I think there's a flip size to each negative or positive aspect of it. Almost everyone struggles with getting tired of it after a few years and maybe it's time to move on at that point. To me, even consistent cold rain and the type of annoyances we're all familiar with seem way better than what I was doing before this (retail). I also quit working at base in order to be back on the road full time and have that freedom. I also suffer from depression and the best therapy I've found so far is messenging, even when its slow. On the other hand, the company I work at is large enough and ive been there long enough that I can come in when I want and as a result, my biggest current challenge is putting in solid weeks (can be tough to get out in the morning). I imagine that's the same for app based couriers. But for me, at least once I'm working, the depression and lethargy goes away. I guess I recommend keeping your foot in or developing whatever other skills you may have on the side. You can always come back to messenging if you pursue something else or you can usually work a day here and there or do it part time. Freedom is one of the biggest draws to this work so I'd recommend pursuing other things when you can. I think a lot of us at a certain point think, yeah i guess I'm a lifer and then our bodies start wearing out and we have no savings or resume fodder. You can play it smart and pursue another career craft on the side or travel.