Today we’d like to introduce you to Chelsea Ragland.
Hi Chelsea, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
My story is a little difficult to tell in a straight line because I’ve never really been just one thing.
Professionally, I’m an attorney. I started my legal career in Big Law, where I spent several years working in finance before eventually transitioning in-house. I’m incredibly proud of that part of my life. Becoming an attorney required a lot of discipline, sacrifice and, frankly, growing up. For a long time, I think my career was probably the easiest way to explain who I was: I was Chelsea, the lawyer.
But outside of work, there was always so much more life happening.
I’m a wife and a mom of three. Motherhood has shaped me more profoundly than anything else I’ve done, both through incredible joy and unimaginable loss. In 2023, my husband and I lost our infant son. There really isn’t a version of my story that skips over that chapter because it changed me. Grief has a way of forcing you to reconsider what matters, who you are and what you want your life to look like. At the same time, life continued to give us reasons to celebrate. Today, we are raising our two daughters, building our family and learning that joy and grief can exist in the same life—and sometimes in the same moment.
Somewhere along the way, I also started sharing more of myself online. What began pretty organically—motherhood, family, things I loved, things I found funny, my opinions on pop culture and everyday life—slowly grew into a community. I realized that people weren’t necessarily following me because I had perfected some particular niche. They were connecting with the whole person. I could be an attorney during the day, come home and be Mom, obsess over reality television after bedtime, talk about something deeply meaningful one day and something completely unserious the next. That was actually the point.
That realization eventually led me to create Mommy Cigarette Break, my podcast. Despite the name, it isn’t really about cigarettes. The “cigarette break” is the metaphorical break—the moment when you step away from everything everyone needs from you and get to be a person again. The show gives me room to talk about motherhood, culture, relationships, grief, reality TV, current conversations and all the complicated things in between. It has also given me a space to use my voice in a way that feels different from anything I’ve done professionally.
My life today is really a reflection of all of those pieces coming together. I’m practicing law, raising my family, creating content, and growing Mommy Cigarette Break, and this journey has taught me that we are allowed to be multidimensional—to be ambitious and deeply devoted to our families, to experience grief and still make room for joy, to take our work seriously and still have fun, and to continue becoming new versions of ourselves. I’m incredibly proud of the life I’ve built, but I’m equally excited about the fact that I’m still building it.
I’m sure it wasn’t obstacle-free, but would you say the journey has been fairly smooth so far?
It definitely hasn’t been a smooth road. The greatest challenge of my life has been losing my son in 2023. There’s no way to adequately explain what it means to lose a child, and I don’t think grief is something you simply overcome. You learn how to carry it while continuing to live.
One of the hardest parts of that experience was realizing that life doesn’t stop while you’re grieving. I was still a wife, still a mother, still an attorney, still someone with responsibilities and people who needed me. There were days when simply showing up required more of me than anyone around me probably realized. At the same time, continuing to live fully became incredibly important to me. I never wanted the worst thing that happened to our family to become the only thing that defined our family.
I’ve also had to challenge my own ideas about what success is supposed to look like. I spent so much of my life following a very traditional path: go to school, work hard, become an attorney, build a career. There is a certain comfort in pursuing things where the next step is clearly defined. Creating content and starting a podcast have been completely different. There’s no roadmap, no guaranteed outcome and no credential that tells you you’re qualified to do it. You have to be willing to put yourself out there, try things publicly, sometimes fail publicly, and keep going anyway.
I think both experiences, in very different ways, have taught me to be less afraid of uncertainty. I’ve learned that resilience isn’t always about pushing through or pretending something isn’t hard. Sometimes it’s allowing yourself to acknowledge that something is hard and still choosing to make room for joy, ambition, creativity and whatever comes next.
Appreciate you sharing that. What else should we know about what you do?
My work as a creator really lives at the intersection of culture, conversation and storytelling. Through my platform and my podcast, Mommy Cigarette Break, I talk about everything from reality television and pop culture to high-profile legal cases, politics, racial justice, motherhood, grief and the experiences that shape the way we see the world.
My legal background is a huge part of what I bring to those conversations. When a high-profile case is dominating the news, I can go beyond the headline and break down the legal theories, the strengths and weaknesses of a case, and what I think the likely outcomes may be. When I’m talking about politics or policy, I’m particularly interested in what happens after the headline—how decisions made by people in positions of power eventually trickle down and affect real families and communities, particularly those who are already underserved.
And then, sometimes, I just want to talk about Love Island.
I actually think that range is what sets me apart. I don’t believe being informed and thoughtful requires being serious all the time. I can spend part of an episode unpacking a complicated legal issue or having a meaningful conversation about race and inequality, and then spend the next segment debating an iconic reality television moment. On another day, we may go somewhere much more personal and talk about motherhood, grief, relationships or what it means to keep evolving as a person. I think people are multidimensional, and I want the things I create to reflect that.
There is also a lot of lived experience behind the way I approach these conversations. I’m still relatively young, but life has given me reasons to grow up in ways I never anticipated. I’ve built a demanding career, become a wife and mother, experienced tremendous accomplishments and tremendous loss, and had to learn how joy and grief can occupy the same space. Those experiences have given me a perspective that I probably could not have developed from professional accomplishments alone.
What I’m most proud of is creating a space where none of those things have to compete with one another. You don’t have to choose between being the woman who wants to understand what’s happening in the world and the woman who has very strong opinions about reality TV. You can care deeply about your family, your community and serious issues and still laugh, be entertained and enjoy the lighter parts of life. That’s what Mommy Cigarette Break and my platform are becoming: a place for smart, layered, sometimes difficult, sometimes hilarious conversations—and I think that feels a lot like the women I’m creating it for.
If you had to, what characteristic of yours would you give the most credit to?
Resilience, without question. I’ve learned that success has much less to do with everything going according to plan and much more to do with your ability to keep moving when it doesn’t. Life has required me to pivot, rebuild and keep showing up through circumstances I never could have anticipated. I think my ability to do that—while remaining ambitious, curious and open to what life can still become—has been one of the most important qualities behind everything I’ve accomplished.
Contact Info:
- Instagram: https://instagram.com/chelsearagland
- Facebook: https://www.facebook.com/share/1BzNtdqDgY/?mibextid=wwXIfr
- Youtube: https://youtube.com/@mommycigarettebreak?si=1-Sjb1Qer4WVel_b
- Soundcloud: https://podcasts.apple.com/us/podcast/mommy-cigarette-break/id1894771088?i=1000787447094
- Other: https://open.spotify.com/show/2QCTbI3VBvrg7dqafkspZt?si=wNGe4ZWXT5qT3hlYgPu4Cg&utm_source=copy-link
