A Satisfying Corporate Career Doesn’t Have to End with Retirement
Five strategies for executives leaving corner offices to help them retire happily, with purpose and to perhaps pass some of their expertise along.
If you’re wondering, “What do I do next?” you’re not alone.
Saying the word “retirement” to a corporate executive in their 60s will warrant one of two reactions: excitement about the future, or complete denial and dread.
Much of the anxiety in the latter category stems from conflicting visions of modern retirement. For many Baby Boomers at the culmination of a successful career, there’s little eagerness for endless days of golf, grandchildren and leisure.
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
For others, there’s a desire to slow the pace, but not trade in the prestige, identity and self-worth that comes from a full-time executive role. This result leaves many nearing retirement (and their employers) at an uncomfortable crossroads.
To get ‘unstuck,’ determine your professional legacy
The good news is that thoughtful planning while you’re still employed can help you figure out a fulfilling and balanced next chapter.
Start by considering:
- What amount of income will be necessary to sustain your retirement lifestyle?
- How much time do you wish to dedicate to various activities, such as part-time employment, corporate board service, charitable work, family, vacations or hobbies?
- Which issues and ideals are important to support in your retirement?
- What distinct leadership abilities and experience can you bring to your future endeavors?
- What assistance will you require to reach these goals?
The ideal mix of retirement activities combines your personal passions with your leadership skills and experience, at a pace that fits your desire for work-life balance.
It can be helpful to involve a professional coach, close friend or trusted colleague in the discovery and planning process. In some cases, savvy employers even provide access to “legacy planning” coaches, who help senior leaders transition into retirement smoothly. This support benefits the organization as well as the retiring executive, by keeping succession plans on track and clearing the way for the next generation of leaders to advance.
Numerous opportunities to offer your executive experience in retirement
As you’re planning your retirement chapter, there’s no need to shelve your professional life entirely. Consider these ways to share your leadership experience and continue to add value:
- Guide other aspiring professionals. Advising younger leaders generates new insights for both sides. Consider volunteering your time in a one-on-one mentorship with a younger professional in your field. Look for opportunities with your current employer, your professional network, through trade associations, local colleges or even national organizations like Menttium.
- Spend your leisure time purposely. Don’t forget to balance value-added activities with fun and family. It can be tempting to say “yes” to every opportunity; instead, stick to your legacy plan. Prioritizing yourself and protecting your schedule gives you time to explore new avenues and make the most of your new situation.
- Join a board. Corporate board service with a public or privately held company is a great capstone in a leadership journey. Expect to commit about 300 hours per year to meetings, committee work and other advisory activities. Start tapping your professional network 18-24 months before you leave your full-time job, in order to find the right board role.
- Serve at a non-profit organization. When you’re passionate about a cause, a full- or part-time role at a 501(c)3 organization channels your leadership abilities in a different direction, while simultaneously making a positive impact in your community. Consider how your skills intersect with a specific nonprofit's mission, then tailor your résumé and LinkedIn profile to support your goal.
- Educate, write or lecture. A corporate career yields a deep base of knowledge. Once you find your voice, there are a number of ways to share your point of view in paid or volunteer engagements. Take time to write the next business bestseller, speak to trade associations, lead community workshops, or offer your story to local schools. Developing an outline of your chosen topic and a short bio with your credentials will help open the door to opportunities.
Longer longevity and larger contributions
Longer lifespans and more flexible retirement ages factor into decision-making. The 20th century added 30 years to the average lifespan—now 77 years—and experts like The Stanford Center on Longevity expect that age to continue increasing. Their New Map of Life addresses the implications and opportunities of coming generations that will foreseeably reach 100 years old.
Americans age 55 or and older are now the fastest-growing segment of the U.S. workforce, with their contributions to the economy expected to triple to nearly $27 trillion in the next three decades. They’re skilled, independent and motivated, with few ready for a complete 180 when it comes to next steps. It all results in the need to reframe “retirement” with new thinking and more possibilities.
Balance is essential to a healthy and fulfilling retirement. You’ll be ready to move forward with confidence and intention once you find the right mix for your ideal lifestyle.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

Anne deBruin Sample, CEO and owner of Navigate Forward, is an experienced HR leader and Career Transition Expert. She has written for CEOWorld magazine and has been published in Fast Company and The Wall Street Journal. Her experience includes high-level positions at PepsiAmericas, Caribou Coffee and Whirlpool Corp.
-
Estate Tax Quiz: Can You Pass the Test on the 40% Federal Rate?Quiz How well do you know the new 2026 IRS rules for wealth transfer and the specific tax brackets that affect your heirs? Let's find out!
-
'The 'Mamdani Effect' in New York: Can the City Afford a Millionaire Tax?State Tax Will higher income taxes drive the wealthy to flee New York in 2026?
-
The November CPI Report Is Out. Here's What It Means for Rising PricesThe November CPI report came in lighter than expected, but the delayed data give an incomplete picture of inflation, say economists.
-
5 Smart Things to Do With Your Year-End Bonus, From a Financial ProfessionalAfter you indulge your urge to splurge on a treat, consider doing adult things with the extra cash, like paying down debt, but also setting up a "fun fund."
-
Are You a Gen X Investor? Here's How You Can Protect Your Portfolio From an AI BubbleAmid talk of an AI bubble, what's the best course of action for investors in their 50s and 60s, whose retirement savings are at risk from major market declines?
-
Hey, Retirees: Put Your Charitable Gifts in a Donor-Advised Fund (and Enjoy Your Tax Break)A donor-advised fund is a simple (really!), tax-smart strategy that lets you contribute a large, tax-deductible gift now and then distribute grants over time.
-
If You're a U.S. Retiree Living in Portugal, Your Tax Plan Needs a Post-NHR Strategy ASAPWhen your 10-year Non-Habitual Resident tax break ends, you could see your tax rate soar. Take steps to plan for this change well before the NHR window closes.
-
Could Target-Date Funds With Built-In Income Guarantees Be the Next Evolution in Retirement Planning?With target-date funds falling short on income certainty, retirement plans should integrate guaranteed income solutions. Here is what participants can do.
-
Your Year-End Tax and Estate Planning Review Just Got UrgentChanging tax rules and falling interest rates mean financial planning is more important than ever as 2025 ends. There's still time to make these five key moves.
-
What Makes This Business So Successful? We Find Out From the Founder's KidsThe children of Morgan Clayton share how their father's wisdom, life experience and caring nature have turned their family business into a respected powerhouse.
-
Past Performance Is Not Indicative of Your Financial Adviser's ExpertiseMany people find a financial adviser by searching online or asking for referrals from friends or family. This can actually end up costing you big-time.