Tom MacWright


I meditate most days. I picked up the habit about four years ago, in an effort to regain some focus and deal with stress. For me, it works pretty well: I feel calmer and more focused when I fit it into my day. Plus, I enjoy challenges and it’s really difficult to develop the ability to focus on one’s breath for ten minutes. There are a few posited health benefits, but the evidence isn’t overwhelming at this point.

I’ve always used ‘apps’ for meditation, starting with the connoisseur’s favorite, Headspace. But Headspace started to annoy me. I have two main gripes.

First, I like things in even increments. I schedule time in 15 or 30 minute blocks. I try to run whole numbers of miles, adding a bit to make it to 3 instead of 2.9. But for some reason, Headspace chooses to wing it. You pick the time of your meditation session and choose ten minutes, and the session lasts… eleven minutes and thirty-two seconds. Mind you, they likely have reams of A/B tests and analytics data supporting this choice, but for folks with a strong attachment to numerical precision that I don’t feel like examining further at this time - it’s annoying. I might have ten minutes before I need to travel and with Headspace I’d open my eyes late by one minute and thirty-two seconds.

The second thing is that Headspace – and most of its competitors – cost the same as other products. By that I mean: startup pricing for subscription products is, roughly, $5-13 dollars per month, regardless of what it is. GitHub is 9. Figma is 12. Notion is 8. And Headspace is $6 monthly or $13 yearly. Now, I think Headspace’s product is pretty well-done, but the current startup bubble has a way of flattening every industry into roughly the same valuation and pricing. Calm, the leading meditation app, was recently valued at 1 billion dollars. Is meditation a multi-billion dollar industry? Does it have to be?

These kinds of valuations require a lot of revenue, so accordingly most of the apps are doing a lot of growth hacking to get there. The UIs for most are full of dark patterns, signup screens designed to look required with close buttons quietly placed in the corner. Free trials by default, and upsells at every corner. It’s pretty unpleasant, and if you don’t require a lot of variation in your practice, then it’s a lot of complication for what could be a folder of MP3s.

I asked online about simply getting MP3s, and came upon some resources:

These do the job pretty well, and if you’ve got an MP3 player you like, go for them! They’re a little funky - UCLA’s specifies to put your “tongue on the roof of your mouth” and MIT’s suggests “loosening your belt.” As an avid The Books fan, I was reminded a little of A True Story of a Story of True Love - “With your eyes closed, close your eyes.”

Anyway, I eventually landed on Oak, the Kevin Rose-founded app. It’s simple, limited, and it works extremely well. And the paid features aren’t put in your face - it truly us usable for free without feeling like you’re missing out. Rose might be playing a long game with a new monetization strategy, or possibly they simply haven’t been devoting enough energy to optimization to make it bad yet. There’s a real value to apps that start off good and don’t change much.

I’d recommend it and think it has few flaws that aren’t shared by other apps. Mainly I’d love to see more apps finding a better way of encouraging consistency than “streaks.” This idea of uninterrupted days of use (derived, I believe, from the Seinfeld productivity secret) is great until it isn’t: it punishes a single day of missing your habit just as much as the inability to do two days in a row. And by resetting to zero, it’s discouraging right at the point when you need encouragement to get back on it.

I’ve only seen one example of habit tracking done really well, in the place I least expected it: a Garmin watch. Garmin, not especially known for technological sophistication, came up with a really good way to do step tracking. It takes a rolling average of the last few days of your activity, and challenges you to beat that. So when you’ve been sedentary, it’s easy to succeed by doing a bit better, and when you’re active, it encourages you to keep going. It’s so much better than setting a round “10,000 steps” target and avoids the guilt of dialing down that number if you’re too busy to get out that much or it’s been pouring rain for the last few days.

Due to the current crisis, I expect a bunch of apps will go free or have extended free content around anxiety reduction. Balance, for example, has a free one-year subscription, Headspace has a ‘Weathering the storm’ series, and Calm produced some… mindful living calendars (?).

I think meditation is a pretty good thing to do, and whichever way works for you, go for it. Hang in there, folks.