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

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]

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]

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]

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]

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]