18 Feb 2026 The Monetization of Free Time
The idea of free time has been on my mind a lot over the last few months, so today’s brief is more of a personal reflection than anything else. Hopefully you’ll humor me.
My son, Jack, recently turned 13 and Emily and I decided it was time for him to get a cell phone. It’s not a decision we came to lightly as we both strongly believe there are tremendous risks that come with putting such powerful technology in the hands of a boy with a pre-frontal cortex that is still developing. After talking to friends, attending a talk put on by our church, and doing our own research, we decided on a Troomi phone. It’s a tightly-locked-down device that only allows him to talk or text with contacts we approve, monitors the content of his messaging with friends and alerts us to anything problematic, doesn’t have an internet browser, and offers only approved apps. The two latter features are of particular importance to Emily and me because we don’t want our kids anywhere near social media.
Our overarching concern, which we share with many parents, is too much screen time. Not only are screens more pervasive, but what’s on the screens is more corrosive. Also, boredom is good, free time is good, and screens are the biggest obstacle to both.
I enjoy listening to The Bill Simmons Podcast (not just because he got his start writing about Boston sports), especially when Chuck Klosterman is a guest. During an episode in late November they were opining on the idea of boredom. Here’s a sampling of what they had to say (cut for brevity):
Bill: …I worry sometimes that there’s too many distractions, that it’s going to ultimately hurt creativity because I think of the way I grew up where a lot of times I read a book or wrote something just because I didn’t have anything else to do. I would be like, I got two hours here. Maybe I’ll write a column, but now if you put, I don’t know, 18-year-old or 19-year-old me in this situation now, I’d be like, I’ll go on Instagram…. I think sometimes the best ideas I ever had, the best things I ever wrote, just in general, came out of like, my brain was just going . . . because I wasn’t on a phone. I was just staring at a tree and all of a sudden think about blank, got an idea and I’m like, oh, that would actually be a good idea.
Chuck: Well, I mean, this is kind of a thing, right? (Y)ou go on a flight, you don’t watch TV, you don’t listen to anything and you don’t read. No, I think there’s something in (our) subconscious about us that craves this . . . I flew four hours and I didn’t read anything. I didn’t watch anything. I didn’t listen to anything. Why do I feel good?
Over the past 18 months, I’ve gone on a series of three-day retreats with 25 other men where a portion of our time is spent in silence. No phone. No computer. No TV. No talking. Just you and your thoughts. I realized many things on these retreats, but two that apply here are: Being still for more than 60 seconds is really, really hard, and Chuck is right: I crave this.
A core idea of capitalism is that if you build a good product that solves a real problem, you’ll make money. While companies still profit by selling stuff we want/need, it was on one of these retreats that I realized they are increasingly monetizing our free time: We listen to podcasts at the gym and on the way to work, we check the internet while we’re at a stop-light, we “doom scroll“, we post on social media, swipe on Tik-Tok or Instagram, lose track of time down random internet rabbit-holes, and burn the midnight oil streaming a movie with a plot we won’t remember in 48 hours. Instead of being bored, “staring at a tree,” daydreaming, or going to sleep at a decent time, we stare at our phones or computers, or isolate ourselves with our Airpods. Kids and adults alike have lost free time, boredom, and the opportunity for stillness, and it’s not good.
Thankfully, we’re waking up to this: Schools are adopting phone-free policies, parents are organizing screen-free hangouts for their kids, products like Brick are creating friction between us and our devices, “digital sabbaths” are a thing, and demand for dumbphones is rising. The more we increase boredom and stillness, for ourselves and our kids, the more psychic deposits we can make into our own souls.
As I said at the start, this is a reflection, not me sharing a solution. I don’t know that there’s one activity or method that offers a fix; it’s probably a mash-up of a few things.
If, like me, you’ve been thinking about this stuff or, better yet, have an idea that’s worked, I’d love to hear from you.
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