Jackson Dean on the Road Mishap That Put Everything in Perspective: 'Funny How Life Shakes Out'

Jackson Dean was feeling good.

Not only was the singer/songwriter coming off a year that had certainly cemented his place within the country music landscape, but the Maryland native had also just received news that his single "Don't Come Lookin'" was the No. 1 song on country radio after topping the Mediabase 24/7 chart.

"I was trying to get my head around that fact and was feeling so grateful," Dean, 22, tells PEOPLE. "I was just trying to really absorb it all."

So, as Dean made his way home from a Thanksgiving trip visiting friends and family on the east coast, he decided to make a video that would essentially capture the happiness he was feeling at that very moment.

But just about 90 minutes after he pressed send on that video, all heck broke loose… literally.

"I was driving down I-65 right outside of Horse Cave, Kentucky, and that drive is so beautiful," remembers Dean. "All of a sudden, I heard a big clank and thought, 'That wasn't good.'"

And he was right. The wheel bearing on his '06 Chevy 2500 Silverado had blown, and suddenly the newly crowned chart-topper found himself stuck on the side of the road, trying to figure out what he was going to do next.

"I pulled over into a Stanton's Garage and met a guy by the name of Billy 'Buck' Minton," Dean remembers of "the good ole country boy" from Munfordville, Kentucky. "He basically told me that I wouldn't be going anywhere any time soon. So, I called my manager, and he was kind enough to drive out from Nashville and come and get me."

It was certainly a reality check for the man who had just become the youngest male artist to get a No. 1 country music hit via a debut single. But despite these impressive stats, on this particular morning, Dean found himself as just a guy with a whole lot of time on his hands as he waited for someone to pick him up.

"I spent that time making phone calls to all of the people on my team and thanking them for their hard work and belief in me," remembers Dean of expressing his thankfulness to all involved in every aspect of the song, which appears on his Luke Dick-produced debut album Greenbroke. "It takes a village to make these major milestones happen between management, A&R, promo, publicity, marketing — the list goes on. I wouldn't have had the time to connect with all those folks and share in that moment if I hadn't been broken down."

And there were many thank yous to be said, as "Don't Come Lookin'" had found its way on everything from Netflix's The Ice Road soundtrack to a John Dutton scene in Yellowstone.

But make no mistake — Dean still was a tad aggravated about the road mishap.

"I was frustrated at first about the breakdown, but then I quickly remembered that I had the No. 1 song in the country, and really, what could I possibly be upset about?!" the country music hitmaker explains. "It's funny how life shakes out sometimes. Also, the irony of it all is not lost on me. Celebrating a song about getting lost and not coming back and then immediately, having my truck break down and needing someone to come lookin' for me?"

And chances are, everybody will be looking closely at Dean in 2023, as the upcoming year will hold new music, new tours, and new opportunities to continue his upward rise to stardom.

"I've got a lot to live up to now," concludes Dean, who will soon head out with Blake Shelton and Carly Pearce on the 2023 Back to the Honky Tonk Tour. "This year was a wild ride. I can't say I've gotten much sleep, but I wouldn't change a thing."