"I'll be signing out in Arizona" next week, he said.
Joining a major league club after being taken with the 41st overall pick in this year's draft is just the latest accomplishment for the 21-year-old Flaherty.
After earning Gatorade High School Player of the Year honors as a senior at Deering High School in Maine, Flaherty took his game to the Deep South and Vanderbilt, where he starred for three years. He led the Commodores in hitting his freshman year in 2006, and the following summer he was a starter for the USA National Team.
Growing up in Maine meant that Flaherty was encased in a region that has produced precious few major league players over the years because, as Flaherty notes, "It's hard to get outside and learn the game like most normal kids."
But Flaherty's father, Ed, has been the head coach at Southern Maine University for 23 seasons, so there was always an open field for his son to hone his skills.
"Having my father there, and having the opportunity to go practice with his team indoors, it worked out year ‘round and it kind of kept me up to speed with those kids that are from California, Florida, and Texas," said Flaherty.
"He's played a huge part in teaching me the game and just letting me hang around his team and kind of understand the game and pick up on things," he said of his dad.
And while the Cubs may have only recently added Flaherty, Chicago Scouting Director Tim Wilken has been watching the infielder since those prep days.
"I always knew he was a good baseball player," says Wilken, who recalled watching Flaherty for the first time at a showcase game in St. Petersburg, Fla. "His father is the head coach at Southern Maine, so he comes from pretty good lineage."
Over time, Wilken's opinions of Flaherty have only strengthened after watching him succeed at Vanderbilt, where he batted a combined .349 in his college career.
This season, Flaherty (listed as 6'3, 210) slugged a career-high in home runs, which he attributed to getting stronger over the years and his maturation as a hitter.
"I think a lot of it has to do with just my physique in general," he said. "I ended up putting on 20-25 pounds since I came to school. The more you become a hitter, the more you have a feel for the bat and the more you can let the ball go deep. You can end up generating more power. I think it was just (about) growing up as a hitter."
But Flaherty also struck out 46 times this season – another career-high. Wilken said that was the result of Flaherty "sacrificing" his swing to accommodate the loss of All-American third baseman and eventual first-round draft pick Pedro Alvarez, who played in just 40 games this season after suffering a broken bone in his hand.
"The swing changed a little bit, and probably he picked his spots to try and drive the ball a little more than he normally would," said Wilken.
Flaherty described himself as a "gap to gap, doubles" hitter, even though the amount of doubles he hit this year (10) were down significantly from last year.
He wouldn't describe himself a power hitter, per se.
"I think this year people started to (think), ‘Oh, maybe he's a power hitter.' But that's not something I necessarily really wanted to be," said Flaherty. "I just wanted to put the ball in play, hit the ball into the gaps and get a lot of doubles."
The Cubs are just asking Flaherty to swing the way they know he can, and they aren't asking Flaherty to go outside his realm defensively, either.
Flaherty played shortstop all three years at Vanderbilt, but some pundits have suggested a move to third base. Wilken rebuked those reports, saying there was no reason to shift Flaherty to another position.
"We'll leave him at short and let him play there," Wilken said. "I think his range will improve just because of his knowledge of the game. Is he fast? No, he's not fast. He's probably not average by timing standards, but he runs well enough and he runs the bases very well. He's got enough of an arm and enough flexibility to his tall frame to play short, so we'll see how it goes the next couple of years."
Flaherty is used to the third base rumblings and only brushes them aside.
"Ever since I've been in high school, there are always people out there that skepticize that I'm going to move to third, and there were a lot of colleges that wanted me to do that," said Flaherty. "Luckily Coach Corbin at Vanderbilt gave me the opportunity to stay at short and that's the position I like the most. It's in the middle of the infield, it's my favorite position to play, and I'm going to keep playing it as long as I can."
Wilken said that drafting Flaherty just made "a lot of good baseball sense for us."
Flaherty, who grew up a Boston Red Sox fan, says he's excited to play for the Cubs.
"Just the opportunity to play for an organization like the Cubs, that's something special," he said. "I'm excited to get it going and to get my pro career started."