Lorraine Whale – Roots, Reinvention and a Really Good Plan

What if the key to reinventing your career isn't a dramatic leap—but a quiet, stubborn plan built one small step at a time? In this warm, deeply honest episode of Legendary Leaders, host Cathleen O'Sullivan is joined by Lorraine Whale, qualified genealogist, house historian, and founder of Time Flies Ancestry—who spent over 25 years in HR and leadership roles before following a passion she'd been nurturing for decades. Their conversation spans career reinvention, the emotional cost of falling out of love with a profession, the underrated power of a good plan, and what it really means to lead yourself forward when nobody else is handing you a roadmap. Lorraine opens with something that will resonate with many—she doesn't see herself as a leader at all. But as the conversation unfolds, it becomes clear that her definition of leadership, building trust, giving others confidence, showing up with tenacity—is exactly what she has been doing all along, in boardrooms, in genealogy archives, and at home as a single mum raising a son she is quietly and fiercely proud of. She shares how she mapped her escape from HR with an Excel spreadsheet worthy of Andy Dufresne, why redundancy felt like liberation, and how a squiggly career can be the most intentional one of all. They also get into the human side of HR—why it too often becomes a ticketing system rather than a true business partner, what real people functions should look like, and the question that changed everything for Lorraine: Do you want to retire working in this? And for anyone wondering whether it's too late to start over, Lorraine's answer is simple: find the thing that lights you up, make a plan, and don't just do nothing. This is a conversation that will meet you with grace wherever you are in your career—and quietly nudge you to take that first step. Episode Timeline: 00:03:54 "I've never seen myself as a leader" 00:06:38 From admin to HR to genealogy — finding her place 00:16:39 Solitude, community, and the AGRA network 00:18:38 Falling out of love with a profession 00:21:19 What great HR actually looks like 00:29:02 The Andy Dufresne escape plan 00:34:02 Squiggly careers and waiting for what's next 00:40:13 The first small step 00:43:32 Loving the problem-solving of genealogy 00:49:43 The village it takes to raise a child 00:56:13 Self-care when there's no time for it 00:58:26 Find the thing that lights you up 00:59:13 How to find Lorraine and Time Flies Ancestry Key Takeaway: Reinvention Isn't a Leap — It's a Long Game: Changing direction doesn't mean scrapping everything overnight. Lorraine spent years qualifying, downsizing, and planning while still in her HR role. The most meaningful career shifts are built slowly, deliberately, and with a very clear goal in sight. Your Whole Career Is the Foundation, Not the Obstacle: A squiggly path isn't a weakness — it's a toolkit. Every function, every stakeholder, every challenge you've navigated gives you a perspective that a linear career never could. Don't discount it. Build on it. Ask Yourself the Uncomfortable Question: Lorraine's turning point came from one honest question — would I want to retire doing this? Sitting with that discomfort is where real clarity begins. If the answer is no, that's not a crisis. That's a starting point. If You Have a Goal, Make It Visible: Good intentions don't create change — a plan does. Whether it's an Excel spreadsheet, a timeline, or a milestone tracker, seeing your progress move is what keeps you going when the goal still feels far away. About Lorraine Whale: Lorraine Whale is a professional genealogist and family history researcher who helps people uncover their ancestral stories and preserve family and house histories. As Founder of Time Flies Ancestry, she specialises in detailed genealogical research that goes beyond online records to include archives, museums, and local history resources across southern England. Lorraine holds a Diploma in Genealogy and is a member of the Association of Genealogists & Researchers in Archives (AGRA) and the Register of Qualified Genealogists, and she also serves on the tutorial team of the Institute of Heraldic and Genealogical Studies. Today, she works with clients around the world to trace their roots and bring forgotten family narratives to life, drawing on decades of experience and a deep passion for the past. Connect with Lorraine Whale: Website: https://www.timefliesancestry.co.uk/ LinkedIn: https://www.linkedin.com/in/lorraine-whale-75634a1b/ Association of Genealogists and Researchers in Archives (AGRA): https://www.agra.org.uk/ Connect with Cathleen O'Sullivan: Business: https://cathleenosullivan.com/ LinkedIn: https://www.linkedin.com/in/cathleen-osullivan/ Instagram: https://www.instagram.com/legendary_leaders_cathleenos/ YouTube: https://www.youtube.com/@LegendaryLeaderswithCathleenOS FOLLOW LEGENDARY LEADERS ON APPLE, ...