What books and articles can you recommend that deal with the philosophy of retirement?

I'm almost 69 years old and many of my friends are retiring and love doing nothing. I've been a real estate developer for 46 years and self-employed for 38, come and go as I please, still love what I do, and have more money than I could ever spend intelligently. The thought of not having an interesting career or just playing golf and losing brain function scares the crap out of me. I don't have the faintest idea of what I'd want to reinvent myself into, or why I should. What articles or books can you recommend for approaching retirement with a positive mindset? 

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Hello,

First of all, congratulations! You are in a very envious position! Being a convivial person and also an active traveler myself, I have met people from all walks of life. I particularly love to converse with folks from the Great Generation, not only do they share the most fantastic stories (many times I wish someone can make the movies out of it), but I also pick up some regrets which I can use it in my practice to counsel pre-retirees. One of those regrets was the boredom of the retirements that no one has mentioned before.

People have the general idea of what a retirement would be like, no more getting up on time and beating the traffic, more time to travel and see the world, etc., but pretty soon people realize no matter how late they get up, they still have so many hours of a day to kill or so many places to visit. Then what?

To avoid that scenario, I ask all my pre-retirees what their plans are when they retire in five years, and again in a year. Since a majority of them are professionals and work the 40-hour a week schedule, a sudden screeching half of work is analogous to coming down from the highest point of a roller coaster. You feel the initial excitement, but soon that thrill wears out. For physically and mentally fit pre-retirees, I encourage them to ease into the retirement. After all, their experience can be so valuable to the companies that they can be great mentors to the new hires. It’s a win-win situation for both retirees and employers. Working part-time not only reduces the burnout feeling, but also enjoy some financial perks, such as the continuations of the health insurance plan and income. Employers are also spared from the talent shortage or reinventing the wheels to train new employees.

Even for people who are retired early due to health reasons, I still encourage them to sign up some volunteer charitable functions. For example, I encouraged a physician client who was forced to retire by an unusual form of the Parkinson’s disease at the peak of his career to sign up a local support group. At the beginning, he was reluctant to go out and became depressed over time. Later, I connected him to a new PD support group and he blossomed. He used his medical background and knowledge of PD to help so many new comers to better understand their diagnosis. He felt useful, and the socialization also improved his morality. All in all, even the sickest may have something to give, whether it’s experience or care, and in turn, they are positively rewarded through the human interactions.

It may seem that I go off on a tangent, but all aforementioned is to encourage you to start a conversation with your financial planner, who may know you and advise you for years about finance and business, what will be the next best thing for you.   

Meanwhile, here are some recommended books (“The Big Shift: Navigating the New Stage Beyond Midlife,” by Marc Freedman; “The Encore Career Handbook,” by Marci Alboher; “65 Things To Do When You Retire,” edited by Mark Evan Chimsky; “Boundless Potential,” by Mark S. Walton; “Master Class,” by Peter Spiers; “Second-Act Careers,” by Nancy Collamer; and “Second Wind,” by Bill Thomas) or websites (Encore; lifereimagined.aarp.org; nationalservice.gov/programs/senior-corps).  Yes, I save the best for the last :-)

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