5 Things I Learned On The Path To Becoming A Festival Headliner

Artist Development
4 min readSep 30, 2022

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Today I’m going to talk about 5 things I learned on the path to becoming a festival headliner in the UK.

If you can be consistent within the bullet points below & stick with them long enough I’m convinced you can accomplish your dream of becoming a headliner at a festival half way around the world just like my band (The Cadillac Three) was able to do.

The Long Road Festival — Leicestershire, UK.

Now, let’s dive in.

Show Up:

It’s essential to be consistent in the music industry. More & more these days out of sight leads to out of mind & any momentum you’ve built up can disappear if you don’t show up. When we first began traveling to the UK we made a point of coming over multiple times a year to raise awareness of the band & to show the audience our commitment to the UK market. We’ve seen many artists & bands come over once or twice only to never come back again & their support has suffered because of it. To have a loyal audience you have to show up.

Be Authentic:

Being authentic is at the core of being successful in all aspects of the music industry. All it means is to truly & unapologetically be yourself. Be authentic in your music, in your performances, in your interviews, in your interactions with fans and in your life and you will stand out. It’s easy to play the comparison game with other artists and bands but their path and their story aren’t the same as your own. Fans can see through a phony lyric, a phoned in performance or an artist that doesn’t know who they are. Fans know when you’re singing something real or just something that you think someone might like. When you are able to be your unapologetic true self you not only will do so without any real effort but you will connect with every audience in a way you never have before.

It Takes A Village:

For us it took 11 years, 3 managers, 4 tour managers, 2 sound guys, 2 lighting directors, a production manager, a record label, booking agents, business managers, lawyers, promoters, travel agents, rental companies, planes, trains, boats, busses & more to get to our first headlining festival in the UK. When we walked on stage and played the first notes I wasn’t even thinking about the song, I was thinking about all the effort of all the people that helped us get the opportunity to play that song. It’s important to take stock of those that are around you and pay respect to their role in what you are building. Celebrate the wins when things are going well and acknowledge and adjust when things aren’t. Your village may change over time but you are nothing without those that have helped along the way and it’s important to remember that as you continue on the path towards your goals.

Never Take It For Granted:

You never know when it’s all going to stop. Covid-19 taught us that really quickly. We were in the UK getting ready to play one of the biggest shows of our career at Wembley Arena when the news came in that the world was shutting down. We went from preparing to play for 20,000 people the next night to being on a plane back home and not playing another show for over a year. The momentum we had built to get to that moment had to sit two and half more years before we were able to get back to the UK to tour and that show at Wembley Arena is still on our bucket list. What that experience has brought us is an immense appreciation for the opportunities we have currently and a focus on not being anywhere but in the present.

Enjoy The Moment:

It can be easy to get wrapped up in everything around a moment and miss the actual moment while you are in it. Like I mentioned above, when we finally after 11 years were on stage playing the first notes of our opening song while headlining our first festival in the UK I was thinking about every person and step it took to get there instead of just soaking it in. This didn’t last long and I was able to really enjoy the show but it’s a prime example of letting everything go when the lights come on. Your job is to leave it all on stage, to give the audience something to remember and if you are locked in they will be locked in with you and everyone will leave having had an experience that will be memorable for a long time to come.

I hope these 5 things will help you on your own journey to becoming a headlining artist or band and that your path is as fulfilling as ours has been. Best of luck and if you’d like to receive more content like this please join the Artist Development Newsletter.

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Artist Development
Artist Development

Written by Artist Development

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