"There’s so much outside of your control": Josh Berry reveals the biggest challenge of being a NASCAR Cup driver

Josh Berry knows exactly how long and unforgiving the climb to NASCAR's top level can be. A grinder who worked his way up from iRacing and local short tracks to finally breaking through with his first Cup Series win this season, Berry has lived both the dream and the struggle.

Now in his first Cup playoffs with Wood Brothers Racing, he admits that the reality of competing at this level is tougher than he ever imagined. Speaking on The Athletic's 12 Questions interview with Jeff Gluck, he was asked about the difference between what he thought life as a Cup driver would be and the reality.

"It's way harder than people realize. When I was racing Late Models and winning all kinds of races, you'd see guys come through the ranks... They'd win a Truck race or whatever. And all of us at that level thought, 'We could do that if we had the opportunity.' But living it, you realize just how good everyone is in the Cup Series and how hard it is to be competitive - and how much is outside of your control," Berry said.

It's a perspective shaped by one of NASCAR's most unusual journeys. Dale Earnhardt Jr. discovered Josh Berry through iRacing and gave him a shot with JR Motorsports' late model program. He turned that chance into winning the CARS Tour title in 2017 and the NASCAR AAA Weekly Series championship in 2020.

Josh Berry (L) with Dale Earnhardt Jr. after the Stewart-Haas Racing announcement, 2023. Source: Getty

It opened the door for him to the Xfinity Series, where he won his first race at Martinsville in 2021. Two full-time years in Xfinity followed, with a Championship 4 appearance that pushed him to the Cup Series. But Berry says the biggest change has been the lack of control behind the wheel compared to his grassroots days.

"When I was Late Model racing, I worked on my car every day. We had a close-knit group making decisions on setup and tracks. Now you get to the Cup Series and there's so much outside of your control. You can have the best car and still have a bad pit stop or bad restart. I knew it would be hard, but it's amazing how good these teams and drivers are," he added.

That grind has been paying off. After his March win at Las Vegas - the first of his Cup career - Josh Berry locked himself into the 2025 playoffs. It was a milestone not just for him, but also for Wood Brothers Racing, marking the team's 101st Cup victory.

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Josh Berry turns toward his first Cup Series Playoffs

Josh Berry (21) during the Grant Park 165 at Chicago Street Race. Source: Imagn

Josh Berry’s Las Vegas triumph secured his playoff spot early, but the summer stretch has been more uneven. He has finished outside the top 20 in five of the last 10 regular-season races. Still, momentum has arrived just in time. With back-to-back top-10 finishes at Richmond and Daytona, his first such streak since March, the 21 team has finally found some rhythm.

The playoffs start on August 31, with the Cook Out Southern 500 at Darlington Raceway (6:00 PM ET). It's a suitable track for Berry, who thrives on old-school, tough venues. A P3 finish there last spring with Stewart-Haas Racing is proof he knows how to get around 'The Lady in Black.'

For a driver who once washed cars and wrenches at JR Motorsports while dreaming of a chance, every lap in the Cup playoffs will carry meaning. His rookie season has already delivered one historic win. Now comes the test of whether Josh Berry can extend that story into a playoff run and keep proving that persistence pays off in NASCAR.