Dream Jobs Exist: Rebecca Fishman Lipsey & Social Entrepreneurship
December 7, 2016
If you’re anything like me, you’ve found yourself in your mid-twenties and dipped your toes into the pool of adulthood, but you’re still struggling to find any semblance of a dream job. We’ve all been here before–we’re stuck in a job we hate or we’re not even sure what kind of career paths interest us. Top that off with our peers, our parents, and the media pushing us to find this illusive yet crucial sense of passion, and you’ve got a millennial crisis on your hands.
Rather than panic, my first thought was to seek advice from rising leaders, creative visionaries, and local entrepreneurs on how they got to where they are today. These individuals have dreamed big, started out small, hit road blocks, and veered course along the way. They’ve found themselves their dream jobs, and give hope to millennials like myself who’re still figuring things out.
Rebecca Fishman Lipsey is one such creative visionary. First arriving to Miami with Teach for America in 2008, Lipsey now serves on the Florida Board of Education and started Radical Partners, which supports social entrepreneurs and nonprofits on how to better address issues that impact our community. Radical Partners is the force behind the 100 Great Ideas Initiative and this month’s Public Transit Day. I sat down with Lipsey to get her two cents on career, failing hard, and stepping out of your comfort zone.
LG: When you were a kid, what did you want to be when you grew up?
RFL: I wanted to be a performer. I really loved theatre and thought I’d be a singer-songwriter. I actually got a job as a wedding singer right out of college but then got accepted into Teach for America and had to switch gears a bit.
LG: Walk me through your trajectory at Teach for America (TFA).
RFL: TFA completely transformed my life path. I started off teaching fourth grade in Harlem. My students came in reading at a first-grade level on average. It’s not because they weren’t capable; it was that something was fundamentally wrong with our educational system. The fourth graders I started out teaching are now seniors in college. To see what they’re doing now and what they’ve overcome is incredibly humbling.
When I was in the classroom, I felt like I had control over what happened with my students, but I didn’t have control over what was determined for our school: what the curriculum was going to be, what tests my kids needed to take. After the two years, I knew I wasn’t done with TFA, so I applied to every job opening in the organization. I was a program director in New York, managing a portfolio of fifty teachers in Harlem, Brooklyn, and the Bronx. The connections I made with the teachers and the schools was eye-opening and fulfilling. The organization was growing really fast, and TFA needed someone to lead the Miami region and they sent me down here. I couldn’t believe that at that age, someone was willing to take a gamble on me at the level and I knew I had to go for it.
LG: What led you to start Radical Partners?
RFL: It was a little bit of an accident. Over the course of my time at TFA, I discovered some core values in myself and beliefs about the world that I wanted to play with. The most important belief was the idea that communities have the abilities to solve their own problems. When I was at TFA, my identity was very connected to the issue of education, but as I started to meet different leaders in social impact, I learned about all these other issues in the community that had nothing to do with my work. I became convinced that we all interplay to create the environment where we can solve all the problems in our community. I wanted to be involved in all sorts of social change issues, so while I was still at TFA, I started coaching different organization leaders. I started realizing that I was having the same kinds of conversations with everyone: how to make a pitch, how to cultivate a donor base. And so I thought that instead of having these one-on-one conversations, I needed to get everyone in a room together. We started getting together these cohorts of bad-asses who were learning from each other and helping each other in what they were doing. This eventually evolved into our Social Entrepreneurship Bootcamp. So Radical Partners organically became a business out of these one-on-one, informal coaching sessions.
LG: Part of Radical Partners is the 100 Great Ideas Initiative. How have these campaigns shaped local awareness and government response?
RFL: If you’ve been to a local commissioner’s meeting, you know they can be pretty boring and almost painful. You need an incredible amount of disposable time to find the meeting, learn what’s happening, and actually be able to follow along. A lot of these meetings are high-level and kind of cryptic. If you get a chance to make a public comment, you’ll get two to three minutes. It’s hard to engage with your community that way.
I remember thinking that there had to be a better way for leaders to understand what their community wants and needs from them. There needed to be a no-barrier method to contribute ideas–what if I created a space on social media where I pick a topic and allow people to share their ideas? That’s where 100 Great Ideas came from. We started off with the public library system. People shared ideas and others liked, commented, and shared them. We synthesized the top ten ideas into a report and with one simple ask, we arranged a meeting with the director of the Miami Dade Public Library System. Since then, we’ve worked with the director of the Miami International Airport and members of the transit team, and we’ve seen a lot of these ideas from these campaigns implemented. Some of the ideas were already in the works but gave government leaders more steam in rolling them out. We’re getting different community members working to solve our city’s problems, and I think we’ve struck a nerve.
LG: What were the biggest lessons in going from an established organization to launching your own passion project?
RFL: This has been an exercise in a couple of things for me. One of them has been belief in myself and the willingness to take a gamble on myself. It’s very difficult to hang out a shingle and say this is what I do, not because I’m an expert but because I am doing it. With things like 100 Great Ideas or Public Transit Day, it was all new ground for me. It’s become an exercise in me believing I can create something good with what I’ve got. I’ve had to get comfortable with the possibility of failing publicly.
When I was with an established organization like Teach for America, it gave me a certain sense of validity and credibility. People were familiar enough with TFA to understand what I did. When I started Radical Partners, all of a sudden people didn’t know what I did or what social entrepreneurship was. I had to be comfortable with defining the vision of Radical Partners and knowing that it fit in with my core values of how I wanted to live.
LG: There’s the common narrative that Miami experiences a brain drain of millennials who become frustrated by the lack of entrepreneurship and civic engagement. How do we break that narrative or go about clarifying those misconceptions?
RFL: We do need more businesses and bigger players especially in the tech space that can hire people at the entry to mid-level position so they can gain the skills to be able to spin off and do their own thing. There’s a lot already brewing here, but Miami is experiencing a growing pain. Businesses are looking for the talent and the talent is looking for those positions to gain the skill sets they need.
What this town is great for is creating things. I think this city is really receptive to new ideas, and if I were try to do what I’m doing elsewhere, it would not be as fruitful.
LG: What are some small, actionable steps Miami millennials can take to engage in our community?
RFL: I would encourage people to play in different fields and get out of their comfort zone. I think it’s important to get involved in organizations that can expose you to issues outside the band of what you do. When I was with the Miami Fellows program, we visited the Port Authority, and I initially thought it was going to be boring and inapplicable to my work in education. But it was fascinating, and I realized that if something goes wrong or right here, the ripple effects in Miami would be huge and because of that, I have to care about this. I was able to build relationships, explore different new passions, and become more whole.
LG: Endemic to the millennial culture is a desire to find your passion and do good. Yet we’re often overwhelmed by a number of options and possible career trajectories. What advice do you have for that millennial who’s struggling to find their path?
RFL: The greatest direction I get is from failing hard. I think the fear of making the wrong choice is the wrong fear. I’d rather learn quickly that I made the wrong choice and learn from that rather than be paralyzed by fear of risk. You get to live this life once so go bold, take risks on yourself, be comfortable with failing, and shift your course if you need to. I’ve found that the wilder I go and the bolder my idea is, the likelier it is to happen. The smaller ideas often don’t have that magnetic energy that get people on board. The most important advice I think I can give is to believe in your big ideas.