Still Yours to Shape: Reclaiming Identity in Times of Transition

In this episode, we’re joined by Amy Stein, Chief Impact Officer at Generations Trusted Family Business Advisors. With over 20 years in her family’s fourth-generation business, Henry’s, and experience launching its mental health foundation, Amy brings a rare perspective on legacy, leadership, and impact. Our conversation focuses on what transition really feels like, how identity shifts, how clarity emerges through change, and how purpose can take on new meaning when familiar roles evolve. It’s a personal, layered look at the emotional side of stepping into what’s next.Amy shares reflections shaped by lived experience and thoughtful observation. We talk about resilience, voice, and the quiet work of preparing for change even when you don’t yet know what the next chapter will hold.About Amy SteinAmy Stein is the Chief Impact Officer at Generations Trusted Family Business Advisors, where she helps family enterprises and their family offices develop values-aligned philanthropic strategies that engage rising generations and create measurable impact. With a strategic, people-centred approach, she supports families in looking beyond financial metrics to integrate business, employees, customers, and community in meaningful ways. Her work focuses on designing initiatives that scale with intention, reflect legacy, and build lasting social capital.For over two decades, Amy was a key leader in her family’s fourth-generation business, Henry’s, Canada’s largest independent imaging retailer. She later spearheaded the launch of the Foundation for Henry’s, a creative mental health initiative rooted in community impact. Drawing on deep experience in governance, strategy, and operations as a family member, executive, board member, and shareholder, Amy brings insight into the complex dynamics of family enterprise. She is especially skilled at bridging generational perspectives and helping families align purpose with action.Resources discussed in this episode:Rotman SchoolPixel FoundationDavid BentallFamily Enterprise CanadaContact Cory Gagnon | Beacon Family Office at Assante Financial Management Ltd. Website: BeaconFamilyOffice.comLinkedIn: Cory GagnonLinkedIn: Beacon Family OfficeEmail: [email protected] Amy Stein | Generations Trusted Family Business Advisors: Website: gtfba.com/ | pixelfoundation.orgLinkedIn: Amy SteinEmail: [email protected] Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.