Evolving the Side Gig —

MAEKAN Session


MAEKAN Sessions are thematic online panel discussions hosted by MAEKAN featuring guests in various creative fields. Sessions allow us to have longer, in-depth conversations on single topics with interesting people around the globe in a format that is open for others to listen in and ask questions.


In this MAEKAN Session we spoke with Josephine Cruz and Dan Sandison on their experiences evolving side gigs into full time occupations.

Josephine also goes by JAYEMKAYEM, her DJ alias. She is a Toronto-based DJ, radio host, music curator and freelance writer. Josephine moved from Calgary to Toronto after leaving a full time office job in marketing. She has played in venues around the world from New York to Shanghai and has opened for artists such as Skepta and Playboi Carti. Dan Sandison is editor-in-chief at MUNDIAL, a football lifestyle magazine based in the UK. While the magazine has been running since 2014, Dan has only dedicated the past two years to it full time. MUNDIAL focuses on the rich culture surrounding football as opposed to numbers and stats. The magazine is now on its 11th issue and is currently working on its expansion to Japan.


Josephine and Dan talked about how they knew it was time to leave their full time jobs and what set them up to succeed on their own. They discuss coping with the anxieties that come with being independent and combatting hurdles or negative influences. Josephine gives advice on establishing a network of resources and having a tight advisory council that gives quality feedback. Dan talks about how a passion project even when it becomes the thing you give all your time to should remain something you find joy in doing.


This Session wrapped up with Dan and Josephine answering a series of attendee questions on finding mentors, branding consistency as a multidisciplinary creative, and how to scale. We found that the topic of turning something on the side into a sustainable full time commitment resonates widely in the creative community. A word of advice Josephine gave, “At the end of the day, you have to be sure with yourself and know that you’re doing things for the right reasons. And if you know that, then nothing can really derail you.”

“I was like, ‘Failure is not really an option, I’m going to ride this until the wheel fucking falls off.’”

Josephine Cruz

Josephine Cruz opening for Playboi Carti shot by Drew Yorke.

Mundial Magazine Issue 11.

“We had enough to pay us for the next three months and that was it. So we just kind of came in and didn’t start looking for work but were just doing the work we’d been given and figuring it out. There was a bit of pressure hanging over us to ensure that 3 months became 6 months, that became 12 months, that eventually became almost 2 years now.”

— Dan Sandison