It has taken him a while to get to the point where he is today, performing acoustic shows. He used to avoid performing full acoustic shows because of "sheer terror."

"I'd say over the last two to three years, my confidence has been built up a little bit just by being on those stages and having a lot of fun. There's a huge opportunity when you play solo — where you're not looking at the other musicians and you don't have a set arrangement. You can pivot through things a little more easily," McMahon said.

Last year's "Pen and the Piano" tour helped him out a lot to get over that stage fright. The tour made a stop at The Jefferson last May, which was a pleasant surprise for McMahon.

"I never anticipated Charlottesville would be such an awesome market for us. The vibe is great! It surprised me how well the show did, and I'm excited that we're going to get to come back for this."

The "Pen and the Piano" tour also helped McMahon "break the cycle" of needing or feeling like he needed to be on stage with a few folks to do a gig. For the upcoming tour, there aren't any plans to have a super-intricate set like he had for the last tour.

"I think a part of it, for me, is the idea of keeping it super minimal and making it about the piano, the songs and the stories," he said. When he hits the stage on Dec. 7, he says there will be some set pieces. "It's too fun, especially around the holidays. Maybe we'll put some lights in a palm tree!"

2020 also will mark some important milestones for him. Not only will he be celebrating his 15th "cancerversary," but his first project, Something Corporate, will turn 20.

After all these years, he's amazed that he's still out doing what he loves.

"I think that the idea of starting where I started and being where I am, and the willingness to shapeshift and change directions and take different approaches to my art and the way I make it [as well as] the way that I write. Making current, modern music that reaches people is the most exciting thing," he said.

McMahon is proud that he's been part of an act that's considered nostalgic now, and that he can still record and release relevant music and maintain that.

"It's a super-humbling thing, and that I've been afforded the ability to do it is the greatest gift I could ask for."

Back in 2005, McMahon was diagnosed with acute lymphoblastic leukemia (ALL), which resulted in a bone marrow transplant. He's come a long way in those 15 years, coming to terms with everything in stages.

"The first five years were pretty turbulent, and was just this kind of trying to deny that it happened and running a million miles an hour in the other direction. The next five were really about trying to get my s—t together. I went to therapy, and I started trying to really tackle that. These last three or four years have I think, benefited greatly just from having taken the time and realizing that that had such an impact on me, and trying to be able to I think, in these last four or five years, settle into that life and be able to look back on the post-cancer years to be, like, 'wow, I’ve made a lot of amazing memories, and I’ve created the life that I’ve got now from the one that I had before.' That, more than anything, has shaped my worldview and the way that I approach each day. It didn’t all happen at once. It really was a process."

In 2006, he formed the Dear Jack Foundation to help support quality-of-life programs and initiatives to help support adolescents and young adults battling cancer to help improve their quality of life by addressing the physical and emotional needs of young cancer patients and survivors.

In all honesty, thinking ahead to that 15-year milestone wasn't on his mind initially.

"It's funny. I think once I got to 10 [years], I really started focusing on the Foundation. When I realized I was past it, there are moments, anniversaries or things that will come up and sneak up on me, and sort of trigger that emotion of what that was like."

He goes on to add, "15 is such a big milestone, if you talk to cancer doctors and you do research. At least in leukemia, they never call it a cure per se, but 15 years is sort of that moment where they say it's as close to a cure as they can call it."

Every year on Nov. 11, he performs a benefit show for The Dear Jack Foundation, where he performs an iconic song from his expansive catalog: "Konstantine."

"Konstantine," a piano ballad that spans more than nine minutes, was written during his Something Corporate days. It's one of the most-requested songs he hears shouted from the audience when he performs, to the point where he coined the phrase "requests are for karaoke bars."

He's a very type-A person, and he tries to prepare for shows to the best of his ability. With the number of songs in his catalog, it takes a lot just to get 25 to 30 prepared for tour.

"Frankly, some of the songs in my catalog might as well be a song that I listened to for the first time today. My memory is just an absolute black hole. For the sake of the audience, if nothing else, I've sort of avoided this idea of being the guy who hears 'Freebird' and then plays it."

Despite hearing "Konstantine" shouted at the shows he's played over the years, the song has a solid place in his heart.

"'Konstantine' is definitely my 'Freebird,' yeah. There's no question. The tricky thing about that is that people think I hate the song because I don't play it," McMahon quipped.

In reality, it's just a song that the band had to stop playing because it took up a large chunk of its set every night. If he plays the song one night, there's always an expectation that he'll play it on other nights. Instead, he's delegated it to be a special performance at the benefit, performing it every year at 11:11. He tries to give it the justice it deserves every year.

When Something Corporate went on its 10-year reunion tour, the song was played every night during the run. It's a song that he loves, and he doesn't mind playing it, despite what fans might think. He just can't perform it every night.

After all these years, there is a bright spot for McMahon and requests: "I would say that these days the shows, the fans are pretty self-regulating. If somebody pipes up and starts yelling 'Konstantine' more than once, there’s usually someone in the audience who’s gonna stare 'em down and tell them to be quiet."

He made a point to say that the Something Corporate chapter is not officially closed, especially since the band never actually broke up. A lot has changed for the members of the band over the past 20 years, and trying to get together is a bit of a challenge.

"I think that the reality of all of our lives, in some ways, we’re even closer than ever; we talk to each other all the time! A lot of that is just ... the effect of everyone has moved in so many different directions. Brian [Ireland] is in Denver now and is really successful in the retail world. Clutch [Kevin Page] is absolutely killing it with these audio installs. Bill [William Tell] and Josh [Partington] have their law degrees. Everybody has moved in these directions away from music and into these other exciting chapters in their life that even trying to get everybody to dinner, let alone get everybody on stage for multiple nights, is a pretty tricky thing."

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Andrew McMahon: The piano, the songs and the stories