While there are many types of exit plans, this article focuses on an extreme exit plan that I experienced. In 2014, my life changed overnight. The night my brother passed away, I went from being the general manager of our family business to the administrator of his probate estate. Then, within three months, my father was gone. It felt like a seismic shift: our family dynamic was turned upside down, and my livelihood was suddenly in flux. In the immediate aftermath, I was in shock. I didn’t have much time to process those feelings because I was consumed with the practical responsibilities of a probate estate which included running and closing several businesses and sold high-end real personal and business properties.
Only later did I realize that, while I had taken care of all the “physical exits,” I had overlooked the emotional, relational, and personal exits that were happening simultaneously. In this post, I’m sharing how I learned to address these internal and external transitions from a coaching perspective. I hope these insights, exercises, and resources help anyone dealing with loss—or any major life change—find a more holistic path to healing and forward momentum.
When something pivotal happens like birth, death, a career change, or divorce, there’s often a domino effect that impacts every area of life. In my case, “multi-level exits” included:
Emotional Exit: Grappling with overwhelming grief while still managing day-to-day tasks.
Identity Shift: My roles changed overnight both personally and professionally.
Relational Changes: Redefining family roles and responsibilities and in business the landscape changed completely.
Livelihood Disruption: My career was over and my new estate administrator position was temporary and I could not accept another position until the estate was closed.
Coaching helped me balance these parallel tracks: the “to-do list” of business tasks and the emotional, and personal transitions. While I did attend individual and group therapy, where I dealt with the trauma, grief and loss, coaching focuses on identifying clear goals, creating action steps, and establishing accountability. Here’s how it helped me:
Self-Awareness: I learned to name and validate my emotions instead of burying them beneath endless administrative responsibilities.
Visioning: Coaching encouraged me to envision my “new normal” and define what I wanted my life to look like once the dust settled.
Strategic Action: Breaking big transitions into manageable steps, such as scheduling time each week to address emotional well-being and family check-ins.
Accountability: It’s easy to let grief and exhaustion derail you. A coach (or a supportive friend or mentor) helps you maintain your self-care and transition plans.
Draw a Circle: Divide it into slices labeled Emotional Health, Family, Finances, Career, Spirituality, Personal Growth, Physical Health, and Recreation.
Score Each Area (1–10): Rate your current satisfaction.
Reflect: Identify which segments suffered the most during your time of loss. Where do you feel most out of balance?
Focus on One or Two Areas: Brainstorm small, achievable steps—such as scheduling daily walks (Physical Health) or planning a weekly call with family (Family).
This exercise gave me a visual snapshot of where I needed the most support and helped me celebrate what was going well.
I started by setting aside just 10 minutes a day to write about whatever surfaced. Some prompts that helped:
Loss and Identity: “In losing my loved ones, how has my view of myself changed?”
Emotional Expression: “Which feelings are right beneath the surface that I haven’t acknowledged?”
Hope and Vision: “Once I move through this storm, what do I want my life and relationships to look like?”
Journaling became a safe space to process the swirl of feelings I’d been ignoring.
I wrote letters to my brother and father, sharing memories and gratitude. Then, I wrote letters back to myself as though they were responding. It was emotionally intense but also cathartic. Imagining their voices offered a sense of closure and connection. I also wrote a letter to myself in a beautiful sympathy card that I did not open for a year. In this letter I wrote to myself that I will be OK and even though I do not understand right now, eventually I would, and for now, know that I am blessed and loved. I occasionally still read these letters and especially the one I wrote to myself. I think because the words are so kind and soothing.
Before diving into estate documents or business calls, I would do a quick check-in:
Deep Breaths: Inhale for four counts, hold for two, and exhale for six—five times.
Body Scan: Ask, “What am I feeling, and where do I feel it?”
Gratitude: Acknowledge one thing I’m thankful for, even if it’s as simple as my morning coffee or a ray of sunshine.
This might sound small, but it grounded me in the present and reminded me to care for my emotional well-being.
"On Grief and Grieving" by Elisabeth Kübler-Ross and David Kessler
"Finding Meaning: The Sixth Stage of Grief" by David Kessler
"Care of the Soul" by Thomas Moore
There’s no magic formula to handle the overlap of business, legal, and personal grief, but here’s what I found helpful:
Schedule Emotional Work: Put it on your calendar just like you would a meeting with an attorney.
Delegate: Enlist help with paperwork or any tasks with friends, family, or professionals.
Open Communication: Let people know you’re juggling grief alongside practical tasks. This invites empathy and support, rather than misunderstandings.
Self-Compassion: Some days you’ll feel productive; other days, not so much. Grief isn’t linear. Be patient with yourself.
Back in 2014, I had no choice but to handle my brother's probate estate as swiftly and efficiently as we could. However, the emotional, relational, and existential aspects of my grief demanded equal attention. Looking back, I see how essential it was to grieve mindfully while also tackling those practical responsibilities.
Going through transition is challenging and I hope these reflections and exercises help you find a path forward that honors both the tangible tasks and the intangible pain. This major transition has helped me deal with later transitions because it was here that I learned to incorporate new solutions and tools.
"Think of yourself as dead. You have lived your life. Now take what’s left and live it properly." -Marcus Aurelius
May we all move through our losses in a way that transforms pain into purpose, allowing us to shape a future that honors our loved ones and ourselves. If you’re in the thick of it, know that you are not alone.