"Don't check in your ski boots"

I have been checking in my ski boots all these years along with my skis ( in the same bag) when i fly. I was told not to do that. I also got new boots so i am motivated not to heed that advice.

With that said, I also carry my laptop ( to get some work done in the evenings and watch porn) . How do i carry-on both my bootbag and laptop bag comfortably. I was able to stuff my laptop in bootbag last time but it wasn't a great solution.

I am willing to splurge some money to get a proper setup.