Local journalism is in the process of reinventing itself, and Rebekah Monson, the co-founder, and COO of WhereBy.Us is one of the leading voices driving change across the industry. 

“We’re all trying to basically rebuild an entire business model, and I think women have been on the forefront of that,” she said. 

Rebekah Monson

I spoke with Monson as part of Women in Journalism, a project published in Solution Set to shine a light on the successes and struggles of women working in news, lift up their stories and achievements, and share their words of wisdom to guide young women in the space toward finding their own success.

At WhereBy.Us, Monson is helping build Letterhead, an editorial email platform. WhereBy.Us’s runs five local newsletter brands, Miami’s The New Tropic, Seattle’s The Evergrey, Portland’s Bridgeliner, Orlando’s Pulptown, and Pittsburgh’s The Incline. Monson also co-founded Commissioner, a local art membership program, and Code for Miami, the city’s first civic hacking organization. Monson serves on several professional and civic boards aimed at improving journalism, technology, and civic life, including LION Publishers and the Miami Foundation.

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Here is a condensed and lightly edited version of my conversation with Monson:

Why did you choose to pursue a career in journalism? 

I was always into storytelling from the time I was a kid. In high school, I worked on the yearbook and I was always drawn to publishing. When I got to college I was majoring in sciences and I realized about a year and a half in that I didn’t want to go to medical school and I didn’t want to do research. I realized that I was sort of “science curious” but I didn’t want to make a career out of it. I started working at the school paper at Louisiana State University, The Reveille, and I just fell in love with it. 

News design was sort of a growing field and I was doing early data visualization and some investigative work. I’ve always enjoyed meeting new people in the community, exploring what our community’s about, and surfacing up these stories and it really stuck. 

I have stayed with it but in a different way than my initial intro to journalism. I started out as a news designer and copy editor, mostly on print products. Over time, my career evolved to make use of digital skills that I had always had since I had been building websites since the 90s. 

Eventually, those things merged, and now I’m in this news product universe which is a dream come true in many ways. I spent a lot of time early in my career not understanding how all the things that I cared about with regard to storytelling and how we communicate and what stories we tell and how we tell them, could intersect. Here I am almost 40 and it’s making sense so that’s pretty cool. 

Do you have any role models or mentors in the journalism field or in general that you look up to? 

So many. I had a professor when I was in college, Dave Kurpius, who was incredibly important to my formative journalism training. I learned about civic journalism under him and I just fell in love with the role that journalism can play in the community and the intersection with social justice. I have had great bosses. My career started with The Spokesman-Review and from there on through the Sun-Sentinel, and I’ve always had very good managers.  

Mitra Kalita is somebody who is very important to me and is a friend, but also someone who I know will tell me straight what I’m thinking and check my thoughts. She’s also a big and ambitious thinker and I admire that. 

I’m always paying attention to what Stacy-Marie Ishmael’s doing and Millie Tran, both of whom are doing incredible work with The Texas Tribune. Both of them have had a massive impact on my universe in journalism, whether they realize it or not, there are huge inspirations to me. 

Also, the News Product Alliance that is forming and establishing itself has been a critical society for news design and has been really important to my career. I have a number of friends and colleagues there who are better designers than I will ever be, but I’ve learned a ton from them and from that organization.  

I’ve had the privilege to work with a lot of really great design thinkers and that’s been an asset, but I would say the person who really changed my career is Miranda Mulligan, who’s now one of my very closest friends. Back when she was at Knight Lab, she did a workshop that I helped coach and she saw that I was drifting and I wasn’t sure where I fit in. 

Her job at the time was to help bridge computer science and journalism so she introduced me to a ton of people. I made a ton of friends in journalism and Miranda really opened those doors for me. I’ve been very fortunate and I’ve found that women in this industry, in particular, are incredibly eager to lift each other up.  

What advice would you give to your younger self when you were just starting out in journalism? 

I think there’s a confidence gap when you’re that age and you’re just getting started. I think that’s the hardest thing to overcome, that impostor syndrome. When you get older, you start to learn that nobody really knows what they’re doing. We’re all making it up as we go along. It’s important to not worry about where you rank so much as what you’re learning and what you’re making.  

I think it’s easy to get caught up in the rat race part of any career. I’ve never been super driven by that, but I’ve always been interested in expanding my skills and experimenting. I was really scared to do that early in my career in ways that I didn’t realize then, but I realize now looking back. 

I would keep my mouth shut when I had ideas because I didn’t think that I was worthy yet. I wish I had that growth mindset a little bit earlier and also the self-confidence to be more open about what I was learning and how we could apply it. I had great bosses who really drew that out of me and I’m lucky for that. The voice in your head is not always your friend when you’re just starting out. 

How do you feel women are represented in your area of reporting? How do you think the business challenges facing the news industry have impacted the representation of women in your field? 

It’s interesting, but I really think a lot of women are leading in this part of the business at this point. Part of that is because a lot of product leaders come through social media at some point in their careers. When social media was forming, almost everybody in that area was a young, smart woman, and there are exceptions to that, but there are a ton of them and a lot of those people have gone on to just broaden their roles over time. 

If you look at News Product Alliance and Becca Aaronson, who’s running it, she is an amazing person. She didn’t come from that background, but she has accelerated very quickly in her career because she has this product mindset and I think that’s true of a whole bunch of these folks. I look around at my side of the industry and I don’t think there is perfect gender parity, but I think some of the really great thinkers and leaders in this part of the universe are really smart women. 

A lot of this started with social media, but some of it didn’t. There are a lot of smart women who early on thought that our business and editorial operations being completely separated doesn’t do us any favors. These women were willing to take on those tough challenges early, and that’s why I think it’s taken them years and years to be taken seriously. And now they are, in part because the industry desperately needs that experience and knowledge and wisdom.  

We’re all trying to basically rebuild an entire business model, and I think women have been on the forefront of that. At every major journalism institution, if you look around, there are really smart women who are figuring out these big questions about product technology, revenue models, and how we bridge the gap between that and our mission. It’s not a perfect representation by any stretch, but I think it’s a very promising part of the industry for women in many ways. 

Do you feel like you need to make sacrifices in your personal life to compete with male coworkers?  

Yes, but unfortunately, I think that’s just a universal experience of women. I think there are going to be times when you’re going to face sexism discrimination. It’s critical for women to have a very strong support network and a very strong mentorship relationship.  

I don’t think anyone coming into any kind of corporate environment should expect that we’ve gotten over sexism. Just like we certainly haven’t gotten over racism. Anything that I might experience as a white gender non-conforming, but female-identifing person is negligible in comparison to what my colleagues of color experience on a daily basis. You need to be prepared for that in this field and in every field, and I think we have an obligation to help support each other and lift each other up. 

One of the things that I think is really exciting about people like Mitra Kalita and Stacy-Marie Ishmael and these leaders who are particularly women of color is that they’re charging forward in this new path of digital-driven leadership that’s super smart, editorially, but equally smart about product and business. As those people gain power, they’re starting to open up all kinds of opportunities for the people behind them, and to foster the careers of other women and people of color. 

These folks are really committed to making diverse news organizations in a way that I don’t think I’ve seen in my career, and that is incredibly exciting to me. I hope that by the time I’m old enough to retire out of this field, we aren’t talking about this anymore. Do I think that that’s likely? Maybe. But I think we can make a big dent in it totally. 

Are there ways that being a woman has been advantageous or helpful to your journalism? 

I think there are always advantages and disadvantages to any lived experience. I think I have a more solid, amazing incredible network as a woman. I don’t know any of my male friends who have that many people in their orbit who are trying to help them along. I have found that women in our industry are incredibly supportive of each other, and I think that’s great.  

I also think that sometimes being a woman gives you a different perspective on an issue or how to get a job done. That is valuable in product development and in storytelling. 

What point in your career was the most difficult for you (either an age, certain role, or specific instance) and how did it affect the way you think about the journalism field now and where it’s going? 

Before we started WhereBy.Us, I was working at the University of Miami. The reason I had ended up there was that in my last job at the Sun-Sentinel, which is a great local paper, I worked a bunch of different roles in the newsroom and I couldn’t see an upward trajectory for myself. 

If I had stuck around for maybe another year or so, there probably would have been something there in the product space, but that doesn’t exist when I left. It was heartbreaking. To think there may not be a space there for you is a hard thing to grapple with. I was very fortunate because I left that role and maintained great relationships with and the utmost respect for my former colleagues. 

I started working at the University of Miami and eventually started taking classes in their interactive media program, which was incredible. It reinspired me and reinvigorated me and was also when I met Miranda Mulligan, who showed me a future that I couldn’t see.   

What’s happening in the product ecosystem now is that there’s just a lot more dialogue about it and more energy behind it. I’m really excited about that because I think there’s a lot of people who are going to be drawn to this work, and my hope is that they’ll have a better guide on how to get into the space, elevate themselves, and move up in their careers, as well as what skills they need to master. We have this community that’s been building over time and now finally getting a foothold. 

Do you mentor other women? What’s your approach to mentorship?  

I do have several mentees; some of them are in media, some of them are in technology and some crossover. I also host open office hours on a weekly basis for people from underrepresented backgrounds in media and technology. People come for a little advice, then we chit chat, and maybe I can make some introductions for them.  

I do that work for a number of reasons. One, because I aspire to be a person who lifts other people up who are smart and may not understand how to play the game or how to open doors for themselves. And a lot of the folks that I end up talking with who are earlier in their careers, they’re seeing entirely different stuff than I am at this phase in my career. It’s an opportunity for me to learn what they’re struggling with, what they’re thinking about, and to help them with career development and personal growth.  

It’s the most rewarding work I do and for me, it’s a cornerstone of my professional practice. I can’t imagine my life without great mentors and I can’t imagine my life without also putting that energy in the universe for other people as well. 

What do you hope for the next generation of young women entering the journalism field? What are your hopes for them? What would you like that space to be like?  

I hope many, many more of them take the leap into entrepreneurship and I hope many, many more of them get the opportunity to build their own destinies. I don’t have a lot of faith that the current, established systems are going to evolve fast enough and so I’m 100% in favor of disrupting them to make other paths for ourselves. 

That’s not everybody’s path, but I just want to see many, many more women taking on this opportunity. If you look around right now, it’s happening. If you look at projects like MLK 50 and Detor, Detroit and Outlier Media, and The 19th, it’s freaking happening. 

Those are all people who are top of their game and they’re carving their own path, making it easier and easier for women to see a way forward that doesn’t involve trying to pull their way up the corporate ladder. I think it’s an incredible skill-building opportunity to start your own business and to create something from the very beginning. I think it’s a very rewarding and exciting thing for journalists to do. 

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