Investigating Ingrid: The Way She Is

By Steven Libowitz   |   October 19, 2026
Ingrid Michaelson plays at the Lobero Theatre on October 16 (courtesy photo)

Most pop bands choose names that are merely drawn from their latest album to describe a series of live shows. For Ingrid Michaelson, Cozy Fall Trio Tour is not only descriptive, but also evokes the same sort of warm and playful feeling the singer-songwriter has exuded over her 20 plus-year career, one characterized by indelible melodies as the soundscape for her largely uncomplicated but decidedly heartfelt storytelling. The result has been several gold and platinum hits, including “The Way I Am,” “Girls Chase Boys,” and “You and I” before Michaelson recently lent her talents to creating the score for the musical stage version of The Notebook. 

We caught up with the singer-songwriter on the eve of Cozy’s first show last weekend in advance of her concert with Allie Moss and Hannah Winkler at the Lobero on Friday, October 16, her first time performing in town in almost a dozen years.

Q. I’m one of those people who think “The Way I Am” is a perfect little song. Sometimes I get in the mood and play it a few times in a row, especially when it makes me cry. My question is, did you realize how powerful this thing was when you wrote it all those years ago?

A. No, no, when I wrote it in my bedroom at my parents’ house. I put the lyrics down on paper, but I didn’t record the melody because I still had a flip phone and my recorder wasn’t handy. I thought, I’ll remember it because it’s a really catchy melody. The next day I was revisiting it, and I couldn’t make the lyrics make sense because I forgot the melody… But the next morning, I woke up singing it. But I really didn’t know what I had. 

Back then, I would play it at the local coffee shop, and this one guy was always coming to see me. He said the Rogaine line is not good. You should change that line. I thought, what am I supposed to say, “I’ll buy you hats.” Like, I really did think about it because he was one of 10 people who came to all my shows. Turns out that it’s probably the line that hooked into everybody’s brain. But I had no clue. You usually don’t know. 

Which leads into my next question about your ability to write with a very simple and conversational style about any subject, but they get deep because of the turns of phrase, or how you sing them. Are you aiming to be simple? Is it a struggle? Or just how they come out?

I’m just a simple girl. In fact, most of the criticism of my work comes from it being too simple. It’s like the albatross that people might misunderstand my simplicity for frivolousness. The truth is, I like to say things simply, but in a way that maybe you’ve never heard before. Maybe the phrasing is a little bit lopsided or inside out, which makes the sentiment hit in a different way… I’ve never been over expository or verbose.

It’s just not in my nature. 

I still get defensive about it because I think that my writing is beautiful and I’m very proud of it and I wouldn’t change it. But it is a sore spot for me. 

Yikes. Sorry to have hit a nerve… I also like the dichotomy of the dark subjects given such pretty melodies most of the time. 

Right. Me too. I have a song called “Be Okay” that if you just read the words, it’s very, very sad. But the melody is so upbeat that everybody thinks it’s a happy song… I like to shroud grief and sorrow in a happy melody. It’s kind of who I am. A sad girl who writes songs. I’m a melancholy person who maybe doesn’t mask but puts on a show to get through life and make people smile. I have the ability to find the positive in things even though I’m a sad girl. My songs are indicative that there’s always a little ray of hope and sunshine.

Do these years of writing about your life and sharing the songs with audiences help you to maybe understand yourself and the ideas of love and loss? Or does it still seem as complicated, mysterious, and unapproachable as ever? 

It’s probably a little bit of both. There’s something about people relating to your music that helps you feel like you’re not alone in the world because other people are feeling the exact same things. It allows you to commiserate, feel things together. But it doesn’t stop pain. It doesn’t stop grief…

Do songs that you wrote a while ago resonate differently now? 

Everything is always about learning and growing and changing and transitioning, you know. Or at least for me. So a song today that I wrote 15 years ago is completely coming from a different place today. I’ve healed and I’ve reopened the wound with listeners. But there are only two songs I don’t sing anymore because they’re about my mother, and I don’t want to go there. Otherwise, it’s just about the journey and the communal element of art – the digestion of art together as a group so you feel less alone. 

That’s a great turn of phrase right there. 

See. I can be deep. 

How was the experience of composing the score for the Broadway musical adaptation of The Notebook in terms of what we’ve been talking about? You’re not expressing your own stories, emotions, and feelings, but instead inhabiting a character? Did doing that let you in some way access more of yourself? 

Actually it wasn’t vastly different. I like to write about internal moments, what’s happening in the person’s head, which I did a lot in the show. They tend to be pretty similar to writing a pop song because, yes you have to drive the plot forward, but you can get really emotional… I lost my mom in 2014, and my dad in 2017, right when I started working on The Notebook. I even lifted some of the lines from things my dad said, but because it wasn’t my story it gave me a cloak of invisibility to spill my guts, my grief, and my joy into the songs. Then I get to watch other people sing them. It was one of the greatest experiences of my life. 

This is your first tour in a number of years. What are you looking forward to?

I wanted to see what it was like to come back to performing, see if I like it and if I am good at it. So it’s a bit of an experiment. I like smaller formats, so this is a good first step. Allie and Hannah are my best friends, and we have a great time on stage. They’re both great singer-songwriters and they’ll be performing a couple of songs each in the middle of the show. I think the audience is going to enjoy it. And you get a little break from me. 

 

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