As San Francisco prices continue to increase, its inhabitants are forced to find creative ways to survive. Craigslist has given way to a new generation of side-hustle platforms such as Thumbtack, TaskRabbit, Upwork and CloudPeeps, which allow people to earn a little extra from their skills. They’ve allowed new industries to flourish, but they also cater to the current tech atmosphere, where people who already work in tech companies offer up their coding abilities and can earn as much as a full-time employee.
But what about the real freelancers? The ones whose skills revolve around their creative passions? The ones who thrive in the gig economy? The ones who hustle not on the side but for a living? We were curious if they still exist in San Francisco, or if the rumors are true, and all creative freelancers have left SF. Here’s what we found:
Sarah Wohl, 31, Design Consultant
On going freelance: [It] was a slow, gradual decision. I was doing some heavy reflecting on the many jobs that I had held: the leadership, the culture, my value, my needs. Things weren’t fitting, and I continued to not know what the answer was. I had thought that I really wanted to work toward design management and building teams, but then there was a louder desire to go out on my own and try to be my own boss. I had a few folks reach out to me serendipitously for some design work, so I began moonlighting. After a few months, I realized this work could be more hours if I wasn’t working a day job. I started to connect with potential clients and found that there was opportunity, at least in the near term, and that was enough.
On managing the high cost of the city: I teach classes at General Assembly for supplemental income. I’m also very lucky to have a rent-controlled apartment that I share with my fiancé, so that’s something. Overall I have to be careful and stick to a budget as much as possible, and that can be hard for someone who loves exploring the city, eating out at all the new restaurants, seeing shows, visiting museums, etc., but it can be done. I also now work from home, so I cut costs on commuting, lunch out, etc.
On what motivates her: I consider myself a pretty driven, action-oriented person, so luckily, I don’t have too much trouble feeling motivated. Though I’ll be honest and say that with everything happening in the world lately, it has become a bit harder. I’ll say that I love working for myself, so I am motivated to make my business successful and keep going! I have been able to create some amazing relationships with great clients, so that has also been a good motivator — to maintain those relationships and continue to help people with my design services, sharing what I love to do and what I am good at. Of course, as a designer, there’s a bit of that self-doubt and that perfectionist curse that things are never good enough, but it motivates me to keep learning and growing.
On whether she would leave SF: I’ve been in SF for just over four years and still feel quite in love with this city. Though I am seeing San Francisco change rapidly, even just within the past few years, I’d like to continue to call it home a while longer. Sometimes my fiancé and I talk about where we would move in the future, but I have a really hard time figuring out which city would be able to be as special as San Francisco.
Christina Simpson, 27, Violist
On going freelance: Before I was a full-time freelancer, I started an unsuccessful start-up with my dad and sister and then worked as a music teacher at a school and started a strings program. I decided when I was eight years old that I wanted to be a professional violist. By the time I had to audition to get into my dream school, however, I was burnt out. I barely practiced and got accepted on a probationary status, which means I had to re-audition. I did a bunch of other things for many years, but I always turned back to playing viola as something I loved. Two years ago, I went to Europe and remembered how much I loved beauty and decided I wanted to try to perform as my job. I quit my day job, started saying yes to more gigs and built my life around the flexibility to take the gigs I wanted.
On managing the high cost of the city: I don’t eat out much. I don’t really buy new clothes. When I started out, I supplemented my income by renting my room on Airbnb and sleeping on the couch or at friends’ houses. I bought an old car a year ago with $600 cash I earned from a serving job at a cafe and kept in a jar in a cupboard. I keep my monthly overhead low. I’m not really poor, but I’m not entirely comfortable either. Also, during my entire professional life, I’ve been doing part-time work and living in the Bay Area, so I am used to it by now.
On what motivates her: I am motivated by the development of myself and the acute awareness that I will die someday. I’ve had an image of myself racing toward the horizon since I was little and have felt the importance of my spiritual and creative self since then. I’ve structured my existence around working on this side of myself. Also, I know that will and effort go a long way in letting one shape one’s own life. If I just don’t give an inch, the wall will come down eventually. What that wall is, I’m not sure yet. My financial success? My ability to communicate? A craft of self-expression I’m developing? My own confidence in sharing myself with others? I’m not sure, but I’m coming at it from all sides.
On her friends and family: My dad is really proud that I’ve built my life the way I want it to be. He’s always tried to empower me and my siblings to take risks. I think I am also fortunate because I’ve seen a lot of money come and go, and I’ve realized it’s not that important. For my friends or acquaintances, there’s a lot of disbelief. People who I meet out in the world look at me like a magical creature when in response to their question, “What do you do?” I tell them I play viola. There are often rude questions about my finances and how I make it all work. Well, I know that technically they’re rude, but I don’t really mind it because I’m sure they are just curious. My friends think it’s really cool and always introduce me by highlighting that that’s what I do. I think it’s because the mythos of California and San Francisco is based around entrepreneurs and visionaries, but not that many people are actually able to do their own thing. I’m not sure if that’s what I’m doing, but to people who don’t really know the sacrifices, “professional musician” sounds very glamorous. Also, my Instagram is filled with me in fancy places in fancy clothes, so that probably adds to the mystique. It’s funny, though—for most of the events where those pictures are taken, I came through the service entrance and ate dinner between stacks of chairs in a hallway.
Ashley Rose Conway, 29, Cocktail Stylist
On going freelance: Before I managed a coworking space called Makeshift Society and worked for lifestyle bloggers (Apartment 34 and Oh Happy Day). Prior to that, I was a teacher. My BA is in elementary and special-needs education. I left the teaching field in Florida and wanted to find a new place that inspired me as I transition into a creative field. My fiancé (now husband) was also looking for a new place to work to inspire him. Through friends we simultaneously found jobs in SF and moved here a few months later in 2012.
On managing the high cost of the city: I am lucky to have a husband with a job that can cover our rent. There is 100 percent no way I could currently do it on my own, but I hope one day to grow Craft & Cocktails to be able to do so! I do try to adjust the rates for my projects to reflect the cost of living here! Buuut small-business/freelance taxes kinda suck—not going to lie. I also often have to pass up events or get-togethers so that I can crank out a project, prop-source at 9:00 p.m. or get through my inbox. I have a small side hustle, but Craft & Cocktails takes up 99 percent of the time I allot for work. I sometimes make premium custom piñatas. It’s called Rose Paper Scissors, and it’s nice to sometimes disconnect for hours to cut, glue and design handmade things that bring people joy.
On what motivates her: I am motivated by my own passion for what I am doing. Is that cheesy?! I also am motivated to continue to spread knowledge (whether about how to make a great drink, photography or styling) to my readers and others. Owning your own business is a constant give-and-take, but I wouldn’t have it any other way. I wake up every day happy to be doing what I am doing.
On what an average day looks like: There really is no average day since my projects range greatly. But if I had to narrow it down, I wake up and check email and IG on my phone…in bed (so, so, so, bad, I know!). Then I drink a metric F-ton of coffee; write down ideas for photo shoots or client work; search for props online; search Pinterest to get additional ideas for the shoots I have concepted (I like to do this toward the end of project planning so photos already out there don’t heavily influence my work); prop-source at stores (including glassware, textiles, decor, sometimes furniture and materials for backdrops); buy ingredients from farmers’ market or stores; pick up flowers for photo shoots; maybe stop to grab food; shoot any projects for that day; edit some photos; cook dinner or order in; edit photos on the couch until 2:00 a.m. Some days I go to restaurant or bar openings or liquor education classes so they get sprinkled into my “average” day.
Macaela MacKenzie, 26, Journalist
On going freelance: After graduation I moved to New York City for a job as a creative strategist at a global PR agency. After two years there, I started to realize I missed writing. Serendipitously, a friend had just gotten a job as an editor at “Men’s Fitness” and asked if I’d like to contribute monthly articles, just to flex that journalism muscle. Six months later, that had turned into a full freelance workload writing for various publications, so I quit my PR job to freelance full-time. I’ve been doing that for almost two years now, and I’m loving it.
On managing the high cost of the city: I will be totally frank—living with my partner definitely helps. We share a one-bedroom and bills, which is great. With my work, I’m able to make six figures, which, some days, seems like just enough to live in a city this expensive comfortably. Coming from New York has also been a leg up. From day 1, having a full-time freelance career has meant having to generate enough income to make it work in two of the most expensive cities on the planet. At the same time, being full-time freelance also puts a weird price on your time — taking off an hour to go to the gym can feel like it costs you $X. Taking a vacation has a direct cost outside of your Airbnb and flights. I’d say the biggest drawback is the constant hustle — if I’m unmotivated, I pay for it.
On what motivates her: What a question! Many things motivate me, but a couple stand out. I don’t believe we spend enough time talking about people with enriching stories. I got into journalism for the very simple and naive reason that I just wanted to tell people’s stories. I’ve stayed in it because I think that passion is contagious. Talking to someone about the thing they’re really passionate about — whether that’s styling hair or empowering formerly incarcerated women at a sustainable clothing label — is such a cool honor. I’m motivated to find those conversations and share them. I’m also motivated to share more stories of substance — which is really, really hard in the age of the clickbait-dominated Internet. If the reality is that hundreds of thousands of people are going to click on an article about Kim Kardashian, I’m motivated to always try to get at something just a little deeper with my writing.
