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Special Reports

Pirates, Treasure, & Your Retirement

David C. Bentall

BURIED TREASURE: Have you ever wondered why pirates used to always bury their treasure chests on a deserted island? As a child, it seemed to me like a reckless game of hide and seek! However, with age, I came to realize the wisdom of this strategy.

If a pirate had successfully accumulated a fortune, and if he kept his booty on board his ship, it was most certainly at great risk. This is because if he ever ran aground, or otherwise sunk his boat, all would be lost! Similarly, if another ship was to overtake or destroy his vessel, all his wealth could be taken in one fell swoop. No wonder then, that the craftiest sailors hid their spoils in a safe place on shore.

The Harvard Business School unearthed a similar pattern when they examined the habits of successful retirees from family business. Amongst the keys to successful retirement, they learned that the wisest family business leaders typically withdraw significant funds from their businesses and invested them in a safe harbor elsewhere. (outside the family business) This not only provides safety and security for their retirement, it also enables them to “let go of the steering wheel’ in the family businesss, so that the next generation is able to steer the ship. (without the elder generation interfering.) As a result, even if the next generation were to fail to captain the family business safely, and the “ship” was to go down, all would not be lost.


Just like the skippeer of a ship may be reluctant to give up the steering wheel, it’s not easy to let go of command, especially if you have had a successful career leading and building your company. The bigger the ship and the more successful you have been, the harder this task can be.

What makes this even more difficult, is that often a family business leaders’ self-worth and personal identity is tied up in their work. As a result, they need to disentangle themselves from the web which binds them tightly to their business.

I asked Susan Latremoille what it takes for executives to free themselves from this trap. As co-founder of New Chapter Lifestyle Advisors and author of 9 Steps to a RichLife Retirement, she has worked with scores of family business executives as they prepare for retirement. She observes that it takes several things for a leader to “let go” But, mostly notably she states that “It is necessary to replace or repurpose the things that made you successful. “ In other words, if you are used to being in command, it is essential to find another place to utilize your skills … but outside the family firm. 

Anne Mulcahy, former CEO of Xerox, put it this way. “The things that work for you as a CEO work against you as a retiree, such as being in command …”

There are many jokes about the ways former leaders try to stay in control – like running the country club board as a CEO would, or reorganizing their wife’s kitchen. But, all joking aside, family business leaders can more easily let go of the need to be in control, if they are able to find a corporate board or charity where they can serve with passion and skill.


But letting go, also requires humility. I explored this theme, in my most recent book, Dear Younger Me, and found Benjamin Franklin to be an inspiring role model. In spite of all his success, this inventor, statesman and entrepreneurial leader purposefully sought to relate to others with humility.

Quoting again retirement expert Susan Latremoille, we learn that “Without humility, old expectations can stand in the way of admitting the need to make changes and to learn new skills” Furthermore, she notes that “ If you are going to succeed in retirement, you will need to humble yourself, and become a student once again.”  


Unfortunately, having climbed the ladder of success, many people have become addicted to achievement. What began as a career, has become a relentless pursuit of achievement and success, and this can become a habit that can be hard to break.. 

The addrenalin rush of the next deal, can cause us to keep running,and  to keep chasing in order to capture that next opportunity. But, over time, many of us get stuck in patterns that keep us relentlessly focused on working, rather than living. Over time, our addiction begins to crowd out all other things,leaving little opportunity to cultivate interests outside of work.

The most powerful antidote for Achievement Addiction is to foster contentment. But to cultivate contentment requires a change in thinking. Instead of looking forward, trying to create more, or trying to find more, we need to change our focus. To be content, we need to learn to focus on the present. Only then will we be able to see, and experience all that we have been blessed with in our lives. Its not a matter of getting more. As Socrates wisely observed:He who is not contented with what he has,would not be contented with what he would like to have.”


Most people’s perception of retirement is naïve and frankly, way off base.  Either they think it will be a 30-year vacation filled with non-stop golf or that it is the end of the road and best part of life is over. 

Both views are largely unhelpful and inaccurate, at least for most people. Retirement can be a totally new chapter of life filled with endless possibilities. And there is more than just leisure to fill your days with. Humility allows you to ask questions and be open to new ideas about what is possible now.

But where should one begin?

Marianne Oehser, retirement guru and author of Your Happiness Portfolio for Reirement, suggests that “… a great place to start is by looking at your mindset about retirement. Your mindset is based on the attitudes and beliefs you have about a situation. If you believe that the best is over and it’s all downhill from here, it will be hard to appreciate this time of life. But if you look at your situation through the lens of curiosity and are open to seeing it differently, it will become clear that the best is not over. Sure, the experiences will be different, but they can be just as enjoyable in different ways.” 

As many successful retirees have discovered, the key to a fulfilling “next chapter” is to Find a passion that equals, or eclipses the passion that you had for your business. 

One former CEO became an opera singer, traveling the world performing. Another focused on raising money to help eradicate the disease that cost him his wife. Others pour their heart and sould into their grandchildren or invest in making their community a better place to live. You have just one life on this earth, why not make it count, by finding and following a new path? 

Retirement is your opportunity to create a whole new life just as you want it to be.


One thing that you don’t need, when facing retirement is a bunch of advice, or prodding from your family or friends. Instead, You need their empathy. What you are trying to do is very difficult. Having spent your whole life building and creating, now you are being asked to unwind it all, and to devolve authority to others. Its almost an unnatural act, to go backwards, when you spent your whole life pushing forward. 

But what does it mean to be empathetic? I believe that, at its essence it is the gift of really “being with” another. Or as Brene Brown puts it communicating “… that incredibly healing message …“You’re not alone.

So, if a friend, or family member, tries to tell you how to plan your retirement, or if you recognize you are struggling with this phase of life, tell them to back off. Let them know that you don’t need them to give you a piece of their mind, instead, you want their presence and their time. In a word, you want their EMPATHY. It is perhaps the greatest gift anyone can give you during this season in your life.


Having spent some time recently with the retirement experts at Next Chapter Lifestyle Advisors, I have been reminded that we can learn a lot from pirates, because they knew how to wisely protect their earthly treasure. I also discovered that Humility, Passion, Contentment and Empathy are qualities that can greatly assist those of you who are wanting to retire as well as those who are walking alongside you on the journey. 

The future is full of limitless possibilities and new frontiers. As you think about retirement you might even say that it’s kind of like a treasure, just waiting to be unearthed!

Written by David C. Bentall. The author would also like to acknowledge the Retirement experts at New Chapter Lifestyle Advisors, whose insights and experience were the inspiration for this article.
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CEOWORLD magazine - Latest - Special Reports - Pirates, Treasure, & Your Retirement
David C. Bentall
David C. Bentall is founder of Next Step Advisors and has been advising family enterprises for over 25 years. He has also personally experienced succession in his family’s real estate and construction businesses. Additionally, he is a gifted author, coach, speaker and facilitator. His new book, Dear Younger Me: Wisdom for Family Enterprise Successors (Castle Quay Books, May 3, 2021), explores the character traits critical for navigating the interpersonal demands of a family business enterprise.

David C. Bentall is an opinion columnist for the CEOWORLD magazine. Connect with him through LinkedIn.