Ep #5: How To Pivot From Freelancing To Your *Dream* Staff Job With Sean Santiago

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 to give yourself the credit you deserve when you’re by yourself as a freelancer

  • The importance of pausing to do a postmortem after freelance projects, even just mentally

  • What you can do to help make sure you’re at the top of the right person’s mind at the right time (aside from, you know, luck)

Friendly reminder: Hindsight is 20/20, so don’t be too hard on yourself when you take the time to look back.