In just his second game with the Ottawa Senators, he made a mistake on the power play and envisioned the consequence as he skated back to the bench.
"OK, that's your last opportunity and good luck on another unit," he told himself.
It's a mentality that comes from playing parts of five seasons under coach Randy Carlyle. Since then, Ryan has run the gamut on coaching personalities through his time with Bruce Boudreau and now Paul MacLean.
Going from one extreme to the other, Ryan adjusted on the fly as he came into his own as an NHL scorer.
"With Randy you had a hard-pressed, aggressive coach and then you went to Bruce, who was fairly lackadaisical in, I wouldn't want to say his approach to the game, but his systematic plays," Ryan said. "He was different like that, but he gave you opportunities to really create offensively. And then I think Mac's kind of that hybrid in between both of them. He gives you space to make plays and do things, but he's also demanding. You have to stick to the structure, and if you stick to those X's and O's that's where he lets the skill come through."
Skill has never been a question for Ryan, a four-time 30-goal scorer who's off to the best start of his NHL career and should be a lock for the U.S. Olympic team in Sochi. It has been more a question of how three coaches approached managing his talent.
Ryan scored 112 goals in the 274 games Carlyle spent behind the bench. Before the Ducks fired Carlyle in late November 2011, a strained relationship with Ryan had the winger on the trade block.
"Everybody knows my history with Randy," Ryan said this week while making it clear that Carlyle was always fair to him. Before the Senators faced the Toronto Maple Leafs during the pre-season, Carlyle was effusive in his praise.
"I think Bobby was a young kid that had a different body make-up from what he is now. He put (in) a lot of time and effort, and it's a tribute to him to get himself in the type of condition that he is now versus where he came out of junior," he said. "Bobby's growing into a pretty mature hockey player both on and off the ice."
Carlyle's heavy-handed style played a role in that growth, but Ryan got more freedom under Boudreau, who learned a little about handling star scorers from coaching Alex Ovechkin with the Washington Capitals.
"Really great players — Ovi, Bobby Ryan, the Jason Spezzas, the (Ryan) Getzlafs — if you try to tell them how to be creative, it's not a smart move because they see things that you can't see," Boudreau said. "It's like they got another sense about them when people are around or where people are or stuff like that. You just have to give them a lot of offensive-free latitude."
But that's not to say Boudreau gave Ryan a free pass. He asked him to try playing centre when the Ducks were weak there and came away impressed with how the young star handled that and other suggestions.
"Bobby was really easy, and he was also very acceptable in anything I asked him to do," Boudreau said. "I'd have him in my office just because I talk to the players a lot, but I'd have him in and he'd be very receptive to any ideas I had. I listened to him on any ideas he had and I thought I was receptive to them. I thought the relationship was pretty good."
That relationship ended July 5 when the Ducks traded Ryan to the Senators following an 11-goal, 48-game season. His days of playing Boudreau's fire-wagon style of up-tempo hockey were over, but MacLean continued the trend of instilling more confidence and trust in Ryan.
The 26-year-old already faced his former team this season and will see Boudreau and the Ducks again Friday in Ottawa.
Ryan saw similarities in Boudreau and MacLean's interactions with players, but not their approaches to hockey. Boudreau won the Jack Adams Award in 2007-08 based on offence and an incredible Capitals turnaround, while MacLean won it last season for leading the Senators to the playoffs amid injuries to Spezza, defenceman Erik Karlsson, goaltender Craig Anderson and others.
"Obviously you don't win the Jack Adams Award by not being able to speak to your players and get through to your players," Ryan said. "I'm looking forward to having a relationship like that and being able to build on that throughout time."
It has started well as Ryan has six goals and three assists in nine games. That mistake Ryan made on the power play earlier this season didn't cost him another chance, and as a result he's not playing scared.
"You don't have to tighten up or whatnot and you can let it go and play," he said. "There's been situations on the ice where I'd like to have things back, but we've had a lot of good talks between us about that kind of stuff. He's given me the confidence to let me know that they're going to put me right back out and get me right back into the situation again."
Ryan is still adjusting to differences in Eastern Conference play compared to the West, like how much extra space he has to gain the offensive zone when he's carrying the puck. But across the spectrum of his play, the transition to Ottawa has been "fairly seamless."
Since seeing Ryan in camp, MacLean never worried about that adjustment and praised his consistency along the way. MacLean wants Ryan to play with a sense of freedom, but he's not giving him special treatment.
"I think it's our job to not just coach Bobby Ryan. We have 23 guys that we have to coach, and that's the same with all of them," MacLean said. "We really believe in the young players, when they get the opportunity to play you have to play them and when they're playing well you have to get them out there and let them play. Bobby's no different than the rest of them as when he's playing well, we'll get him out there, and when he's not, we won't."
Ryan has learned that lesson under each coach and is thankful for the extra chances that have followed when he faltered. He doesn't like the comparisons to Daniel Alfredsson — who signed with Detroit the same day Ryan was dealt to Ottawa — which will undoubtedly linger, but filling that role as a scoring winger suits him well.
"They're giving me an opportunity to, I guess, be one of the top players, one of the go-to guys and putting me in situations where they feel like I can have success," Ryan said. "That's all I really wanted and that's the opportunity that I think I knew I was going to be given."
Follow Stephen Whyno on Twitter at @SWhyno