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8 Ups and Downs of Freelancing

By Lauren Mayer

Are you just out of school and trying to decide between following your passion or heeding your parents’ advice to “get a good steady job and play music for fun”? Have you worked for years in one of those “good steady jobs” while fantasizing about what a life on the road would be like? Or are you juggling miscellaneous gigs and wondering if it’s worth it?  

If you answered “yes, that’s me! How did she know?” to any of these questions, then this article is for you.

Since freelancing lives in the gray areas of our business, there are no black and white answers to your questions or even clear “pros” and “cons” in the nature of the work. But as someone who has supported myself as a freelancer in the arts for 42 years, I’m in a unique position to share some of the ups and downs from my own experience – or at least to amuse you with some of my weirder gigs along the way.

A few of my favorite looks from some of my “weirder gigs along the way”.

1.) Being your own boss means you have to supervise yourself

Comic Rita Rudner joked about the perils of being her own boss, “because she’ll know if I’m lying when I call in sick”.  However, since most musicians are already hard workers and perfectionists, unlikely to call in sick even if we need to, our biggest challenge is planning time and making decisions.

I have a choreographer friend who used to joke that her apartment was never cleaner than when she sat down to start a new show and was itching for excuses to procrastinate. Since I dislike cleaning even more than making decisions, I have used a few techniques to keep myself on track:

  1. Get to know what works for my employee (i.e. me). In my case, I’m better at creative projects like writing first thing in the morning, and afternoons are better for administrative tasks.
  2. Decide when you’re the boss and when you’re the employee. As the boss, I start each day by looking at my calendar and blocking out the day’s tasks. Then as a dutiful employee, I do what my boss told me to do.
  3. Optimize your workflow with organization tools that work best for you. For example, the Calendar app on Mac computers and Google Calendar allow you to color code your different appointments. Additionally, Be Focused is a free timer app that’s a great way to remind yourself to stand up and stretch every half hour. I figure I can do anything for 30 minutes, so it helps me get past my reluctance to start more challenging assignments.
Me in music director mode coaching vocal ensemble work from the piano.

2.) Being your own boss means being nice to your employee (and that means you)

I know being kind to employees brings out their best, so I apply that to myself – if I’m having an especially frustrating day, I tell myself to take a break. In fact, when I do my morning planning for the day in “employee mode”, I block out time for meals, exercise, an occasional social phone call, and other much-needed pauses in my work day. Those breaks are much easier to take when I see them on the calendar and give myself permission to take them, knowing my “boss” won’t get mad at me for slacking off!

A biography of composer Stephen Schwartz details that when he was facing a huge deadline for one of his earliest scores, his wife asked him why he was goofing off doing crossword puzzles instead of being hard at work, and he explained that the “goofing off” was part of his creative process. So I try to allow myself similar license – jigsaw puzzles or rereading Jane Austen are favorites. 

Of course, I always laugh at stories about composers with dutiful wives taking care of their every need so they could indulge in whatever hobbies enhanced their creative processes. I wrote my first album by getting up at 5 a.m. to have some writing time before I had to get my kids ready for school, and I wrote the first of my weekly political satire songs sitting in a Starbucks waiting for my son to finish his improv class in San Francisco. This was after he’d gotten his learner’s permit, so I let him drive us there (in rush hour traffic) and spent most of the time in that Starbucks trying to get my heart rate down.  But I digress…

Image courtesy of Your Teen Magazine.

3.) You have to reinvent yourself more than Madonna

Most types of freelance work evolve: teachers have to adapt to ever-changing teaching standards, lawyers have to keep up with current laws, and I can’t imagine how hard it is for auto-mechanics to deal with today’s computerized vehicles. However, it feels like music and theater are especially quick to change. If you want to keep working, it helps to be a master of reinvention.

The turns I’ve taken include:

  • I started as an aspiring comedic singer-songwriter until I found comedy clubs weren’t open to anything with music.
  • I discovered the piano/bar cabaret scene and became a music director/songwriter for cabaret singers.
  • The AIDS epidemic wiped out the cabaret scene so I switched to writing/performing custom shows for parties and fundraisers.
  • After having kids, travel became too challenging, so I switched to writing/directing corporate shows.
  • 9/11 wiped out most corporate events, and I got divorced and became a single mother, so I switched to vocal coaching and teaching school music.
  • My kids got old enough that I had time to put out some albums, as well as create YouTube videos in the hopes of becoming a viral star and earning big payouts.
  • YouTube changed their monetization policy and streaming services wiped out real income from self-producing albums, so I resumed teaching (but kept doing comedy videos as a creative outlet).
  • During the pandemic, I switched to Zoom shows and wrote an original musical with a collaborator.
  • Currently, things are opening up and comedy clubs seem more flexible, so I’m working on a one-woman show based on my newest album. It’s all about to come full circle back to comedy clubs!

If you find all these zig zags terrifying, then you probably should avoid the freelance life. But if you think the variety sounds intriguing, I also hope it reassures you that it IS possible to adapt, and even to thrive, in an endlessly-changing environment. And given that most of what I’m doing now didn’t exist when I started out, who knows what you’ll end up doing in 10 or 20 years?

A promotional image from my Jewish mother-inspired album Don’t Mind Me (I’ll Just Sit Here In The Dark).

4.) You have to be more flexible than an Olympic gymnast

As you’re re-inventing yourself over and over, you’ll end up taking all sorts of random gigs, which if nothing else may give you great stories. Here’s a sample of mine:

  • Playing background piano in a shopping mall and getting so bored that I amused myself by doing TV show theme songs as jazz standards (which is really easy to do with The Flintstones!).
  • Writing a song for Pia Zadora and being one of her backup singers at a benefit, where she gave football star Ronny Lott an award for having the cutest rear end in the NFL.
  • Writing and performing a corporate show for the California Association of Funeral Directors, where I was a tap-dancing casket, and then later sang “When Will I Be Embalmed” to the tune of “When Will I Be Loved” .
  • Singing three-part harmony Christmas carols in the shoe department of Lord & Taylor’s in New York City, where a well-dressed gentleman complimented us and then explained he wasn’t hitting on us, he knew good singing because he was the policeman from The Village People.
  • Dressing up as Sarah Palin for a local news segment (after winning a lookalike contest), and because parking (and people) are nuts on Halloween in San Francisco, I had to walk several blocks in costume, carrying an enormous stuffed fake moose head. In classic San Francisco fashion, no one gave me a second look!
  • Singing a song I wrote about having a crush on Congressman Adam Schiff to him at a Zoom fundraiser.

5.) Get clear on what you enjoy and are good at (as well as what you don’t & aren’t)

I love making people laugh, writing songs, and making a difference for students. I don’t love playing background piano and I’m not great at pit conducting – it doesn’t mean I won’t ever do either again, but at least those aren’t the types of gigs I pursue or accept for “exposure” instead of income. (Spoiler alert: very few landlords will let you pay rent with “exposure”. )

My husband was a freelance performer for years, singing with a big band and doing singing telegrams in between theater gigs. He had some highs (like appearing in one of the first West Coast productions of “The World Goes Round” and lows (like a singing telegram where he was supposed to sing “Bésame Mucho” while riding into an office on a donkey – and the donkey was having none of it). He went back to school and became a substance abuse counselor. 

There’s nothing wrong with deciding that you’d prefer the stability of a steady job that allows you to pursue your artistic goals on the side (and that will probably mean you’ll never have to do a gig riding on a donkey or dressed as a tap-dancing casket).

My husband still sings occasionally with his band, making demos, or performing with me.

6.) It’s hard not to take rejection personally when you’re what they’re rejecting

Well-meaning friends and family will counsel you not to take it personally when you don’t get a gig or opportunity you really wanted, which just means they don’t get what it means to be an artist. They’ll say things like “you’ll get the next one!” or “it was a lousy gig anyhow”, which doesn’t really help much (especially if it’s paired with “if it’s this hard, maybe you should consider a real job”). Unfortunately, the struggle with rejection is unavoidable since what we do is a huge part of who we are.

My best strategy has been to accept and even embrace that rejection and disappointment are simply a part of the deal. Every field has unpleasant aspects – kindergarten teachers wiping noses during cold season, CPAs at the peak of tax season – so it helps to view rejection as a basic occupational hazard. And who knows, (once again) you might even get good stories out of it.  

For example, I can boast about being invited to write a new song to submit to both David Hasselhoff and Barbra Streisand, both of whom said “no thanks”. However, in Ms. Streisand’s case, I think her manager felt a little guilty over how much time and effort I’d put into the lyrics she’d rejected, so he gave me house seats for one of her concerts (a rare but rewarding consolation prize).

And if nothing else, all the rejections will make you doubly grateful when someone says yes! 

A group photo with the full crew at a demo recording session I music directed.

7.) Plant enough seeds and some will sprout 

You never know where an opportunity will seemingly come out of the blue, but it’s often because someone remembered you or ran across your old work. You improve those chances both by doing good work and by nurturing relationships and being kind – you never know when that lowly production assistant you never yelled at becomes in charge of hiring, or the trumpet player you gave a ride to is looking for a sub and thinks of you first. 

Granted, sometimes those seeds take a LONG time. For example, in the late 1980s, I wrote & performed parodies at several annual Sondheim celebrations in San Francisco, and the producer wrote an article quoting my lyrics, without asking or compensating me or the other parodists. I decided to let it go, figuring I’d gotten a couple of gigs out of the shows and it wasn’t worth making a fuss. 

Several years later, cabaret/Broadway star Liz Callaway ran across the article and added one of my parodies to her act. This was pre-internet and she had no way of locating me, but every time she performed it she credited me by name. Sure enough, someone from my college a cappella group heard her, told her she knew me, and helped her contact me. Since then, not only does she credit me, but she has promoted my albums, given me wonderful quotes, and paid me royalties from her recordings of the song.

In another turn of events, I got a licensing deal from a Brazilian educational book publisher and a commission, who found an old children’s album of mine online, and landed my current job teaching musical theater at the San Francisco Conservatory of Music because the program director sang in a church choir with my husband. 

The longer you stick it out, the better the odds are that something you’ve done or someone you’ve met will lead to an opportunity that’s creatively fulfilling, lucrative, or at least makes a good anecdote.

A moment between songs at a house concert with the Raging Grannies.

8.) Freelancing isn’t stable, but stability isn’t everything

The only aspect of freelancing that stays consistent is that it’s feast-or-famine, and it doesn’t spread itself out evenly. 

For example, I had almost nothing going on this past December, and then spent January balancing music directing a high school production of Drowsy Chaperone, music directing a workshop of a musical by Jon Anderson (lead singer of the band YES), teaching a two-week tap intensive for music conservatory graduate students, and prepping for a benefit concert with The Raging Grannies. 

(For my Maestras who have never heard of the Raging Grannies, check them out! They’re a long-standing musical activist group of older women with chapters around the country who stage concerts and events, such as protesting cuts in state funding for Planned Parenthood by crocheting a giant uterus. Note: the middle song in the video below, “If My Uterus Were a Gun”, is one of mine.)

My experience is probably weirder than most freelancers because of the type of music I write and perform. However, among my freelance colleagues, it remains common to combine high-level professional work with odd jobs, teaching, and one-shot gigs. Like me, you may ping-pong between periods where you worry you’ll never work again and crazy months like I had in January. But if you’re self-motivated, adaptable, and willing to cope with the ups and downs, it’s a rewarding life – and never boring! 

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