Bowdoin College, his former employer in Brunswick, Maine, wouldn't mind if he cleared out his former office so the new soccer coach could move in.
And he'd like to see his family in person, rather than on a smartphone. Or stop having to worry about finding time to pay bills from afar.
But the Irish native appears to be having the time of his life, despite a whirlwind month.
O'Leary broke away from the UEFA Pro Licence coaching course in Scotland to fly to London and join Nelsen for the flight back for the Jan. 8 Toronto FC news conference announcing their hiring. After that, it was the MLS Combine in Florida and the MLS SuperDraft in Indianapolis.
Then it was home for a day, and back to Toronto FC.
The longtime collegiate coach likes what he has seen from the MLS club, whose roster and culture president and GM Kevin Payne has been hard at work remaking.
"I think there's a real eagerness and hunger to turn this thing around," O'Leary said in an interview at the team's Florida pre-season hotel.
O'Leary is no mug, however. He knows it's early days.
"Obviously we're in the romantic phase right now," he added. "It's just us right how. There'll be difficult times ahead and we'll all learn about each other when it gets really difficult."
O'Leary, a Dublin native, has carved out a successful career as an assistant coach at Boston College, the University of New Hampshire and then head coach at Elmira College, Kenyon College, Dartmouth College, George Mason University and Bowdoin.
He has had other opportunities to leave the collegiate ranks for MLS over the years but says Toronto trumped all of those.
"There was one reason I came in and that was Ryan," he said.
O'Leary is giving up the security of a long-term college contract to join a 5-21-8 MLS team. But he is confident in TFC's new regime.
"I know Ryan and I know what he'll bring here," he said simply.
O'Leary says it took him 10 minutes to take the Toronto job, a time frame that convinced him he was making the right move. His rationale is if you have to debate a job's merits or talk it over with others, you're trying to convince yourself.
He knows the new job will mean longer hours and a little more stress.
"But stress sometimes is good, it keeps you young. Sometimes it keeps you vibrant, you're out of your comfort zone, it's exciting," said O'Leary, who just turned 50.
His American wife — they have a six-year-old son and eight-year-old daughter — was a slightly harder sell.
"Luckily she knows Ryan well and she's always been very supportive," he said, admitting he had to have "a wee word" with her.
On the practice field, he and the 35-year-old Nelsen are obviously close.
"Fran knows what I want and I know when I turn my back his instructions will be to the letter from what I want," Nelsen says.
In typical Nelsen fashion, he then widens the praise.
"And that's including all the assistants as well, Jimmy (Brennan, J (Jason Bent) and Stewart (Kerr), all the way to all the staff," added the former New Zealand international defender.
O'Leary has a nice way about him, with a ready smile on a world-weary face. He'll sidle up to a player getting ready for practice and ask the "big man" how he's feeling.
If you were casting a movie, the soft-spoken entertaining Irishman would fit nicely in "Jaws," swapping stories with Quint (Robert Shaw) aboard The Orca.
But his role has always been soccer coach.
O'Leary was a right back during — in his words — "a very mediocre" playing career.
"I played at decent level in Ireland, but I think my lack of pace was always going to be a ceiling on where I went. I knew that at a fairly early age."
O'Leary played under some good coaches, however, and started looking to that side of the game by taking the first of many courses.
He came over to the U.S. in 1985 to attend the NSCAA (National Soccer Coaches Association of America) convention in Washington, D.C. That led to some summer camp work and he was offered an assistant coaching position at Boston College.
He says it didn't take him long to know he would stay in North America.
Most recently, in his seven years at Bowdoin, he led the Polar Bears to a record of 74-39-14 and, in 2010, its first ever appearance in the Division III Final Four.
He remains a passionate advocate of the college coaching system, listing off the coaches he learned from, including many from other sports.
O'Leary points to the likes of now retired Kenyon College swim coach Jim Steen, who won more NCAA national championships (50) than any other coach in any NCAA sport. "He's viewed as one of the most innovative swim coaches in the world."
At George Mason, he pointed to former basketball coach Jim Larranaga who led the Patriots to five NCAA tournament appearances, including the Final Four in 2006.
"Every day you've huge resources to help available aid with your coaching development," he said. "So it was a fantastic learning experience for me."
Early courses taught him Xs and Os, O'Leary said. But other coaches helped him learn how to help and manage people.
"To them, I'm eternally grateful. I learned an awful lot from coaches outside of the world of football."
He also notes that the U.S. made it to the quarter-finals of the 2002 World Cup with 17 players on the roster with college experience.
"Ireland went once to the quarter-finals of the World Cup (in 1990) and we're still celebrating, still talking about it," he said. "If Scotland ever went there, the place would be shut down for a yearlong party."
"I always laugh at when people take a pop at the role college soccer has played in developing players," he added. "It's sent many players to professional leagues around Europe."
There was disbelief in some quarters when Toronto FC hired Nelsen and O'Leary, with critics decrying their lack of MLS coaching or — in Nelsen's case — any coaching experience.
O'Leary says he was too busy to pick up on any negative vibes.
"There's so much work to be done here, I don't read anything," he said with a laugh. "I'll always choose to decide what I'll allow to get in my head."
He reminds skeptics that Payne, who chose the new coaching staff, has four championship rings (from D.C. United) and also hired Bruce Arena and Bob Bradley.
"He's seen what I know about Ryan. I know how strong a person he is, I know what a strong football brain he has and I know how he handles people. ... So I would always say 'Well, look at Kevin Payne's track record of identifying talented coaches,' and I think he's nailed another one in Ryan Nelsen."
The paths of O'Leary and Nelsen first crossed more than a dozen years ago.
Nelsen switched to Stanford in 1999 from Greensboro College. At the time he had already played for the New Zealand under-23 and full senior side, along with former Stanford players Gerard Davis and Simon Elliott. Former New Zealand coach Bobby Clark was coaching Stanford at the time.
O'Leary had succeeded Clark as coach of Dartmouth in 1994 after the former Scottish international took chare of New Zealand.
"So we're all intertwined in a way," O'Leary said.
O'Leary met Nelsen briefly at a couple of camps in Stanford and had to scheme how to play against him when the two teams met.
O'Leary remembers watching video of Nelsen playing for New Zealand against Brazil in the 1999 Confederations Cup before 53,000 fans in Guadalajara, Mexico.
"And we were going to be facing him a few weeks later," he recalled. "So it wasn't a happy experience, my first experience (of him)."
Even back then, the word on Nelsen was he was an intelligent player with great leadership ability. He was also a good athlete, having represented New Zealand in cricket at the youth level.
Nelsen had big shoes to fill at Stanford, following Elliott — who went onto play in MLS and the English Premier League.
"Ryan didn't miss a beat," said O'Leary.
Nelsen also fitted in well off the field.
"He's a humble guy," said O'Leary. "He maybe had a better resume than a lot of them from a playing perspective but the way he carried himself, you would have never guessed it. I think it stayed that way today. Now he's built up — over the course of many years — a very very impressive playing resume, but if you met the lad you'd have no idea he even kicked a ball."
In 2001, O'Leary took over the George Mason University program in Fairfax, Va. D.C. United drafted Nelsen fourth overall that year and it wasn't long before Nelsen and then D.C. United 'keeper Nick Rimando dropped by to ask if they could help at training.
"I think, at that stage, they both had a real brain for the game and had an eye on going into coaching when their careers ended. So even they were at the front end of their playing career, they were already looking to the back end and a career in management.
The 33-year-old Rimando is still playing in MLS, for Real Salt Lake.
O'Leary and Nelsen worked together for four years. Nelsen would train in the morning with his MLS team, then help the college players in the afternoon.
Nelsen and O'Leary have stayed close since their George Mason days. O'Leary ended up doing some scouting for Blackburn Rovers while Nelsen was there and has also commuted to Britain regularly for coaching courses.
They also talked on the phone once or twice a week, dissecting training sessions.
"From there, we're pretty confident we see the game the same way," O'Leary said.
For Nelsen and O'Leary, opportunities in today's game often come out of transition. So they look to build a sound defensive foundation — and then use it as a springboard to attack.
"We don't just talk about defending, we more talk about defending to attack," said O'Leary.
On the ball, Toronto will take the cue from its opposition. If they are sitting up at the halfway line, one pass might expose them. If they are sitting deep, you have to be more patient and use passing to break them down.
"It's not a case of 'Do we play long (balls), do we play short,' it's a case of how do we get behind the team," O'Leary summed up.
"The term we like to use to our players is 'Trust your brain.' See what's on. Have a strong defensive foundation but in possession, trust your brain."
When it comes to formation, O'Leary does not seem bothered. Formations change on attack and in defence, he argues. Play a good team and it will pull you into a different shape.
"It's too early to say what we'll do. But I don't think we're going to get too caught up on formations."
Both Nelsen and O'Leary are looking forward rather than back at TFC. O'Leary says that won't change, even in the good times.
"I had a wise old coach who would always call me after games. He'd leave a voice mail and he would say 'Don't know how you did today but you either won, you lost or you drew. Either way it's history now, move on.' And that's the way I've always been."
The result can't be changed, after all. So for O'Leary, you address it and then move on.
O'Leary has gone as high as you can in terms of coaching courses. He has just finished the two-year UEFA Pro Licence course, needing only to make a final presentation next month.
He took the course under the auspices of the Scottish Football Association in a 21-person class that included David Weir, David Unsworth, Alan Stubbs, Scot Gemmill, Gary Locke and Canadian under-20 coach Nick Dasovic. Others from North America were Vancouver Whitecaps assistant coach Paul Ritchie, and Dartmouth coach Jeff Cook.
The course has included time with managers Sir Alex Ferguson of Manchester United and Andre Villas-Boas of Tottenham. Everton's David Moyes spent two days showing the class how he operates.
The course has taken them all across Europe in search of soccer expertise.
"You pick up a lot of valuable information as you go that I think will stand us in good stead here," O'Leary said.
O'Leary says this latest course was more about handling situations than Xs and Os.
He recalls former England manager Howard Wilkinson telling them that being a soccer coach is not a job for those who don't like dealing with problems.
"You'll have 10 problems a day," O'Leary recalled Wilkinson saying. "The day you walk in and there's no problems means there is a crisis and they're keeping the problems away from you, so worry."
The UEFA Pro License is needed to manage in many top leagues in Europe but not in MLS. Nelsen has not taken coaching courses, saying he was occupied with his playing career.
Away from the field, O'Leary is a sports and music buff who looks forward to taking in Toronto's vibrant concert scene. He counts Queen — twice in Dublin — as his all-time favourite show.
"Best concert by a mile," he said with a smile.
He still rues missing a David Bowie show at George Mason's basketball arena. The former Ziggy Stardust had flu that night.
O'Leary will miss Maine, which will remain his American home. The coastal town of Brunswick and its people, not to mention the lobster, will always have a place in his heart.
"I always said and I meant it, that I'd never leave for another college job. I just felt that that (Bowdoin) would be the place I'd stay. We were very very happy. But this is a fantastic opportunity," he said.
"I'm going in with a guy I believe will turn this around."