1. Name: Rebecca Fishman Lipsey

2. Current job, past jobs: Currently CEO, Radical Partners; previously executive director of Teach For America Miami-Dade

3. Schools attended; major: B.A. from University of Pennsylvania (Psychology and Communication majors) and M.A. from Bank Street College of Education, New York City.

4. Did you need to have an internship to help get your jobs? I’ve had an assortment of internships, most of which taught me what kinds of work and workplaces I love, and what kinds to avoid. I struggled painfully as an intern because I wanted so much to be in a leadership role and had a hard time taking a back seat. I learned quickly that I was going to need to find a job where someone would take a gamble on me early on, because without that permission to bring my full self to the table, I found myself getting into all sorts of trouble! I feel seriously blessed that I joined Teach For America upon graduating from college because it is an organization that charges every member to lead without limits. The work was incredibly meaningful and inspiring, and the organization introduced me to an entire movement of people with shared passions. Another great career-builder was participating in the “Miami Fellows” program, a local fellowship focused on developing local leaders. That experience linked me to a network of ambitious, talented professionals who are now my close friends.

5. Did you contact prospective employers cold? What were your best and worst interviews? My career path has been a bit organic (read accidental). I applied to Teach For America right out of college and fell in love with the mission and the people involved. Many of my clients today are people I built relationships with through my work there. My best interviews have involved laughter and a real connection: I want to work with people who bring out my best, who ignite a spark within me and who feel that same spark in return. On the other side of the spectrum, I still have nightmares about my interview for an investment banking job during my senior year in college. The interviewer showed me someone else’s résumé and asked me to explain why I was a better candidate. I could tell right away that wasn’t going to be a company that would bring out the best in me.  Interviews are a great way to discover the values of a company.

6. What is the biggest obstacle you deal with now? School debt; life-work balance; job satisfaction; lack of promotion opportunities; time management? Radical Partners, my business, is an accelerator for social entrepreneurs. We partner with leaders who have incredible ideas for businesses that will transform their industry to the betterment of society. Our goal is to help them take great ideas and turn them into something HUGE. The most important challenge I face is selecting the right partners, and knowing when to walk away from a proposal. The allure of getting paid by someone in the short term is not worth the time investment in the wrong partner. The goal isn’t more clients; it’s to have absolutely game-changing clients. On a personal front, my other greatest challenge is finding time for hobbies. I’m a closet musician, and if I don’t get my fix with a microphone and a piano once in a while, I get cranky.

7. Who would be your ideal mentor? How have you sought a mentor and how has that person played a role in your career? I love vibrant women who take risks, and I try to build as many of those relationships as I can—as a mentee, as a mentor and as a friend. I’ve been surprised how willing people are to meet strangers to offer advice and perspective, and I hope to always pay that favor forward.

8. How and where do you network with others in your field? The best networking happens on boards of non-profits. I love to join boards for organizations that are still being discovered. I’ve met amazing people like that who share a common interest, and who usually are DOERS. I am a huge fan of being set up on “new friend dates” by other friends and connections, and am not above cold calling random executives to introduce myself and see what comes. In fact, after checking out the other features on GlassCeiling.com, I contacted the founder of RainTees, an organization you spotlighted. Now we’re in discussions to create a joint-partnership for an upcoming adventure. Thank you for connecting me to an incredible woman and a great organization!

9. What challenges do you still see facing women as they rise in business? What helps you navigate those challenges?  I struggle at times when I want to make bold leadership choices because people assert all sorts of expectations on women to be nurturing, to be risk-averse, or perhaps polite in places where directness, confidence, and willingness to fail might be critical. I sometimes have to give myself special permission to follow my instincts instead of pleasing people.  I’m also working hard to overcome my secret wish to be perfect at everything. As I think about these 10 questions I’m actually replaying my answers in my own mind, wondering how others will perceive me: It’s hard to be vulnerable publicly! A few things help in those moments. Having a set of core values that drive my decisions has always been a source of stability. Most importantly, though, I have found that laughter and friendship really get me through. When I take myself too seriously, I lose my spark. My friends help me fail and succeed lovingly and remind me that the best version of myself is the one that comes naturally.

10. What helpful advice can you give to someone who wants to follow in your field? Are there specific classes that should be taken in high school or college? What internships should be applied for? Two pieces of advice: First, raise your hand. It’s amazing how frequently huge opportunities go to the people who actually apply, offer, or have the nerve to put themselves out there. People often think it’s talent that gets someone a big honor; often it’s that they were willing to self-promote. Second, get comfortable with RISK and JOY in the workplace. How you spend your daylight hours….that’s the most precious thing you have to offer. Don’t study something because you SHOULD. Don’t take a job because someone expects you to. Find a way to bring out your inner strength, talent, and sparkle, and give yourself permission to do something professionally dangerous once in a while.

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