Preparing For Life After the Corner Office
April, 2026
What happens at the end of your career?
Do you want what comes next to include meaningful work, ongoing learning, giving back, healthy living, and time for personal pursuits and leisure? If so, the goal is not simply retirement—it’s building what Irish economist Charles Handy called a portfolio life: a mix of activities that together create purpose, engagement, and pleasure.
Many of my clients initially come to me focused on their next leadership role. Increasingly, however, they are also exploring alternatives to traditional retirement. Their concern is not purely financial, but existential: Will I still feel relevant? Engaged? Useful?
If that question resonates, the time to act is earlier than you think.
Think of your transition as crossing a gap. Where you stand today is familiar. Where you want to go—a fulfilling portfolio life—is visible, but not yet fully formed. The risk is trying to leap too quickly without something beneath you.
Instead of jumping, you build a bridge.
One of the most effective ways to do this comes from a model I have adapted from Ronnie Brooks of the Shannon Institute. She described the process as “dropping mattresses”—creating a series of platforms below you before making the leap. Each “mattress” reduces risk and builds confidence. This process is depicted in the graphic above and is best understood from the bottom up.
Rather than waiting until your final day of work, you begin constructing your next chapter while you are still in your current role.
Start with a foundation:
• Clarify what a portfolio life means for you
• Reconnect with your strengths and interests
• Understand your financial timing, preferences, and flexibility
Then begin building forward by experimenting in five key areas:
• Working in the form you want
• Learning and self-development
• Giving back
• Health and well-being
• Personal pursuits and leisure
Also begin shifting your connections toward people who have successfully “crossed the chasm” and can offer guidance and partnership along the way.
You don’t need to have everything figured out. What matters is momentum. Small, intentional steps allow you to test ideas, build relationships, and refine what your future could look like.
The result is not just a safer transition—but a better one.
Instead of stepping away from something, you are stepping into something you have already begun to create.
A Bridge in Action
In the next section, Ken Sobaski, recently retired CEO of America’s Thrift Stores, shares how he applied this approach during a nine-month transition period. Rather than waiting, he actively “dropped mattresses” across each of the five portfolio elements—testing, learning, and building his next chapter before leaving his role as CEO.
His story brings this concept to life.
Dropping the Mattresses: Ken Sobaski’s Nine-Month Transition
When I was preparing to step away from my CEO role, I didn’t want to “retire” in the traditional sense, focused primarily on travel & leisure. I wanted a fuller life with more variety and a greater sense of purpose. Having recently divorced, there was a risk of a huge hole in my life, so I committed to a nine-month period, before leaving my job, to work with George to actively build what my next chapter could look like—what George calls a portfolio life.
Instead of waiting for clarity, I focused on action— “dropping mattresses” across five areas and adjusting as I went.
Working in the Form I Want
For me “Working in the Form I Want” is all about “Giving Back,” taking what I’ve learned over my 45+ year career and sharing it. As such, I’ve stayed engaged in ways that feel purposeful, allow me to give back, but flexible. I’ve been a formal mentor for 8+ years and love it, so now I’m coaching several early stage “Baby CEOs” and looking to add a few more. I also facilitate a monthly on-line, virtual, private equity CEO group with 10–12 leaders per session and remain active in a Birmingham CEO and founders’ network that I’ve been part of for 10 years.
In addition, I’ve been collaborating with three other executives to do for/with them what George did for me and facilitate a “Retirement Reimagined” process, with the potential to expand later this year.
Finally, I’ve had the opportunity to share my story more broadly. I’ve participated in several podcasts, with more scheduled. Podcasts were a conscious, easier to execute, choice instead of pursuing writing a book or public speaking. I’ve learned it’s just as important what not to pursue and I’m comfortable setting those aside for now.
Learning and Self-Development
Learning has taken on a different tone—more personal, less professional, mainly about trying new things for new experiences. I’m working with a vocal coach, singing in a church choir, and preparing for a local theater performance.
I’ve experimented with new interests like bird watching. On a trip home to Minnesota last fell along the Great River Road, I discovered that I love road trips with my dog Brutus, just like John Steinbeck and “Travels with Charley.” So I am actively planning another road trip in May through several states I want to explore.
I continue to read widely, from health and longevity (Outlive) to relationships and world history.
Not everything sticks—but that’s part of the process.
Health and Well-Being
This has been one of the most transformative areas with a focus on BOTH Health & Wellness and Building Community.
In terms of health & wellness, I’ve joined the yearlong Astride Health program. Through Astride, I have established strong daily habits: eight hours of nightly sleep, working out six days a week, practicing transcendental meditation twice daily.
The results have been significant—I have lost 40 pounds and feel better physically than I have in years. Some activities, like pickleball and tai chi, are temporarily on hold due to an Achilles injury, but overall momentum is strong.
Numerous studies show that long term health is also about building community and relationships, and that has been a key focus for me. After several years without a church home, I’m now deeply involved in my new church—serving on the stewardship committee, joining small groups, and participating in leadership activities. Another part of this is that I have started dating again—meeting new people, learning along the way, and staying open to the experience.
Lastly, I am consciously trying to reignite old relationships, reaching out to people who have touched me along the way and trying to reconnect. While successful, this is an area where I need more discipline—particularly maintaining consistent outreach and follow-up. This continues to be a work in progress. It hasn’t all worked out, but it’s been energizing.
Giving Back
My primary form of giving back is actually Working in the Form I Want. They are one and the same for me. In my mind, mentoring Baby CEO’s, facilitating CEO Networks and doing podcasts are all fundamentally about me giving back from my 45+ years of experience.
I am also giving back by joining a small group of my choir and singing monthly at memory care facilities around Birmingham. Having had a grandmother and 2-aunts with Alzheimer’s, it is something that really resonates with me.
Down the road I look to add to this set of activities by serving as a guest lecturer at the University of Alabama Business School and by finding 1-2 additional volunteer activities.
Travel and Leisure
Except for Road Trips with Brutus, travel is my lowest priority. Through my work with Astride Health, I expect to live well into my 90’s so travel can wait. That said, I have a trip to Santa Fe planned in May. This is a place many told me I need to see. And I am actively planning a trip to Croatia by early 2028, hopefully with my 5 children. Finally, I am looking ahead to a 2027 trip to Egypt for the longest solar eclipse ever.
At the same time, I’m letting go of things that no longer fit—like golf and not overcommitting to leisure activities. But…I may join a bowling league this fall, who knows?
What I Have Learned
Life after the corner office isn’t about slowing down—it’s about redirecting. As I shared in my most recent update to George:
“Life is good. Most of my friends can’t believe how much is going on with me being retired. But it’s great—I’m very happy and fulfilled, and it’s all on my time, at my pace.”
I’m not finished building my bridge, am not sure what other mattresses I might add in the future, but I’m no longer standing at the edge.
