Q: Is it possible to have one apple watch paired to two iPhones at once?

Hi

No - that is not presently possible.

Apple Watch can be paired with one iPhone at any given time. To switch between phones, you can first unpair your watch from the iPhone that you are currently using and then pair it to the other one.

The Watch app on iPhone takes backups of the watch automatically, including a fresh backup when unpairing. Each time you re-pair, during setup you can restore the watch from the backup that is stored on that iPhone. Most data and settings will be restored, with some exclusions (eg cards used for Apple Pay, passcode).

Unpair your Apple Watch and iPhone - Apple Support

Set up your Apple Watch - Apple Support

If you would like to suggest that Apple considers adding the ability to pair with two iPhones as a new feature, you can do so here:

https://www.apple.com/feedback/watch.html

I guessing you have separate iCloud accounts for your personal and work phones?  If you do, you could share your work calendar with your personal account.

http://help.apple.com/iphone/9/#/iph7613c4fb

I Have the same scenario.  My company won't even let me share outlook calendar outside of biz.  so I have to keep two seprate calendars and maintained on separate devices.  ill ask apple to consider incorporating