He's tired of telling the media how sad he is, he's tired of telling his sponsors how sorry he is and he's tired of telling himself how he'll get 'em next week.
There's only one thing that can solve all of his problems. It's as simple as finding a way to qualify on Fridays and race on Sundays, but that is much easier said than done.
"I'll be honest with you," Waltrip said. "I did not think we would struggle the way we have because we have all the support we need from Toyota."
Though he is only about two months into his inaugural season as the owner of Michael Waltrip Racing, he already is battle-tested.
Trying to develop a brand-new three-car team into a competitive organization has been tough enough, but Waltrip also has spent a good deal of his time fighting misconceptions. He spent the offseason trying to convince fans that having Toyota in the Nextel Cup Series is a good thing and dispelling rumors that the manufacturer had enough money to buy its way into victory lane.
The reality is that Waltrip hired 200 employees last August, essentially building a race team from the ground up in a matter of months. When bringing together 200 people from various backgrounds, communication and coordination will certainly be an issue - and it's shown. Waltrip qualified for just one of the first four races, the Daytona 500, and his troubles continued Friday at Bristol Motor Speedway.
Waltrip and teammate David Reutimann both came up short of making the Food City 500, the fourth race in a row that Waltrip will miss.
But now, Toyota's rough start has altered the misconception. Waltrip can only shake his head at the claim that the automaker was focusing on the Car of Tomorrow all along and will have an advantage in the future.
"I didn't get the memo that the current car wasn't a priority," he said.
"We race that car more than we race this car."
Waltrip has been a fan of the CoT since it was proposed, but is under no illusion that it will be a magical cure-all.
"It's just a race car," he said. "There's no tricks, there's no shortcuts, there's no getting an advantage over anyone."
Waltrip is going back to the drawing board, re-evaluating his plan of attack and restructuring his troops in the areas where he feels it is necessary. He's also bringing in Toyota to help him get the most out of his equipment.
"We're looking at how our competition side operates, and we're making adjustments," Waltrip said. "We have strong people, but maybe they all weren't in the right places."
For what it's worth, Toyota has been through this before. When the manufacturer entered the truck series a couple years ago, the Toyota teams struggled to be competitive. But through steady improvement and the passage of time, Toyota's teams are now close knit and very competitive week in and week out.
Bill Davis Racing also can provide Waltrip with some light at the end of the Toyota tunnel. Dave Blaney is part of an established team, and he's appeared in every race and run well at times.
"The experience they gained in the truck series allowed (Toyota) to show up in the Cup series ready to race," Waltrip said. "Now it's just a matter of judging how they stack up in Cup.
"Sure, it helps us be better prepared because of the truck experience, but now that they're in it, they learn more every day."
So Waltrip will take the knowledge gained in Bristol with him to Martinsville next week. He'll take two laps next Friday like he always does in hopes of getting his shiny blue Camry into the field, moving him one small step closer to where he wants to be.
"Hopefully we'll come out the other end with a better race team," Waltrip said.