Sharpen Your Songwriting Tools: Q&A with Jud Caswell

Jud Caswell, an award singer-songwriter from Brunswick, Maine, is returning to teach at SummerSongs East this year! We’re so excited to have him back! He’ll be teaching two classes: The first, is “Sharpening Your Tools: Whole Brain Songwriting,” focused on taking your craft to the next level. The next is a class focused on workshopping your new song and getting feedback.

Q: How did you get your start as a songwriter? What was your jumping-off point?

A: I fell in love with songwriting as a freshman in college. It was the first time I had ever been around people my age who wrote songs, and it blew me away. Everyone was learning how to play acoustic guitar, and a friend down the hall taught me how to Travis pick and it was all downhill from there. I spent my whole time at school listening to John Gorka and learning James Taylor songs and started writing my own stuff almost immediately.

There was another more important starting point for me, though, around ten years later. I had been writing and recording and playing all the local watering holes. I felt like I had gotten about as far as my gift was going to take me, and it wasn’t enough. I had always harbored a pretty “Romantic” notion of what it meant to be creative; to be an Artist. I placed a lot of value in doing things myself, having my own voice and my own style and unique approach, and as such, I was resistant to learning more about the craft of writing. I felt like that would taint my art somehow. I decided if I wanted to be more successful, I was going to have to let go of that notion. It was the best decision I ever made — and it was really only through that focus on craft that I was able to really find my voice as a writer and find the audience that wanted to listen.

Q: Let’s talk about your class, “Sharpening your Tools: Whole-Brain Songwriting” — what can students expect at SummerSongs 2016?

A: “Whole Brain Songwriting” means making room for both halves of your brain in your creativity — with the right brain offering creativity, insight, and intuition and the left brain offering analysis and structure and reason. I feel like there’s a lot of focus on the importance of the right brain in creativity — and that’s natural and appropriate. It really is the well that we draw from. But the left brain is incredibly important as well, and finding a way to engage it more fully and seamlessly in your creative process is a way to really take your songwriting to the next level.

In this class, we’re going to focus on tools that you can bring to bear on your writing to help you make the songs that you want to make. It’ll be a kind of Swiss Army Knife approach, with lots of specific tools for specific problems, but the overarching question that we’ll be looking at is “what’s another way to do that?” I think that as we begin writing songs, we make choices intuitively. That’s a beautiful approach, and if your intuition is strong enough, it’ll take you far. But sometimes you can be left high and dry — after all, when you do things purely intuitively, you don’t really “know what you’re doing.” What I want to do is introduce a whole slew of ways to look at your writing — to break it down and look more closely at the myriad choices that you make. When those choices are clear, you are given the ability to make different choices. And different choices lead to different results. And different results sometimes are better results!

Topics we’ll cover are music theory, melody, song form, and lyrics. We’ll also have a one-session short capo workshop. In music theory we’ll try to give writers a deeper understanding of how their chords work together. We’ll look at keys, scales, and chord numbering systems to make it easier for writers to try new chords and to always find their way back home. With melody, we’ll find some simple tools to increase your melodic ideas and improve the flow and fit with your lyrical content. Song form is maybe the most important element to me, and taking a look at overall song structures will help writers make better decisions about hook, title, song length, and musical ideas as they balance novelty and familiarity to keep their listeners glued to the song. Zooming in on lyrics a bit more, we’ll break down the rules of meter and rhyme and look for ways to bend them into the shapes we want. And if you’ve ever wanted to throw a whole new spice into your guitar playing, come by the short capo workshop and prepare to search for the lost chord with me.

This class is for any level of student, though different levels will understandably get different things out of it. If you’ve written songs before and you feel like you just can’t take your songs to the next level, this may be just the thing for you!

Q: Your other class is about workshopping your song…what is so powerful about asking and getting feedback about a new song, no matter what level songwriter you are? What level student will fit in best for this class?

The song workshop is also open to any level of songwriter — the only thing I hope of participants in these workshops is that we all want to write better songs. I have run a workshop for years and the one thing that all the stalwart regulars have in common (aside from a great sense of humor) is that they are interested in the craft of songwriting and are always looking for ways to improve. We always have fun, we care a lot about each other, and we all are willing to look deeper into the nuts and bolts of our writing in hopes of reaching our own individual goals. I would love to have that kind of experience at SummerSongs as well!

In my experience, the one thing we all want to know about any of our songs — no matter what level we’re at — is, “how good is this song?” And preferably the answer is some version of “WOW!” I try to avoid that conversation at all — for a lot of reasons. For one, we all have different taste. And liking a song is, at heart, a matter of taste. I’m much more interested in trying to discover what a song is trying to do, and to delve into how it is achieving (or not achieving) its goals. I always try to make observations about specific techniques, and how those choices affect the tone or the pacing or the novelty or the predictability of the song, and then let the writer decide whether these things are goals they are striving for or not.

I have a ton of respect for songwriters of all levels — it’s an incredibly vulnerable and personal thing to share your songs, and it’s very important to me that writers feel safe in a song workshop. But I also respect the writer’s desire to learn about the craft, and I think one of the most valuable things we can do for each other is to offer an outside perspective. It can be very hard to really see what is so close to us, and I think the job of the song workshop to help the writer see the choices they are making and hopefully understand the effects those choices have.

Q: Why do you think a retreat like SummerSongs is a great way to spent a few days or a week?

As I mentioned at the outset, songwriting really started for me when I got a chance to be around other songwriters. We’re a tribe, and there’s just nothing like being around your tribe. I can’t wait to see the experience of first-timers here — I know that it’ll be life changing. And I can’t wait to get back to my people — it’s been way too long!

SummerSongs, founded by singer-songwriter Penny Nichols in 1999, offers seasonal songwriting camps (summer and winter) for adults on both the East and West coasts of the United States. The songwriting camps take place in the Hudson River Valley 30 miles north of New York City; and on the beautiful California Central Coast, overlooking the Pacific Ocean. Both locations are perfect havens for songwriting and creative inspiration.

Join us at SummerSongs East: July 31-August 6 (half-week and full-week available), Stony Point Center, Stony Point, NY — 35 miles north of NYC! 

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Got questions? Email founder Penny Nichols at or Sharon Goldman, marketing director, at