When I first put out the call out for interviewees, I was really hoping that a musician would answer the call. I was absolutely thrilled when Jessica, an avid follower of Bay of Quinte Young Entrepreneurs, answered that call! A lot of people discount that musicians are entrepreneurs too. Think about it: they work their butts off to get to the level needed to begin performing, they need to market themselves, network, track their expenses/revenues, differentiate themselves from the competition, and still make a living. Sounds like a true entrepreneur to me!

Everyone, please welcome to the #MyDaySeries stage, Jessica Yarrow!


Question 1: Describe yourself in 3 words only.

  • Determined, goal-oriented, adaptable.

Question 2: Tell me more about your business(es)? What kind are they?

  • My business is working as an event musician for events, weddings, busking (seasonally), long-term care homes and more. I play clarinet and saxophone with accompaniment tracks (a performance strategy I once dubbed “Sax and Clarinet Karaoke” and the name stuck!). I rarely turn down a playing opportunity because you never know what other events it may lead to.
  • I also have a full-time Monday-Friday job as a concierge, a part-time (mostly weekends) job as a server/bartender, and a part-time teaching position at Pinnacle Music as the clarinet and saxophone instructor. It is difficult to support yourself financially as a full-time musician, especially when so many people only want to pay in “exposure”, and most musicians I know have multi streams of income from a combination of performing, teaching, and/or a day job. There is a silly old musician joke that says “What do musicians say at work? Do you want fries with that?” that sometimes rings painfully true when trying to make a living doing music.
  • Eventually my goal is to have most, if not all, of my income from music related work.

Question 3: Where does your entrepreneurial drive come from? What are your sources of inspiration?

  • I have always had an entrepreneurial drive. I started making and selling jewelry at 8 years old. My parents had a big influence on my work ethic and taught me the value of earning what you have rather than just having everything handed to you. Because of this, I have always had the drive to work hard and find a way to turn my passions and hobbies into sources of income so I can do what I enjoy while still making a contribution and earning income. I have been fiercely independent since I was a child and still enjoy the feeling of accomplishment of relying on myself to thrive successfully and financially.
  • I am incredibly goal driven, and constantly set new goals and aspirations to keep myself moving forward and doing more.
  • My inspiration to become a musician started at a young age. I started playing in high school in class, bands, and taking lessons independently. The more I got involved in performing, the more I was inspired to continue working towards taking music in university.
  • I completed a Bachelor of Arts Honours with an honours major in music and minor in psychology at Queen’s University. I also took a diploma program and graduated on the Dean’s List in Recreation and Leisure Services at Loyalist College. The combined educational and employment experiences have helped me greatly in my entrepreneurial endeavors related to skill, organization, communication, customer service and more.
  • I enjoy performing so much that it was a natural and inevitable transition into figuring out how to earn a living from it. I believe a big part of being an entrepreneur is having a diverse set of skills, creativity, and a real passion for what you do. It often takes over your life and thoughts so you definitely need to enjoy and have a deep love for what you do (even if you do not love every single minute of it!).

Question 4: Considering how fierce competition is among your industry, what are your business(es) competitive advantages? What makes you stand out in the crowd?

  • Many working musicians play guitar and sing because that is typically what is in demand. I work as a soloist with recorded accompaniment that I play though a PA system. I have also been contracted as a soloist with an ensemble, and for musical theatre productions (some paid, some not). Instrumental music is fantastic but a guitar or piano player singing is just more commonly seen than an instrumental soloist.
  • Clarinet and Saxophone in particular are also often only seen as classical or jazz instruments and expected to play those styles only. One of my favourite things while performing is to see people walk past, pause and say “is she playing Michael Jackson on a clarinet?” or “I recognize that song! That’s Bruno Mars!”.
  • When approaching potential clients, I try to maintain an effective balance of not being aggressive with marketing while still representing my business with passion. I have been quite successful in performing for long-term care homes because I have had formal education and experience working with seniors. Many musicians that play in long term care homes will have a strong performance background but may not be as comfortable interacting with residents. I enjoy the challenge of performing so many different styles of music and for a variety of events and the satisfaction of leaving a happy audience and organizer!

Question 5: No two days are often the same for an entrepreneur, but what does a typical day look like for you?

  • I try to schedule performances around my other jobs, but sometimes I will have to book time off in advance to accommodate an event. If I have an evening event, I will often still work a full or part shift during the day, go home and have a small snack (it is unpleasant playing a woodwind instrument with a full stomach!), get changed and load my equipment which I have set out the night before, travel to the destination, set-up, perform for the allotted time, pack up my equipment, re-load it back into the car, and travel home for a late meal. It makes for a long day when I work a full shift, and instead of going home to relax, I am now in performance mode for another several hours.
  • Days where I only perform feel a little less rushed. I will eat a meal a couple of hours in advance, sometimes while commuting if the gig is far away, and follow the same routine of loading my gear into the car, travelling to the destination, set-up, perform, pack up my equipment, re-load into the car, and travel home or to my next gig. I will sometimes try to schedule two performances in a day, such as busking in the morning and a nursing home in the afternoon or event in the evening.
  • Being a musician is a lot more physical of a job than people realize. Even though it is a fun job, it is still hard work and often physically and mentally draining.
  • There is also all of the behind the scenes work that clients do not see. It may seem expensive to hire a musician for an hour, for example, but that “1 hour” also includes all of the preparation and creating an appropriate set list, practice time to ensure you play well, travel time to and from the event, set-up and take-down time, maintenance and supply costs on your instrument, wear and tear on your vehicle from travelling and loading oddly shaped and heavy equipment into your vehicle, purchasing music, and other operating costs that may occur. With all of that being said, I am so thankful I get to share my love of music with others and earn an income while doing so. Seeing smiling faces or people dancing and reminiscing about what a song means to them is just as valuable to me than the financial compensation.

Question 6: What do you do daily to grow as a person?

  • I am very goal-oriented. I believe it is important to set and achieve goals in order to grow as a person. I like to discuss my goals with others to keep me accountable. For example, this year I have decided to take my Grade 10 Royal Conservatory of Canada exam on clarinet. I am not required to take this exam or hold the certificate to be an employable musician, but it holds me accountable to keep working on my skills and is an accomplishment I have wanted to achieve for several years.
  • Music is a lifelong endeavor that requires constant learning and changing while still maintaining a base of fundamental skills, which is one of the reasons I enjoy it so much!

Question 7: What tricks have you discovered to keep you focused, productive and achieve a decent work/life balance?

  • My best advice to stay focused and productive, especially as a multi-employed person, is to genuinely enjoy what you are doing and it does not feel so much like work. Factoring in my 4 jobs, I work approximately 55 or more hours per week. I enjoy all of my jobs but do strive to adjust my work more towards music-related employment.
  • It is important to embrace every opportunity but also rest well when you can! It can be difficult to have a work-life balance as an entrepreneur because we love what we do but being rested and healthy is important to sustain yourself as an effective business. I play in 2 bands and as a soloist and would love to do more, but I know I still need downtime.
  • I’ve learned there is no shame in taking a break from performing if I am recovering from an illness or just need a quiet day at home. It is better to take care of yourself and prevent burning out rather than struggling to come back from being burnt out. It is also important to eat healthy and be active as often as you can! The busy times for an entrepreneur can lead to some pretty serious sleep deprivation and low energy but eating healthy and building good endurance through physical activity helps get you through until you can rest! I am also a big believer in participating in passion projects related to your business, even if they are unpaid, to keep your mind happy and focused on why you do what you do!

Question 8: What popular entrepreneurial advice do you agree/disagree with?

  • My advice about advice is to have a healthy balance of listening to advice but going with your instincts. Every business, even of similar products or services, are all going to be different based on the business owner and customers. Here are a few of the statements I agree with and some I do not!
    • “Do what you love”
      • This is so true! You are going to be spending a lot of time thinking about and providing your services and if it is something you do not enjoy doing, you will not put forward the passion you need to show your clients that you care.
    • “Value your time”
      • Building a business requires sacrificing a lot of time to get your name out there, but do not let others take advantage of your time or generosity. This can be very difficult, especially in the early stages where you want to take every opportunity you can. Find a balance of providing time and being compensated fairly for the time you are providing.
    • “Connect with your community through donations and volunteering”
      • Being connected with your community is important. I try to volunteer for a few worthy events per year, but set a limit for yourself, because people may try to take advantage of your time and generosity.
    • “Put yourself out there!”
      • You are the only one who can make your business succeed. You get out what you put in. It does not always feel natural right away but it does get easier the more you try it, and you never know where it may lead to! Give out business cards as often as you can. Give business cards to your family and friends to hand out for you. I once contacted a small farmer’s market regarding busking on Saturday mornings, became a regular performer, and a year later I was at the same market performing for Prince Charles and Camilla when they made their royal visit to Prince Edward County.
    • “Take constructive criticism”
      • If I perform at an event I always check in with the organizer to see if they were happy with what I provided, and if there is anything I could do differently for next time. Constructive criticism is a big part of growing as an entrepreneur, and as a person. Take the advice humbly with cautious consideration, as you are the expert in the field, and be weary of negative people without the knowledge base giving you unsolicited or malicious advice.
    • “Celebrate small victories”
      • The little victories add up to the big victories! I celebrate the weeks where I have so many bookings it is not worth taking all my equipment back into the house after a gig because I have another one coming up the very next day. It seems like a silly thing to be happy about, but it means I have been successful that week. Celebrate, but do not get smug and let your work ethic slip under the false pretense that work will just easily flow your way. You still need to continue putting the effort in if you want your business sustained.
    • “Don’t be a diva!”
      • You are there to serve your clients, not the other way around. Some musicians unfortunately develop a bad attitude, making them difficult to work with. Your reputation will suffer if word of mouth gets around that you were demanding, difficult, unprepared, or did not provide the services the client was promised. It takes much longer to build a business than it does to make an error in judgement and ruin everything you have worked for. Word of mouth is a powerful marketing tool but it can go both ways. I treat every performance as a potential audition for more bookings, no matter how small or what venue or event I am at.
    • “Know when to say no”
      • This one was difficult for me to learn, especially at the beginning. The majority of the time, I will play anywhere for anything! I’ve done everything from weddings and galas, dinner parties, luncheons, and rarely say no when I am asked to provide my services.  I’ve learned that there are some bookings that are just not worth it. For example, one long-term care facility I used to play for offers an insulting payment and have flaws in booking which resulted in being double booked and brushed off without payment for the work I already completed preparing for a performance, and income lost from booking time off from a job I would have been getting paid for. I was contacted after the double-booking to schedule a future date and I decided I would no longer offer my services to them. This was the first time I said “no” to a job but was thankful for the empowerment I gained from it.
    • “Launch before you are ready”
      • This strategy may be effective for some businesses, but not for music. Not being ready for a performance can be disastrous (not to mention unpleasant to listen to for the people attending the event!). When your product as a musician fails, it fails publicly and can be humiliating and discouraging. That being said, music is a lifelong learning and changing profession, but at the very least you have to be comfortable performing and being in front of people, and you have to be prepared for the hours and hours of practice and dedication it takes to be successful.
    • “Business will come to you once you are successful”
      • I’ve been performing for over 10 years but I still take the initiative to seek out new performance opportunities. I will find out about events and offer my services if they are interested, and if I see a friend advertising for an event I may offer a donation of performance time for the event, an hour of performance as a door prize, or get the contact information of the organizer to arrange a paid performance. I gave a donation of an hour performance once for a door prize which led to booking 5 events with people who had attended the performance that was won. There will always be ups and downs in bookings but be determined and creative getting new work!

Question 9: What’s your favourite metaphor to describe entrepreneurship?

  • I think the best way to describe being a musical entrepreneur in particular is feast or famine! Sometimes I have 6 upcoming bookings on my calendar and sometimes I have none. Unfortunately, there are times I have to turn down last-minute bookings because I’m working at my day job. The busy times will more than make up for the slow times!

Question 10: What was the toughest moment you have experienced in your business practice? How did you succeed to get over it and move forward?

  • When I first started performing as an entrepreneurial venture, I found the most uncomfortable part to be discussing payment for services. I did a lot of events and bookings for free or accepted compensation that was not appropriate for the amount of service I was providing. I performed for friends’ weddings twice under the assumption that I would be paid and I was not. I did not want to develop a bad reputation for being demanding or unreasonable. It took me a fair amount of time to acknowledge that when you provide a service you deserve to be properly compensated.
  • While I acknowledge and appreciate that some opportunities may, in fact, be good exposure and may lead to future bookings, simply paying in “exposure” does not help me pay my bills. Yes, being a musician is a fun job, but the key word is a job”. I always compare it to a tradesperson being asked to work for free. You would not expect a plumber to make a house call, provide a service, and pay them by promising to promote their good work to others, and the same expectation should be held for entertainers. I do still commit to providing 3-5 volunteer or donation-based performances per year for charitable or fundraising events. I am still working on being more assertive and asking for fair payment for entertainment.
  • A turning point moment for me asking for fair payment happened the evening before I was scheduled to perform for an event and had already agreed to perform at the event at a reduced rate. The set list and all the pre-work was completed for an event lasting several hours and was a significant amount of preparation time. The organizer contacted me to reduce the rate further and I agreed but only on the condition I could perform busking-style with an optional basket for tipping to balance out being paid less by the organization. After a lot of back and forth we moved forward with the event, I was permitted to use a busking basket, and the organizer paid the original amount that I had asked for. I learned that I could be assertive enough to ask for fair payment without seeming demanding or unreasonable.

Lastly, if someone wants more information, what is the best way to contact you?


If you would like to be featured in an upcoming “My Day” series post, please send me an email either through the Contact page or directly to boqyoungentrepreneurs@outlook.com