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How You Livin?: Jacob Winterstein

by Jasmine Combs

“At some point your idea has to stop being an idea and start being a plan, and at some point your plan has to start being an action” -Jacob Winterstein


I don’t think he knows this but, my dear friend and colleague Jacob Winterstein is one of the most influential people in my life. When I first started performing poetry in 2014, it was mainly at the poetry slam venue that he and Alyesha Wise organized and hosted. Since then, I’ve been able to work closely with him both artistically and professionally, and I’ve learned so much about what I want to do for a living from him. One of the things I admire most about Jacob is his ability to turn his ideas into realities. It doesn’t sound that impressive, but I know first hand the difficulty of 1) believing in your ideas enough to pursue them and 2) the work ethic required to bring those ideas to fruition, especially in a society where we’re primarily conditioned to work hard for others instead of ourselves. Jacob is many things, but his primary titles include: self employed Teaching Artist, Co-founder and organizer of The Pigeon Presents: The Philadelphia Poetry Slam, and Co-director of Camp Bonfire: Summer Camp for Adults. Personally, I find the thought of being a self employed artist terrifying. I love my art but I also love stability and I’m working on gaining the courage to risk my stability to try being a full time artist. Jacob took that leap of faith roughly four years ago. He saved up a nice cushion of money and quit his job as Director of Development for the Philadelphia Student Union to start working for himself.


Jacob’s primary source of income comes from working as a Teaching Artist, a hybrid profession that is part practicing artist and part educator. In his sophomore year of college he began teaching poetry through Youth Art and Self Empowerment Project, an organization that brings different programs to young people awaiting trial in adult jails, which don’t have programming catered towards young people’s needs. He now works as an independent contractor brought into different schools and community groups to teach poetry, spoken word, and even freestyle rapping. There are several organizations that Jacob works with that function somewhat like a liaison between teaching artists and the places looking to hiring them. Some of them include: Young Audiences, Live Connections, Ruckers-Camden Center for the Arts, Al-Bustan, and Art Reach. As an independent contractor Jacob is only paid for the days that he works which means there’s no sick days. “Like I got sick for a week, I had the flu, and if I don’t show up for work I don’t get paid. And if I don’t have room in my schedule or the school can’t reschedule me, not only do I not get paid that week, that might be money that I just miss out on and can’t ever make back.” This also means there’s no company providing him with health insurance, workers comp, and he has to pay his own taxes and do his own book keeping.  


There are typically two scenarios in which a school will bring in a teaching artist. Worst case: a school cuts their art program and doesn’t want to pay a full time art or creative writing teacher, so they hire a teaching artist to do a little bit of arts programing to make up for it. Best case: a school already has arts programing and want to bring in a practicing artist that spends time creating their own art to enhance what the students are already learning. “That can be a really cool experience because I am someone that’s actively writing and rehearsing and performing poems and I also have teaching skills,” Jacob added, “So when I come to them I’m thinking more of my creative process whereas their teacher is a really amazing teacher but maybe hasn’t developed a creative process.”  


In 2011 Jacob co-founded The Philly Pigeon with his former poetry slam teammate and friend, Alyesha Wise. The two wanted to create a major poetry show in Philadelphia, something bigger and better than your typical event held in a cafe or bookstore, with lights and music that brought out a huge crowd. So they created it! After their first year they received a grant from the Knight Foundation which snowballed The Philly Pigeon into an even more professional endeavor. The two then needed a fiscal sponsor to manage their grant and applied to make The Philly Pigeon a Limited Liability Company (LLC). He explained that an LLC is, “a business designation that ideally protects the partners of the business. So If someone, God forbid, sued The Pigeon, they’d be suing a business and not me. It also means that anything I do that’s business related, I can write that off on my taxes and it allows us to open a bank account so it’s very clear what’s The Pigeon’s money and that it’s not my money.” Although Jacob hasn’t gotten paid from The Philly Pigeon since that first year, this project is valuable to him in other ways. Aside from being another creative outlet for Jacob and a way to engage with the other artists in Philly, Jacob says, “it has a name that’s bigger than my own and it’s something I can point to that gives me legitimacy as I explore other professional opportunities.”


Another source of income for Jacob is Camp Bonfire: Summer Camp for Adults. Like The Philly Pigeon, this is another example of turning an idea into a reality. The idea actually sparked from a misinterpreted email about a similar adult summer camp in California. The sender told Jacob that he should do it, meaning he should attend the camp, but Jacob thought it meant that he should do his own adult summer camp. Around this time Jacob was working on a different project with Ben Camp (a childhood friend from summer camp) who runs a theater company, and he agreed that starting a summer camp for adults was a great idea. So, together they created Camp Bonfire! “It was beyond anything that either of us had ever done before but it wasn’t so far beyond that we couldn’t do it,” Jacob said, “with any event the first thing is to find a space and find a date. The second part is to convince people to come to it and at the same time make sure once they get there, there’s something great for them to do.” Aside from their annual summer camp, Jacob and Ben also organize custom retreats for individuals and organizations.


“Something that I learned working for myself the last four years is that I have to have a lot of pots on the fire at the same time. I need to make sure that lots of diferent things are cooking so that when one organization loses funding or doesn’t get a grant and can’t hire me to teach that year, that another pot is on the fire and ready for me to dip into. I think the thing I’ve enjoyed most about working for myself is that I have a lot of flexibility and that my days are really different and everything I do out in the world, I enjoy. I don’t always enjoy like, accounting or doing my quickbooks or answering a lot of emails, but I really love organizing a summer camp for adults and I love how different that is from teaching fourth graders how to write poems and I love how different that is from running a monthly poetry slam. I just like how varied my week is and even how varied my year is, and how I get to do really fun things….and it’s also all scary as shit”  




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