i had a very similar issue with ice skates. Played hockey for 35 years, and always had my toes turn numb by the end of a game. Started speed skating a few years ago, same issue and never thought much about, as I've always liked skates very snug fitting. I commented about it to one of club coaches in the "post-skate rehydration sessions" aka beers, and he said "relax your foot, and focus on putting pressure on the whole sole". D'oh!!!!!
It took me a few months to implement this, and lots of focused training, but numb toes are gone. Nice bonus is that the skating stride is very similar to pedaling, so it made a significant improvement when I ride. Not so much speed, but comfort and control.
the comment on nerve pinching. Get that checked out ASAP, as it will get much worse before it gets better. There are occasionally non-surgical solutions if it isn't too bad. This issue can create all kinds of havoc beyond your toes.