Typical solution: Make the timeout much longer so you don't need to keep doing the work
Correct solution: Deploy a second factor that isn't annoying
If your second factor is a FIDO Security Key then you just touch the key. Doing this a dozen times per day feels about as much trouble as how you have to hit the spacebar to make spaces when typing, ie you aren't even aware of it.
The VPN couldn't easily do this out of the box today (as OpenSSH demonstrates, where there is a will there is a way but I wouldn't trust a typical proprietary VPN client to not open massive security holes this way) but all the web stuff you mentioned could use WebAuthn, and Okta supports that if your employer deployed it as I understand it.