So when he was asked on Sunday afternoon following New Orleans' 130-119 loss to the Orlando Magic -- setting a new record for franchise futility with 12 consecutive defeats -- Holiday remembered back to some of those losses from before.
"I've been a part of losing streaks before," Holiday said. "I've been on the other side of it where coming out of it, it feels great. I just think to be able to stay positive and push through it. But I've also been a part of it where we've been on a losing streak and it's been a negative. That's even worse than what it is now. Just have to stay positive."
Pelicans coach Alvin Gentry didn't even make it to the end of Sunday's game.
With 1:46 left in the third quarter, Josh Hart was given a technical foul after staring down a referee on his way back up the court after he thought he was fouled on a layup. Gentry protested the call and picked up one of his own, and after Magic point guard D.J. Augustin shot the technical free throws, Gentry picked up his second technical and was tossed.
"We just have to play better," Gentry said. "We gotta play better. The frustration boiled over for me tonight. I have to do a better job of that also."
Gentry admitted it was a bit of frustration boiling over from the entire losing streak that ended up playing into his ejection.
The Pelicans had lost 11 games in a row twice in franchise history before this streak: Nov. 23-Dec. 14, 2004, when the team was still the New Orleans Hornets, and then again Dec.5-22, 2012, in the franchise's first year as the Pelicans.
A common thread during this current streak has been the team's defense. In the 12-game losing streak, the Pelicans, who entered Sunday 29th in the league in defensive rating and scoring defense, are giving up an average 121.4 points and losing by an average of nearly 12 points a game.
It was the sixth time in the past 12 games that the team had given up at least 127 points, and the fourth time the opposing team has scored at least 130 points.
When Gentry was asked if he was concerned about his job after a 6-20 start and a 12-game losing streak that is the longest of his head-coaching career, he said he wasn't going to worry about something he didn't "have control over."
"You'd have to ask that question to the people who control that," Gentry said. "I just know I'm going to come to work every day and do everything I can to get this turned around. That's what I do know."
The Pelicans held a six-point lead after the first quarter but were trailing by a point a halftime. Things didn't get better for the home team in the third quarter, as the Magic pushed the lead to 15 before the final frame.
In the second and third quarters, Orlando outscored the Pelicans 75-54, as New Orleans couldn't carry the first-quarter momentum any further. The Pelicans allowed 41 points in the fourth quarter, which is a league-high eighth time they've done so this season.
It's a problem that has plagued the team throughout the year and something they'll have to correct to win games, according to Holiday.
"Play even harder. Play desperate for 48 minutes," Holiday said when asked how to turn things around. "I feel like we do it a lot of the time, and then when they make they run or swing and punch us, that kind of gets is. Just play hard for 48 minutes and try and come out with a victory."
Pelicans forward Brandon Ingram said the team has to stay together to come up with wins. He doesn't feel like the team hasn't stayed together yet, but he knows it will help in the long run.
"I don't think anybody has wavered," Ingram said. "I think we just have to continue to push and just figure out ways to execute better and win basketball games."
Holiday, who had a game-high 29 points, said it's hard on the team to continue to lose but that he also knows how hard it is to win in the NBA. He continued to preach the message of positivity as a means to break the streak.
"From a personal standpoint, I feel like we're all competitors and losing isn't in our nature," Holiday said. "We're going to keep pushing and try to figure out a way to win, and as soon as we find a way to win, then try to replicate the results. Being positive is the biggest part."