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AS FOLKS HURTLE toward retirement, they often wonder whether they’ve saved enough, debate when to claim Social Security and fret about how they’d pay for long-term care. Make no mistake: Such issues are hugely important.
But amid these financial musings, we should also spare a thought for four other questions:
How can I transform myself from a diligent saver to a happy spender? This sounds so easy, and yet many struggle with it, including Ken Begley and including me—and including those who amassed vast fortunes, as Marjorie Kondrack recently discussed.
To be sure, we don’t have to spend our money to get pleasure from it. Simply sitting on a pile of dollar bills can deliver happiness, thanks to the sense of financial security it offers. Similarly, giving away money, whether to loved ones or to charity, can also deliver ample happiness.
Still, I think every diligent saver should ponder whether there are ways to spend more on themselves that could improve their retirement years. I have no clever strategies to suggest that’ll help you go from avid saver to joyful spender. But I’ve found that practice helps.
My advice: Don’t start with a big purchase—a super-lavish vacation or a luxury car. That’ll likely make you uneasy, and there’s a risk you won’t get much pleasure from the money involved. Instead, try buying some smaller items, which often deliver disproportionately greater happiness per dollar spent. If you part with a little more money than usual and it enhances your life, perhaps your attitude will slowly shift and you’ll find yourself enjoying the fruits of your earlier thrift.
What will get me out of bed in the morning? I’m a big fan of daydreaming. Assisted by the internet, I muse about vacations I’d like to take, restaurants I want to try and musicians I’d like to see perform. Daydreaming costs nothing except time, and—I suspect—often delivers just as much pleasure as the real thing.
As you approach retirement, I’d encourage you to daydream about how you’ll use your time once you quit the workforce. Indeed, I think it’s worth creating a lengthy wish list. That wish list will no doubt include fun stuff, like trips you want to take and hobbies you might pursue.
But I’d also include a few items that have the potential to deliver eudaimonic happiness and that could put you in a state that psychology professor Mihaly Csikszentmihalyi referred to as “flow,” where you become completely absorbed in what you’re doing and time just whizzes by. We’re talking about activities that you consider important, that you find challenging, that you’re passionate about, that you feel you’re good at—and which could provide your retirement with a sense of purpose.
That sense of purpose will make your retirement more fulfilling and help to compensate for the identity you lose when you leave fulltime work behind. I’ve seen folks mourn the end of their career, with that deflating sense that not only were their accomplishments modest, but also there’ll be no more chances to rectify that. To ease this “grief,” it’s helpful to have something to look forward to—another chance to do good work.
Who are the friends I’ll see regularly? During our working years, we often count our colleagues among our friends. Yet these friendships often peter out when we change jobs or shift into retirement. How will we make new friends? I wouldn’t leave this to chance encounters, and instead have a plan for how you’ll meet others.
And, no, don’t count on family to fill the friendship void. Our adult children often have busy lives, and don’t necessarily want to spend big chunks of their limited free time with Mom and Dad. Moreover, as Dennis Friedman has noted, we spend time with friends because we think we’ll enjoy it, whereas with family it’s not solely about enjoyment—there’s also a sense of obligation.
I’m no great fan of retirement communities, but I could imagine my attitude changing in the years ahead. Those who live in retirement communities seem to find it easier to make friends, so these communities might be a good choice for those who fear social isolation and struggle to meet others.
What will my future self think of the decisions I make today? This is always an important question to ask—but it’s especially important for newly minted retirees, because so much will change in the years ahead.
Our mobility may be sharply curtailed or we may find ourselves devoting large chunks of time to medical issues. The activities that appeal to us at age 65—travel, pickleball, caring for the grandkids—may hold scant appeal a dozen years later. Because so much is unknown and things can change so quickly, it’s hard to imagine who we’ll be just a decade down the road.
And yet, despite all the uncertainty, retirement tends to trigger “end-of-history illusion,” where we assume that our life’s constant change will finally come to an end. Will it? I wouldn’t count on it. Our time in retirement could be marked by major upheaval, and the initial choices we make might get quickly thrown out.
Rick Connor touched on this recently. In 2021, he and his wife Vicky sold their home in the Philadelphia suburbs and moved to a New Jersey beach community, imagining this would be their final stop. And yet they’re already wondering whether they might move again.
I, too, wonder whether the retirement plans that Elaine and I are making today might get torn up just a few years down the road. What to do? Make sure your home will be suitable for your older self. Think long and hard before making major financial commitments, such as a second home or an RV. Don’t rule out options that might seem unappealing today, such as a 55-plus community or a continuing care retirement community. I think flexibility is the key—especially when it comes to housing.
Jonathan Clements is the founder and editor of HumbleDollar. Follow him on Twitter @ClementsMoney and on Facebook, and check out his earlier articles.
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I retired from government service after 31 and getting hurt on the job. After a couple of years, got bored and found a part time gig in the rental car business, work a few days a week. Now it’s over ten years later and though with a different company, still working a few days a week and loving it. Nice to get out and be with other people who are retired also plus nice to work because I want to. Between a pension with a year COLA, social security & investments, living the same life we always did. Empty nesters who’ve always lived under our means and still do, lessons it seems our kids also learned.
Nice to choose to work now even though we don’t have to, puts a whole new spin on working. Best part is I get to choose when I stop again, the choice is mine & mine alone. But continue to keep on working now & happy with this choice.
I retired at the age of 60, that was seven years ago. My experience is that if you were living a full and rich life before retirement with many shared and a few independent hobbies with your spouse, with many different social circles centered around an activity (church, tennis teams, pickleball groups, blogging friends, hiking, fishing buddies, grown children) there is almost no retirement planning required. It’s just about having a rich life every year of your life, not trying to find one when you retire, that’s too late to start. Not too late in that it’s hopeless, it’s not, but too late because you missed out on a lot of fun during your working years you can’t get back. Because I had a very visible high powered job I did think I needed an off ramp approach with work that involved some limited consulting after retiring. I worked eight hours a week at that which kept me in my same business social groups and also paid 100% of our living expenses since we had only been spending about 25% or our income prior to retirement. After four or five years I ramped the work down to even less, maybe four or five hours a month, but it still requires some intense focus which I think is good for the brain. Plus I chair three boards as a nonpaid volunteer, a hospital, a college and a foundation. I loved my job but this retired life is twice as good!