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