SONG PREMIERE: Ashley Riley Conveys Passionate Sincerity with Infectious Americana Tune “Second Guessing”

“I know it meant more to me, and I’m setting you free…” Honest and disarming declarations like this fuel singer-songwriter Ashley Riley’s upcoming new release, Set You Free, due out June 18th. The album is rife with songs about holding on and letting go, giving in and giving up, and the peace that comes from making it out on the other side.

The 10-song collection finds Riley stronger and wiser than before, her down-to-the-bone vulnerability on display, tempered with an understanding and sincerity that only comes with time. The gritty, rootsy moments that garnered favorable comparisons to Patty Griffin and Stevie Nicks remain, backed by lush instrumentation that incorporates genres such as indie rock and pop into her Americana-folk niche. “This album really encompasses everything that I do, from the really slow ballads to full on rock songs,” says Riley.

With Set You Free, Riley made the decision to plant both feet firmly into the more hopeful side of her sound. The result is a gorgeous and heartfelt collection of songs that pulls you in close and holds your attention.

Today Glide is excited to premiere the single “Second Guessing,” a clear standout on the new album. Light and upbeat, the song is a folky romp through a flower field of infectious senses. Riley deals with heavier subject matter while also translating it into a form of catchy Americana. Her strength as a vocalist is on display in the soulfulness of her delivery, but we also get a moving passion in the lyrics. Complemented by dreamy, washed out guitar, Riley sings her heart out and conveys her sincerity. 

Listen to the interview and read our chat with Ashley Riley below…

What is the inspiration behind this song? What is the story you wanted to tell with it, and what do you hope that listeners take away from hearing it?

“Second Guessing” was inspired by looking backwards and dealing with ghosts. I had a friend totally ghost me, and it definitely haunted me. I spent a lot of time looking back and trying to figure out what I did wrong, because for some reason I was always willing to take the blame. In the end, it was me recognizing that I’m kind of a people pleaser and I don’t like it when I upset people. I used to back down and away instead of having a hard conversation. I’m strong-willed enough that I would still do what I wanted, but I’d do it in a smaller way to keep the peace. In this particular situation, I stood my ground, and it ended the relationship and left me second guessing myself. The song is me working through all of that and at the end resolving to not feel that way again, which is probably impossible but really just means I’m going to stick up for myself when I need to. When I really looked back, though, I realized that that was a pattern for my friend. They would just drop people who didn’t agree with them, and it wasn’t even an election year! Kidding. 😉 It took me a long time to process and not still feel hurt by that. In a way. I guess this song is my goodbye to them since it was left in such a weird place. It’s like when a show you’re into gets abruptly taken off the air and they don’t even finish the storyline — I’m not a fan of that! I think what I’d hope for listeners to take away from the song is maybe a sense of trusting yourself, and also a catchy melody. 😉

When you wrote this song, which came first — the lyrics or the music? Did it take some time to make it all fit together, or did it all pour out quickly?

I started with the groove and chord progression on this one. I think it took me about a week to figure out all the lyrics and melody. I record voice memos on my phone because I’ll usually write a verse or chorus and then I like to see where the melody takes me. It can be fun and funny to go back and listen to those, but it’s a good way to explore possibilities and melodies; a lot of times I have little snippets of lyrics appear in those memos, and I go back and craft it better from there. The lyrics did come pretty quickly, but the arrangement took a little time to get right. When I brought it to James Treichler (producer, Wave Upon Wave Studios), he helped me finish the arrangement in terms of timing and moving from section to section, so the song really came to life in the studio.

Tell us about the recording process. What went into this song in particular?

I’ve recorded most of the upcoming album, Set You Free, remotely, with all that was going on in the last year, but fortunately I did get to start on “Second Guessing” during an in-person session. I’m working with James Treichler at Wave Upon Wave Studio in Champaign, IL. We had a demo session where I took a bunch of songs over and did a guitar/vocal take. From there, we would think about feel and intent of the song and build around it. It’s been great to work with someone who is really intent on serving the song, and James is very intentional with that. I hadn’t really thought about it much but I guess working remotely could be a disaster if you’re not on the same page, and it’s felt really easy to me. With “Second Guessing,” I remember wanting to add more to it… more guitars, more layers, just more. It was funny, because we gave it a try and it was pretty clearly like, no, I don’t think we need all that, and we stripped it back down to what it was. Sometimes recording can be an exercise in restraint, and leaving space can be as important as filling it.

What do you think this song adds to your forthcoming album, theme-wise and music-wise?

Well, as I’m starting to think about these songs as an album and analyze them to talk about what they mean to me, I’m finding that this album is really a journey. It’s about doing what you can and letting go. It’s about trusting yourself and staying the course. It’s so easy to give up, and this album is about not giving up. I think “Second Guessing” is a bit of an emotional turning point in that way. It kind of turns that corner into starting to trust yourself and stay that path, theme-wise. Musically, I think it lives in a cool space of its own on the album.

You’re from the middle of Illinois. What influence has that place had on your music overall and on you as a performer?

Yes, I grew up right in the middle of Illinois in Decatur and the surrounding areas. I wrote a song called “This Town” (on my 2016 album, Through the Thin) that’s inspired by Decatur, but I’ve never really put much thought into how where I live has seeped into my music. That is an interesting question. Decatur was a booming industrial city up until the ’90s when it started to decline, and now I think we’ve been the fastest shrinking city in Illinois for the last couple years. It’s the kind of town where everyone is always saying there’s nothing to do and is always wanting to get out of town! Maybe that’s made me always search for hope or meaning in places. I try to write songs about ordinary moments, and that’s probably a bit inspired by a pretty ordinary blue collar town. Good question!


Photo credit: Joe Riley

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