Yes, and it usually has to do with technology. Sometimes, when a "new and improved" version of some computer app comes out, it's more complicated to do something as simply as the version prior.
I most certainly have, and quite recently too, by the way. My reward vs punishment method for increasing quotas isn’t as effective as I imagined it would be. Grrrrrrrr.
I can now give you a specific example of "there must be a better way." I had to provide my employer with a photo of my current vaccination status. My phone doesn't take pictures, so when I was at the dentist yesterday, I asked his assistant to take a photo of it and email it to me. This morning, it took me over 45 minutes to figure out how to convert that photo in the email to a pdf and then upload it on some app my firm uses to track these things. These are the kinds of things that will push me to retire sooner rather than later.