Pivoting With Purpose: How to Transform Your Life’s Work Without Starting Over

In today’s episode, James Marland sits down with coach, consultant, and visual practitioner Jill Greenbaum to uncover what it really looks like to pivot your business — and your life’s mission. If you’ve ever wondered how to build something new without abandoning your past, or how to move into more meaningful work (even around tough topics like end-of-life conversations), this episode will show you the roadmap. You’ll leave inspired, equipped, and ready to take your next big leap.

Show Highlights

00:00:00 Why We Must Talk About Death (And Why We Don’t)

00:00:40 Meet Jill Greenbaum: Teacher, Coach, Visual Thinker, Lifelong Learner

00:02:00 How Decades of Experience Built a Pivot Foundation

00:03:00 From Fortune 500 Training to Visual Facilitation Magic

00:04:00 Buddhism, Singapore, and Finding a New Mission

00:05:00 Facing the Whiplash of a Business Pivot

00:06:00 Taking Skills With You: Coaching, Curriculum, and Visuals

00:07:00 Building a New Offer With Old Expertise

00:08:00 How to Design Coaching Products That Feel Natural

00:09:00 Facing Fear: Pivoting From Secure to Uncertain

00:10:00 How Jill Uses Intuition and Values to Guide Decisions

00:11:00 Meeting People Where They Are (Not Where You Are)

00:12:00 Shifting Into Grief, Loss, and End-of-Life Conversations

00:13:00 Using Visuals to Make Hard Conversations Easier

00:14:00 How to Launch a New Offer With Just 6 Questions

00:15:00 Email Scripts, Quick Conversations, and Honest Research

00:16:00 Moving From Research to Real Customers

00:17:00 Why People in Their 50s and 60s Are the Real Audience

00:18:00 The Relief of Having a Plan for End-of-Life

00:19:00 Funerals Are Better Than Parties: A Life Perspective Shift

00:20:00 Leaving a Legacy: Living Life On Purpose

00:21:00 How Different Life Experiences Shape End-of-Life Wishes

00:22:00 Fighting Over Funerals: Why Advance Conversations Matter

00:23:00 Managing Grief, Confusion, and Family Conflict

00:24:00 Where Jill Is Now: Mid-Pivot and Loving It

00:25:00 What’s Next for Jill Greenbaum and Her New Programs

00:26:00 Closing Reflections: You Have More Choices Than You Know

Links and Resources