It's okay to want the big dream. The trick is learning to hold it loosely.

Chris Hutton graduated right before the world shut down, and he rebuilt his music career one piece at a time: teaching, vocal production, session work and songwriting. In this conversation from the archives, he names the quiet trap so many singers fall into, wanting nothing so nothing can let you down, and shares how he's learning to want things again. Still true today.

🎧 In this episode

• A working singer's career is rarely one job. It's a mix of teaching, production, session work and live gigs, and that mix is what keeps the music going.
• Being "defensively apathetic" can feel safe, but it quietly shuts down the part of you that dreamed in the first place.
• You can chase a dream with your whole heart without needing it to define your worth.
• Singers are storytellers first. Technique serves the story, not the other way around.

About Chris Hutton

Chris Hutton is an LA-based singer, songwriter, vocal producer and voice teacher. In this 2021 conversation, he had worked with LA contractors including Tim Davis, collaborated with Grammy-nominated producer Bruce Vanderveer on his single "Rewind," and held a bachelor's in commercial music from Biola University.

Moments worth your time

• 02:13 — "Rewind": a shower idea that took off on TikTok
• 05:45 — Writing a song from the other side of the relationship
• 12:17 — "Between like 3 and 6 and a half different jobs": what a working singer's week really looks like
• 25:11 — The wingback chair, the baritone, and the "pick a lane" speech
• 33:58 — Why singers are storytellers before they're technicians
• 41:52 — Not knowing what a demo was until after graduation
• 47:52 — Learning it's okay to want things, and to hold them loosely

"I'm gonna chase it, but I'm not gonna chase it because I, I need it." — Chris Hutton

Curious where your career momentum is leaking? The Singer Momentum Snapshot shows you what deserves your attention first.

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Pay yourself first, even if it's fifty dollars a gig.

Keyboard player and producer David Yuter and hip-hop artist Raymond Harper join me for a candid conversation about musicians and money: learning to say no, writing something every day, why finances feel like such a touchy subject, and the simple habit of paying yourself before anyone else.

A note before you listen: this conversation was recorded in 2021. Part of it covers investing ideas the guests were excited about at the time, and a lot has changed since. Nothing in this episode is financial advice.

🎧 In this episode

• You don't always have to be the yes guy.
• Write something every day, even a single line, or the idea is gone.
• Pay yourself first: a small, automatic “life tax” on every gig.
• Musicians can make a great living. Start by believing it's possible.

About David Yuter & Raymond Harper

David Yuter is a San Diego keyboard player and producer who plays upwards of 150 shows a year and works in artist development. Raymond Harper is a hip-hop artist and songwriter from Detroit, an Army veteran now living in Los Angeles.

Moments worth your time

• 02:16 — From Detroit lunch tables to the Army to Hollywood
• 03:15 — Learning not to be the yes guy
• 07:24 — Write something every single day
• 09:55 — Why money feels like a touchy subject
• 35:27 — Yes, musicians can make a great living
• 39:15 — The life tax: paying yourself first
• 1:00:27 — Parting words: it's all a mindset

“If you get $300 for a gig, take $50 and put it in this side account.” — David Yuter

Curious where your career momentum is leaking? The Singer Momentum Snapshot ($47) shows you what deserves your attention first.

Explore more conversations and join the community at The Unstoppable Singer.

Sometimes the most serious lesson shows up in the middle of a game night.

Recorded a few months into the shutdown, this one is pure play: one-word check-ins, guilty-pleasure music, would-you-rather (singer's edition), and a running joke about falling down a well. Along the way, Mariela Contreras and Veronica May get honest about the songs they're tired of, promoter pressure, and what it means to sing what you love. Still true today.

🎧 In this episode

• Laughter is part of the work. Rest and play keep your love of singing alive.
• Notice which songs you reach for when nobody's requesting anything.
• Original shows can feel exposing. That's part of why they matter.
• Showing up early still says a lot about you as a pro.

About Mariela Contreras & Veronica May

Mariela Contreras and Veronica May are singers, songwriters and teachers, and both have been guests on the show before. Mariela was writing songs for an EP; Veronica was teaching virtually and planning new recordings with San Diego friends.

Moments worth your time

• 01:43 — One word for how you're feeling, and one thing to brag about
• 03:34 — Putting on a real shirt for Zoom
• 10:27 — Would you rather play naked, or with a set you don't know?
• 19:54 — Ten minutes late or twenty minutes early?
• 24:54 — The song you dread singing
• 28:06 — “Why have I been singing the songs I don't want to sing?”
• 36:06 — Asleep at the gig: accompanist or audience?

“why have I been singing the songs that I don't want to sing?” — Mariela Contreras

Curious where your career momentum is leaking? The Singer Momentum Snapshot ($47) shows you what deserves your attention first.

Explore more conversations and join the community at The Unstoppable Singer.