Conventional wisdom says that planning a successful retirement is all about financial security—you focus on saving and growing a nest egg and creating a financial plan so that you never have to worry about running out of money in old age.

But financial advisor Wes Moss, CFP, noticed a paradox—many wealthy r­etirees did not seem significantly happier than retirees who had just a few hundred thousand dollars. His conclusion: Big retirement accounts let people sleep well—but may not give them enough reason to get up in the morning.

Moss wanted to see if he could reverse engineer what makes for a great retirement, so he launched multiple studies of more than 2,000 older folks to find out what happy retirees were doing right. Among his surprising findings: Having more money in retirement makes you happier up to a point, then plateaus. Having hobbies to fill up your time isn’t enough—you need activities that you are passionate about. You want to live close to your kids—but not too close. And having a busy social life isn’t as important as having a few meaningful friendships.

The desire for a realistic vision of retirement has been stoked by the pandemic. Many people working remotely got a trial run at what staying home every day looks and feels like. Bottom Line Personal asked Moss to highlight the data from his study and explain how to use it to plan a richer, fuller life once your working days are over.


In my “Retirement Happiness” study, participants answered dozens of questions about their lives and rated their overall satisfaction on a scale of one to five (five being the best). I divided the respondents into two groups—happy retirees and unhappy retirees—and looked for meaningful patterns in the data.

Social data…

Happy retirees had an average of 3.6 “core pursuits”…unhappy retirees, fewer than two. A core pursuit is an activity that brings you an ongoing sense of excitement and fulfillment. The top four core pursuits among the participants were travel…activities with kids and grandkids…playing tennis or golf…and, by far number one, volunteering. For interesting ideas about where to volunteer: Contact AmeriCorps Seniors (, a federal program with more than 200,000 members that engages volunteers ages 55 and older to serve their communities.

Happy retirees maintained at least three close connections beyond their spouses. The study defined “close” as people you would confide in about good or bad news. Unhappy retirees averaged just 2.6 close connections. Also: Retirees who took at least one trip a year with a close connection were twice as likely to be happy as the average retiree. And the more close connections retirees had, the greater their levels of satisfaction.

Retirees who visited or attended one large “social epicenter” a week were twice as likely to report being happy over the average retiree. Social epicenters include places of worship, an exercise or golf group, senior centers and/or a charitable or neighborhood group.

Relationship data…

Happy retirees stayed married. Those who were not married were 4.5 times more likely to be unhappy than the average retiree. Being single in retirement didn’t doom retirees to unhappiness, but those who were single needed to be very intentional about their support networks and realistic about making lifestyle changes to match their expected income.

Happy retirees had sex at least once a month. If you had sex at least once a week, you were twice as likely as the average retiree to report being happy. Less than once a month, you were twice as likely to be unhappy.

Personal financial data…

Retirees who had paid off their mortgage—or who were within five years of paying it off—were four times more likely to report being happy. While there can be solid tax and investment advantages to keeping a home mortgage, my study found that older folks got a sense of security from owning their homes debt-free. I typically recommend to my retiring ­clients the one-third rule—pay off a mortgage only if they can use no more than one-third of their nonretirement savings.

Happy retirees had at least $500,000 in liquid net worth. This included easily accessible investments such as stocks and bonds but not their home and illiquid possessions. Millionaire retirees did report higher happiness levels than others overall. But a half-million dollars was the trigger point for diminishing returns. Happiness levels increased dramatically for retirees who had $500,000 in retirement savings compared with those who had $100,000. But retirees who had more than $500,000 in retirement savings reported far less of a happiness boost.

Happy retirees talked about personal finances with their partners one to two hours each month. Once you spend more than that, satisfaction levels plateau. And discussing finances 3.5 hours or more a month actually was counterproductive.

Family data…

Retirees whose adult children were financially dependent on them were 1.5 times less likely to be happy as the average retiree. The unhappiest retirees often had adult children still living in their homes. Also: More than 40% of respondents still provided their adult children with some financial support, but happy retirees gave their adult children an average of less than $500 a month…unhappy ones, more than $700.

Retirees who live close to at least half of their adult children were five times more likely to report being happy than the average retiree.


While every retiree’s circumstances are different, by emulating and incorporating some of what we learned above, you can reduce the traumatic adjustment that you might experience when you retire. To implement these ideas…

Write up a nonfinancial plan. The unhappiest retirees had vague and superficial notions of what retirement would look like, which often led to isolation and boredom. Better: Set social and lifestyle goals for yourself. The list doesn’t have to be comprehensive, but you need to plan enough to create a vision and structure for how you will spend your weeks. This is especially important for men who retire and don’t maintain the social support system of their “work families.”

Practice a faux retirement. Consider taking an extended vacation without leaving home to experiment with retirement routines and test out what feels meaningful. What you think you need when you stop working may have to be redefined or rethought.

Don’t count on your to-do lists and bucket list to keep you occupied. Many people expect to fill up their days with time-intensive tasks and activities that they had been putting off for years, ranging from taking vacations to renovating the kitchen to organizing all the photos on their computers. Reality: You will get through those lists quickly and need to find ongoing ways to stay busy and maintain a sense of purpose.

Get on the same page as your spouse. Start small. Talk about what your first month of retirement will look like. Be sure to address how your financial situation supports and affects your lifestyle. Example: If the stock market takes a beating and your finances are tight, what cutbacks are you prepared to make? How long would each of you like to stay in your current home, and what alternatives would you consider?

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