Interview questions Karen is ready to dig into. Copy them, tweak them, or bring your own.
1You’ve worked from a ski lift in Bulgaria and a beach in Mexico—what does a ‘typical workday’ look like when your office is everywhere?
2Most people think location freedom requires passive income or a huge audience. What’s a first step someone with a 9-to-5 and limited time can take this week?
3You talk about ‘escapreneurs’—what’s the biggest misconception people have about building a business that funds freedom?
4Automation scares a lot of small business owners. What’s one thing they can automate within 1 day that’ll save them 5+ hours a week?
5If someone’s drowning in apps—Calendly, Stripe, Teachable—how do you help them simplify without starting from scratch?
6You worldschooled your kids for 9 years. How did you handle work deadlines while also being present for your family in new countries?
7What’s your response to parents who say, ‘I’d love to travel, but my kids need stability’?
8If someone wants to leave their job but can’t afford to travel yet, what’s your ‘staircase approach’ to testing location freedom?
9What’s the most unexpected challenge of running a business while traveling—and how do you solve it?
10You’ve helped your clients design freedom-focused businesses. What’s the #1 trait you see in those who actually succeed?