How To Retire When You're a CEO

Tips for Transitioning Out of a High-Powered Leadership Role and Into the Next Phase
Kathy Longo, CFP®, CAP®, CDFA Wednesday, 29 January 2020

How To Retire When You're a CEO

Retirement can be a difficult transition for anyone, but it can pose an even greater challenge for those leaving high-powered leadership roles. Since their positions are so incredibly demanding, CEOs often don’t have the time or focus to plan their next move. Also, since the average age of retirement for a CEO is just 62, that leaves quite a few years to plan for. CEOs also frequently define themselves by their work, which can make retirement feel like a loss rather than a milestone to celebrate.

If you find yourself planning to retire from a leadership position, read on for tips to help you adapt to your new, non-career driven lifestyle.

Acknowledge Feelings of Loss

CEOs often achieve career success because they are highly driven, competitive and appreciate a challenge. They put more time, effort and brain power into their work than the average person, making it all the more difficult to give it up. If you’ve measured your self-worth by your career success, retirement can become a confusing, isolating time. It’s common to feel a loss of purpose, or even to suffer from depression. In fact, research shows that highly successful individuals may actually be more prone to depression and related mental health concerns. Taking time to acknowledge any feelings you’re having about retirement is a healthy step, and there’s no shame in seeking professional help when needed.

Plan for What’s Next

The average American lifespan is 78 years, so if you retire in your early sixties, chances are good that you have quite a few years left. What will you do with them? Having a plan in place for your retirement years can help with feelings of loss by allowing you to focus on an exciting new venture. Many retired CEOs continue working in some context, be it part-time as a consultant or even in philanthropic ventures. According to recent studies, remaining active in some kind of work is actually good for your health. Retirees who work or volunteer part-time have lower blood pressure, fewer major diseases and report greater satisfaction in life. So, think about your accumulated skills and experience and make a plan for continuing to use them in retirement. Since retired CEOs are a valuable commodity, you may be surprised at the options at your disposal. Be selective and choose organizations and causes that will be fulfilling for you. Also, don’t forget to pursue hobbies and leisure activities that you may not have had time to explore during your busy working years. Now is the time to focus inward a bit and plan a retirement that is both purposeful and meaningful to you.

Focus on Family and Friends

One of the true blessings of retirement is the option to spend more time with the people who are important to you. Your high-pressured job likely kept you from investing as much time into family and friends as you would have liked, and retirement gives you the opportunity to refocus your energy. Simply being more present in your home may be a transition at first, so keep the lines of communication open with family members. If you have a spouse or children living in your home, be mindful that your retirement will be a time of transition for them, too. Talk together about how you might spend your days and whether there are opportunities for making more meaningful connections together.

Explore Mentorship Opportunities

If you’re still hoping to use the skillset you developed as a CEO without a formal part-time or volunteer position, consider taking a young leader under your wing – perhaps even someone who reminds you of your younger self. You can still enjoy the retirement lifestyle by making your own schedule, but you’ll have the opportunity to provide guidance, advice and problem-solving acumen that an up and coming leader may be hungry for.

Be Patient with Yourself

Going from the high-stakes business world straight into a phase of leisure will take time to come to terms with. It won’t be easy to leave the working world behind you at first but try to be patient and allow yourself some grace in the transition. If it helps, work to change your mindset from one of loss to one of opportunity – specifically, the opportunity to reconnect with what’s truly important to you in life. What will make retirement fulfilling for you? Are there goals you’d still like to accomplish? Who do you want to spend your time with? You may not have answers to these questions right away, but slowly gaining an understanding of what you want out of your post-career years will be the ultimate panacea for your transition challenges.

Retiring as a CEO may mean saying goodbye to the corner office and work that defined and fulfilled you. However, it’s also the start of a new phase of life in which you can find continued meaning and purpose.

Related Articles

About the Author

Kathy Longo, CFP®, CAP®, CDFA

Kathy Longo, CFP®, CAP®, CDFA

Kathy Longo brings over 25 years of expertise and experience to Flourish Wealth Management. Kathy is wholly dedicated to improving the life of each client and finds joy in making complex matters simple and easy to understand. She excels at asking the right questions, uncovering new possibilities and implementing the most advantageous strategies for success. Playing such a pivotal role in her clients’ lives remains an honor and a privilege. After earning a degree in Financial Planning and Counseling from Purdue University, she began her career at a small firm in Palatine, Illinois where she worked directly with clients while learning to build a viable, client-centric business. Over the years, she gained extensive knowledge and wisdom working as a wealth manager, financial planner, firm manager and business owner at notable, various sized companies in both Chicago and Minneapolis.


  • This email address is being protected from spambots. You need JavaScript enabled to view it.

Top Financial Advisor in Minneapolis

Contact Us

  • 3300 Edinborough Way
    Suite 420
    Edina, MN 55435
  • FAX: 952.953.3310
Listen to Flourish Financially on Your Favorite Streaming Service

Copyright © 2020 Flourish Wealth Management, Inc. All Rights Reserved. Powered by AdvisorFlex.