Is travelling with confidential data really necessary? Wouldn't it make more sense for me to have a 'empty' notebook and store my data out of harm's way (but accessible via a VPN).
Yes.
The whole travel with a clean laptop isn't feasible beyond a simple "access data remotely via VPN" scenario.
Company laptops are often so full of custom software (bootloaders & up) that it's impossible to replicate/reinstall a working environment over VPN.
They're crazy sensitive: e.g. On ours if you go too long away from the core network it freaks out and locks everything down. And recovering from that...well:
I've literally had IT tell me that my options are 1) Fly to the nearest office and connect to core network 2) They fedex me a fresh laptop that has recently been connected to the core.
Don't travel with sensitive data, and openly explain that you don't do so.
The frustrating part is the UX, and the fuss when you land.
I've found that this works:
- Burner android (burner account explicitly for travel) for music, podcasts, light browsing, etc.
- Cheap ThinkPad for headscratching / hacking (work over SSH, keys on a Yubikey, IP in your head. YubiKey as second factor for password manager as browser extension (uninstall before the border))