The peril of the check box lifestyle

If you know me or have read stuff I’ve written over time, you probably know I’m not a huge fan of checking boxes, personally (“I got the three-bedroom, the three kids, and the Golden Retriever with the flower crown!”) or professionally (which tends to be work that’ll be automated within 10 years anyway, even though the people who are doing it keep claiming how essential and relationship-driven it is.) But instead of belaboring that, I’ll start with a story.

Probably in September ’18, I went to Chicago for a trade show in the recruiting industry. At the time, I had just had an interview with this place in Texas that I thought would be cool to work at. I ended up getting that job, but I was a shitty employee and I lasted eight months there. At the time of this story, though, I was waiting to hear back from them. So the whole time I’m in Chicago I’m chasing Texas phone numbers, and around 11:03am, I got a call. Answered it! Was this the moment? Nope. It was someone trying to sell me insurance. Oh well.

Conference goes well, ends about 3pm, and our flights back aren’t until like 8pm. So I go check out Soldier Field, because I like football, then stop by a bar near there, because I like beer, then I head to O’Hare, and I’m drinking there because it’s an airport and that’s what 30-something males do in airports. Flight gets pushed, and so now we’re not leaving until like 9:30pm. Tincup, who is a big name in the recruiting space, joins me at the bar and we are BS’ing, even though I am more lubricated than he is at this point.

Somehow we get on broader life stuff — I think, at the time, my girlfriend (now wife) had about five friends pregnant — and Tincup says something like “There are three things people always think will make them happier, but never do.”

So I say, “What are those three things?”

“A ring, a baby, and a threesome.”

We had a good laugh, and talked to some people at this O’Hare bar, then rolled out. I think I got home around 1:20am. Hell of a 36-hour period.

I think about that quote a lot, though. We do have a mentality, broadly, that the next thing — the next box to check — is going to be the big winner that pushes us over the emotional and Instagram-worthy top. In reality it’s usually just another progression and what you do with it (the marriage, the parenting, the aftermath of the threesome) is more important, but that’s not usually our cognitive approach to it.

So we chase certain boxes, and those boxes don’t necessarily make us happier. I know women who had the three kids and got the big house — men too — and they’re like “Oh, is this it? This was the grand promise? Now I have vomit in my hair and I keep stepping on Legos?”

The Platform Economy has made some, if not all, of this more confusing because now we see the highlight reel of other people, as opposed to the behind-the-scenes. The highlight reel always looks nice. To see the behind-the-scenes, you gotta be there Saturday morning or Tuesday night, and that’s not when people take IG photos, generally speaking. It creates a lot of false equivalencies and comparisons and social want and Joneses stuff, and I’m not sure any of it is good for us.

Simpler equation: go to a bar/restaurant and look at a family of four. Are the kids behaved? Are the parents interacting? In a 45-minute span, how many beers did the husband have? How many screen devices are involved? Has a waiter been kicked? Is the mom only laughing when she looks at an app, as opposed to because of her children or conversation?

See, that’s the peril of the box check.

Life is weird, and the journey can be tough, but do things because you want to do them at a certain time, not because you need to hit the box or keep up with other people. Live your life and run your race. It’s OK. Right?