How do freelancing artists do it? How do they piece together work to create a sustaining and stable career?  Through this interview series, I aim to get to the heart of those questions by talking to various artists about how they make freelancing work for them.

In this tenth installment, Janelle Reichman at Continuum Design & Web spoke with trumpeter and electronic musician Gerald Bailey. Originally from Indianapolis, Gerald earned a bachelors degree in jazz trumpet performance at the University of Cincinnati College-Conservatory of Music before moving to Chicago, where he has lived for the past 13 years. Gerald’s musical career has varied greatly – from performing at the White House with Balkan brass band Black Bear Combo, to touring with bands like Belle and Sebastian and Mumford & Sons, to playing lead trumpet in bands at Chicago’s famed jazz club The Green Mill, to touring with his own electronic based music project Charles Mantis, which blends trumpet and beats with elements of Electronic, Jazz, Balkan, and Dance music into one unique style. Gerald’s new Charles Mantis record Datura Inoxia is available for streaming or purchase HERE. In this interview, Gerald spoke to Continuum about maintaining a mobile lifestyle, making lists, practicing in the car, the importance of time away from music, why a freelance life might be the way of the future, and a lot more. Enjoy!

(photo credit: Roxy De La Torre)

When did you start playing the trumpet?

I started trumpet in sixth grade. A year earlier I played drum pad at a public elementary school and switched to trumpet as soon as my family moved to a new school district with a larger band program.

What made you want to play that particular instrument?

Sound and versatility attracted me to the trumpet. As a kid I spent a lot of time with my grandfather and he listened to jazz every day. It was common to hear a wide range of trumpeters in the car on road trips. Early into learning the instrument he gave me my first Miles Davis record and I was immediately hooked.

Did you always want to be a professional musician from a young age or was it a decision that came later on?

Becoming a professional musician wasn’t on my radar until about age sixteen. I was lucky to have great music teachers early on. Matthew Harrod (high school band director) and Mark Buselli (Indianapolis area trumpeter) were both influential in my choice to pursue music. They are both still teaching and playing music in the Indianapolis area to this day.

Have you ever had any non-music related “odd” jobs? If so, what were they?

Yes! I have had an array of side jobs over the years. Those experiences were vital. One of the more interesting “odd” jobs was working as a test subject for the Cochlear hearing implant. Test subjects were paid to transcribe short sentences that were recorded at a wide range of frequencies. I’ve also worked as a fast food burger slinger, bartender, dog walker, house sitter, theater usher and barista.

Have you ever had a full time (9-5) job?

After graduating from the University of Cincinnati, I spent a year working in customer service at a theater in Ohio. My lunch breaks were spent either practicing trumpet in my car or working on an escape plan to move to Chicago.

What’s your ideal typical day?

When things are running smoothly for me I like to start early with composing/mixing, teach a short class, move to emails/booking around lunch, shoot some promotional photos or videos, practice trumpet before dinner and then head to an evening gig or catch another artist performing. The Chicago area is rather large, so anything listed needs to be able to be accomplished outside of my home at any given time. Over the years I have adapted to the mobile lifestyle. Composing, mixing, booking and promoting may happen just as often in a tour bus, plane, high school band room, hotel lobby or coffee shop as it does in my home studio.

Would you consider yourself a “hustler” when it comes to getting work?

Hustling does not work for me. Ideally the people I want to work with want to work with me. Hustling feels unnatural and the results can be superficial by design. Don’t get me wrong here, I have shaken many hands and handed out my fair share of business cards over the years, but when things are going well it does not feel like hustling.

What factors do you consider when deciding whether or not to take a gig? Has this changed over time? If so, how?

Type of experience, pay and the people involved tend to play the greatest roles in deciding whether or not to take a gig. The order of importance changes with my needs at the time. A lot of times, if you are dealing with good people the experience is great and the pay is right.

Who or what are your main sources of income these days?

It helps to keep a diverse list of income sources, so if something falls through it doesn’t totally sink the ship. A typical week in Chicago might require me to work as a session musician, at a jazz club, teach a college class and play Turkish music at a wedding.

In your experience, how long does it take in a new city to build a sustainable freelance career?

It is important to think of your career as sustainable right out of the gate. There really isn’t a finish line where an artist feels like they have now made it. I would imagine the wait time depends on a variety of factors, including things like city size and profession.

What is the opportunity you made for yourself for which you are the most proud?

Just recently I helped start a technology-based composition class in the Chicago Public Schools through the After School Matters program. This July my teaching partner Max Davis (Style Matters DJs) and I will help high school musicians learn composition and theory using Ableton Live software. Over the last few years I have been using Ableton on stage in my own original projects. The plan is to take what we have learned using technology in a performance setting and apply it to our class.

Within the course of a day, do you have any specific tactics for making sure everything gets done?

Making a list is my go-to method. I make a list for the day, week, month and year. My medium of choice is an old school ledger. The romance of writing in that dusty old black book motivates me to blaze through each list.

How do you balance work time and off time in your daily life?

Time away from music is crucial. I try to devote one day a week to cooking or photography and a week or so of vacation per year. The people I spend time with and the places I visit on my days off become inspirations for new music. For example, this past winter I played one night in New Orleans, but I spent my days off touring the area with my wife Leighann. Many of the places we visited and photos we took have become inspiration for some the projects I am currently working on.

How do you tend to spend your time when you encounter lulls in work?

Fortunately down time can be slightly predictable. There are a couple months that are generally slow every year. It might make sense to use a down month to work on a web page, or focus on a new creative project that has yet to take off.

How often do you turn down work and why? How do you handle situations where a much better offer comes along?

At every level it is common to turn down work from time to time. This is why the good experience, good people, good pay scale is so important in weighing what opportunities you take and pass on. If you agree to something and need to back out it is important to make sure the job is covered.

Have you ever had a mentor who helped you figure out how to make a freelance lifestyle work?

I take cues from friends and acquaintances of mine who are freelancers. Artist/digital designer Benjamin Miles (Director of Interactive at the Uprising Creative), Toronto based photographer Scarlet O’Neill and Kyle Hodges (director of branding for Dark Matter Coffee and Press Pot Recordings) have been major influences on me as professionals. Benjamin is making things work from Chicago in an industry that is dominated by Los Angeles, New York and San Francisco while Scarlet is a great time manager, using her downtime to catch up on things that cannot be accomplished during her busy periods. Kyle is a master collaborator, and collaboration is key! Dark Matter Coffee is taking inspiration from music (jazz and metal influenced coffees like Giant Steps and Mastodon) and releasing new music with their record label.

Were there any books or other resources that were instrumental in how you manage a freelance career or running a business?

The freelance world is moving too fast to document in a book how to approach this flying-by-the-seat-of-your-pants lifestyle, but I have found articles featured on and to be very helpful!

Is networking something that you actively make time for or something that happens naturally?

Networking is natural when there is a common goal in mind. If someone wants to work with me towards a common goal, then I will make time for it.

How do you use the Internet/Social Media for your career?

Social media seems to change every year, so adaptation is key. It helps to use a platform that compliments a specific project. The picture/video/audio first design of Instagram seems to work well with some of the newer music I’m working on (@charlesmantis). Other platforms are tied deeply into an algorithm and seem to lend themselves to commercial projects like wedding bands, success stories and personal life. It helps to choose a social media platform specific to the kind of audience you are trying to reach.

Describe how you market yourself as an artist. Do you have a personal brand? If so, how did you develop it?

All artists have a personal brand and discovering that brand is a part of the journey. An artist’s product should match their brand. I’m not a great actor, so by design my music and brand needs to match my personality.

Would you say being a freelance musician is easy or difficult? Why?

Easy. You cannot fail in music. In fields outside the arts you can definitely pass or fail. You can definitely fail as a mechanic.

To what do you attribute your success?

Self-discipline has been key in continuing to work as a musician. With every passing year I feel more equipped and organized.

What are the benefits of having a freelance career and what are the pitfalls?

Freelance work could be the way of the future. The New York City Council unanimously voted this past fall to give freelance workers protection against wage theft. Regulating the industry should help to change the overall image of self-employment in the United States. I don’t see any pitfalls in working towards one’s own interests.

What advice would you offer to other artists trying to make it as a freelancer? If you had to do it over again, what would you change?

I have learned a ton on this journey and I wouldn’t change a thing. Moving forward I plan to pursue the projects I love with even more deliberation.

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