My eighty-nine-year-old father passed away in April. As I wrote his eulogy, I was reminded that he lived decades in a “retirement lifestyle” that many of us aspire to—a life filled with purpose-filled work, spiritual grounding and rich connection with family and friends.
In my coaching work I see many alumni that reach a retirement “moment”—a point where they want to keep going, to stay engaged with work in a way that feels purposeful, but also to live more intentionally, on their own terms and timeline.
I say “moment” because there is no longer any typical or mandatory age to retire; gains in healthy longevity mean many of us will stay engaged in careers longer. Also, that moment may be forced on us by something we hadn’t planned, like a health crisis or a layoff, and we find ourselves needing to reassess quickly.
It’s a laudable goal, to live and work intentionally in retirement, but be prepared to encounter challenges along the way. I’ve found there are two key areas of exploration that can lead to lasting satisfaction in the retirement years.
First, have a Process Orientation
Retirement is a path made up of variable phases, not a singular “event.” You do not need a perfect, detailed plan from day one. Instead, approaching this time as an iterative journey made up of many small transitions through phases helps to make it a more comfortable evolution. Here’s how I think about the phases:
✅Plan: This is when you become more intentional, reflecting on what you want and making initial choices. It might be a financial health check-up or a first pass at designing your future. It’s a time for exploration and curiosity.
✅ Pause: Sometimes we need a break—from responsibilities, routines and roles we have lived in for years—to clear our heads and reconnect with ourselves. The pause isn’t aimless; it’s a key part of letting go and making space for whatever comes next.
✅ Reengage: After some exploration and reflection, we typically start to re-engage with the world in a new way. We might pursue different roles—a small business venture, a non-profit board, a part-time consulting gig or a portfolio career. The form it takes depends on your values and goals.
✅ Life at Leisure: Eventually, many find a more settled rhythm—a lifestyle filled with friendships, passions, mentoring and service—a rich, purposeful phase without the pressures of a full-time career.
Second, re-evaluate your Values & Mission—Your North Star
Values and mission help illuminate this path forward. Your values reflect what matters most to you at this moment in your life—connection, creativity, service, legacy, independence, adventure—whatever feels true for you.
Your mission is a clear, guiding statement that expresses your intentional purpose during this phase. It answers questions like: Where can I make a unique contribution now? How can I use my skills, knowledge and passions to live a rich, purposeful life?
For some, this might be mentoring the next generation of leaders, developing a longstanding passion into a small venture, serving a community in need or simply deepening relationships with children and grandchildren. Whatever your mission, it guides choices about how you will use your resources—your time, your expertise and your network—to find fulfillment.
If you’ve reached a retirement moment and want support in your journey, I hope you’ll explore the resources that Darden Alumni Career Services offers:
ACS Website – Here you’ll find further reading and resources on the topic of working in retirement, including this simple Values worksheet.
Coaching – whether it’s a job search or a pivot to an entirely new kind of work, we help you explore how to get what you want.
Life Design Workshops – Designing Your Life, while not a book not specifically intended for retirees, has an excellent set of mindsets and exercises for intuiting, planning and prototyping your way forward. Our ACS small group workshops go in-depth with this material, meet on-line and are free to all alumni; reach out to join our wait list, and you’ll be contacted about upcoming workshop dates.
ACS Virtual Events Library – Our growing catalog of panel discussions and webinars explores a wide variety of topics and includes a series devoted to “Second Act” Careers with panels on Teaching in Higher Ed, Writing a Book and Independent Consulting (with more to come…..reach out and let us know what other topics you would like to see!).
