What Matters to You Now: Laura Shepherd on the Question That Starts Every Career Change

Laura Shepherd's mother sat her in front of the moon landing when she was four years old. She wanted to be an astronaut. Laura was not good at science, so that dream fell away. But the the explorer did not. It is still the strongest driving force at 61. It is why mid-career she left a six figure marketing job to make forty bucks a day plus tips teaching scuba in the Caribbean. Why she left that too when it had given her what it had to give. She is a leadership and transitions coach now, running her own practice, with a Kilimanjaro climb booked for October. What moved her from one of those lives to the next was never a plan for the whole path. It was one question, asked again every few years: what matters to you NOW. Not what mattered five years ago, or even imagining what will matter if a few months or years. We talk about the pivot everybody in her life called crazy, why she says the leap only looked like a leap from the outside, and the difference between the discomfort you can live with and the discomfort that actually grows you. CHAPTERS 00:00 Welcome to The Scenic Route: Meet Leadership and Transitions Coach Laura Shepherd 02:21 Astronaut Dreams and the Life Script She Did Not Follow 04:36 Leaving a Six Figure Corporate Job to Teach Scuba in the Caribbean 06:17 Goals Give Direction: The Cost of Chasing Them With Blinders On 10:24 How She Decided: Five Job Offers From Four Days at a Trade Show 18:31 Hiring a Coach: When Asking for Help Felt Like Weakness 19:01 What Matters to You Now: The Core Values Check 25:50 Two Years In: The Toddler Stage of Building Her Own Business 30:00 Pink Elephants and Red Cars: Training Your Brain to Notice 34:48 Avoidance Is a Choice: The Two Kinds of Discomfort 37:48 Laura's Best Advice: Find the Gap in Your Core Values 41:13 Kilimanjaro in October: Mind, Body, Soul Connection ABOUT LAURA SHEPHERD Laura Shepherd is a leadership and transitions coach helping high achievers who are stretched thin figure out the next path and supporting them along the way. She spent 25 plus years in corporate marketing before pivoting into coaching. Her company is North by Northwest Coaching and Consulting: be your own compass. Website Laura is climbing Kilimanjaro in October and documenting her training on Substack. Follow: On LinkedIn On Instagram ABOUT VICTORIA Victoria Steward is a Corporate Exit and Financial Empowerment Coach, helping senior corporate women stuck in the 'one-more-year' loop build the self-trust and financial clarity to leave corporate on their own terms, their own timing, their own scenic route. Curious? Book a Pivot Clarity Call. Follow On LinkedIn On Instagram Resources The Engineer's Exit Decision Toolkit The Can I Pivot Yet? Exit Roadmap Website