Yeah, I've done that with PIVX already. All the PIVX I own is profit and I probably should have sold to re-enter at a lower level, but... I just haven't been able to. Maybe I just like staking. :)
So much comes back to our why. For me, at this stage in my life, my why involves supporting projects I think will make a big positive impact on the future while also (hopefully) becoming financially free in the process at levels I've never known.
The only regrets I think I'd face would be if I sold something I believed in and then bought it back higher or just watched it go be successful without me.
Yeah that risk always exist.. Maybe by keeping a stake no matter what in the things you believe in will be the right call I think.
But yeah, there is always the gambling element since no one really knows. Part of life I guess, chance that we can't control.
Great WHY btw. I hope you keep reaching those levels man!