For Hire

How To Pivot From Freelancing To Your *Dream* Staff Job With Sean Santiago

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On today’s show, I talk to Sean Santiago. Funny story: When I asked him to be on the show, he had been a freelance art director and creative consultant, and had worked with companies like Converse, Target, Architectural Digest and Refinery29 (though we actually didn’t cross paths at Refinery29). He’s also the founder of Cakeboy, an independent LGBTQ+ zine. But, by the time we were able to sit down for this interview, he had JUST started his first staff job in three years, like that week. So, technically, Sean’s not freelance at the moment, but I still wanted to talk to him because, as a freelancer, he was able to cobble together the kind of work he wanted to be doing, the kind of stuff that his prior staff experience didn’t necessarily allow—which ultimately turned into him getting a dream job kind of job: He’s now the Art Director of Out Magazine. No big deal. Despite that, Sean is one of those people who is so humble and truly doesn’t know how talented he is. On the show, we talk about: How hard it can be