One of the most valuable insights to emerge from our April Alpine Songwriting Retreat—hosted with Grammy-winning artist Daisy Chute—came from Dr. Ben, one of our attendees. After our time together in the mountains, Ben shared a detailed roadmap he’s developed throughout his own artistic journey. It’s a practical, honest breakdown of the performance milestones that can help artists build confidence, skills, and a sustainable career.
We thought his roadmap was so helpful that we wanted to share it with our entire Talent Is Timeless community. Whether you’re just starting out or already performing at festivals, Ben’s stages offer a valuable framework for understanding where you are—and where you might be heading next.
Dr. Ben’s Artist Performance Roadmap
Stage 1: The Karaoke Circuit Start here. No pressure, just fun. This is where you can test material in a low-stakes environment and get comfortable performing in front of people.
Stage 2: Open Mics The traditional stepping stone. Open mics are where you’ll meet other musicians, build confidence, and get honest (if sometimes quiet) feedback from an audience.
Stage 3: Volunteer Gigs with Forgiving Audiences Ben’s brilliant tip: start with nursing homes. As he points out, audiences here are either hard of hearing or might not remember if you made a mistake. But they’re super appreciative and playing for them is priceless. It’s a gift—you can focus on the performance itself without the pressure of a critical ear. Other forgiving venues might include community centers, charity events, or small local gatherings.
Stage 4: Pay-What-You-Can Gigs You’re moving into spaces where people are choosing to pay for your music. There’s no guaranteed income, but there’s intention from the audience.
Stage 5: Guaranteed Pay Bar Gigs Even if it’s just $100 for background music while no one’s paying attention, this is where you start earning consistent money for your work. You’re a professional now, even if it doesn’t feel glamorous.
Stage 6: Opening Act or Guest Artist You’re warming up the crowd for someone else, or you’re invited as a special guest. This is where collaboration with other musicians becomes key.
Stage 7: Ticketed Event as the Main Act Now people are buying tickets specifically to see you. This is a pivotal moment—your name on the bill matters.
Stage 8: B Stage at a Festival You’re part of a larger music event. There’s infrastructure, a real audience, and recognition within the community.
Stage 9: Main Stage at a Festival You’ve arrived at a place where you’re headlining or performing on the biggest platform at a major event.
Ben’s Essential Tips for the Journey
As you move through these stages, Ben offers three pieces of wisdom that go beyond the roadmap itself:
a) Enjoy the process and the ride. This isn’t just about reaching the end goal. Every stage has value. The open mic nights, the nursing home gigs, the bar shows—they’re all part of your story as an artist. Find joy in where you are right now.
b) Take copious notes and learn from each gig. After every performance, identify something to improve: a technical glitch, a forgotten lyric, a missed note, an awkward interaction with the audience. Each gig is a lesson if you’re paying attention.
c) Take your time mastering each level before moving to the next. Rushing through the stages might get you to the main stage faster, but it won’t give you the foundation you need. When you take time to really master a level, you control your jitters, build genuine confidence, and actually enjoy what you’re doing.
Where Are You on the Roadmap?
One of the most powerful aspects of Ben’s framework is that it allows artists to self-identify where they currently are in their journey. This isn’t about competition or comparison—it’s about understanding your own path and recognizing the progress you’ve already made. For Dr. Ben, stages 8 and 9 are aspirational and what he is hoping to aim for next.
Are you just starting with open mics? Celebrate that. Are you playing your first ticketed show? That’s huge. Already headlining festivals? You’ve earned it.
The beauty of this roadmap is that it shows that every step matters. There’s no “too small” venue, no “too early” to start. Every performance is building something: your skills, your confidence, your story.
About Ben
Dr. Ben is a folk-blues recording artist who writes songs of heartache, hope and healing, based on over 30 years of experience as a travelling doctor to almost 100 rural communities across Canada. His songs describe his experiences helping people with mental health challenges, addictions and chronic illness, using a mix of intricate fingerpicking guitar styles, soulful blues licks and poignant lyrics. Dr. Ben performs in bars across Ontario in the same small towns on his doctor schedule, and also sings for patients in hospitals and nursing homes in his down time. Since the release of his first single in 2024, Dr. Ben has won two awards for his music videos and five semi-finalist or finalist nominations in major songwriting contests. Dr Ben lives in Toronto and his side-gigs include university professor of healthcare management and global health advocate.
If you’re part of the Talent Is Timeless community, we’d love to hear where you are on this roadmap. Share your story with us, and remember: every stage of this journey is worth celebrating.
You can Connect with Dr. Ben on Talent Is Timeless here: https://www.talentistimeless.com/members/benchan/
Talent Is Timeless is a global community of 29,000+ songwriters aged 50 and over, proving that creativity doesn’t come with an expiry date. Our members connect with like-minded artists, participate in monthly songwriting challenges, attend expert-led masterclasses, and compete in our annual contest—with winners recording at iconic studios like Abbey Road. Whether you’re returning to music after years away or writing the best songs of your life, you’ll find encouragement, feedback, and genuine connection here.