Underground Railroad by Colson Whitehead book cover

Sarah Rinaldi whisked into my life when she marched a crew of men into my kitchen to film a documentary on my husband. Within minutes, I knew she would make an excellent interview subject. She was a skilled, heart-led producer and an engaging conversationalist. While there to interview Shaka and me, she gamely allowed me to quiz her on the spot and follow up with a phone interview.

Her career path from lowly production assistant on “The Winner Next Door” to Emmy Award-winning producer is inspiring—and instructive. She exemplifies success earned through a signature mix of audacity and industry. Read on to discover how a “just say yes” mantra has fueled her achievement, and what she wishes older women had told her about the pursuit of excellence.

  • Name: Sarah Rinaldi
  • Age: 37
  • Work: Television Producer/Director
  • Education: Bachelor’s degree in English and Spanish from Amherst College

What did you study at Amherst?

I was a liberal arts major, so nothing. My major technically was English and Spanish. That was as close to film and journalism as you could specifically hit. I didn’t know what I wanted to do. I enjoyed writing, and I enjoyed languages, obviously, so that’s what I did.

Then I got to my junior year in college and finally took a video class over at Mount Holyoke [College] I loved it, and I loved it in a way that I didn’t love writing. I always enjoyed writing, and I still do, but when I was doing video, I would just forget to eat. I’d say that’s a really good benchmark for me, since I also love to eat.

I would be working on these projects, and I would just stay in there. I loved it, and I took a couple more of those classes before I graduated.

I had no idea what I was going to do when I got out of school. It was a bit of jumping into the abyss. I don’t know that it would be possible today in this climate.

I’m not sure I would’ve had the same perspective knowing how hard it is to get jobs. I felt like when I was leaving college, anything was possible. It wasn’t about if you were going to get a job. It was just, what job.

Times have definitely changed. Tell me a little bit more about that first video class. Was it video production? Were you out there physically with a camera working on stories? What did you do that got you so excited that you forgot to eat?

Whatever I cut was definitely terrible. I was working with a VHS recording camera at the time. What I loved was being in the edit room. That’s still what I love.

It’s twofold. It’s transformed a little bit for me, but what I loved then and I still love now is being in the edit room and piecing together a story that works and that flows.

I think there’s a lot of storytelling out there. Some of it is phenomenal and some of it is awful. Then a lot of it falls somewhere in between. I really enjoy the process of making something that speaks to people’s personal stories as much as possible because that’s what I’m constantly doing. I’m telling other people’s stories. I like to be very true to their perspective.

Tell me about your first job after college and how you pursued it.

My parents gave me $1,500 because I wanted to take two unpaid internships in New York City. They gave me enough as a graduation present to cover three months of rent, $500 a month.

I took two unpaid internships in TV, and I worked as a juice bar girl at Crunch to earn some cash. The goal was by the end of the summer to have a real, full-time, paying job, so I could support myself in New York.

There were two internships, and one of them I got fired from. It still amazes me that I got fired from an unpaid internship, but looking back, the job wasn’t that great, I didn’t love the people, but at the same time, I was so impatient. I had just graduated and thought I was so ready and had so much to offer.

I didn’t have much in the way of patience. They’d say, “Can you fax this? Can you do that? Can you organize the videotape library?” I did all those things, but I said, “Hey, guys, what else do you have? I really want to dive in.” These guys didn’t want to have anything to do with this sort of rash, upstart, right-out-of-college girl who was trying to do all the good stuff, so I got fired.

From that job where I got fired, I actually made a connection. For some reason or another, [a colleague] connected with me, and he led me to my first production assistant job in New York, starting in September.

My first real job after that was working on a show called “The Winner Next Door.” Maya, this is a lottery-sponsored television show for local NBC to basically present the positive side of the lottery–that lottery winners weren’t just people who blew their money and were destitute somewhere under I-95. To say it was not my dream job would be a mild understatement.

All the people who were working there at this crappy little TV show were all new graduates–NYU film people, myself and a couple of other people.

I still know almost every person that I worked on that show with. They’ve all gone places, their own paths, in television. It is one of my fondest memories and interactions when I reconnect with those guys.

Were they all guys?

It was probably 50/50. There were men and women. It was a pretty good mix.

What advice would you offer for people who are in
those very early, awkward stages of career building,
in terms of maintaining relationships even
if you don’t maintain the job?

The best advice I’ve ever gotten was from Mary Carillo, a sports announcer. She is one of the few women sports announcers, and she’s amazing. The advice is: Just say yes. If someone asks you to do something you’re not sure how to do or there’s an opportunity, say yes.

I feel like the way I’ve made my way through is by constantly just saying yes, even at times where I probably shouldn’t have said yes. Maybe sometimes I should’ve said maybe, but I just said yes.

I think it’s particularly important in careers and job paths that aren’t structured out and that are uncertain. The best thing you can do is just dive in to opportunities, even when you don’t know how they’re going to turn out. Every time I think I know which opportunity is going to be the one that sits well and which one is going to be the one that doesn’t, I’m always wrong.

Talk about the uncertainty about the kind of work you do, since it’s project based and not as linear as some career paths. You’re pitching projects, people can accept or reject them, you can have multiple things going on at one time, and you’re responsible for managing yourself and other people.

It’s not the kind of job where you report in at 8:00 a.m. and stay until 5:00 p.m. and you know exactly what’s happening from day to day.

All of the things you said are exactly how it unfolds. When you say “uncertainty,” the first thing that pops into my mind, which maybe isn’t what you meant, is that when I first got out of school, everybody was going to be a consultant or banker. If you weren’t one of those two things, maybe you were going to be a lawyer or doctor.

It felt like there were four or five clear paths toward particular careers and not a lot of advice or guidance about anything else.

I think that was the biggest challenge for me. For a long time, I continued to question what I was doing, where I was going, and how I was going to get there when I didn’t even know where I was going.

I just kept moving. I guess I just kept saying yes, honestly. Sometimes it was hard to believe in something when I didn’t even really know what I was doing. I’m not necessarily the kind of person who has a five-year or 10-year plan, or anything like that. I had ideas about what success meant for me, but those have certainly changed a lot over time.

What helped you stay firm in your path and never venture to law school?

I took my LSATs when I was 25. I thought, “Maybe all this TV stuff—I don’t know.” I took them and thought, “I don’t know that I actually want to be a lawyer.” I had many moments of uncertainty, where I was wondering if I should maybe go in another direction.

At the beginning, when it was hard and I was just making my way, the ratio was a lot of stuff I didn’t particularly enjoy and a little bit of things that really got me going. The things that got me going excited me enough that I wanted to continue down that path.

As I started telling more stories and getting to work on more features, and as they got better, and I really understood what I was doing and putting out work I was proud of and excited about, I started to feel much more certain. Maybe “certain” is not even the right word, because I don’t ever feel really certain. I was much more confident that what I was doing felt good.

A lot of those relationships I mentioned with editors and producers were really important to me staying in it, because when you don’t have a structure in place around you that’s constant, then the one thing that for me provided a lot of stability and grounding was the really great relationships that I formed.

Give me a few steps in the path from “The Winner Next Door” to where you are now.

I spent a number of years at CBS as a broadcast associate. That’s similar to a PA. They just use a different name. I was a broadcast associate and then an AP, an associate producer.

I was doing a lot of live events. Live events aren’t really my thing, mostly because there’s not a lot of room for the kind of work I do, which is the storytelling. I was kind of following the preset path that CBS had, even though it wasn’t a particularly great fit for me. On the side, whenever there was time, I would do features and stories when they arose.

In 2006, I got up the courage to leave CBS. It was really hard. I had kind of made this goal for myself. It was like an anti-goal. I basically said that if I ever get to 30 and I’m still at CBS doing this stuff, I’m going to be really upset with myself. I knew it wasn’t the direction that was going to be the most satisfying.

In 2006, I was offered a job at the Olympics doing features with a figure skating crew, which was a pretty high-profile, high-pressure event. They have a lot of resources.

In order to take the position, I had to leave CBS. I literally left this job that was certain, that I was working at year-round, for a position that was going to go for six weeks.

It was a terrifying decision, even though I had assurances from CBS that they would hire me back on a freelance basis for projects as they came up. Beyond that vague reassurance, I thought, “What am I going to do with myself?” But I did it. I did it because I knew I had to do it.

I left, and that was kind of the pivotal moment for me. I just kept going from there. I started doing features. I would come back to CBS to work on projects as they came up, as I’m doing right now.

Slowly those projects got bigger and bigger. They started out with small pieces for small events. Then they grew to big pieces for bigger events, and finally to shows, overseeing shows, developing them and coming up with creative ideas to execute them. Then I started doing it for people outside of CBS. It just has unfolded in its own way.

Would you say that you’ve had any mentors throughout your career? You’ve talked about colleagues and people who started with you at “The Winner Next Door” and people you’ve stayed in touch with. Have you felt like there’s been a senior person that showed you the ropes?

I don’t. I’d say my biggest regret is that I don’t have a specific mentor. If I had to give someone advice, I’d say, seek one out. For me, the challenge was that I work in such a niche industry that there weren’t many people who were literally like me.

I did seek out a lot of women, and I’d say I have really good relationships and people I go to for advice. I think the most traditional mentor is someone you have a longstanding relationship with and call weekly, monthly or annually.

Maybe I have a bit of a romantic vision of mentor in my mind. I certainly have significant relationships with people in different areas of the industry that have a lot more experience than I do.

Where I feel I have a little less is that in the specific area that I do, it’s been such an odd path. They always say, “Seek out someone who has the job that you want to have one day.” I haven’t found it. I guess I haven’t quite figured out what the job is that I want to have one day. I’m not sure where I’ll be in five or 10 years.

How would you describe your niche?

It’s storytelling. It’s programming. What I love about my job is, I’m so super involved with people’s personal stories. I love interacting with people. I like looking into their lives and telling their stories.

The stuff you saw me do is a little bit light. This isn’t that heavy. With a lot of the stories I do and the things I tell, there’s a very significant life-changing event around them. Those are the ones where you’re really telling someone’s story that is so meaningful for them.

I think that strikes me the most. I feel very beholden to those stories and to those people, and I want to make sure I tell it as sincerely as possible.

Down the road, I’m probably going to turn in a direction where I’m less hands-on, but right now I still love being in those stories, as opposed to overseeing them. It definitely is what makes me get excited.

It also still makes me get excited to start at the beginning of a project and have no idea how I’m ever going to get it done or what it’s going to look like at the end and be anxious, panicked and worried. “There’s no way. I don’t have enough money. We don’t have enough time. What’s it going to look like?”

No matter how many times I do it, there are always those feelings at the beginning of a project. Then at the end, you look back, and there’s a lot of pride, ownership and satisfaction in feeling like you took it to the opposite side of that street where you really love the product you put out.

I really value that process. If I ever stop feeling that way entirely, I don’t think I would do very good work.

What did your 20s teach you?

I would never want to be in my 20s again. What’s the saying? You don’t know what you don’t know. That’s how I felt about my 20s. Thank God I didn’t know, because if I knew, I might not have made all the choices that I did.

I guess my 20s taught me to be bold. I had a bit of fearlessness that probably came mostly from a lack of awareness. It was almost a blessing. I feel like I was so young and naïve that I made decisions and took chances that maybe I wouldn’t have, if I had known what the heck was going on, or what I was really doing.

In my 20s I probably spent, as I’m sure everyone does, a lot of time figuring out who I was. I think that’s a loaded thing to say, “Who are you?” I don’t know if any of us can define it even now. It was having confidence in what I was doing, and really believing in myself.

You can say the words, but to really mean it when you say you believe in your opinion, the things that matter to you and what you’re doing, and to really inhabit those words, it’s something different than to just say them. I think in my 30s I started to really be able to do that, based on all the experiences and things I’d gone through.

What are you teaching your 30s?

My 30s are about action, I think. They’re about coming to terms with the choices I’ve made.

What you said to me really resonated when we spoke: making choices and learning that the idea of having it all is a ridiculous standard to hold ourselves to, but I think only now in my mid-to-late 30s am I really coming to terms with what that means.

I’m very career oriented in a way that I’m very satisfied with, but it’s not as easy a path as I thought it would be coming out of Amherst, where everyone just tells you, “You’re awesome, you should go do your thing, and the world is a great place.”

Then you get out there and say, “They don’t necessarily like these smart, aggressive, go-get-‘em women as much as they say they like them.” They say that’s what they want out there and that we’re all equal, but it’s actually kind of not true.

That was a surprise for me. I came from a very padded background where I was constantly nurtured and told that things were great. I appreciate that that’s where I came from, but it was a bit of an awakening to go out into the world and find that there were still very serious degrees of separation between expectations, limitations and freedoms for men and women in different careers.

Saying it, I almost feel naïve. There are a lot of people out there that would say, “Duh.” I was just so bought into that sort of lovely liberal arts education, saying, “You can do this.”

I’m glad I did, because if I hadn’t had that naiveté to me, I probably wouldn’t have gotten as far as I have. At the same time, it’s made me aware now in my 30s of how important it is to continue the conversation, and not let go of talking to women about why you need to stand up for and speak for women’s rights and feminism.

I think this is the biggest thing for me. When I was in my 20s, I didn’t want to be identified as a woman. I just wanted to be a director and a producer. I was not interested at all where my gender fell in that. “Don’t single me out for that.”

Now I really want to be a woman. I really want to talk about it, and I really want to be someone that other people can talk to. It’s incredibly important.

I’m not really embarrassed that when I was in my 20s I didn’t have that awareness, but I can see now that it was really short-sighted of me.

I feel like feminism has become this dirty word. And that there are a lot of people in the younger generations that don’t really want to identify themselves with that because it feels very aggressive, which I can relate to, because it felt so to me as well.

I’m looking for a different environment. I want to create something where women feel really comfortable being really proud to be women and standing up for that, without feeling like that’s an aggressive stance. I feel like we were in one place in the ‘60s, and somehow we’ve gone backward at times.

You talk about being very career-oriented. Can you talk about some of the things you decided not to do in the pursuit of your career?

I don’t know if they were conscious decisions. I never decided not to get married or not to have children. I’m not sure where I stand on those things.

If you ask me if I want a family, my answer is yes. If I’m being honest, I’m getting older. I’m facing different choices than someone who is 25. I certainly feel like doing what I’ve done was the right thing for me. I’m not sure that I could’ve done both.

I was never in a position where I met someone and wanted to be in a relationship and then have a kid. That didn’t arise. It wasn’t like I had the choice and then said, “No, I don’t want to have kids,” or “No, I don’t want to get married or end up in a serious relationship.” It was more that it didn’t come up.

I don’t think I would’ve made the decision to stop working and raise kids as a stay-at-home mom. I don’t think that would’ve been a decision that worked for me. I’m well aware that by constantly working and doing this kind of stuff, I’m not doing other things.

That’s a tough one because it’s one I’m still dealing with. I’m not 45 looking back. I’m right at the place where I think, “If you want to have a family and if you want to have a kid, do it now.” I wish I had more of an answer for you on this one. I think I still have questions for myself.

I’ll interview you again in 10 years to get that answer.

Interview me in 10 years, and I’ll tell you what happened.

It’s not easy. I’d like people to know that it’s not easy. Along with that, I want them to know it’s okay for it not to be easy.

I feel like there are all these romantic notions about life, and they’re not dispelled very much. It’s okay that life isn’t easy. It’s okay that there are hard choices. Instead of looping around with this “you can have it all” notion, let’s be more up front about the hard choices people have to make in terms of choosing between or balancing with their career, partners, jobs and lives.

I certainly spent a considerable amount of effort over the years trying to go after the ability to be everything. It’s always been challenging to come up short. Only recently have I realized I can’t have it all. That’s when you start to make peace with your decision.

I don’t regret anything I’ve done. I wish I had a little more knowledge and awareness of these things on a more realistic level earlier, but I certainly don’t have any regrets.

I reviewed a book called “Wonder Women” on the blog. I hate the cover and the title of the book, but it makes some really good points and observations about what it’s really like as a woman at different phases in your life, all the way through to when you’re in your 70s trying to ward off wrinkles. It gave me some foresight I needed.

That’s really interesting. I’d love to read it.

On a side note, I’m a big fan of reality. It sounds so silly. I think reality is a lot more interesting, nuanced and attractive than these stereotypes that we perpetuate, like about what things should be like. It’s messier and dirtier, but I’ll tell you on a personal level and a professional level that it makes for a hell of a more interesting story.

I’m going to pick up that book. You think you’re smarter than that. We’re all 15 and we know the movies aren’t the way life is. We know that, but we’re still confronted with feeling like we come up short when we don’t achieve these ideas of beauty, success and what it means to be a woman, even though we know they’re unrealistic.

It’s this battle. It’s like you’re running yourself in a circle. You know intellectually that it’s wrong, yet you’re fighting these feelings like you secretly should be achieving them.