Independent Contractor Spotlight — Musician

Folk musician Ali Sperry gets honest about eking out a living on stage and in the recording studio

Ali Sperry is a singer-songwriter based in Nashville, Tennessee. She’s toured cross-country to promote her albums and played some of her favorite local haunts, as well. Ali hails from the small town of Fairfield, Iowa, known as a hub for transcendental meditation. She grew up practicing yoga and meditation in school and now is a prolific yoga instructor. She also works as a nanny to supplement her income. Her love of singing, playing the guitar, and writing her own tunes started in childhood under the guidance of her parents who are also both musicians. Ali discusses the ins and outs of chasing her dreams.

What inspired you to become a musician and how did your music career take off?

Ali Sperry: As a kid, I walked around with my first Sony tape recorder and would just make up songs all the time. Later, in middle school and high school, I sang a lot, but it translated more to musical theater. For a long time, I thought that I wanted to pursue musical theater and take my singing into more of an acting realm. Then I was living in Chicago and pursuing acting, but nothing really was taking off. Through a family friend connection, I heard about this band, Sweetwater Rose, that was auditioning in Nashville, and I was like, Oh, that sounds fun. I’m going to audition to be in an all-girl band. And I got in.

You’ve since branched out on your own and are making a go of it as an indie musician. What are the unique challenges of making a living or finding success?

AS: There’s really no set way to do it. In a corporate kind of environment, it’s pretty clear-cut: you start with a company and you can work your way up the ladder, and then maybe you move to a different company and you do the same thing. But in music, the thing that has been really challenging for me is just that there are no ground rules. There’s no format of, OK do this and then this will happen.

How do indie musicians make their income? Is it through touring or downloads or are there other revenue streams?

AS: There are different angles. You can be the band or the artist that just tours hard all the time, and you can make a living from that definitely. But it’s not easy, because you have to tour enough to work your way up and start to get guarantees at venues so that you’re not just playing for some cut of the door… In the beginning, it’s hard to cross over to that point where shows are actually lucrative and not just that you’re playing for the sake of being out in the public eye and getting your music out there…

Now with Spotify playlists, you can actually make decent money from that. I have not yet gotten on a Spotify playlist…That’s definitely a goal. But I’ve talked to friends who were like, Oh, now I have this passive income from getting on a Spotify playlist. So that is actually working for some people, which is great.

Then another way is with syncs. Getting songs in movies and TV shows and commercials is a really great way to make money because you’ve already recorded the song and invested all the money into recording the song…

And you’ve actually done a few syncs, is that correct?

AS: I did have something in a Lifetime movie. Yeah, it was exciting. And I had something in a friend’s indie movie that they made last year. So that was also really cool. It’s something that I aspire to do more of is getting my songs to music supervisors that do the placements and find songs for TV and film.

As a yoga instructor and a nanny-for-hire, you’re an expert side-hustler. Can you talk about these pieces and how they fit?

AS: I’ve been teaching yoga for 12 years now. For a long time, I just thought of yoga as like, Oh, this is just a day job that I’m doing until I can make a full living doing music. And while I still would love to really make a living doing music, I recently have been reinvigorating my yoga teaching and doing some training and starting to do more private sessions and corporate sessions and stuff. I want to treat it with as much intention as music so that it can keep growing and developing.

With nannying it’s always been something I’ve done since after college. I did some on-tour nannying with Bela Fleck and Abigail Washburn. I got to go on tour with them and experience what a bus tour was like, and that was a blast. Now, I have about seven families that will just call me sporadically. So it kind of works out great because I don’t have a set schedule with any one family, and I can use it to kind of fill in the gaps when I need to make extra money or when my schedule’s a little lighter.

Your soon-to-be husband is a drummer. What are the challenges of having a life partner who is also an independent contractor in the music industry?

AS: He’s on the road a lot more than I have been in the past couple of years. Then there are some periods where we both are. But I think that is kind of both a challenge and a blessing. We always say that’s, in a way, what keeps us going because we’re constantly in a state of missing each other. Then we get to be reunited, and it’s so exciting. But sometimes we have to miss birthdays or important life moments. Or he’ll have some special show that I wish that I could be at. Or I’ll have something going on that he wishes he could be at. So there are definitely challenges that come with the territory.

Then in terms of the independent contractor thing and planning…with money, there’s this sense that you never really get to relax all the way because even if things are going really well musically for a certain period of time, it could be really slow the next year. Again, you don’t have that stability, you don’t have that corporate ladder of like, Oh, next year I’ll get a promotion.

What, if anything, do you envy about your friends who have nine-to-five jobs?

AS: I think the biggest thing I envy is the being able to set it aside—to come home at the end of the day or come home on the weekend and really let go of work and be fully off the clock. I think, for myself and for a lot of independent contractors and self-employed people, you just always have a little voice in the back of your mind that says, Oh, well don’t forget you have to do this thing. And it kind of feels like it’s all on me. I can’t drop the ball on these things because, you know, it’s not like I show up to work at nine on Monday and get paid. I just have to be creating the work and creating the income for myself. I’ve been trying to build more rest time and playtime in and trying to have days where I say, OK, I’m really not going to do work today.

What’s your advice for fellow singer-songwriters or independent contractors?

AS: Don’t give up—because I feel like it is frustrating sometimes. There are times when you wonder, Am I making progress? And it’s hard to gauge how much progress you’re making. But I think if you are doing something you really love, and it’s bringing you joy, then hanging in there is the best thing. You will get past those wells, and then you’ll get to another place where you will be able to say, Oh, look at this. I have a lot going on. And this is actually working!