When you were a kid, did you ever think, “I want to grow up to be a freelancer and work on a contract basis”? Probably not – does anyone? I know that was not what I thought about as a child, even though I always knew I wanted to work in theatre. Freelancing and working as an independent contractor is rarely talked about in high school and college – is it even mentioned in college courses, other than perhaps an Entrepreneurship class? Unless someone you live with is doing it, or there’s a specific class in your department geared toward the business side of your intended career, you probably aren’t familiar with that lifestyle (and its specifics, tax implications, and other ripple effects through the rest of your life) until you’re living it. Like many people, I picked a career that has a ton of variables – there’s no one path to success, there’s a vast number of environments and organizations in which to work, and though some of the work is as an employee, a lot of it is as an independent contractor. How it Started I am primarily a stage manager. I first learned the job in high school, but it wasn’t my focus for a long time. Since then, I‘ve had approximately 20 jobs that were not stage management, and I took a long, meandering path to become a professional stage manager. Once I decided to cast off the safety nets of part-time jobs outside the industry, apply to grad school, and pursue it as a full-time career, I was laser-focused on working in regional theatre. But even once I felt I’d “made it” – I had my AEA card, I had a professional credit, I had an MFA – when the theatre jobs did not come frequently enough, I had a hard time calling myself a stage manager. How can I give myself this title when I’m not consistently doing what I was trained to do? After a few years, I realized that this narrow definition of my career didn’t serve me. I discovered I wasn’t meant only to do one thing. I’d always considered networking difficult – my impression of it was that I’d have to constantly talk to people I didn’t know and ask them for something, which didn’t appeal to my introverted self. But I reframed that too. I built up my network by connecting online and/or keeping in touch with just about everyone I attended graduate school with (and meeting the students who arrived after I’d graduated), plus everyone I’d enjoyed working with on past gigs, and through those connections I started trying new things and saying yes to almost anything entertainment-related. I was a Production Assistant for corporate events at the Convention Center. I stage managed large choral concerts, and one-day jazz and classical music concerts. I tried non-traditional opera, and college dance shows. I was a Production Coordinator for a site-specific interactive experience, and a local touring devised Shakespearean production. I (reluctantly) became an off-and-on production manager. Through all of these experiences, I learned a LOT about myself, my work, and the people and organizations I do and do not want to work with. Still, the most valuable thing that emerged was the realization that I could take my skill set, be thrown into any live-event situation, and add value to it by helping it all come together. Over time, with experience, I was able to start saying no to the jobs that weren’t right for me, and make room for more of the work I really liked. I had to make a conscious decision not to leave my schedule wide open “just in case” a theatre called and actively pursue other work that felt interesting to me. I wrestled a long time with this big shift: was I a failure if I wasn’t working consistently in theatre? If I filled my schedule with other work, how bad would I feel if I suddenly got an AEA contract offer? I wasn’t in a position to go wherever the work was, so I saw few choices if I wanted to continue in my field – either pivot to another role like administration, production management, or company management, or cast my net wider and see what else was out there for a stage manager. A sidebar that I think is especially relevant for entertainment freelancers – because of the passion we usually have for our work, and the constant need to hustle for more work, sometimes our job title becomes our whole personality. When I wasn’t consistently working in theatre, not only did it feel like a professional crisis (“Am I even a stage manager?”), but it also felt personal (“When I’m not working or trying to find work, who even am I?”). This can be a lonely career path, as we often say no to vacations, family events, and social gatherings due to work. Friends and family might even stop inviting us because they assume we are always working. We often work erratic, long hours or six days a week, leaving little time for hobbies. In the early-career stage, it can be easy to sign up for this life, thinking you have to say yes to everything to build your resume, and there’s going to be time later to re-prioritize family and friends and work/life…