Unobstructed

Right In Front Of My Face

Written by Derek MacDonald | May 29, 2026

Ever heard of the meditation app Headspace?

No? How about their competitor, Calm?

Well, I'm a paying subscriber to Headspace. And after working in the brand marketing world for years, I constantly find myself looking at things like websites, commercials, or ad campaigns and thinking about why they did it that way.

Lately, I've been thinking about that kind of stuff for Headspace.

Like today. I'm getting myself moving this morning and I realize I almost forgot to meditate. Which feels silly because it's just part of my morning routine. But I'm someone who really needs reminders I can see or it's like my brain forgets it was ever a thing. That's why I put my running shoes in front of my door. Otherwise, I'm pretty sure I'd never run. But today I almost forgot to meditate, and so I start thinking about the Headspace brand as I go to open the app. I've already been sort of wondering about what they might be going for with some of their recent emails. They kind of just feel... generic. Which is a bummer because I really like Headspace. So I'm curious now and I actually go and pull up their website. I'm looking at the layout and messaging, then the navigation, buttons, and links. And... my mind takes off and starts running through the ways I'd go about tweaking stuff.

In my opinion, Headspace has a superior product to others on the market. And, sure, it's entirely possible I'm biased and/or I like an underdog. They have strong branding and consistent messaging that makes them recognizable. I don't know for sure what's going on behind closed doors, but I'd guess their biggest issue isn't that they lack brand appeal, but that consumers don't realize the benefit they'd get until after they've already bought-in and become users.

I'm looking at the screen and smirking as I realize, sometimes, I kind of feel like people aren't sold on liking me until after they get to know me, too.

Perhaps Headspace and I share a similar struggle of gatekeeping our value.

Anyway, this is where most folks I've worked with would jump in and suggest they create a demo or a free trial to generate more interest. Maybe that's because we all grew up experiencing show-and-tell in school as a way of explaining why we should care about something. I haven't seen that work a whole lot, though, because people need to understand why something would be worth paying attention to in the first place. Otherwise, they won't feel all that strongly about trying it. So I'm thinking about ways I'd make it more appealing to people, without fucking with their branding, and here's what I'm seeing: expand access by providing additional entry points, instead of only pointing to the app.

What I'm thinking they should do is make it possible to opt-in to email subscriptions where folks  could click straight to the next course module. Creating the option for users to subscribe to courses via email extends the surface area of their library. I'm imagining that seemingly innocuous feature would dramatically increase utilization of their app, because it changes the story you can tell about the product from something where people have to think of the app first and then go use it, to something where people self-select their reminders and get prompted to continue.

I want it right in front of my face, please.

Otherwise I'll forget.

And I'll keep going down this rabbit hole instead of meditating.

Our Daily MAP Year Prompt
270/365

What's your thing that you can't help but notice when moving about the world?

onward.

For more on this daily column and The MAP Year Project, read the backstory here. And if you know someone who'd appreciate this, pass it along.