If you do so, it's essential to have a reliable method of steering the boat while you're busy handling the pole and
lines.
A good
autopilot, or in calm condition a way to lock the helm. but even a 30' boat will tend to turn as you gybe due to the shifting of the sail forces from one side to the other. So you have to be quick and sure enough to get the maneouver done and back to the cockpit in time to correct.
Any sort of sea running will cause difficulties so pick your days.
An "A" sail and a sock makes life much easier, thought gybing in a breeze can still be a challenge.