Roberts, who has moved from coaching first base for the Padres to bench coach this season, first gave television a whirl, serving as a studio analyst and occasional color commentator for NESN, calling Red Sox games.
He later joined the Padres as a special assistant to baseball operations, where Roberts got a look at how an organization ran from the inside.
"I wanted to see the different facets of the game from different viewpoints," Roberts said. "And it was interesting, seeing it from the broadcast booth and then from the suite. I learned a lot from that, like how hard the guys in the front office work."
After the 2010 season, the Padres promoted Roberts to first-base coach, giving him a third job in as many years. But here, surrounded by players, coaches and the game, this is where Roberts found his true niche.
"After my playing career, I wanted to see what the next chapter of my life was going to be ... where my passion was going to be, whether it be the TV booth, the front office or back on the field," Roberts said.
"I think after doing the first two and after a year on the field, there was no doubt [coaching] was where I needed to be."
He'll get the chance to add another chapter to his coaching file this season as he's moved from the first-base box to a seat next to manager Bud Black, as Roberts replaces Rick Renteria, who was named manager of the Cubs during the winter.
"The thing I'm looking forward to the most is looking at the game through a different lens," Roberts said. "Also, it's a chance to work closer with Buddy while trying to study other managers and bench coaches, the catchers. I look at it as a new challenge."
His duties will differ from his previous post in ways Roberts probably doesn't know yet. Black empowers his staff and leans on his bench coach, before and during a game. Roberts, who worked with outfielders and headed the team's baserunning efforts, will train new first-base coach Jose Valentin to handle those duties.
But one thing will remain constant with Roberts -- his daily contact with players. Black made sure to make that abundantly clear early on.
"The interactions are something that Buddy wants from me," Roberts said. "I like to touch the players. I want to teach and be involved. This is a perfect opportunity to teach some people I didn't have before."
Black is excited to see Roberts in this new role. And, as he said this week, don't let that Roberts smile fool you one bit.
"I think he's going to do great," Black said. "He understands the game, he understands players. He's got a feel for the clubhouse. You add those up with his personal qualities, his aptitude, his passion and feel for players, there's a lot there to like.
"There's a competitive edge to Doc that a lot of people don't see. People see this nice guy, great smile. But he wouldn't have achieved what he did as a player if he didn't have a strong competitive edge to him."
Black said he can easily envision Roberts as being managerial material, though you won't get Roberts to bite on that one.
"I haven't taken much time thinking about that," he said.
Instead, he's devoting every minute he can this spring to getting to know the new players in camp and also working with Valentin, the newcomer to the coaching staff. Roberts, and that smile Black talked about, bounce from drill to drill and from locker to locker. He's in his element in uniform.
Nothing against working in television or in the front office, but there's an absolute understanding each and every day that this is where Roberts should be.
"Ultimately," he said. "I missed the camaraderie of being in the clubhouse."