What happens to our judgment when grief has shaken our sense of safety? Why can the simplest practical decisions suddenly feel overwhelming? And what does it actually mean to live again when life cannot return to what it was? In this episode of What's the Point?, I sit down with Christopher Dale, a certified financial planner, grief educator, author, and founder of Life After Grief Financial Planning. Chris explains that grief reaches far beyond sadness. It can affect concentration, executive function, confidence, and decision-making. From a financial perspective, that matters because people may be asked to make some of the biggest decisions of their lives at exactly the moment clear thinking is hardest. Money can also become tied to much deeper emotions: guilt, control, fear, safety, and responsibility. Chris knows that intersection personally. In his early twenties, his mother developed Alzheimer's and his father's health was declining. Chris found himself becoming the caregiver and financial problem-solver for both of his parents—learning systems, handling expenses, and trying to make decisions with very little guidance. Then his mother died. His father followed just two and a half months later. The grief was overwhelming. Chris describes turning to alcohol at night simply to escape the physical and emotional pain. Eventually, he recognized that what was helping him get through the evening was beginning to hurt him instead. Support from his priest, counseling, and journaling gave him another outlet. Those journal entries later became the foundation for his book. His grief became even more complicated when, on the day his father died, Chris discovered a decades-long affair and another family. That discovery forced him to grieve someone he loved while also confronting anger, betrayal, and financial consequences that had shaped his childhood. Chris talks candidly about forgiveness—not as an excuse for someone's behavior, but as a way of releasing its hold on your life while still maintaining boundaries. Years later, Chris and his wife experienced another profound loss when one of their twins, Christopher, did not survive. Their surviving son, Eli, became what Chris describes as his first real glimmer of hope in a long time. That experience changed the way he viewed fatherhood, work, and what he wanted his life to become. Eventually, that perspective contributed to Chris leaving the traditional financial world and building his own practice—one that gave him more time with his family and allowed him to combine financial planning with what he had learned about grief. One of the most important ideas in this conversation is that living again does not mean returning to who you were before the loss. Chris describes it as finding a new normal. Grief remains part of the story, but clarity begins to return. Hope begins to return. You start wanting things again. As he puts it, life after grief is different—but it can still be deeply fulfilling. We also talk about what meaningful support actually looks like. Instead of simply telling someone, "Let me know if you need anything," Chris encourages people to make specific, practical offers. One of his closest friends took a week off work to help him clean out his parents' home—exactly the kind of concrete support that can matter when grief has made ordinary tasks feel impossible. And when Bill asks the question at the heart of every episode—What's the point?—Chris' answer is about doing better and remembering that there is a way forward. We do not have to remain only the product of what has happened to us. What's The Point? is a podcast hosted by Bill Ellis featuring real conversations with people who've figured out what matters—their purpose. Each episode explores what motivates them and how they find meaning in what they do. Connect with Bill: bill@billellis.com www.billellis.com www.brandingforresults.com IG - @wcellis Facebook - @CoachBillEllis Facebook - @bill.ellis LinkedIn - linkedin.com/in/wcellis Book: Women Who Won Links for This Episode: Life After Grief Financial Planning™ http://Lifeaftergrieffp.com Life After Grief Consulting® http://Lifeaftergriefconsulting.com LinkedIn: https://www.linkedin.com/in/lifeaftergriefchrisdale/ Facebook: https://www.facebook.com/profile.php?id=100087776514969 Instagram: @cdd2dale Twitter/X: @LifeAfterGChris Current Projects Life After Grief: Holding the Numbers with Shaking Hands—When Money, Trauma, Grief, and Racism CollideChristopher's book exploring money, trauma, grief, race, caregiving, and family through lived experience and the perspective of a financial professional. The Advisor's Guide to Grieving Clients Professional training and continuing education for financial professionals serving clients experiencing grief and loss. Real Talk with Life After Grief Chris A podcast about grief, money, family, caregiving, race, resilience, and life after loss. Life After Grief Collective A community focused on education, conversation, and support around grief and financial transitions. Quick Episode Summary: 00:00 – What grief does to our sense of safety 02:00 – Why clear thinking becomes difficult after loss 05:00 – Money, guilt, and control during grief 07:00 – Knowing when you need more time or outside help 10:00 – Why clients began relying on Christopher differently 12:00 – Becoming a caregiver for both parents 14:00 – Navigating financial and care systems alone 16:00 – Losing both parents within months 18:00 – When coping becomes harmful 20:00 – Finding help, counseling, and spiritual support 22:00 – Replacing alcohol with journaling 23:00 – Grieving someone you're also angry with 24:00 – Forgiveness without excusing behavior 26:00 – The financial consequences of family secrets 29:00 – Forgiveness, boundaries, and responsibility 30:00 – The phone call that revealed another family 33:00 – Protecting grieving clients from financial pressure 35:00 – The role hope plays after devastating loss 36:00 – Losing one of their twin sons 38:00 – The first glimmer of hope 39:00 – How grief changed Christopher's priorities 41:00 – Talking to his sons about their brother 44:00 – How do you know you're starting to live again? 46:00 – Happiness after grief feels different 47:00 – Where someone overwhelmed by grief can begin 48:00 – What meaningful support actually looks like 51:00 – Why trusted mentors and advisors matter 55:00 – Christopher answers: "What's the point?"
