I used to jerk my wired earbuds out of the jack all the time.
I haven’t tried running with my AirPods yet, as I feared they would eventually fall out.
Did they ever fall out? Only a small portion of the time. Half the time I noticed it and caught them.
Was the idea of them falling out stressful? Hell yeah. Nothing like a $50+ bud to stress the hell out of you when you're trying to get a run in and it just will. not. sit. in. your. ear. correctly. Add sweat to the equation and things get messy quick. And the fact that in some places, like public transit, you have a good chance of losing the bud forever if it falls out.
I am much happier with the IEMs I've been using for a half a year or so now. They hook over my ears optionally, so they're never really in danger of falling out and I never have to mess with them. And they're wired to me anyway even if they do fall.
I used to run with Bluetooth over-ear headphones, which was great in winter, and, uh, less great in summer (the foam would get completely soaked and foul-smelling).
The ear supports on the Pixel Buds are pretty secure, though, I expect it to be OK, especially at my pace.