Jason Singer On Michigander’s Fall Tour, Importance Of The Business Side For Indie Musicians

For Michigan born singer, songwriter and guitarist Jason Singer, road trips from Michigan to Chicago were a common occurrence. 

It’s an experience documented in the song “East Chicago, IN,” a tale which references the symbolic change from central time to eastern that motorists encounter crossing between Illinois and Indiana en route to or from Michigan which appears on the 2018 Michigander EP Midland. 

“A lot of times we came to Chicago to play. We’d play and, on the way home, we’d pass that East Chicago sign and stop at a truck stop there. The time changes right around there coming back so we’d lose an hour heading back to Michigan – we’re extra tired and it’s dark,” explained Singer in July downtown in Chicago, perched atop the Chicago Transit Authority’s Madison and Wabash elevated train platform prior to a performance blocks away at Lollapalooza . “We would usually play a show and then immediately drive back to Michigan. Because it’s only two and a half hours back to Kalamazoo – and it’s always weird. Because you just played a show for like 500 people or whatever – or less – and then you get in the car and it’s just quiet. Everyone is asleep and you’re just driving. You can be alone with your thoughts and reflect upon how the show went.”

Michigander began as a Singer solo project that grew into a band, one which crafts anthemic dreamscapes and catchy, guitar driven songs built around melody. With their latest EP, the aptly-titled Everything Will Be OK Eventually, Singer and company began to experience some of their first success on FM radio in America, with songs like “Let Down” gaining heavy Tripe A rotation. 

As the group launches a fall tour of the U.S., Michigander’s first major headlining tour, Singer is clear on how he hopes his latest music resonates despite uncertain times across the country.

“We’re in a weird time right now. Hopefully things get better. But I kind of want these songs to be like a soundtrack to the return to normal,” he said of the Everything Will Be OK Eventually EP. “I want to stick to that. Because I think we’re still on a good path, even though it’s uncertain and scary at the moment.”

Aside from a performance in Grand Rapids, Michigan as the opening act for Senator Bernie Sanders in March of 2020, Lollapalooza stands as the group’s single largest performance to date. On stage in Chicago, Singer worked a snippet of Radiohead’s “Karma Police” into a triumphant performance which featured songs from his latest EP as the centerpiece.

“It’s OK to be lonely / It’s OK to be lonely sometimes,” he sang at Lollapalooza during “OK,” one of several songs on the latest Michigander EP which seem tailor-made for the times. 

“This is a dream come true. I will cry by the end of the set,” joked Singer on stage in Chicago’s Grant Park. “We put a record out last year called Everything Will Be OK Eventually and right now it feels like we’re getting toward eventually. And this really helps,” he said, referencing the return of live music while introducing the group’s live take on “OK.” 

Age-old showbiz wisdom dictates that to find success in an entertainment field, one must ship off to New York or Los Angeles (or, in music, Nashville). But Singer has achieved success on his own terms without leaving Michigan and a midwestern sensibility defines Michigander’s finest musical moments.

“I think there’s a certain type of attitude that comes with living here,” he said of life in the midwest. “We’re a little bit spaced out from the rest of the major cities. Chicago is like the biggest city – but Chicago still feels kind of small. Not that there’s not a work ethic in other places but I think how we’re brought up here, it’s a little harder to get out – so to get out, you have to work a little harder. There’s a quaintness to the midwest. You can go to so many different places in a day whereas out west, it takes like a day to get between each city. It’s just special.”

Before he even started writing songs, Singer developed a fascination with the music industry itself, an artist interested in more than just writing songs. 

A keen eye on the business side of things, especially early on, has helped Michigander grow from local favorites to an increasing presence on stage and on the FM dial across the country. 

“As an independent artist, and even still now, I have to be very aware of what I’m doing with my time – because unfortunately there’s a lot more to the music business than just playing music,” said Singer. “You can write the best song but if you just make the best song and it can’t get to anybody, then no one is ever gonna hear it. Which is kind of sad. So I think it’s important to be aware of both sides. Now I have management and a team so they help a lot with that side of things which helps me focus a lot more on the music – but even when you do have a team you have to still be aware of it,” he said. 

“I think something that I learned was if you want to get ahead in things, you need to be valuable in a monetary way – like selling tickets,” Singer explained. “Because if you can sell 100 tickets, the promoter will be like, ‘OK. You just sold 100 tickets. Here’s some cash.’ You make money. Or, ‘Hey, this cool bigger band is coming to town and they need a local opener. Can you play?’ So it’s that kind of thing over and over where you just put the work in and the opportunities come. It’s the same with any kind of business – show that you’re valuable, get moved up. And that’s kind of what the vibe was for us for so long.”

On record, Michigander has existed only since 2018. Amidst the current fall tour, the group is gearing up for a December 6 return to Chicago in support of The Lumineers with a tour alongside Manchester Orchestra scheduled for early 2022. Building upon the musical growth that defines Everything Will Be OK Eventually, Singer is already hard at work on new music.

“It’s going really well. They’re some of the best songs that I think I’ve ever written. I’m really, really excited about them,” he said. “The best part about the job is to make the music. And sometimes it’s a little daunting trying to top yourself. But I’m learning that you can’t have that mindset. You’ve got to just sit down and make the best thing you can make in the moment. So that’s what I’m attempting to do. I think the songs I have out right now, the new EP, I think those are the best songs that I’ve made. I hope the new stuff is the same way.”