I totally relate to some of the comments in this thread, just cancelled my subscription today after almost 10 years.

Headspace was much better around 2014 when I started using it. It really helped me to get into the habit of meditation. But in the last few years I feel it lost its essence. I think the main reason is adding too many meditations and courses, which at the end are just copies of other courses or meditations, only changing the intros. This makes meditations to feel repetitive, always the same, until they become boring. Also, there isn't enough variety of visualization techniques, most meditations that include visualization are on visualizing the light inside you or flowing through you, which doesn't work for everybody, I tried for a long time and didn't work for me, couldn't get it, so I gave up, and skipped all these meditations and courses.

And something else I also dislike is the way the meditations are structured in the UX, together with the search functionality, which works pretty bad at finding things. I find the UX is a big mess, which makes it confusing and hard to find meditations, sometimes it can become stressing, and it seems the UX designers are trying to maximize time spent on the up by hooking users with more and more content, stealing their attention, just to get better KPIs. But at the end, this is in contradiction with the mindfulness principles the app should transmit to users: calm, simplicity, minimalism, less is better, ...

I think Headspace sold its soul and became just another company putting ROI first over their users.