The former Drive-By Truckers member penned a host of brutally honest songs for last year's Southeastern album, detailing his struggles with alcoholism and a stint in rehab, as well as material based around cancer and sexual abuse.
He retains that same honesty when being interviewed, too.
"If you're not writing about the things that terrify you sometimes then you're not giving people enough," says the Alabama native, who plays Oran Mor this Saturday with his band, the 400 Unit.
"I choose to reveal those things on the album for a lot of reasons.
"For one, I thought it might help some people. If you can connect with other human beings, then the best way to do that is to say things that you're afraid of, that make you seem a little uncool and don't present you in the best light.
"The audience you attract won't turn their backs on you if you do that. They're not going to be surprised, and they're not going to be burning my records if I say something they disagree with."
Southeastern, Isbell's fourth album, certainly achieves an intimate honesty, displaying his flair for both language and melody.
Yet it's also the first album he's recorded while sober, after he spent two weeks in rehab following an intervention by his wife, the singer Amanda Shires, and various friends.
Now, however, the 35-year-old is in good spirits.
"I put myself through hell in some ways, although I wasn't being put upon by anyone else, it was all me," he says.
"So when I stopped putting myself through that I felt a whole lot better and I'm having fun now… It was gradual for me - I could see the bottom before I hit it.
"The job I have, you're not going to get fired from, you'll drink yourself to death before you get fired. It was having a few bad days, and you realise you're having diminishing returns."
Channelling his experiences into Southeastern, the singer has emerged with arguably his best album yet. Making the album sober also led to a different recording process than before.
"The writing process wasn't easier but it was more focused," he adds.
"It probably would have been a different record if I hadn't been sober as I wouldn't have had the same stories to tell.
THIS time I didn't have hangovers to recover from, and I could sit and work on a song without wanting to go out drinking."
Southeastern is also Jason's first album since 2007's Sirens of the Ditch to not feature the full 400 Unit, although members of the group do appear on it.
The Unit will, however, be back in place for this coming tour, including the gig at Oran Mor.
As for what they'll be playing on the tour, the singer is a believer that gigs shouldn't be the same routine every night.
"Every crowd is different, and I don't want to treat people the same from one day to the next, plus I like to mix it up to keep it interesting for myself as well," he says.
"It's easy to get complacent and play the same songs every night in the same order, and I try not to do that.
"We're not like a jam band or a jazz band, but we like to keep it interesting."
While the material on Southeastern is heavily personal, Jason doesn't mind revisiting those places every time he performs the songs live, even if it can be draining.
"I try to go mentally to the situation I was in when I wrote them, so I can deliver them with the same intensity," he explains.
"So they stay the same to me as far as the emotion goes. It's exhausting, but performing, that's a reward for me more than anything else."
l Jason Isbell, Oran Mor, Saturday, 7pm, sold out