I had been considering reading Ulysses this year. Then found out this week it was the 100th anniversary so I started reading it last night. Not totally sure why I was so intimidated. Maybe Portrait of the Artist gave me an undeserved impression of what it would be like.
Nevertheless, if you were able to enjoy Kerouac's On the Road, you'll be able to enjoy Ulysses. They read similarly. Someone else here commented "enjoy it like a scramble down a hill" or something to that effect. Pace is very important.