Look Both Ways Podcast

About Look Both Ways Podcast

Look Both Ways is a podcast about building careers while raising children, and the stories of women who are doing both. Hosted by Jenna Randolph, each episode dives into honest conversations about ambition, identity, resilience, and motherhood. From career reinvention to burnout, from raising babies to letting them go, from chasing dreams to rebuilding from scratch — Look Both Ways explores what happens when we let ourselves be fully human: messy, brilliant, complicated, and constantly evolving. This is the space where women stop apologizing for wanting more, tell the truth about the hard parts, and learn to trust the journey — even when it looks nothing like they planned. lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast)

Publisher

Jenna Randolph

Category

business · kids & family

Language

en

Explicit

No

First episode

7 Nov 2025

Latest episode

2 Jun 2026

Latest episodes

16 episodes in the feed.

1. 

   2 Jun 2026

   Passionate, Beautiful, Chaos: Kathleen Ferguson on Grief, Grit & Betting on Herself

   We talk about resilience like it’s a personality trait. We don’t talk nearly enough about what it looks like while you’re inside it. The messy middle.The destructive phase.The fork in the road where you either keep numbing… or you decide to build. This week I sat down with Kathleen Ferguson. Founder. CEO. Mother of three. Competitive bodybuilder. Community builder in the fitness industry. But none of that is where her story starts. At 26, she lost her first husband to melanoma. Six months after their wedding. There was a period that followed where things got dark. Grief rarely behaves politely. And eventually she hit a moment that so many of us recognize — the quiet, internal choice: Stay here.Or redirect. She redirected. She became a personal trainer in 2009. No Instagram. No apps. No scalable business model. Just 5 a.m. clients, long split shifts, and belief. Then came motherhood. Three kids. Fifteen and seventeen months apart. Working through pregnancies without real maternity leave. Building other people’s brands. Absorbing limiting beliefs about what she was capable of. At one point she said, “I didn’t even remember what music I liked.” There’s a phase of motherhood that feels like a tunnel. You are feeding everyone else first. You are trying to be fully present at home and fully competent at work. You apologize for running a load of laundry between Zoom calls. And somewhere in there, you disappear a little. What I respect about Kathleen’s story is that she didn’t frame that season as failure. It was evolution. She hired a life coach. She started unpacking the beliefs she’d been carrying for years. She realized she had been building everyone else’s vision but shelving her own. So she stopped. She launched Coach 360 — a platform designed to address retention in the fitness industry — even when the timing felt anything but perfect. There is something powerful about building before you feel fully safe. And then, because her reinvention wasn’t complete, she stepped on a bodybuilding stage in her 40s. Not because she needed validation.But because she wanted to see what she was capable of. Her three words for this season: Passionate. Beautiful. Chaos. Motherhood isn’t balanced.Ambition doesn’t disappear.Identity shifts.You evolve. If you’re in the tunnel right now — it won’t last forever. And if you’ve been sitting on something that feels too big or too late… Maybe it’s neither. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

2. 

   20 May 2026

   Intentional, Becoming, Unbecoming: Lindsay Tigar on Writing Her Own Next Chapter

   We talk a lot about following your dreams.Not nearly enough about what it looks like to follow them before everything is figured out. This week, I sat down with Lindsay Tigar, award-winning journalist, fractional brand and storytelling executive, and mother of two, who is packing up her family and moving from Asheville, North Carolina to Copenhagen, Denmark. The visa is not fully approved.The house is on the market.The boxes are not packed.And they are going anyway. Lindsay built her career the way many of us were taught to, intentionally, ambitiously, and with a plan. From interviewing strangers at the grocery store at age five to writing for National Geographic, Vogue, Travel + Leisure and Time, she has always known who she wanted to become. Motherhood disrupted that certainty. We talk about the identity shock of early motherhood. The pressure around breastfeeding. The moment she realized that if she was not going to be with her daughter all day, the work she was doing had to matter. The quiet grief of leaving a “dream house” that does not actually fit. And the courage it takes to move toward joy, even with so many uncertainties. Enjoy. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

3. 

   5 May 2026

   Everything that Matters: Hillary Applegate on Choosing Her Own Path

   How Hillary Applegate Designed a Career She Never Had to Choose Between We talk a lot about women “doing it all.” Not nearly enough about the women who actually planned for it. This week I sat down with Hillary Applegate, founder and CEO of Digital HQ, a social-first marketing agency working with brands across industries from “aerospace to guacamole”. Hillary is one of the rare people who looked five years down the road, made a calculated bet on herself, and then had a baby, not the other way around. She grew up in Silicon Valley in the nineties, when the whole region felt electric with possibility. Both her parents were entrepreneurs, so watching her dad drop her off at school and disappear into a flexible, self-directed day imprinted on her early. She didn’t have the language for it yet, but she knew the 9-to-5 mold wasn’t going to fit. She started college studying psychology. Partly her mom’s influence, partly her own curiosity about how people think, until a lab experiment involving a stage, a heart rate monitor, and an audience sent her straight to the registrar’s office to change her major to marketing. Same day. What followed was a front-row seat to the early days of social media as a legitimate career. She was pitching Snapchat to university marketing heads in 2013 while one guy across the table asked if it was “the sexting app.” She was right. They eventually figured that out. She had already moved on. She spent five years growing a social department from zero to nearly a million in revenue before making the move that mattered most: in January 2020, she launched Digital HQ. Not because the timing was perfect. Because she knew if she waited until after kids, the risk would feel impossible. Five and a half years later, she was pregnant. What I kept coming back to in this conversation was how deliberate all of it was. The decision to go out on her own before having a baby. The decision to build a team rather than stay a solo consultant. The decision to take Fridays off and spend them eating whipped feta with her one-year-old daughter. We also got into the realities nobody likes to say out loud… the loneliness of freelance, the ebbs and flows of client work, the way motherhood didn’t change her ambition so much as it quietly reoriented where her sense of self actually lived. Her advice for women trying to figure out their own version of this? Pick your partner carefully. Build your village. And stop waiting for a version of the plan that feels completely safe, because that version doesn’t exist. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

4. 

   21 Apr 2026

   Bumpy, Exciting, Rewarding: Margot Denommé from Crown Attorney to Digital Safety Advocate

   We spend a lot of time talking about building a career with a clear destination in mind. Not nearly enough time talking about what happens when that destination evolves. In this week’s episode, I sat down with Margot Denommé, and in a lot of ways, she always knew what she wanted to do. At 12 years old, she was reading real murder trial transcripts. Not for school. Not for a class. The criminal judge who lived across the street would give them to her. She’d read them, go back, ask questions, and try to understand how it all worked. From that point on, the path felt pretty clear. She was going into criminal law. And she did. Law school, then into a career as a Crown attorney that lasted 26 years. She saw things most of us will never see. Not just the cases that make headlines, but the ones that don’t. And for a long time, that was the work. Until something started to shift. It didn’t happen all at once. It started in classrooms. She began taking time away from work to talk to kids. At first it was about self-esteem and self-worth. What she calls the culture of comparison. But over time, what she was seeing in court and what she was hearing from kids started to connect. And then the research started to catch up. Studies around social media. Rising anxiety. Depression. Self-harm. The realities kids are dealing with online, often without any structure or guardrails. She paid attention to that. And eventually, she left her career and started building something new. Today she runs RAD, Raising Awareness about Digital Dangers, and wrote the Family Smartphone Guide to help families understand what kids are actually navigating. Things like digital footprints, cyberbullying, online predators, and the mental health side of all of it. There’s a moment she shared that stuck with me. The same day she gave her notice, she heard on the radio that school boards were suing major social platforms, and the lead litigator was someone she went to law school with. She took that as confirmation she was on the right path. Whether or not you believe in signs like that, I think the bigger point is this: Sometimes the things you’ve spent years doing are exactly what prepare you for what comes next. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

5. 

   7 Apr 2026

   Intentional, Demanding, Rewarding: Paula Comfort on Hard Work and Betting on Yourself

   Paula Comfort arrived on a boat. Not metaphorically. Literally — on the HMS Corinthia, crossing the Atlantic from England to Canada because her family couldn't afford to fly. She didn't know she was on a boat. The ship was too big to comprehend. Looking back, it's the perfect metaphor for Paula's entire life: moving toward something enormous without fully knowing what it was yet. Just trusting the direction. Just doing the work. Her parents had already shown her how that worked. Her father — a gifted athlete, a high academic achiever, a man who could have gone further if his family had the money — became an electrician. Then an engineer. Then a man who came home from a long day and went straight to his books. Her mother started as a bank teller, spent thirty years at the same institution, and became the person every young employee came to for advice. Paula watched all of it. And she learned. By grade seven she was getting cut from teams. By grade nine she was sitting on the bench — again. But something in her kept pushing. Her basketball coach, Linda Kirkpatrick, saw it early. Even as the youngest and the shortest, Paula was the one people gravitated toward. The one who debriefed the game on the bus ride home. The one back in the gym the next morning at 7 AM. She didn't just build resilience on that bench. She built a blueprint. From kinesiology at Waterloo — 20 hours of classes, 20 hours of labs, weekly — to a part-time job at a health club where they handed her the keys within a month. From a fitness director role to running a $3 million business at 23. From five clubs to eighteen years with Sports Clubs of Canada, eventually overseeing 23 locations as their most senior executive. Paula didn't walk a straight line. She ran. She got married at 34. Had three daughters at 36, 38, and 40. Got promoted to the most senior role in her company — while seven months pregnant. Managed international travel across 13 global openings while making sure she never missed a Christmas concert. The nanny. The carpools. The 9 PM calls with China on a Sunday night. She made it work. Until the moment everything fell apart. A toxic new leader. A public shaming. Legal battles. Her husband's own career restructure. Two mortgages. Three daughters. The realization that the company she had helped build — the one she called her baby — had changed beyond recognition. Everything stripped away. What came next was the chapter no one plans for — and the one that defines everything. Consulting work that barely covered the gap. An executive coach helping her get back to her why. A retainer from an Orange Theory owner that closed the financial gap just enough. A slow pivot toward recruitment — something she was uniquely positioned to do better than anyone, because she had actually lived the business from the inside. Today, Paula is the founder of Higher Ground Talent, an executive recruitment firm placing senior leaders across the health, fitness, and wellness industry. She brings something no one else in the space can: 30 years of operating at the highest levels of the industry she now serves. When I asked Paula to describe her career and motherhood in three words, she gave me three good ones. Intentional. Demanding. Rewarding. Intentional — because every year, she scrolls through every photo she's taken and writes down her reflections: the highs, the hard moments, and how she came through. She did goal-setting exercises with her daughters when they were small. She has a folder for every year. Demanding — because her husband still says he can't keep up with her, and her daughters might argue she kept them in gymnastics a little too long. And rewarding — because she looks at those daughters today, and their networks, and their discipline, and she knows something about how those things were built. Paula's story isn't about having perfect timing. It's about a woman who was handed a work ethic before she was old enough to name it, who built a career one unglamorous rung at a time, who lost almost everything and rebuilt — and who found that the relationships she tended through all of it were the thing that held everything together. "The minute you start pulling away from your core values," she says, "they're out." She's been tested on that. More than once. She's still here. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

6. 

   10 Mar 2026

   Be Your Own Prototype: Marie Berry on Bone Health, Rucking & Reclaiming Her Roots

   Marie Berry’s story starts before she was even born. Her German parents received a fax about a baby in Bolivia who would soon be available for adoption. Two days later, they decided to adopt her — and within a week they were on a plane to Bolivia to bring her home. That beginning set the tone for a life defined by bold moves. Marie grew up the only brown-skinned child in a small German town, surrounded by blonde-haired siblings. Instead of seeing her adoption as something that made her different, she saw it as a superpower. From there, she chased the world. London. Madrid. Paris. Shanghai. Roles at Adidas, Chanel, and Ford. Then New York — where she built and exited a marketing software company during one of the most chaotic seasons imaginable: a newborn, a pandemic, and a cross-country move to Miami. But the next chapter of Marie’s story didn’t start with a business idea. It started with a diagnosis. At 38, despite being a lifelong athlete and triathlete, Marie was diagnosed with osteopenia — early bone density loss. The more she researched the statistics around women’s bone health, the more shocked she became. So she did what entrepreneurs do. She started solving the problem. That journey led her to rucking — walking with weighted vests to improve bone density — and eventually to building YVO Warrior, a wellness brand and community helping women in midlife build strength, literally and metaphorically. Along the way, Marie also reconnected with something deeper: her indigenous Bolivian roots. And she realized the most important lesson of her career and life. Be your own prototype. In this episode we discuss Marie’s adoption story and upbringing in rural Germany Growing up feeling different — and why she experienced it as a superpower Living and working across London, Madrid, Paris, and Shanghai Building and exiting her marketing software company during COVID Giving birth while running a startup and navigating early motherhood The mindset shift from “I’m a founder who also has kids” to “I’m both” Her osteopenia diagnosis and the overlooked bone health crisis for women Why she’s on a mission to make bone health sexy The rucking movement and building the YVO Warrior community Reconnecting with her indigenous identity Why flow state matters more than hustle Memorable Quotes from Marie “I didn’t experience my adoption as a wound. I experienced it as a superpower.” “Fun was my biggest KPI in my twenties.” “Before I would’ve said I’m a founder who also has a kid. Now I say I’m both — equally.” “One in two women over 50 will have an osteoporosis-related fracture, and we’re not even talking about bone health.” “How can we turn the burden of life into strength, opportunity, and communal power?” “Find out who you are and do it on purpose.” “Be your own prototype.” Who This Episode Is For This conversation is for the woman who: Is building a career while raising kids Has followed an unconventional path Is entering midlife and rethinking strength and health Wants permission to evolve Feels the pull to build something more aligned with her truth YVO Warrior A wellness brand and community helping women build bone strength through rucking and community movement. Follow along for: - Bone health education - Rucking workouts - Community walks - Midlife strength training This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

7. 

   24 Feb 2026

   It’s a Balance: Norma Hogan on Burnout, Boundaries & Intentional Leadership

   When Norma Hogan describes her life a few years ago, it doesn’t sound dramatic at first. She was successful. She was leading. She was delivering. She had spent over a decade in senior customer success and operational leadership roles in tech. She was the kind of leader companies rely on — high output, deeply committed, capable of doing in three days what others might take five to finish. And then, slowly, her body started speaking. Her cholesterol climbed. Her blood pressure rose. She became pre-diabetic. Her doctor asked her a simple question: Are you stressed? Her answer was the one so many high performers give: “Well… isn’t everyone?” But there was a moment she couldn’t ignore. She had earned a work trip to Europe — including a stop at a breathtaking spa in Iceland. It was beautiful. Quiet. Restorative by design. And she couldn’t relax. Not mentally. Not physically. Her nervous system was so locked in fight-or-flight that even stillness felt impossible. That’s when it started to click: this wasn’t just a busy season. This was burnout. In this episode of Look Both Ways, Norma walks through how she got there — and why so many women in leadership roles are on the same path without realizing it. We talk about: * The subtle stages of burnout (and why high achievers often miss them) * The culture of overperformance in tech * The invisible labor of motherhood layered onto leadership * The trap of “you can have it all” becoming “you must do it all” * And the cost of being the one who can always handle more One of the most powerful parts of our conversation was hearing Norma reflect on her children telling her recently, “You’re nicer now.” It was both heartbreaking and clarifying. Because burnout doesn’t just affect performance.It affects presence.It affects relationships.It affects who you are at the end of the day. Norma now runs Intentional Leadership (https://intentionalleadership.ca/), where she works with founders and leaders to prevent exactly what she went through — or to rebuild after it. Her work blends leadership development, boundaries, nervous system regulation, and values alignment. When I asked her to describe her journey in three words, she said: It’s a balance. Not a daily time-management hack. Not a productivity framework. But a recognition that life happens in seasons. There are seasons to push. Seasons to build. Seasons to recover. Nothing in nature blooms all year — and neither can we. This episode is for the woman who: * Feels constantly “on” * Has built something impressive but feels depleted * Can’t remember the last time she truly relaxed * Or suspects her body might be whispering what she’s trying not to hear Norma’s story isn’t about abandoning ambition. It’s about building ambition that doesn’t cost you your health, your joy, or your family in the process. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

8. 

   27 Jan 2026

   Forgiveness, Grit, Becoming: Tammy Soares Does Not Believe in Failure

   Forgiveness. Grit. Becoming. Tammy Soares’s story is what happens when fierce ambition, deep love for family, and a nontraditional path collide—from a small mountain town to the president’s seat of a global digital agency, all while raising two kids and reinventing herself more times than she can count. This episode isn’t about “having it all.”It’s about becoming—again and again. From Mountain Roots to Big Possibility Motherhood was always part of Tammy’s DNA. She grew up with humble beginnings—camping in the Sierras, wearing hand-me-downs, watching her dad work for the school district. She could see the appeal of summers off and stability, but she was hungry for more possibility. She imagined becoming a kindergarten teacher, taking early childhood education classes while working full-time. Then Silicon Valley intervened. A tiny startup called Career Mosaic. A salary that dwarfed teaching. A leap that changed everything. The Degree She Didn’t Finish—and the Career She Built Anyway Tammy didn’t finish college—and for years, that fact was both a wound and a superpower. She left school assuming she’d go back “someday,” only to find herself promoted quickly, out-earning expectations, and building a track record that spoke louder than credentials. Still, she was warned she’d “hit a ceiling” without a degree. When Accenture later offered her a senior role, even their online application required a college field she couldn’t honestly complete. Ten anxious minutes after flagging it, the recruiter called back: “We don’t care.” Her work had already answered the question. Motherhood Didn’t Slow Her Down—It Split Her in Two Tammy had her son, Sam, in 1999. After preterm labor, she spent bedrest working from home—propped up with a turquoise iMac beside the bed. Six weeks after birth, she was back at the startup, nursing in her office with a pack-and-play nearby. She and her husband, Matt—her high school sweetheart—ran a relay. He took early shifts. She took late ones. Their baby had a full-time village even while both parents worked more than full-time. Office freezers filled with breast milk. “Do Not Disturb” signs during pumping sessions. A young leader modeling that a woman’s body and career could coexist in the same room. The First Big Reset: Staying Home When the startup sold and relocation wasn’t an option, Tammy made a radical choice for someone so driven: she stayed home. Sam was 15 months old. She was pregnant with Alyssa. She spent a year as a full-time mom—grateful, present, and slowly losing sight of herself. Everyone called her “Mama,” including her husband. Somewhere between laundry, dishes, and nap schedules, Tammy disappeared. The itch to work wasn’t a lack of love for her kids.It was a longing to feel like herself again. Reentry, on Purpose (and on Her Terms) Coming back wasn’t glamorous—and that was the point. Tammy took an inside sales role close to home: eight hours a day, no laptop, no late-night email. A way to rebuild confidence and income without sacrificing every moment with her young kids. She was wildly overqualified—and said so. “You get to benefit from this.” She crushed it: salesperson of the year, quotas shattered, grit sharpened. At the same time, she navigated a different kind of challenge—raising a strong-willed daughter whose big emotions were often mishandled by adults, leaving Tammy wrestling with guilt and heartbreak she couldn’t fix from the office. Another Pivot: The Deli Then came the deli. Tammy and Matt bought a small shop next to a cluster of schools, imagining community, flexibility, and ownership. Reality looked more like 4 a.m. openings, six-day weeks, and slipping out of camping trips at dawn to bake cinnamon rolls while her family slept. The sacrifice outweighed the return. She missed technology. She missed learning. She missed the version of herself who thrived on complex problems and big ideas. Selling the deli wasn’t failure.It was Tammy choosing a new path when the old one no longer fit. The Rocket Ship, Restarted Her return to digital started quietly—with an instant message from a former colleague. A new agency in San Luis Obispo. Small town. Big ambition. The perfect bridge between the mountain kid who loved trees and the woman who loved tech. That message led to leading major global accounts, building teams, and eventually becoming president of Rosetta. It also meant long stretches on the road—trips to Waterloo, Canada—while her daughter cried on the phone because she missed her mom, and her husband became the day-to-day parent at home. Tammy carried both ambition and absence. Seeing Gender Clearly—For the First Time In her 20s, gender felt invisible. She laughed off strip-club lunches. Snapped at a VP staring at her chest: “My eyes are up here.” Raised with brothers, she was comfortable being “one of the guys.” It wasn’t until she became president that women began pulling her aside to ask, “How did you break through?” Only then did Tammy look back and see the pattern: being passed over for roles she was already doing, brought in as the token female leader, called in last-minute so the room looked balanced. The role that changed everything? She had to walk into her boss’s office and say it out loud:“I want it. And I can do better than this.” A Redefinition of Failure Tammy doesn’t believe in failure. To her, failure means giving up—and she doesn’t. Lost clients, stalled roles, parenting missteps, even businesses that no longer fit aren’t dead ends. They’re data. You learn.You adjust.You choose a new route. That mindset is what allowed her to navigate career leaps, economic realities, and the complexity of raising two very different children while holding big jobs. Where She Is Now Today, Tammy is a seasoned executive, a human-centered technologist, and the mother of two grown kids who still call her “the best mom ever.” Her kids carry what they watched: independence, resilience, and permission to define success on their own terms. Her decades-long marriage—shaped by lean years, dual careers, deli dawns, and global travel—remains her anchor. Her leadership philosophy is simple:Stay human as you rise. Protect your people like a mama bear. Make more room for others. Three Words That Say Everything When I asked Tammy to describe her journey in three words, she chose: Forgiveness. Grit. Becoming. Forgiveness — for herself, for imperfect seasons, for the years she felt “behind” or “too much.” Grit — the daily choice to keep going, ask for the job, open the door at 6 a.m., book the flight anyway. Becoming — the understanding that there is no final version of you. You’re allowed to pivot, grow, and rewrite the script at 25, 35, 45, and beyond. This episode of Look Both Ways is honest and unvarnished—about ambition without a roadmap, motherhood without a tidy work-life-balance bow, and the courage to define success outside a traditional résumé. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

9. 

   20 Jan 2026

   You Got This: How Midori Charles Just Kept Going

   This is one of the most meaningful episodes I’ve recorded. Motherhood is not easy — and even in the most “ideal” circumstances, it can feel like a constant series of quiet and not-so-quiet battles. Midori’s story was not ideal. Hard hit after hard hit, the kind that could have taken her down — and nearly did. But she kept going. Small acts of kindness from strangers.A fierce determination to build a better life for her boys.And the decision, again and again, not to quit. This episode is a reminder to look around us — to notice the moms who are barely holding it together — and to be the hand that reaches out when it matters most. Trigger warning, this episode mentions suicide and suicidal thoughts. At 18, Midori enlisted in the Marines — much to her father’s dismay. Not because he didn’t believe in her, but because he was afraid. Afraid of what that choice would demand of his firstborn daughter. Afraid of the physical and emotional toll. Afraid, too, of a quieter truth: her parents made just enough money that college financial aid wasn’t an option, but not enough to pay for it outright. So Midori made a decision that would shape the rest of her life. She joined the Marine Corps.She learned discipline, leadership, and responsibility far earlier than most.She rose quickly.She led — even in rooms where she was the only woman. And then life intervened. A devastating knee injury.A medical retirement she didn’t choose.A pregnancy that complicated recovery.Postpartum depression.Isolation.No nearby family.No village. What followed wasn’t a graceful transition — it was survival. There were moments she questioned everything: her worth, her identity, her future. Moments where staying meant strength, not quitting. Moments where rebuilding meant starting over in ways she never imagined — learning to sew quilts just to make ends meet, returning to school while raising babies, redefining ambition in a body and a life forever changed. And still — she kept going. When I asked Midori to describe her journey in three words, she didn’t hesitate: “You got this.” Not because it was easy.Not because she always believed it.But because sometimes, those words are the only thing that carry you through. This episode of Look Both Ways is one of our most honest conversations yet — about career disruption, motherhood, mental health, and resilience. The kind that doesn’t look pretty on paper, but is earned the hard way. If you’ve ever felt like your path broke in half — this one’s for you. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

10. 

    13 Jan 2026

    Change, Strength, Love: Alexa Starks is Rewriting the Rules of Working Motherhood

    There's a moment many working mothers face that no one prepares you for: You return from maternity leave. You've done everything "right." You're exhausted, overwhelmed, maybe still healing. And instead of support... there's silence. No plan. No check-in. Just an expectation that you'll pick up exactly where you left off. That's why my conversation with Alexa Starks hit so close to home. Alexa Starks — founder of Executive Moms and a workplace culture innovator — built her entire career around climbing the corporate ladder. She had her path mapped out: SVP, C-suite, the works. She was ambitious, driven, and good at what she did in the fast-paced world of advertising operations. And then she had children. What followed wasn't just hard — it was isolating in a way she never expected. Despite working remotely, despite having flexibility on paper, Alexa found herself completely unsupported. Her first manager never mentioned a return-to-work plan. Her second pregnancy came with severe reflux that had her baby up six to seven times a night — and still, there was no conversation about adjusting her workload or checking in on how she was managing. She was visibly struggling. And no one said a word. Until she got sidelined for promotions and realized: this wasn't just her experience. This was the experience for so many working mothers. So instead of finding another job, Alexa Starks decided to fix the problem. In this episode of Look Both Ways, we talk about: Why the return to work is the most overlooked phase of new motherhood The moment Alexa realized she'd been pushed out — and what she did next How she's helping moms advocate for themselves with language they actually need The corporate workshops teaching managers how to actually support returning mothers Why having two babies in two years was intentional (the "bandaid method") The 5 PM Slack test — and why proving yourself never ends What made her family pack 10 suitcases and move to the Netherlands Life after leaving the U.S.: bikes, daycare four days a week, and no regrets The global study she's conducting on working motherhood (dropping December 2024) What I loved most about this conversation was Alexa's clarity. She didn't sugarcoat the struggle. She didn't pretend flexibility alone is enough. She named the invisible tests, the lack of language, the exhaustion of trying to prove you can still "hang" — all while running on no sleep and holding a screaming baby. Motherhood doesn't break your ambition. But the workplace often does. If you're in the thick of it — wondering why no one told you it would be this hard to come back, or why you feel like you're constantly failing some invisible test — I hope this conversation reminds you: you're not broken. The system is. And people like Alexa Starks are building the tools to change it. Resources mentioned: Executive Moms Reentry Blueprint Workshop — 15% off with code LOOKBOTHWAYS Free self-advocacy script at executivemoms.co (http://executivemoms.co) Global Working Motherhood Report (December 2024) You're not alone. And you deserve better than silence. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

11. 

    6 Jan 2026

    Roller Coaster Ride: Nazli Senyuva Offringa on What Nobody Warns You About

    From ER Hallways to Health Communication — Building a Career While Raising Two in a Pandemic What does it mean to grow up in an operating room — and then become a mother yourself? In this episode of Look Both Ways, I sit down with Dr. Nazli Senyuva — a health communication scholar, University of Southern California faculty member, seasoned journalist, and mother of two — whose work bridges research, media, and the lived realities of modern parenthood. Naz shares her journey from growing up in Istanbul with two surgeon parents — where the ER literally doubled as her playground — to moving to the U.S. for college, navigating academia, and unexpectedly becoming Turkey’s go-to COVID expert overnight during the pandemic. We talk about the shock of new motherhood despite writing a dissertation on pregnancy, the sleep deprivation no one truly prepares you for, and why she almost didn’t have a second child without her mom’s hands-on support. Together, we unpack identity loss, invisible labor, unrealistic media narratives around motherhood, the importance of flexible expectations, and why “just do it” isn’t always helpful advice. Naz also opens up about her new project, The Village — a platform designed to recreate the honest conversations and community many parents are missing in modern life. If you’re juggling career and kids — or wondering how anyone actually does this without crumbling — this conversation will make you feel seen, validated, and a little less alone. Topics We Cover Growing up with a surgeon mom who “just did it” — and the pressure that creates Why hospitals feel like a place of comfort (and what that says about childhood) Becoming a public health voice overnight during COVID Pandemic pregnancy, Zoom lactation consultants, and unmet expectations Sleep deprivation as a legitimate form of torture Why comparing your postpartum to social media is a losing game The difference between grandparent help and paid help Birth in the media vs. birth in real life Letting go of control — the hardest job of motherhood Why leaving your kids sometimes makes you a better parent This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

12. 

    16 Dec 2025

    Never Give Up: Mia Bjorkroos on Reinvention and Rebuilding from Survival Mode

    What does never give up look like in real life — not as a slogan, but as a survival skill? In this episode of Look Both Ways, I sit down with Mia Bjorkroos — a fractional COO, operational strategist, and global fitness industry leader who helped scale Piloxing into more than 90 countries, all while raising two sons. Mia shares her journey from growing up in Sweden, where parenting and partnership were modeled as deeply equal, to becoming a young mom in the U.S. We talk about navigating financial instability, building a travel-heavy international career, and later rebuilding her life after divorce. Together, we explore ambition, guilt, work-from-home boundaries, the emotional importance of support systems, and the self-development work that helped Mia move from survival mode to intentional living. If you’re navigating career + kids — and sometimes relationship + identity too — this conversation will make you feel seen and remind you that you’re not alone. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

13. 

    9 Dec 2025

    Beautiful, Chaotic, Transformative: Beth Potter Was Made For More

    Beautiful, Chaotic, Transformative: Beth Potter Was Made For More Jenna sits down with Beth Potter, who became a mom at 16, got emancipated, dropped out of high school, and bought her first house at 18. Beth opens up about running an in-home daycare for 12 years, not recognizing herself in family photos, and her pivot into the fitness industry. She talks honestly about climbing the corporate ladder while raising kids, hitting rock bottom with burnout in January, and what happened when her body finally said "enough." This conversation gets real about the pressure to prove everyone wrong, the guilt of missing your kids' events, and finding out what success actually means when you've spent your whole life chasing it. Key moments from our conversation: 🏡 Getting emancipated at 16 and starting a daycare business by 18 that she ran for 12 years 📸 The Easter photo moment when she didn't recognize herself and everything changed 💪 Selling $100K in personal training in three months in a small town and discovering she had a gift for sales ⚖️ Missing dance practices and football games while building her career and the guilt that still sits with her 🔥 Proving wrong every single person who said a high school dropout wouldn't amount to anything 🪫 Burnout that lasted two and a half years before her body completely shut down in January 🎯 Chasing titles and salaries until she got to the top and realized it meant nothing ☕ Taking a full month off to romanticize her life, journal, nap, and figure out what she actually wanted 👩👧👦 Her daughter telling her "Mom, you're building your empire and I can't wait to be you someday" 🏌️ Finally picking up golf this year as her first real hobby outside of work 💭 The Rachel Hollis conversation about being "made for more" and learning that the chase never ends This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

14. 

    2 Dec 2025

    Persistence, Positivity & Collaboration: Sarah Ray on Joy-Based Delegation and Building Career Momentum With Two Under Five

    When I sat down with my second Look Both Ways guest, Sarah Ray, it reminded me why I love talking with her so much. She takes what could be one of the most exhausting seasons of life and reframes it with clarity and optimism. To her, parenting is its own version of progressive overload—the gradual increase in stress that ultimately builds strength. In other words, the hard stuff is what makes us stronger. We talk about her philosophy of joy-based delegation, raising grounded and well-rounded barn kids who can tack up a horse before they can recite the alphabet, and the sanity-saving reminder that every phase of parenting is just a season. Sarah is hungry, driven, and endlessly curious—qualities that have fueled her career in health tech. But her story also includes postpartum anxiety, imposter syndrome, and the too-familiar blurring of work and life (including a conference call with her six-day-old baby on her chest). With baby number two, she’s finding her stride. And yes, you’ll also hear mentions of Taylor Swift, Jimmy Buffett, and the classic business book The E-Myth. Here is Sarah’s story. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

15. 

    25 Nov 2025

    Anything But Linear: Redefining Success with Rose Ann Mullet

    The Tombstone Test: Redefining Success as a Working Mom with Rose Ann MulletIn this episode, Rose Ann Mullet doesn't hold back about the chaos of switching careers mid-pandemic while pregnant, finishing a master's degree with a newborn, and eventually walking away from teaching altogether. She and Jenna get into the specifics, like why she wore safety goggles to teach while pregnant, what it actually felt like to leave a profession she excelled at, and the moment she realized her childhood writing dream was burning her out instead of lighting her up. They talk through the guilt of feeling like you're failing everywhere, the surprising relief of redefining ambition, and why asking "what would my tombstone say?" changed how Rose Ann thinks about success entirely. Key Takeaways 🎯 Career paths twist and turn in ways you never expect, especially when marriage and motherhood enter the picture 👶 Managing work during COVID with a newborn meant every single minute had to count, there was zero room for casual water cooler time 💍 Rose Ann's husband took over cooking when she was pregnant and never stopped, which shows how much the little decisions about who does what can reshape your entire life 🔄 Some things will break if you drop them (like your kid's health), but most things (laundry, emails, that stack of papers) can absolutely wait 📚 Waking up at 5am to write for years taught her that even the things you love can hollow you out if you're not careful 🏫 She left teaching because fighting with administrators over grades and standards was bleeding into family time, and that wasn't worth it ⏰ After bedtime, you get maybe an hour to yourself, your spouse, or that show you've been trying to finish for three months 🎓 Her years in the classroom convinced her that helicopter parenting backfires, kids need to struggle and fail while they're still at home 💭 What looked like ambition at 18 (becoming a bestselling author) looks completely different at 30-something with a four-year-old who needs you 🔄 Your capacity changes day to day, and giving everything you actually have is different than giving some imaginary 110% all the time This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

16. 

    7 Nov 2025

    Introducing Look Both Ways

    Trailer: Why “Look Both Ways” Exists — Ambition & Parenthood Without the Either/Or Episode Summary Welcome to Look Both Ways, a podcast for women doing both — building meaningful careers while raising kids. In this first episode, host Jenna shares why she created this show, how her own experience of burnout and motherhood sparked the idea, and what she hopes Look Both Ways will offer: a space for honest, unfiltered conversations about ambition, identity, and the messy middle of working motherhood. This is the beginning of a community built on stories, support, and the belief that we can keep building something better — together. 💡 In This Episode The moment Jenna realized there was no “map” for working mothers. The years of depletion that led her to reimagine what balance really means. Why “doing it all” is a myth — and what it looks like to do both instead. How Look Both Ways will explore the nuance, trade-offs, and realities behind modern working motherhood. What listeners can expect: honest stories, practical wisdom, and zero performative perfection. ✨ Memorable Quotes “I realized there wasn’t a map for where I was trying to go — so I decided to start making one.” “It’s not about the hours. It’s about the energy, the messy middle, not the perfect outcome.” “Ambition isn’t optional for many of us. And if society isn’t going to hand us what we need, we can share what we’ve learned and support each other.” Subscribe to the Look Both Ways newsletter for new episode drops and behind-the-scenes reflections Share your story or nominate a guest: https://lookbothwayspod.substack.com/ (https://chatgpt.com/c/690e6b79-ba80-8329-83f8-26c375905c9e#) Get in touch with Jenna on LinkedIn (https://www.linkedin.com/in/jennarandolph/) 💬 Join the Conversation Whether you’re in the carpool line, between meetings, or hiding in the pantry for five quiet minutes — you’re not alone. Subscribe, leave a review, and share this episode with a friend who’s doing both. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit lookbothwayspod.substack.com (https://lookbothwayspod.substack.com?utm_medium=podcast&utm_campaign=CTA_1)

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

3 ratings

Contact Look Both Ways Podcast

Guest appearances

Books guests

Based on episode analysis; this does not confirm that the show is currently accepting guests.