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Cindy Sherman, “Untitled Film Still #21”
Cindy Sherman, “Untitled Film Still #21” (1978). Gelatin silver print, 8 x 10 inches (20.3 x 25.4 cm)Courtesy of the artist and Metro Pictures, New York

8 artists who had surprising side hustles before they made it

Fancy a pint poured by Nan Goldin or being welcomed into a gallery by its receptionist Cindy Sherman – these are the past lives of the world’s biggest artists

The phrase ‘side hustle’ entered the English language in the 1950s, but only became a buzzword defining the Millennial and Gen Z generations in the late-2010s, meaning young people are now collectively termed ‘Generation side hustle’.

For those of you living under a rock, a side hustle is a method of making extra cash, without it deterring from your long-term career prospects or forcing you to quit your day job, whether that be selling clothes on Depop, Uber driving, or dog-walking.

For many artists and freelancers, a side gig is crucial for both economic and creative survival. In the last few years, it has been estimated that Creative Arts and Design students will earn disproportionately less than students working towards science, law, or business degrees.

Those committed to ‘making it’ in the arts (reminder: it’s never too late to back out), must resort to making alternative, and often less-than-ideal income streams – unless of course, they have enough privilege to stay afloat in a highly-competitive creative sector.

As The White Pube and others have brought to light, these socio-economic issues also have broader ramifications on diversity and inclusion within the arts, where regular working hours are simply not enough to excel and earn a decent London wage. Aptly worded on a billboard in 2016: “What creativity can there be when only money can buy you your next opportunity?”

Fear not if you are a creative losing hope against the backdrop of rising rent prices and stagnating salaries (on top of the current COVID-19 outbreak, which, at the time of writing this, was only a looming threat). These seven highly-successful artists also did a number of odd jobs in their teens, 20s, and 30s. Some of which actually helped them grow more resilient or find artistic inspiration.


Known for his monumental steel sculptures, Richard Serra hails from humble origins. His Spanish father Tony was a candy factory foreman and shipyard worker in San Francisco, while his mother, Gladys, was a Russian Jewish immigrant and housewife.

Serra excelled academically as a young man and studied English Literature at prestigious American universities, before earning a place at Yale’s art school. To make money, Serra worked in steel mills while also training to be an artist – an experience which would have a profound impact on his practice which adopted the materials lead and steel.

But the artist’s side hustles didn’t end there. In the early 1960s, he founded a furniture removal business, named Low-Rate Movers. Based in New York, the company hired struggling art students and even Serra’s friend the minimalist composer, Philip Glass.


Barbara Kruger worked in relative anonymity as a photo editor and magazine designer before she could call herself an artist in the mid-1970s. Now, she is highly revered for her confrontational feminist work juxtaposing image and text while satirising a capitalist-driven consumer society.

Born in Newark, New Jersey in 1945, Kruger told Dazed, “I grew up in a working-class home… that experience determined very much what my work later became – my childhood informed my ideas about power, control, hierarchy, and marginalisation.”

She spent the 1960s and 1970s offering freelance design and photo editing work to magazines such as House and Garden, Aperture, and Condé Nast (then called Mademoiselle). But she hated it, confessing to Interview Magazine “there’s just no way I’m cut out to create someone else’s image of perfection as a profession.” 

In 1973, at the age of 28, she got her first big break when she was invited to exhibit work at the Whitney Biennial, but after many years of struggle, reminiscing: “For me, the idea of being an artist didn’t have to be tied to a bohème melancholia. It’s because I come from a different class. I didn’t finish college, my parents didn’t graduate college; we didn’t have a pot piss in…I had to work. I didn’t think it would be possible for me to be an artist without having a job.”


Before becoming a world-famous artist, Jean-Michel Basquiat was homeless and selling postcards in New York’s Washington Square Park in the early 1970s.

At the age of 15, he ran away from home and slept on park benches. To survive, Basquiat designed and distributed hundreds of colourful postcards merging together drawing, watercolour, and text. An early example of creative marketing, they were all signed “Jean Basquiat.”

At the same time, Basquiat created street and graffiti art with his friend Al Diaz – establishing the collective SAMO©, a pseudonym for ‘same old shit’.

In 1979, at the age of 19, Basquiat got lucky when he bumped into Andy Warhol in a restaurant and sold him a few postcards. Enamoured with Basquiat, Warhol introduced the young artist to a new frenetic and lucrative art world, irreversibly changing his life forever.

Tragically, Basquiat died at the age of 27 in 1988 from a heroin overdose after remarkable success.


Photographer Nan Goldin is known for her uncompromising and unfiltered “social portraits” of American subcultures as well as for documenting the Aids crisis in the 1980s.

Born in 1953, as a teenager, she ran away from home, before being looked after by different foster families. By her late teens, she was experimenting with drugs, but she still managed to get into art college, having taken up photography from the age of 15.

In the 1970s, she moved to New York, where she worked in bars to pay the rent. “I was working as a bartender, at Tin Pan Alley, this tough bar on Times Square… for this amazing woman who politicised me… there were a lot of street people, a lot of prostitutes and pimps, and gang kids.”

Goldin’s formative experiences as a bartender undeniably influenced her work, which often centres on the themes of sex, heartbreak, LGBTQ culture, intoxication, and marginalised peoples.


A friend of Warhol and Basquiat, Keith Haring had a bumpy start before becoming a popular artist and LGBTQ activist who symbolised 1980s New York street art and the Aids crisis – the cause of his premature death.

Born in Pennsylvania in 1958, Haring graduated from high school before joining a freewheeling, drug-taking hippie community who hitchhiked across the country and sold anti-Nixon t-shirts designed by Haring – part of younger generation’s protest against the Nixon administration’s “war on drugs”.

He attended a commercial art school but dropped out. He later explained his reasons for quitting “the people I met who were doing it seemed really unhappy; they said that they were only doing it for a job while they did their own art on the side, but in reality that was never the case – their own art was lost.”

Nevertheless, when Haring relocated to New York in 1978, he worked at Danceteria nightclub as a busboy cleaning tables – the same club where Madonna worked before she became famous.


Cindy Sherman started her career as a gallery receptionist before becoming one of the highest-selling photographers at auction. Known for her uncanny art of disguise through photographic self-portraiture, Sherman’s work subverts concepts of feminine identity and sexuality.

Sherman worked front of house at the Downtown, non-profit grassroots gallery Artists Space, where she eventually exhibited her most famous collection the Untitled Film Stills in 1980. Foreshadowing her artistic trademark, Sherman occasionally turned up to work in disguise, once dressed as a 1950s secretary and another time in a nurse’s outfit.


One of the most famous contemporary artists who emerged from the 1990s Young British Artist scene, Tracey Emin is known for her intensely personal and confessional artistic practice. 

The Margate-born artist had a turbulent upbringing, something which propelled her to document her anguish, pain, and trauma from sexual assault and abortion. In 1979, she moved to London, where she lived in a cupboard in Clapham Junction. She worked in odd jobs, including as a shop assistant at a boutique. 

Shortly after graduating from both Maidstone College of Art and the Royal College of Art, Emin entered her wilderness years, recounting “I was terribly scared about my future. I sold some paintings, and made about £2,500, but nowhere enough to pay back the bank. After I left, I was homeless, became pregnant, and had a total breakdown.”

She eventually got a job working as a youth tutor for Southwark council, while also studying a philosophy course part-time. By the early 1990s, she was back on her feet and opened The Shop on Bethnal Green Road with fellow artist Sarah Lucas, selling t-shirts bearing slogans such as “I’m so fucky” and “Have you wanked over me yet?”


The most famous Chinese dissident and artist, Ai Weiwei didn’t become a household name until later in life. An active opponent to his country’s authoritarianism, Ai’s studio has been demolished more than once by authorities and he was detained without charge for 81 days in 2011, eventually losing his Chinese passport (it was finally returned four years later).

But before he became one of the most influential artists of our time, he was a blackjack guru while living in an unfurnished apartment in New York’s Lower East Side in the early 1980s. Earning the status of a “rated player”, Ai was often chauffeured to casinos or driven to Atlantic City to gamble.

While briefly attending Parsons School for Design and trying to make ends meet in New York, where he lived until 1993, Ai had a string of odd jobs, from renovation, collecting rubbish, construction, cleaning houses, barbering, lawn mowing, and babysitting. Always curious and restless to keep creating, Ai has come a long way doing manual jobs. 

However, in a recent interview, he commented: “I think it is more fun to be a barber than an artist.”