When Bose asked independent singer-songwriter Will Dailey to showcase their portable PA system at Sweetwater Sound, he had one request.

“I work on a lot of their products that are kind of for the traveling troubadour lifestyle,” he said of his partnership with Bose. “I’m going to be out there for that, so I told them, ‘I’m on tour. I’ll go out there for you guys, but if I’m in Indiana, I want to have a show.’ I don’t get to Indiana enough. I’m really on the East Coast, sometimes Chicago, and Southern California — that’s where I play the most, and Europe. I have this indie career that I can make work for me, but America is a big place and I rarely get to Indiana.”

You can get a chance to see this top 20 Billboard-charting artist when he stops by Sweetwater for a free show on Wednesday, May 24.

Cutting out distractions

“The traveling troubadour” has been on the road opening for The Wallflowers and Rhett Miller. He’s also been doing solo gigs as part of his innovative 10 Dollar Song Tour. 

The 10 Dollar Song Tour features Dailey performing his regular show, but there’s a song you can hear only via an “antique” Discman. After paying what you’d like to hear the song, you put on the headphones and get a listen to his song “Cover of Clouds.”

In a phone interview from the road, Dailey said he enjoys putting his music out on streaming platforms. However, “Cover of Clouds” is an ode to Joni Mitchell and highly personal to him. He fears it will get lost in the avalanche of content that now engulfs us on a daily basis.

“Writing songs is what I do for myself, and putting them out is what I do to connect,” he said. “I love when a song connects on a platform. But this particular song, it’s six-and-a-half minutes long, and it’s a tribute to an artist that influenced me and the people that introduced that artist to me. I thought, ‘Wouldn’t it be a shame to put this song into the abyss of all our content.’ And not just music platforms, but all of our content. They might click on it, then get a text message in the middle of it, and they’re out. I just thought, ‘Not this time. Not this particular song.’ ”

Instead of getting distracted while listening to a song, putting the headphones on and immersing yourself in this one might be a bit different.

“Some people are like, ‘This is the best song you’ve ever written, and now I’m angry that I can only listen to it once.’ Some people are getting very emotional,” he said. “Some people are getting emotional because they wonder if they’ve been listening to music correctly because they didn’t look at their phones.”

“I feel like I’m doing the right thing, even though it’s something I have to explain,” he said.

Life-changing album 

What makes the song so important to Dailey is the role hall of fame folk icon Joni Mitchell played in his life while he said he was just trying to learn to play Guns N’ Roses and Nirvana songs.

“Someone just said, ‘Here’s this record,’ and it was Clouds,” Dailey said. “I was still trying to learn to play a C chord, and this person who was dating my mother at the time, then became by stepfather, had a guitar and showed me the open tuning to ‘Chelsea Morning,’ which I had no right learning. I couldn’t play a C chord, and he’s trying to show me this thing she did. That window and door was opened in my mind at a young age. That album always stayed with me.”

Dailey said while he thoroughly enjoys the likes of Led Zeppelin and Pearl Jam, it’s those artists that fly under the radar that really intrigue him. Citing Joan Armatrading, he said he was so “upset” that he only learned about her seven years ago.

Trying something new

Having shared stages and studio spaces with the likes of Eddie Vedder and Willie Nelson, Dailey has won numerous Boston music awards. And though it might sound like he prefers the days of yesteryear, he’s not against streaming platforms, saying he had just been listening to Spotify on his road trip. However, for this song, he was looking for something more intimate.

“It’s a real quagmire that we’re in,” he said. “It’s really wonderful that everyone has access to this same platform. There’s so much beautiful work out there, and I’m talking television shows, books, articles, blogs, videos on YouTube, tutorials, and a 100,000 songs every day. I’m excited to put new music out online. This one song fosters a healthier relationship for me with the people I’m asking to participate in it.

“Come to the merch table and listen to a song that is only available on a Discman on a headphones that you can only listen to once,” he added. “The responses are wonderful, but also far more fulfilling for me for his particular piece of music.”