But while he has fond memories of the successes, it was those dark stretches when the White Sox underachieved, the frustrating games that quickly slipped away, that put him to the test.
Like any other die-hard White Sox fan, Williams had coping mechanisms, and one of those was to simply get up and walk away from the live action. For example, on May 21, 2009, when the Twins pummeled the White Sox, 20-1 at U.S. Cellular Field, and Jake Peavy said "not yet" to approving a trade from the Padres to Chicago, Williams walked away and cleaned out his garage.
"I could probably write a book on what to do when your team is frustrating the [heck] out of you," said a smiling Williams during a chat with MLB.com after his recent promotion to executive vice president, with Rick Hahn taking over as general manager. "You know what's funny? Trying to discern who is worse: [White Sox chairman] Jerry [Reinsdorf] or I.
"We are very alike in the way that we can get to a point of just total disgust, just like a fan. You are not down there and you are not on the coaching staff and you are not on the field, so there's no way to burn off that anxiety unless you go out and do something."
Handling that anxiety or "dialing it back" over the course of a 162-game season, as Williams said, was the greatest lesson he learned on the job. It also was one of the things he never did very well. Williams promised to exhaust himself in trying to bring a championship to the White Sox and he took that responsibility to heart both for the organization and for the fans who were putting the day's woes behind them by watching the White Sox.
"If we can give them that 2 1/2- to 3-hour diversion and we can be something that they can feel good about, positive about, root for, then great," Williams said. "When it doesn't work that way and we turn into yet another disappointment in their day-to-day living, then it affects me on a personal level."
Williams believes his experience in dealing with the stress of a GM job will make him a valuable asset for Hahn, his new GM. Balancing work and family is another common thread he shares with Hahn, who has two young sons, a dynamic Williams dealt with when he first took the job.
"Certainly I would like to take away some of the guilt maybe of putting so much time into the job that you miss things at home," said Williams, who has five kids. "I want to tell people right now that I'm going to encourage this man. ... The White Sox may be playing at 7 o'clock on a Tuesday night, but if [Hahn's sons] have something where they need their dad there, yes, the general manager of the White Sox might be at a recital or at a soccer game.
"That's just as important as the work that he puts into the team, the ability to disconnect and be there for your family. It's paramount. I'm going to be very sensitive about that, and again, I think it's part of the role I've got to play for him."
As far as Williams' early goals on the new job, he smiled and mentioned getting more sleep and being there for his children as well as his girlfriend, Zoraida Sambolin, who is a CNN news anchor based in New York. Sambolin was in attendance for the press conference to announce the promotions.
"There hasn't been a summer where I had flexibility to do what they needed me to do since I've been an adult," Williams said.
Now, the stress of the job falls upon Hahn, meaning there will be fewer in-game escapes, like the time in Anaheim when the White Sox gave away a big lead, causing Williams to depart early, only to realize he forgot his pass. When the White Sox rallied, he almost couldn't get back into the stadium.
"Someone with a cell phone had to go on our website and say here's a picture of me in order to get me back in the stadium," said a laughing Wiliams, who joked that he might have missed the bus to the airport if he couldn't get back in. "The day you sit in that chair and it's your record on the line, it changes a whole lot of things.
"I'm going to miss the job. I love the job. But I know that I'll probably live longer not doing it. It's healthier for me not to do the job anymore."