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  • Writer's pictureEmmy Rozanski

Navigating Life after Music Music School: Choosing Solidarity Instead of Scarcity with Olivia Dobbs

It's has been inspiring for me to learn Olivia Dobb's philosophy towards music and being a musician. I love Olivia's thoughts on supporting each other and understanding that the success of others benefits us all. Olivia has performed with a wide variety of ensembles, including a band that improvises accompaniment for comedy shows!

ER: Tell us about your musical background and what you currently do. OD: I started playing the flute in elementary school, and performed for church services and pretty much any other occasion when people would allow it. In middle school I began private lessons, joined the Milwaukee Youth Symphony Orchestra’s flute choir (and later, their jazz band), and I was off to the races. In high school, I was especially keen on playing in pep band and pit orchestras, and I picked up saxophone and clarinet. After studying flute performance in Chicago, I returned to Milwaukee and started working. Pre-Covid: I am a freelance woodwind doubler, doing about 150 shows a year, mainly in pit orchestras, as a backing musician (that’s the best I’ve got for “sideman” in gender-neutral), and subbing with regional orchestras and big bands. During-Covid: I’m taking advantage of the extra practice time, my private studio has expanded, and I’m also working on some personal recording projects I’d been putting off.

ER: I understand that you decided not to continue majoring in music after your first year of college. Was it difficult to keep up with music while majoring in a different subject? OD: Yes, but the challenge was very rewarding. During that year studying at DePaul, I had been granted amazing opportunities - played in several ensembles, got an internship at a venue, attended tons of performances, and spent hours on end in the practice rooms. Leaving that environment pushed me to discover and create my own opportunities with more autonomy. I continued taking private lessons, financed by a part-time job tutoring high schoolers in AP Music Theory, and later a job in a music store. I had the freedom to study saxophone and clarinet, get internships and gigs in a variety of scenes, and meet amazing mentors. One strategy that helped me through it (and that continues to pay off today) was creating a very structured schedule to keep up with all these commitments.

ER: What was your biggest challenge after college graduation? OD: Auditions, for sure. It took a lot of time and experimentation to learn how to deal with the psychological challenges and that intense performance anxiety, which I’d rarely experienced in other settings. Fortunately, I had patient and generous mentors, family, friends, and neighbors who listened to my mock auditions, and frequent self-recording has helped too.

ER: Have you ever had a big disappointment relating to music? What did you do to get back up? OD: This pandemic year is the thing that’s disrupted my relationship with music the most. My motivation to play has always come from live collaboration and live performance. So this year I’ve been exploring solitary musical outlets that aren’t performance-oriented, such as writing and production. I’m also keeping a pretty strict practice routine, for its own sake. Teaching has been really inspiring as well.

ER: Have your career goals changed over time? OD: Yes, a bit. When I was applying for colleges, I just knew I was heading towards a career as a performing musician, but truly didn’t have much understanding of the business. I liked seeing my friends’ bands and playing in musicals. When I left Chicago, I planned to study up and apply for a masters degree program in multiple woodwinds and earn a chair on Broadway. After graduation, my primary goal was to tour with a show. Lately, I still love playing for theatre and symphony orchestras, but I’ve also really enjoyed traveling with bands. There’s something so electrifying and intimate about those performances. And now Covid is actually helping me get to know myself better as an artist, and I’m more excited than ever to get back to live there’s definitely some refining and reevaluation happening along the way :)

ER: What actions did you take during the first year or two after graduation that were successful? OD: Expanding my comfort zone socially was very helpful. I’m quite an introvert, but I devoted lots of time to seeking out masterclasses, festivals, networking opportunities, etc. to learn more and meet people. I also took up running and yoga, which have been great for my playing and health.

ER: Looking back, what do you consider to be the most important step that you took for your music career? OD: I’m not sure there was one most important step for me, but a million small steps along the way. One was playing with The Improvised Musical at ComedySportz. While I was in school, I was looking for regular groups to join that would challenge different aspects of my playing. What better way to practice improvising than by playing in a band that makes up accompaniments to long-form improv comedy, in front of a live audience? Not only did my improvising and doubles improve, but I also learned important skills from the actors - "yes, and”, make your partner look good, keep the focus on the story, keep moving the story along, etc. Those lessons and relationships have shaped my approach to performance, business, and life.

ER: I know you've worked hard to master doubling instruments. What opportunities have you gained from your woodwind doubling skills? OD: Going back to my early days in MYSO’s flute choir, I always got called on to play the alto and bass flutes, which was amazing. Later on I’d play a lot more piccolo in orchestral contexts. Nearly all of the musicals I work on call for woodwind doubling (or as some have described it, “flair bartending with instruments”), and so do a few of the bands I play with. The time I spent studying clarinet and saxophone made me a much stronger improviser and prepared me for gigs outside of the classical and theatre scenes. I teach all three instrument families, too.

ER: What advice would you give someone in music school or recently graduated from music school? OD: Practice, study, network, but not because you’re concerned about landing a job in a cutthroat industry. That way burnout lies. Do it because you love it, because your craft is your pride and joy, because it brings people together, because it benefits all musicians when any one of us is thriving. Solidarity is a much stronger mindset than scarcity.

ER: Anything else you want to add? OD: Thanks so much for these great questions, Emmy! This blog has introduced me to fascinating musicians over the last few months and I’m honored to be included in your project.

ER: How can people find you? Website:

Instagram: @livdo_ww

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