Press Pause to Leave: Sean O’Rourke on Knowing When It’s Time to Step Away

Send us Fan MailHow do you know when it’s time to leave, even when you’re the owner ? In this episode of Time To Press Pause, Ellen Williams is joined by Sean O’Rourke, a cyber liability consultant, CFO, and former IT company co-founder, who shares the moment he realized he could no longer live in a millisecond-by-millisecond business. After more than 25 years in technology, including 12 years running the IT firm he co-founded, Sean made the difficult decision to step away from day-to-day operations. Not because he couldn’t do the work, but because it no longer aligned with the life he wanted to live. Together, they explore what it means to pause without quitting, how identity and motivation shape leadership decisions, and why being honest with the “reflection in the mirror” matters more than external expectations. In this conversation, you’ll hear: How to recognize burnout before it defines youWhat it really means to leave, even when you’re the bossWhy technology became a 24/7 pressure cookerHow Sean reshaped his career without walking away from his expertiseThe importance of being honest about what truly motivates youThis episode is a powerful reminder that pressing pause isn’t about stopping, it’s about choosing what comes next. 📘 Ellen Williams’ upcoming book (pre-launch): Creating Time: The Key to Productivity and Peace 👉 https://shopbooksdirect.com/product/creating-time/Learn more about Sean O’Rourke and his work at Combs & Company: 👉 https://www.combsandco.com 📰 Subscribe to Ellen’s newsletter for updates on new episodes, insights, and the book launch: 👉 https://api.transpond.io/form?am=42668&fid=49041&host=true