Jackson Shepard is Keeping it Freeform
Leaving room for humanity and flow is the name of the game for guitarist Jackson Shepard. His music is rooted in community, connection, and the simple but powerful act of being present. His playing is an invitation; to slow down, reflect, and really feel.
With his debut album Say Yes to What Is, Jackson opens a new chapter — one that explores love lost, perspective shifts, and the quiet beauty of growing through it all. It’s an honest reflection of where he’s been and where he’s heading, both as an artist and as a person learning to take life as it comes.
But Jackson is no stranger to releasing projects. As the guitarist and founder of Human Bloom, he’s spent years shaping sound and story through albums like NightShade and Ex+Ordinary, and through singles like Capillary — the song that first put the band on the map. Through those projects, he’s learned what it means to meet a creative match, to listen deeply, and to make room for play.
These days, you might find him onstage anywhere in Chicago, playing with local scenes, a local church, adding color to someone else’s story, or taking his own sound abroad. No matter where he is, that “Jackson-ness” — his warmth, his openness, his willingness to surrender to the moment — always shines through.
At his core, Jackson Shepard is driven by love, by letting go, and by a desire to be fully present with every note. His art is a conversation with the universe — one filled with curiosity, courage to show up, and heart.
We talked with Jackson about the making of Say Yes to What Is, the inspirations that started it all, and the people who ground him and push him to get better along the way — those who remind him that the journey of music is really a journey back to one's self, again and again.
Jackson, how did you get started in music, what’s the lore? Is there a favorite first musician or style you can remember?
I started messing around on piano and drums from as early as I can remember because they were already in the house. My dad played in a rock band in high school and my mom inherited the piano from her mom. The Beatles, Michael Jackson, and the Wiggles (lol) were definitely some of my first inspirations and obsessions. Specifically Sgt. Pepper, the White album, and MJ’s History compilation CD. From there I started taking guitar lessons at age 9, getting mostly into classic rock and blues!
Are you doing music full time? What does a typical week for you tend to look like?
Yes! A typical week usually includes rehearsals and shows for other artists or my own projects. I play gospel music at a church every Sunday and I love it. I also teach guitar, piano, or music production lessons off and on. But my favorite thing to do is to record music, either at home or in the studio.
Since the release of your first full album “Say Yes to What is” how has the response been and can you tell us more about the making of this album? Like, how long did it take, how was it produced?
The album took 6 years! The first song, “Say Less” was created in 2018, and I released the full project in 2024. “Say Less”, felt like a new world to dive into. I was starting to feel like I had found a place where all my influences and experiences could collide into a unique sound. I wanted my first solo project to show as much range as possible, while still being one cohesive flow.
In that time frame, I was most inspired by Marcos Valle, Radiohead, Laraaji (and meditative music in general), James Blake, D’angelo, Stevie Wonder, Luiz Bonfá, Dorothy Ashby, Madlib, Flying Lotus, J Dilla, Louis Cole, and Italian soundtracks from the 60’s/70’s (Piero Piccioni, Ennio Morricone). Most of the album was produced at home but I did one session at Rax Trax for live drums, and two of my favorite drummers- Johnathan Hulett and Luke Titus, sent me files from their home recording set ups.
The response has been great! People have reached out here and there about how much it means to them, and some people have even purchased the album on bandcamp.
What were some things you learned about yourself and your music making this project? And why the title, Say Yes to What is?
This album was just as much of a creative exercise as it was a way for me to take care of myself. I had some challenging experiences in different friendships and romantic relationships, and this music was a way for me to process these experiences and then grow from them. I made at least 2 albums worth of material, but the songs that I kept were the ones that felt like a space you could live in when you’re going through a difficult time, or just a time to reflect and feel. This album was a major step for me to stop hating myself and start truly loving myself. It helped me find a style with clothes, visuals, and confidence in general. It also forced me to get more comfortable with singing and the vulnerability that comes with that. After a breakup in 2020, I was listening to a podcast with comedians Pete Homes and Duncun Trussell, and Pete said that “Say Yes To What Is” is one of his personal mantras. It was exactly what I needed to hear in that moment, and it helped me focus on embracing things as they are even when they are difficult!
You play with many different singers and poets specifically in town, including J.Hoard, Alysha Monique, Blake Davis, Iyana Brown-Bey, SiLo, Silas Short, Luke Titus, Angèle Anise, Jamila Woods and the list continues to grow. How do you approach playing others’ tunes?
I always aim to internalize another artist’s music and vision while still bringing my own style to it. It can be overwhelming at times learning so much music, but I’ve gotten better at it over time, and it is an amazing way to gather new ideas and experiences. In the past, I think I had more uncertainty about whether I was playing other artists' music “right”. But I’m learning that if people want Jackson, I’m gonna give them all the Jackson that I can (haha). It’s better to bring our full selves to a project instead of minimizing ourselves to fit into a box.
I love the artwork for this album, who designed it & what does it mean to you?
Thank you! The artwork for “Say Yes To What Is” was done by Kala Cree Kullars, an artist based in Chicago. I saw Kala’s work at the Hyde Park Jazz Festival and I was instantly mesmerized by it. It felt like we had a good creative chemistry as well. I just sent Kala the album while I was finishing it up, and she quickly started creating while listening to it. To me it’s this perfect collage of faces, bodies, instruments and emotions, all symbolizing different people and experiences in my life that taught me different lessons. For visuals, my favorite works of art are the ones that you can stare at infinitely, and there’s always a new detail to catch or interpretation to make. To me, this is definitely one of those pieces.
You have a band called Human Bloom you created back in 2015. The group contains yourself, Imani Rouselle, Josh Jessen, Leonard Maddox Jr. and Josh Griffin, give or take rotating members. Recently at Copper Still and The Hideout new songs were being tested out. If so, what’s been the inspiration for this next project? Since you live here and Imani in New York how did the songwriting process go for that?
We’re still early on in the process of shaping this next batch of work. I’m excited to bring old and new songs into the studio, while still leaving lots of room for experimentation. I’ve also been inspired to create more live band recordings, sometimes with no metronome, to feel those natural tempo fluctuations. With how out of control technology and AI is getting, I’m wanting to lean in the humanity of music now more than ever. That is definitely a theme I’ve been thinking about lately.
I also have been inspired by my own spiritual journey. Learning how to communicate better, to let go. Learning different kinds of rhythms and percussion, learning about nature. Spending time studying great composers and arrangers like John Coltrane, Alice Coltrane, Antônio Carlos Jobim, Billy Strayhorn, Duke Ellington, Charles Stepney, and more.
The distance is very difficult! But both of us like to visit each city so we make it work. I always get a ton of inspiration just from being in NYC. Sometimes I’ll have a song with everything but lyrics, and then send that to Imani, sometimes we get to build it from scratch together, or sometimes I’ll create music around one of Imani’s melodies or lyrics.
What’s your favorite song of yours to play for your solo stuff? with Human Bloom? Can you also relay the history of how you all met and started playing together?
It changes daily. For solo stuff, I have a new song called “I’ll Shine Anyway”, that’s super fun to play. For Human Bloom, I’m stoked about a new song called “Scavengers”.
Imani and I met at Columbia College Chicago around 2015. I booked someone else to sing with us for a show, but they got sick, and then recommended Imani. After that first show together, I knew there was a special connection!
Over the summer you played at a festival in the UK called “We Out Here” with the epic band Rotary Connection 222, how did you make that connection? How was the whole experience? Were you flown out?
That connection started with the brilliant bassist/bandleader/artist/arranger/DJ Junius Paul. We played one church gig together, and that led to me joining this group (Rotary Connection 222) that honors the work of Chicago's own Charles Stepney. Just a little backstory, Charles worked with Muddy Waters, Howlin’ Wolf, Minnie Ripperton, Earth Wind & Fire, the Dells, his own group Rotary Connection, and many more amazing artists.
Playing this festival was incredible! They have a very deep appreciation for Charles’ work in the UK so the audience was losing their minds over every song. Playing in this group has been such a loving and mind-blowing experience where I’m always growing as an individual and as a musician. It’s one big family. I was flown out, and I got to explore London for a couple days too.
You were also playing guitar on a project with the legendary Kamasi Washington, Maurice “Mobetta Brown”, and Mononeon. How did that come together?
That track, “Odyssey”, started from a last minute session in 2020 at RCM studios. Mike Mitchell started the groove on drums, I came in with a progression, and then Mono fell in on bass. Everyone else's parts were overdubbed later. Insanely magical! Still can’t believe I got to be on that song.
I'm curious to know how you listen to music? Can you listen anywhere? When do you need music during the day? Do you have to be doing something while you listen to music or do you have to be still?
Usually on Spotify, Youtube, or Bandcamp, with some good headphones. I have a pretty decent vinyl collection as well. Although, I just saw that Spotify is changing their terms so that they can basically use artists' work however they want to, forever, so I don’t love that. I know some people are switching to other platforms, but we’ll see.
I can listen anywhere, and I love to listen while running or being in nature. I’m usually learning someone’s show or working on my music. Sometimes I need it to get through the day, and sometimes I just need silence or a podcast.
What's your favorite thing about being a musician in Chicago? What values in being a working musician can you speak ?
The community! We all lean on each other, learn from each other, and push each other to keep getting better!
It has really taught me discipline and consistency. To always bring my full self to a project or performance, even on the days where I might be tired or dealing with something else. The more I give, the more it all comes back to me in some way, shape or form.
Who are some of your favorite artists in town right now that you have to let people know about?
So many. So many artists have inspired me, poured into me, and have seen me at my best and worst. And I’m so thankful to be in a place to learn from all of these incredible people. Blake Davis, Qari, Manesseh, Marquis Hill, Makaya McCraven, Junius Paul, Denzel Lavell, Alexis Lombre, Sam Thousand, Meagan McNeal, Jamiah Rodgers, J Bambii, Dai, Boukepra, Nashon Holloway, Josh Griffin, Greg Artry, Leonard Maddox Jr., Joshua Jessen, Josiah Maddox, Imani Rousselle (NYC), Iyana Brown-Bey, Otez Gary, Shawnee Dez, Ryan Person, Sen Morimoto, Ekoliii, Left Jones, Adam Ness, Family Junket, Aliyah Jones, Ariana Thomas, Wyatt Waddell, Kameron Lowe, Anaiet, Gabe Wallace, Illville Vanguard, Emoni Brown-Bey, Amyna Love, 99 the Producer, Patrick Jasper, Creature Fight, Alysha Monique, Isaiah Sharkey, Slique Jay Adams, Mamii, Melvin Knight, Chris Alli, Silas Short, Peven Everett, Isaiah Collier, Matthew Skillz, Jeremiah Collier, Brooklyn Skye, Zara Zaharieva, Jamila Woods, 7k, Johnathan Hulett (LA), Jahari Stampley, Alfonzo Jones, Brendan Doshi, Sparklmami, Resavoir, William Courdoroy, Shawnee Dez, Elisa Latrice, Aliyah Jones, Ariana Thomas, Wyatt Waddell, Caitlin Edwards, Akenya, Adam Ness, John Cunningham, Irvin Pierce, Thaddeus Tukes, Brandice Manuel, The Christ Universal Temple Musicians: Montage Pheloan, Darren Nichols, Matt Jones, Marcus Kincy, Jerrel Johnson, Garrett ‘G Body’ Body. It goes on and on. Till the break of dawn.