Look Both Ways Podcast

Jenna Randolph

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

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

    3d ago

    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

    48 min
  2. May 5

    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

    1h 1m
  3. Apr 21

    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

    1h 3m
  4. Apr 7

    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

    59 min
  5. Mar 10

    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

    1h 4m
  6. It’s a Balance: Norma Hogan on Burnout, Boundaries & Intentional Leadership

    Feb 24

    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, 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

    1h 5m
  7. Forgiveness, Grit, Becoming: Tammy Soares Does Not Believe in Failure

    Jan 27

    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

    1h 6m

Trailer

Ratings & Reviews

5
out of 5
3 Ratings

About

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