Realising the importance of being comfortable on my board, as opposed to only skating to learn tricks.
I've stopped and started skating many times over the years. Having recently skated with some old friends for the first time in a while, I realised how inextricably linked my board comfort is with my general life contentment (i.e., when I feel awkward skating I tend to have a pretty miserable outlook on things.)
Whenever I would start skating again, I would focus on relearning tricks. I always found this approach frustrating - trying to be the same skater you were in the past - which would cause me to quit again a few months later. After years of this, I've finally realised that what keeps me coming back to skating is my love for the feeling of riding around. As such, I've found that I'm at my lowest when, after months of neglect, my board control is bad and I feel unnatural pumping about. I now care less about tricks - tricks come and go for reasons that'll always be mysterious - and care more about feeling 100% comfortable on my board to the point it just feels like walking. (The irony is that, through this approach, new tricks happen way more fluidly, almost incidentally.)
Realising this has caused me to relearn the importance of skating almost everyday. And when I say "skate everyday", I don't mean a full session everyday, but trying to do something on the board each day. A lot of days, after work, I'll just go and push around my neighbourhood for half an hour, maybe hitting little spots that I pass. Alternatively, I'll try and skate into town whenever I need to run errands, even though it's a bit of a trek. The main point of this is to keep my board feel. Being able to cruise around comfortably, manoeuvring terrain with ease, is directly linked to my satisfaction in life.
In short, when I feel unnatural on my board my life in general starts going askew.
This may sound obvious to some of you, but for years I always saw skating and life as being in conflict, with one always getting in the way of the other. But now I realise that, in order to be responsible and diligent in other areas of my life, I need to feel comfortable on my board, or psychologically it all falls apart.