Meet Jason Wexler

Alright – so today we’ve got the honor of introducing you to Jason Wexler. We think you’ll enjoy our conversation, we’ve shared it below.

Jason, first a big thank you for taking the time to share your thoughts and insights with us today. I’m sure many of our readers will benefit from your wisdom, and one of the areas where we think your insight might be most helpful is related to imposter syndrome. Imposter syndrome is holding so many people back from reaching their true and highest potential and so we’d love to hear about your journey and how you overcame imposter syndrome.

Early in my career, I ended up working with a lot of musicians who were much older and much more experienced that I was, and I definitely felt that I was in over my head on certain gigs. As I gained more experience, I realized that all that matters is your work ethic, both in the ability to be prepared, and to make sure your skills are sharp so you can fit into any situation you find yourself in.

Thanks for sharing that. So, before we get any further into our conversation, can you tell our readers a bit about yourself and what you’re working on?

I started my career primarily as a keyboard player, working with an original band that toured throughout the mid 2000s. Once that band had run it’s course, I started to freelance with original artists throughout NYC, which found myself touring, performing on television, music directing, and also producing records for some of these artists.

Once I had children, I wanted to stay closer to home, and found myself involved in the wedding industry, working with bands through the NY/NJ/CT area, which was fun and also very lucrative.

During the pandemic, all of my live performance work dried up, and that’s when I decided to focus most heavily on my own music. I now have 5 instrumental recording projects under a label, The Chillest Records, that I own, and it’s become one of my primary parts of my career. I’ve been placed on numerous Spotify Editorial playlists, and my music has been streamed over 50 million times across platforms. My main two projects, The Chillest and Chillzy, have become my primary focus in my career as an independent musician.

I continue to perform with a live tribute band, and teach some private piano lessons as well. I’ve found that diversifying your income streams as a freelancer is the key to having a successful career.

If you had to pick three qualities that are most important to develop, which three would you say matter most?

1. Being on time. Half of the battle is showing up. If you’re known to be reliable and will be where you’re needed, when you’re needed, you have a much higher chance of being called for future work.

2. Being prepared. As a musician, I have to learn new music for every gig I take. If I show up and I can play the entire set down cold, without any rehearsal, that’s a huge win for everyone in the band.

3. Being a team player. Knowing when to set aside your ego for the benefit of the group makes people want to work with you. Having knowledge to share without being pushy makes you an invaluable part of a team.

The biggest takeaway from this is to be a reliable, responsible team player. You want people to feel that they can depend on you in any situation.

Any advice for folks feeling overwhelmed?

I frequently found myself getting overwhelmed when I had multiple projects going on at the same time, along with touring and teaching.

What I found worked for me is to write everything down in a list, and figure out which tasks feel like I have the least amount of understanding of the time it will take to complete them. These are the tasks that make me feel overwhelmed.

Once I know which tasks those are, I complete them first, resulting in a list of tasks that I know how long each will take, and I can schedule out the rest of my week/month with that list.

My feeling of being overwhelmed always come from the unknown, so removing the unknown from the equation early on rids me of that feeling.

Contact Info:

• Website: jasonwexler.com and thechillestmusic.com
• Instagram: @jasonwexler

Image Credits

Personal Photo: Alex Roldan

1 Manish Gosalia
2/3 Phil Lebowitz
4 Amanda Wexler