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

Jeannie, thanks for joining us, excited to have you contributing your stories and insights. Earning a full time living from one’s creative career can be incredibly difficult. Have you been able to do so and if so, can you share some of the key parts of your journey and any important advice or lessons that might help creatives who haven’t been able to yet?

I never thought that I’d become a professional musician.

The story of how I started to earn a full-time living from music is a little convoluted, but if beleaguered teachers and first-generation immigrants are your thing, then settle in. Cast your mind back to 2017; three full years before COVID-19, I decided to become an Elementary School teacher.

I’d picked teaching for two reasons. First, as a Thai passport holder who’d just graduated from college in Canada, I needed to find a way back to my girlfriend in Seattle. Going for another degree was the easiest way to obtain a visa, and since said college only offered liberal arts degrees – here comes reason number two – I knew I’d need a graduate degree to find a “real job” either way. Teaching Elementary School seemed … fine.

This next part may surprise you if you aren’t intimately familiar with international student visas. I graduated with a Master’s in Teaching in the spring of 2018 and, even prior to receiving my certificate, accepted a contract as a fourth/fifth grade teacher in Highline School District, just south of Seattle. The start of my first year was three months away, and I was confident that my post-grad work visa, known as Optional Practical Training (OPT), would kick in soon.

What people don’t tell you about immigrants who “come in the right way” is that our propriety is no match for unfriendly, backlogged, and uncommunicative government systems. I started to panic when I still hadn’t heard back from US Citizenship and Immigration Services (USCIS) by July and, when I spent one frantic afternoon pressing every possible button in their automated call service, finally spoke to an officer who told me that there was no way I’d be approved for work before the start of the school year.

So I struck a deal with the school district: if they were alright paying a long-term substitute teacher to be in the room, I’d teach as the lead teacher without pay so that my students – almost entirely from low-income families – wouldn’t have to adjust to a new teacher partway through the school year. UW had taught me what that kind of upheaval does to children, especially those from communities with high rates of poverty and trauma. My visa would come along soon enough, right?

Well, no. I would teach without pay (or back pay – remember the substitute teacher?) for almost four months. So how was I feeding myself?

It was a little crazy, but I decided to try my luck at busking. First on sidewalks in downtown Seattle, and then tentatively on the more deserted corners of Pike Place Market until I worked up the courage to play at the most popular and coveted spots. I would teach from 8AM-4PM, and then run down to the market for a set or two in the evenings, sometimes making $50/hour. Luckily, my girlfriend and I were living with her parents so we didn’t have to worry about rent, but this meant that I could buy my own groceries!

When OPT was finally approved, I started to make good money as a teacher. But the stress of teaching – I could write an entire novel about why teaching there was so awful – combined with my initial lack of income resulted in a Jeannie that I barely recognized. I couldn’t sleep, often forgot to eat, and was turning into an angry and traumatized adult in a room full of children that needed me at my best. So I quit teaching at the end of the school year, in the summer of 2019.

I didn’t realize it at the time, but I would turn towards music and away from teaching forever. I immediately took up busking at Pike Place full-time, sometimes playing for five hours a day, for four or five days a week. I learned the microculture of the Market, learning more songs and singing louder until I became one of the top earners in the community of buskers. Over time, I began to see busking as a “real job” and started calling myself a “musician” when people asked me what I did for a living.

But just as I was getting comfortable as a street musician, everything changed. In 2020, due to COVID-19 ordinances, live music came to a temporary but devastating halt, and my income disappeared overnight. Luckily, I had savings from my time as a teacher, and I spent them on a proper website, professional studio recordings, and music equipment. I now knew that simply relying on busking wasn’t sustainable; even when the world opened back up, I needed to be prepared and more versatile as a musician. So when restaurants and wineries began hiring live musicians in 2021, I cold-called and emailed as many as I could, hoping to create a schedule with a guaranteed income.

Gradually, as more folks heard my voice – honed by hundreds of hours in the Market – and as I made friends with other professional musicians in Seattle, my calendar filled with gigs. Good gigs, with kind people in the service industry and a slowly growing fanbase that would return week after week. Seattle was hungry for live music as the pandemic began to fade, and I was more than happy to sing all weekend, sometimes hitting 15+ hours in four days.

Today, my biggest struggle is finding balance between taking care of my body and feeding my need for financial security. I’m often offered more gigs than my vocal cords can handle and some are hard to turn down – especially weddings, which I’d like to prioritize in 2025 and beyond. Sometimes, such as during the slow months of January and February, I worry about my bank account. But I’m no longer tied to a hellish 9-5 job nor do I endure hours of (unplugged!) singing in the cold with no guarantee of good pay.

Ultimately, I am endlessly thankful for my experiences as both a teacher and a busker. I’ve experienced two very different careers, both of which built me an unusual set of skills that make me a successful musician. If nothing else, they taught me to be grateful for what I have: stability, warmth, and community. As I grow, endeavoring to release more original music or aspiring to larger stages, I’ll always remember my roots as an educator and a hard worker.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

I talked a lot about how my past careers as an Elementary School teacher and a street musician (busker) influence my conduct as a professional musician, but in this section I’d like to dive into more of the nitty gritty details to paint a picture of what it’s like to be in my shoes for a day.

The Greater Seattle Area and surrounding cities like Woodinville and Bellevue have access to so many talented musicians. When I started out, I felt despair at the prospect of distinguishing myself from the others; I was just one more singer-songwriter with a guitar, after all. But as I continued to work, I found that several things set me apart and had folks coming back specifically for my performances.

1. Vocal ability. My time as a busker doubled as a rigorous training regimen because loud, bustling Pike Place Market doesn’t allow amplification from its musicians! I therefore learned to project my voice and, in doing so, mastered singing in a way that no other environment had ever forced me to. I’m decent at the guitar, but my vocal control really does make me stand out from the crowd.

2. Storytelling. Teaching taught me how to entertain and captivate an audience, and what started as a strategy to save myself some vocal strain became a hallmark of my performances. Most musicians simply aren’t good at telling stories about their songs. How many times have you been to an open mic where folks get on stage, mumble a hello, and proceed to play three songs while hardly looking up at the audience? I use my stage time to introduce myself, tell my story as a human being, and describe the inspirations behind each of my original songs. I even have emotional anecdotes about many of the covers that I play — we all have associations with certain artists that make their songs more meaningful to us.

3. Adaptability. Now that I’ve been both a busker and the focal point of folks’ nights out at a bar, I understand how to be more or less visible depending on the event that I’m performing at. I can command a room — such as at ticketed events or when I’m the entertainment break during a fundraiser — or I can slide into the background for hours on end, such as during wedding receptions and happy hours. Understanding what kind of presence I need to provide is also good for my mental health; many musicians struggle to feel fulfilled if their expectations don’t align with their experiences. For example, I don’t expect folks to applaud after every song during cocktail hour! But if the MCs at a gala need me to run interference because their AV team is struggling with setting up a projector, I can step in and entertain.

4. Responsibility. Musicians are notoriously difficult to work with, seemingly governed less by discipline and more by their mood that day. I defy that stereotype by being extremely organized and communicative. It’s the little things, like showing up at least a half hour before every show, having back ups of every cord and microphone, or being dressed appropriately for every occasion that show my clients that I’m thoughtful and prepared. I also believe that I have a responsibility to the audience: I always perform to the best of my ability, and I take the time to say hello to as many tables as I can.

Do you think there is something that non-creatives might struggle to understand about your journey as a creative? Maybe you can shed some light?

The biggest lesson I’ve learned about being a “professional creative” is that in order to succeed, you have to define the scope of your own job. I’m a “musician”, but that can mean a million things! I could be a recording musician, spending most of my time in the recording studio. Or I could be a touring musician, interested mostly in selling tickets to small and large stages with the goal of growing a fan base for my original music. But if I try to do all of it, I feel overwhelmed and unsuccessful.

So my current goal is to simply do a mixture of things that allow me to live a good quality of life. Right now, that means performing at wineries, bars, and restaurants — with the occasional wedding or corporate event thrown in — about four times a week. If I muster the energy to write songs and get into the recording studio, great. But I’m no longer chasing thousands of social media followers or tens of thousands of streams on Spotify.

Don’t let anyone else’s success bog you down, because we’re all chasing different things.

Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?

The amount of tips that I make have almost nothing to do with my singing or guitar playing ability.

This was a hard lesson to learn because I had spent so much time perfecting my pitch, technique, and memorization of song lyrics. I wanted all of that to count for something! But being a street musician through spring, summer, fall, and winter in Pike Place taught me that there are so many other things that get folks to pay attention to musicians. Some of these things are within the performer’s control, and some aren’t.

For example, people’s moods are influenced by the weather. Sunnier weather puts people in good moods, and because the sunshine makes the outside warmer, folks can afford to take their time and linger. In contrast, the rain or cold temperatures had people dashing from building to building, or just set them up for a gloomier mood. Another element outside my control was the holiday or event just around the corner; people were usually more generous during Christmas, but tightened their purse strings after Black Friday.

What I did learn to use to my advantage was volume, storytelling, and song choice. If I could be louder, sing at a higher pitch (which would cut through crowd chatter/white noise), or sing a popular song, people would pay attention. If I then also strategically told stories about the next song, people would be more inclined to pay attention.

Contact Info:

• Website: https://www.jeannierak.com
• Instagram: https://www.instagram.com/jeannierakmusic
• Facebook: https://www.facebook.com/jeannierakmusic
• Youtube: https://www.youtube.com/@JeannieRakMusic
• Other: https://open.spotify.com/artist/7jSPRJZwbAeXpkOHC89xiZ?si=KIjR7p-bSc2s5MkqrmWGTw

Image Credits

Kimberly Person (Into Dust Photography)
Austin Quach
Janette Casolary