In this episode of We’re Not Recording, Melanie Naranjo sits down with Andrea Cooper, Chief People Officer at Talkspace, to unpack her winding career journey — from working on the retail floor at Walmart, to spending over 20 years inside one of the world’s largest organizations, to stepping into the uncertainty of consulting and ultimately finding alignment in smaller, mission-driven companies. Andrea reflects on the fear and freedom that came with leaving the “safety of familiarity,” the steep learning curve of working for herself, and the confidence that comes from having to pitch your own value, set your own rates, and risk rejection. She shares candid lessons on building a consulting network, negotiating pricing without underselling yourself, and why relationship-based, authentic networking mattered more to her than personal branding or social media hustle. The conversation also explores the differences between large enterprises and lean teams, why smaller companies force deeper business understanding, and how retail experience shaped Andrea’s people-first but business-grounded leadership style. Throughout, Andrea emphasizes growth, resilience, and the power of discomfort as a catalyst for long-term confidence and clarity. This episode is especially valuable for HR leaders, consultants, and professionals considering a leap away from traditional career paths — or anyone questioning whether staying comfortable is holding them back from their next chapter.