This is the latest in a monthly series in which industry leaders describe the projects and products that give them the most joy and pride. This month, singer-songwriter Ted Leo talks about how The Both, his collaborative project with Aimee Mann, changed his perspective on creating art.

I’ve been an active musician for about 28 years, and I’ve spent the majority of them as the principle songwriter of one group or another. Except during the times when I was writing and performing truly alone. Like, ALONE alone — in a car alone, on a train alone, on a stage alone, on a floor alone, on a couch alone, in a hotel room alone. Alone alone alone alone. There was never a specific drive to work alone, but I often found myself at least driving alone, nonetheless.

It worked to a certain degree. I got a lot done. We’ll never know how things might’ve been different had I been less uptight at times, or had other people been less uptight at times, or had we inspired more openness in each other at other times. Generally, things as they’ve happened have been OK, and I have a history of decent art and great relationships to look back on.

But there are those times one wonders: Has it all been too monolithic? Have I pushed too hard? What would real openness look like; feel like; result in? In those times of questioning, I never made too many moves to find the answers, but recently, an opportunity fell into my lap. It started out as simply a reinvigorating bit of fun and ended up forcing me to confront those questions, and to answer them. It left me able to point to this as the greatest thing I have done: to truly understand — and find (self-defined) success in — collaboration.

About two years ago I entered into a partnership with a friend who has been called one of the greatest songwriters of our time, Aimee Mann. It started as a friendly end-of-tour back and forth about how “we should do something together someday.” However, Aimee threw down the gauntlet by sending me an actual verse and chorus of a song and suggesting I take it from there. All of a sudden, I was at sea.

Songs are craft, able to be crafted according to certain rules and desires, but they’re also precious. Unless you pointedly don’t care what you’re saying, there’s a very real and vulnerable something of you that winds up in those words, notes, chords, and beats. And now a well-regarded artist whom I personally possess the deepest respect for was asking for this piece of me to exist next to that piece of her.

As hard as I worked, I couldn’t come up with the goods. I couldn’t get out of my own way. I had my own idea of where the song was going, and I had a primal fear of that being rejected — probably because, in part, that would mean I was being rejected.

But here was a partner who could help me through this. Let’s tease out what our goals with this song are. What have we said? What does it mean? What do we want to say further? Are we using the right words? How can we make it better? Most importantly, can we find excitement in agreement instead of resignation and acquiescence? Can we respectfully challenge each other and remain open to being challenged, trusting that there is no personal rejection?

I had to learn to divest the ego from the creative process in ultimate service of the creation, which freed each utterance from the turgid entanglements of self-worth and allowed for each piece to become a puzzle to be solved. This process also allowed me to better appreciate the piece itself. Finding the people you click with, recognizing the moment, and taking the risk to trust can get you to places you never even knew you wanted to go.

Collaboration isn’t settling; it’s using each other’s talents and skill sets to support and propel; to offer without fear; and to receive with thoughtfulness and grace. Aimee and I have a growing body of work that I’m proud of, but it’s been the work itself, and all that I’ve learned from it, that I treasure more.

To learn more about The Both, visit them online, and explore Ted Leo’s career in more depth on his official website.