His alarm was set for a few hours later, but he couldn't sleep. The tossing and turning never ends for Northwestern's athletic director.
The NU football program just earned its elusive bowl victory and has momentum reaching new heights.
Its basketball program is going in an exciting new direction under a new head coach. The athletic department's marketing efforts have seen strong results, and continue to flourish under Phillips' leadership.
Factor in how Northwestern finally got its facilities master plan off the ground–and has already raised nearly 40 percent of the necessary funds–and how the department is in its best shape ever. Phillips should be sleeping soundly each night, but he's not.
"I'm worrying and thinking about what the next project is," Phillips said.
Since coming to Evanston in 2008, Phillips has changed the culture of Northwestern athletics. Now, it seems like the football program is in position to contend for the conference crown each year.
Phillips believed in Pat Fitzgerald, whose enthusiasm and promise didn't quite match the results when he was given a 10-year deal in 2011. Phillips, though, is reaping the rewards of his investment.
"He's the perfect fit for us," Phillips said of the eighth-year football coach.
The most recent gamble by Phillips may have been his greatest yet. In March, he fired Bill Carmody, and replaced with him Duke assistant Chris Collins. The move was made to bring a new energy to the program, and of course with the hopes that the successor could lead NU to its first NCAA Tournament appearance. That's the next hurdle to leap, and it's fresh on Phillips' mind.
The response to Northwestern's new basketball coach has been overwhelmingly positive. The program remained stable through the transition and has taken a significant leap in recruiting.
From the athletic department's end, increasing fan support has translated to ticket sales and corporate sponsorship reaching all-time highs.
"It's been terrific," said Phillips. "If you talk to our ticket people, they're going well. They're excited about the season. I think our numbers are going to be strong again. What I'm most excited about is sustained success."
Lying ahead for Phillips are greater challenges. He must continue to guide fundraising efforts for the lakeside athletic complex, and then the focus turns to renovating Ryan Field and Welsh-Ryan Arena. It's a process that will take several years and many more sleepless nights.
"You've got to stay true to your priorities," said Phillips. "And this was our priority."
At Northwestern, the string of accomplishments is only mounting. The Wildcat football team could be unbeaten heading into an October primetime matchup with Ohio State, and there's an incredible feeling that surrounds Pat Fitzgerald's program.
On the court, there are hopes that Chris Collins could be the perfect fit for Northwestern's basketball program, which is now filled with promise.
"There's no question, we've got great momentum right now," said Phillips. "There's a real excitement there about Northwestern athletics overall."
The success of Northwestern's athletic department is at an all-time high, but far from its pinnacle. Phillips struggles to enjoy each triumph with his focus on the next task.
During a recent staff meeting, Phillips emphasized to the department that the best is yet to come. NU is striving for greater, just as its athletic director does.
"There's a better destination for us," said Phillips. "And no one's satisfied."