It's possible if you do one of the following:
1. Turn down the difficulty
2. Grind skills
At around level 15, I tried to go from 2H (level 53) + HA to 1H (level ~28) + Shield (level 28) + HA. I had to turn it down the difficulty from Master to Adept. Granted, I don't have a companion following me, so I might have been able to do expert if I had picked one up.