It's a question executives such as Commissioner Gary Bettman and COO John Collins ask themselves and any of their business associates after each NHL Winter Classic.
How do we go bigger? Can we enhance the fan experience?
Each year they seem to find a way. Whether it's going to an iconic baseball venue or adding dozens of ancillary community events around the big game, the League keeps trying to top itself.
While the window of opportunity in Pittsburgh is short, only seven days from the League's takeover of Heinz Field to practice day on Dec. 31, once again the NHL along with NBC and the Penguins are going for gold.
"This day is a lot of fun," Bettman said. "It has become a huge event. It has become bigger than anyone could have ever imagined on New Year's Day. It has become a tradition after only three years."
Outside of the obvious -- the center stage rivalry between the Penguins and Capitals, between Sidney Crosby and Alex Ovechkin -- the League has added a few wrinkles this season to make the 2011 Bridgestone NHL Winter Classic memorable for as many fans and viewers as possible.
Bettman said HBO has brought "even more buzz to the event" with its real-life documentary, "24/7 Penguins-Capitals: Road to the Winter Classic." Episode One created a stir around the sports world and the highly-anticipated second installment in the four-part series will air Wednesday at 10 p.m. ET with an encore at 11 p.m.
This is the first time a Winter Classic will be broadcast in 3D. Bettman announced Tuesday that Direct TV, Comcast and Cablevision have all signed off to show the game in a way that requires the viewer to wear glasses.
The Penguins are building a community rink outside of Heinz Field that will be available on Christmas Eve. The Winter Classic Community Rink at Stage AE will be available until Jan. 1 with 13 public skating sessions planned as well as several youth hockey games. Teams from Evgeni Malkin's hometown of Magnitogorsk, Russia and Crosby's hometown of Cole Harbour, N.S. are scheduled to participate.
Fans who want to cash in on the Winter Classic experience inside of Heinz Field before the game itself can do so on Dec. 31 by scoring tickets to a pair of morning events. Former great Mario Lemieux will lead a group of ex-players in an Alumni Game at 9:30. That will be followed by the Penguins' only practice on the makeshift rink atop the gridiron, scheduled for 11:30.
"Even with 65,000 tickets being sold (for the game), there are so many people who really want to touch this event and can't get tickets," Collins said. "We worked with the Penguins to figure out what are the windows that we didn't want to create in the other markets but we wanted to create here. The window was to do something early in that practice day or not do it at all. With Mario's interest in doing it, why wouldn't you do it?"
The fact that the NHL is going bigger in terms of venue size also shouldn't be undersold.
"Obviously in terms of iconic cold weather stadiums, where the stadium itself would be the draw, that list is short and we've gone through the two best with Wrigley and Fenway," Bob Costas, who will again serve as NBC's in-studio host for the Winter Classic, pointed out Tuesday.
"This day is a lot of fun. It has become a huge event. It has become bigger than anyone could have ever imagined on New Year's Day. It has become a tradition after only three years." -- Gary Bettman
"This isn't a (sport) that is typically played in front of crowds greater than 20,000, so to be in a stadium with 65 or 70,000 -- I remember walking on the field in Buffalo for the first time during the game, looking around and going, 'Whoa!' " Bettman said. "This is a different experience just in terms of the sheer mass of people focused on the game and cheering."
As the NHL prepares to outdo itself, another question gets asked:
Where to next?
That one will have to stay unanswered for now.
"What we typically try to do is build off of what we did the first year, second year, third year -- that's why we haven't made any plans for next year yet," Bettman said. "We'll digest this experience, look at the possible matchups and the availability of venues and figure out what we think will make sense.
"There is no shortage of clubs and cities that have expressed interest. Boston petitioned us to have it every year at Fenway because it was so good. The Bruins would like that, but we have 29 other clubs."
Follow Dan Rosen on Twitter at: @drosennhl