands tight to the chest, where instead of a heart and lungs you’ll find a TI-90x and a stopwatch.

I hate that there’s this selfish part of me I’ll never outgrow. No matter how successful I become, no matter how much money I make, and spend on others, I am still:

  • The brother who never made it to a single (out of three!) graduations

  • The friend who’s watching the clock when he meets you out for a drink

  • The boyfriend who weighs the opportunity cost before spending time with you


The point isn’t that I don’t know how to make the time. I do know, and I put it to action (which is how I went to the event with Amy.) What I can’t stand is that this selfish part of me is so intrinsic, I feel like I can never turn it off.

I know how to make the time, but I’m always painfully aware of the cost.

Let’s Not Kid Ourselves

“But you’re building your career! You’re building your future! It’s not like you’re choosing between spending time with people and mindlessly watching Youtube videos or playing with apps.”

I know — what do you think I tell myself every fucking day?

I say things like:

  • “I work this way because I’m building something for us.”

  • “If I work like this for the next 3 to 5 years, I’ll be able to slow down when it’s time to start a family.”

  • “I want to inoculate my family against all the things this world can throw at us.”

On the surface, the intent is sincere… but it doesn’t look much different from the parents I see who neglect their kids. They kiss ‘em on their cheek, hand them to their nanny, and wave goodbye.

When pressed about what their kids like to eat, watch, read, they laugh and say, “I don’t know. I’m too busy providing for them, I don’t actually spend time with them!”

When I was a kid, my dad worked in NYC while we lived in Albany. He got one day off a week, which he saved until he had a total of two. Then he came home, slept for one day, and spent time with us on the second day. Then he left again.

I imagine he said the same thing to himself, for the few years he did this. “I’m doing this for my family.”

working with dad

It sucked.

I’m not saying it’s not true. For anyone who’s guilty of this, there’s truth to it.

But it’s not the whole truth.

For me, the whole truth is: I’m addicted to the climb. I’m addicted to:

  • Taking something completely foreign yet important (e.g., film options and writer agreements) and saying, “ok, I don’t know what any of this shit means, but I KNOW I can break it down” — while most people never bother because there’s nothing sexy about entertainment contracts.

  • Admiring the top figures in different spaces (representation, screenwriting, marketing, etc.) and being blown away at their level of thinking… yet knowing if I work my ass off, I could play in the same league (maybe never reach their star-level, but definitely could ride the bench).

  • “Building my house,” so to speak. I’m addicted to creating this foundation of skill sets and career choices that will serve as the bedrock for my family, my friends, my colleagues, so that if they ever need shelter, I can provide it.

Prioritize So Hard It Hurts

There are worse addictions out there.

Addiction to the climb is quite a few degrees to the left of, let’s say, porn or nicotine. Still, it needs to be managed.

The problem is our mid-20’s and early-30’s seem like the PERFECT time to pile on the work. At no other point will we have so few responsibilities (children, parents, mortgage, college tuition, lunch boxes, medical bills), and enough mental and emotional stamina to put in the 9, 10, 12 hour days.

We have the ability to do real work. Because at this time, our output can be so high, not working has a high opportunity cost.

How do you manage the addiction? I think the answer lies in prioritization — prioritizing both how I want life to look in 10 years, and what I want it to look like today.

BJ Fogg had this quote: “I’m prioritizing so hard it hurts.”

It took me a long time to understand what he meant by this. I used to treat prioritization like a bucket list, or a list of neverending to-do’s.

When you prioritize properly, however, you realize: you will drop balls. An idea you love is never going to get the attention it deserves. Your darlings will die.

It’s like Robb Stark sending off 2,000 of his men to lose the Battle of the Green Fork, so his force of 18,000 could win the Battle of the Whispering Wood.

Wolf and Jaime

Sacrifices must be made.

When we prioritize properly, we give up late night drinks with friends, to do the work that’ll pay off in 10 years. Other times, we skip the work that’ll benefit us in the long run because what’s the point in reaping the rewards of work if you can’t enjoy it?

This is inevitable. No point in torturing ourselves by dwelling on it. But I do look at both these things and think, “well, fuck, that’s PLENTY to keep me busy for a lifetime!”

If that’s true, then shouldn’t I strive to eliminate the activities (there are plenty) that contribute to neither? This list of activities is very personal — no one can tell you where your priorities should lie — and for me, a shortlist of the activities to STOP are:

  • Shopping

  • Mindlessly checking email every 20 minutes

  • Mindlessly scrolling through social media

  • Mindlessly watching Youtube videos, e.g. binge-watching 45 minutes worth of 3-minute BREAKING BAD clips

  • Checking blog statistics

I can’t stop these activities in one shot. But I believe I can get there.

This post leaves me with a few questions:

What are you prioritizing?

What are you eliminating?

And… does it hurt?

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