Lilly Winwood Hits on Heartbreak, Mistakes and Growth on Debut Album, ‘Time Well Spent’

It’s said that patience is a virtue, but if we’re being honest, it can be pretty damn hard sometimes.

With the release of her debut album, Lilly Winwood wanted to make sure everything was perfect. Having completed recording in 2019, a hands-on approach to each pillar of the release process held the album until a late January release. The culmination of those efforts is Time Well Spent.

Winwood navigates through the 11-song effort with tales of heartbreak and self-destructive behavior, but at the same time, recognizing and promoting growth and lessons learned. Winwood’s smooth, compelling vocals are layered onto the entirely self-penned album that showcases the 25 year-old’s sonically diverse chops, all combining to produce an early album of the year candidate.

We chatted with Winwood about the release process of Time Well Spent, many of the songs on it, her approach to songwriting, what she hopes listeners take away from the album and more!


Pro Country: You released your debut full-length album, Time Well Spent, at the close of January, an album that you’ve said has been finished since 2019. What was the release process of the album like for you? What went into ultimately deciding to release it independently?

Lilly Winwood: Because of this album being a debut, I went into the release process head first and a little blind. I wanted everything to be perfect, hence such a long wait. After not finding the certain responses I was looking for, I decided to follow my gut and release Time Well Spent independently, before I sat on it for too long and it got swept under the rug.

PC: What went in to the decision to release “California” as the lead single from Time Well Spent?

LW: “California” was always in my head the first song I wanted to release without hesitation. It summarizes the feel of Time Well Spent, and for the longest time, it was my favourite song on the record, and most certainly the song I have been playing live the longest and gotten the best responses. 

PC: “Few More Records” is a song that you’ve said discusses being burnt out on the road. With the way things unfolded last year in the live music industry, what does that song mean to you now? Has it taken on a different meaning?

LW: I think “Few More Records” stays true to what I wrote about because you could apply it to any situation, not just touring on the road. I think everybody has things, chores & jobs they don’t want to do, but if you think about the positivity of the outcome, it makes it all worthwhile.

PC: “Indiana” is one of our favorite songs on Time Well Spent. Can you talk about the inspiration behind that song?

LW: Thank you! “Indiana” was a hard song for me to write. There was a period of time where I was going through some intense heartbreak and I couldn’t quite let go of the person, so to feel closer to them, I would drive up to Indiana and have long weekends full of self-sabotage and unhealthy behavior; this song is all about that period in my life and how it’s easy to overcome a hard time if you just ‘cross that state line.’

PC: “One Step Behind” is an introspective song of karma and guilt. How important do you feel it is to continuously look inside of yourself and draw inspiration from your past?

LW: I think it’s important to some extent; you could say that letting go of your past is one of the most important things you can do also. My advice to others is always forgive yourself and allow yourself room to grow; reflect on your past to keep you humble.

PC: The title Time Well Spent comes from a line in the last song on its album, “You’ll Know Where to Find Me.” What was it about that line and phrase that drew you to name the album after it?

LW: My producer, Allen Thompson, and I brainstormed for a long time on names for this album, we thought “Time Well Spent” was a good representation and summary of all the songs on this record. I sing about hard times, travel, good times & learning curves, and at the end of the day, all of the time, no matter what, is “Time Well Spent.”

PC: You solo-wrote each of the eleven songs on Time Well Spent. How important is it for you to inject as much of “yourself” and your perspective into the songs on the album?

LW: I think the best way of connecting with your audience is by giving something they can empathize with, and the best way of doing that is by being completely honest and raw in your writing. No one wants to connect with something fake.

PC: In an interview with American Songwriter, you said that you did a bit of sonic exploration on Time Well Spent. Is it at all important for you to have a maintain a certain level of sonic versatility and exploring your various influences?

LW: I definitely think sonic versatility keeps things interesting when it comes to music, and my music taste changes every day. I think exploring your influences is important, but also staying true to yourself.

PC: Do you have a favorite song on Time Well Spent? If so, why is it so special to you?

LW: Following the release of this record, I’ve been listening to it just as much as way back when we recorded it, and as I’ve been listening, I’ve found new things that I love in each and every song. I’d say right now at this point in time, I’m favouring “Bruno;” I really like the guitar riffs that Laur Joamets does. 

PC: What do you hope listeners take away from Time Well Spent after listening all the way through?

LW: That mistakes will be made, but control what you can and move forward into the world with no hesitation, and explore, explore, explore!

PC: Of the things you can control, what are your plans for 2021?

LW: Writing more songs, setting myself goals & staying safe while keeping others safe!

*Lilly’s music is featured on The Best of Pro Country playlist!*

One thought on “Lilly Winwood Hits on Heartbreak, Mistakes and Growth on Debut Album, ‘Time Well Spent’

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  1. Just blown a way by Lilly and her talent. The apple doesn’t fall far from the tree. Have followed the family talent from Birmingham in the sixties. Lilly..please tour in the UK ..I know you’ll go down well!!!

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