The 3 Retirement Traps That Derail Successful Executives
For many successful executives, retirement looks nearly perfect on paper. The financial plan works. The calendar is open. There is time to travel, exercise and see family.
Then Monday morning arrives.
There is no leadership meeting, no urgent decision and no team waiting for direction. The title that once opened doors is now part of a biography. The daily signals of importance — calls, invitations and requests for judgment — begin to fade.
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The traditional corporate career is also less predictable than it once was. Reorganizations, mergers, buyouts and layoffs can push executives toward the exit before they have given much thought to who they will become afterward.
Three traps often follow: holding too tightly to a former professional identity, assuming freedom from work will produce purpose, and filling the calendar with consulting, board work or another demanding role to recreate the old job.
This transition can also involve grief. A career provided meaning, recognition and a familiar measure of personal value. Losing that role can leave even a confident executive wondering: Who am I now?
When the title becomes part of you
(Image credit: Getty Images)
In 2016, Carolina Migliaccio, 63, stepped away after more than 30 years in Fortune 500 brand strategy, innovation and design, including work with Kraft Foods and ConAgra Brands.
She began consulting. Two years later, she received an attractive offer for a senior corporate role. She turned it down.
“After three decades, my title and self-worth had quietly fused,” she says. “When the title was gone, I had no language for what I was feeling.”
She wanted work with meaning, even if it carried less corporate cachet. Yet she kept asking herself, “What would they think?”
The “they” were former colleagues who probably were not thinking much about her next move at all. “The identity free-fall definitely caught me off guard,” she says.
It took about five years for her to feel grounded again.
“It perplexed me that a smart, successful executive like myself had no idea who I was,” Migliaccio says. “I even questioned what I believed. Were my beliefs really mine, or had I become so indoctrinated by everything and everyone around me that I had lost my own sense of self?”
Migliaccio eventually built Soulful Moxie, an advisory practice focused on identity and leadership transitions. Her advice to people still deep in their careers is to begin loosening the bond between employer and identity before retirement arrives.
“Your job is just a part of what you do,” she says.
Today, she is increasingly drawn to experiences and friendships. When a close friend turned 65, Migliaccio hosted a celebration at her home instead of simply arranging another dinner at a restaurant. It was a small example of a larger shift: She was making choices based on what felt meaningful to her, rather than what might impress someone else.
“The goal is to trust a sound financial plan while recognizing that some anxiety is human. Feeling uncertain does not mean the retirement decision was wrong.”
Beware the rush to stay important
Cohen Taylor has seen how quickly the retirement honeymoon can wear off. As a behavioral wealth specialist at Mission Wealth, she helps clients and advisers address the emotional side of money and major life transitions.
She shared two recent client stories. One East Coast couple in their late 50s left careers in finance and celebrated with an extended trip around the world. Coming home was harder. Everyday routines and family dynamics returned, but the structure of work did not.
A West Coast biotech executive reacted differently. After retiring around age 60, the executive quickly pursued another role because life without clear direction felt uncomfortable.
But don’t jump too fast. Consulting, board service, or a new job can be rewarding. The trap is making the decision primarily to quiet the discomfort of no longer being needed.
“If you’re pursuing a new role later in your career, remember that the compensation may not outweigh the constant travel and stress the new job might require,” Taylor says. “Money is not everything.”
She encourages clients to think about their values, relationships and preferred daily life before committing. A phased retirement can help. Reducing workdays, taking an extended vacation or testing a lighter schedule gives people a preview of life when work occupies less space.
Retirement also requires a shift in your financial mindset. People who spent decades accumulating wealth may start checking their account balances repeatedly once the paychecks stop.
“A number of mindset shifts will occur,” Taylor says. “That’s normal.”
The goal is to trust a sound financial plan while recognizing that some anxiety is human. Feeling uncertain does not mean the retirement decision was wrong.
Turn experience outward
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Perry Solomon, 82, took a different path.
After running a high-end electronics business, he created the eco-friendly consumer-products brand ProSumer’s Choice and sold it in 2021. Today, he advises younger entrepreneurs through Solomon Growth Advisors in Santa Monica, CA.
His two daughters were not interested in joining his businesses, but they helped him broaden his view of legacy. Passing something on did not have to mean handing down a company; it could mean sharing judgment, family values, stories and focused time with his seven grandchildren.
His book, Grandpa Day, reflects more than 20 years of intentional time with them.
“I’m an advocate for retired executives to give back to the business community,” Solomon says. “Share your wisdom and experience with younger generations through blogs, articles or books. You can still influence a lot of people in very positive ways.”
Solomon remains active, but the purpose has changed. The work is less about proving his own success and more about helping other people build theirs.
A painful transition becomes a new mission
Atlanta resident Nancy Treaster’s reinvention began with caregiving.
Treaster was a senior software executive who managed a large support organization. As her husband’s frontotemporal dementia progressed, she reduced her travel and work responsibilities. She also helped care for in-laws with Alzheimer’s disease.
Eventually, the demands became too great, and she retired in August 2023.
Both her husband and father-in-law died in 2024. After years of work and caregiving, Treaster needed time to decompress. She also discovered that she still needed a mental challenge.
“I left Corporate America for good, but I still needed a project,” she says.
That project became The Caregiver’s Journey, a nonprofit and “how to” podcast she co-founded with Sue Ryan.
Treaster had no clinical health care background. She did have years of experience solving problems, leading teams and navigating a fragmented care system. She completed a Certified Caregiving Consultant program and began turning her hard-won lessons into practical guidance for families.
The shift required her to let go of the compensation and status attached to her former role. Over time, the nonprofit stopped feeling like a bridge to something else. It became the work she wanted to do.
Treaster now points families toward hopeful brain-health research while avoiding false promises. The 2024 Lancet Commission estimated that about 45% of dementia cases worldwide are potentially attributable to 14 modifiable risk factors. That does not mean every case can be prevented, but it suggests that some risk may be reduced or the onset delayed.
Her larger message is practical: Get an accurate diagnosis, understand the type of dementia involved and give caregivers information they can use today.
Expect an emotional adjustment
As a retirement coach, I often see retirement unfold in stages:
The honeymoon: Relief and freedom.
Disenchantment: Boredom, restlessness, or feeling lost.
Reorientation: Testing new routines and forms of contribution.
Stability: Developing a life that feels natural rather than improvised.
There is no standard timetable. Some people adjust quickly. Others need several years. Both are normal.
Before accepting the first consulting offer or filling every empty day, create enough space to notice what you actually miss.
Is it the work? The people? The intellectual challenge? The authority? The income? The recognition?
Those answers lead to very different next steps.
Try a short purpose exercise
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Try a little “values archaeology.”
Think back to the person you were before the executive title. What originally attracted you to your field? Which problems energized you? Did you enjoy building teams, teaching, negotiating, inventing or helping people make difficult decisions?
Then look outside work. When no one was evaluating your performance, where did your attention go?
Your next purpose may grow from an old interest, a transferable strength or a problem you now feel ready to solve. Test it through a class, a volunteer role, a short project or a limited consulting assignment before making a large commitment.
Find your zone of genius
Chicago-based Migliaccio tells clients leaving corporate life to find their “zone of genius” and choose work that reflects their values rather than outside expectations.
“It’s your time to tap into who you really are and let the world know it,” she says.
You are never too old to start something. You are never too young to think about what comes after the current career.
Be curious. Leave room to experiment. Retirement does not require you to abandon ambition. It gives you the chance to decide what your ambition is now.
“There is always another way — and often a better way,” Migliaccio says. “But you need the time, space and support to discover it.”
