Check-Off Your Bucket List
With Fun (but Meaningful) Goals

4 minute read

Woulda, coulda, shoulda.
It’s time for will, can, did.

-Cyrus Bamji

In the 2007 movie, The Bucket List, Morgan Freeman and Jack Nicholson play terminally ill cancer patients who decide that rather than spending the rest of their days focused on tubes and tests, they’re going to escape and go on one last adventure. In the scenes that follow, they check off all the items on the bucket list that Freeman’s character wrote and Nicholson’s supplemented.  Among them: Skydiving, racing classic cars, going on safari, flying over the North Pole and – of course – visiting the Great Wall of China.  Good thing one of them happens to be a billionaire.

The film takes a number of inevitable twists and turns but what happens in the end (spoiler alert) is that the adventure pales in comparison with the friendship that forms between the two men – and how it contributes to repairing the important relationships in both of their lives.   That’s not too far from how bucket lists work in reality, says Chris Farrell, senior economics contributor at Marketplace, American Public Media’s nationally syndicated public radio business and economic program, and the author of five books, most recently, Purpose and a Paycheck: Finding Meaning, Money, and Happiness is the Second Half of Life.

This is important information for the massive Peak 65 group of Americans to keep in mind.  Next year, 2024, will mark the year that more Baby Boomers turn 65 than ever before – roughly 12,000 will hit the milestone on a daily basis.  In Farrell’s many conversations with retirees – and soon to be retirees – he has found the bucket list phase to be front of mind, and undeniably important, at the start of retirement. Like Freeman and Nicholson in the movie, travel and spending time with family and friends tops the bucket list of things people want to do in retirement according to the Alliance’s latest Protected Retirement Income & Planning Study (PRIP). “People who retire from their full-time job want to go out and do things,” he said, “[they want to] take vacations and visit friends or maybe take art classes. But within about 2 years,” he notes, “about 40 percent of people go back to work.”  Not traditional work (more on that in a second) but they’re doing something that takes into account their skills, knowledge and experience and importantly asks the questions: “What is it about how I’m spending my days that says, ‘I’m making the world a better place?’

A bucket list doesn’t necessarily have to include big or expensive things. It could include the simple, more meaningful things you’ve always wanted to do, like volunteering or working part-time at your favorite charity, or starting a small but meaningful business.  The most important thing is to get started.  Or, as Cyrus Bamji, Chief Communications Officer for the Alliance Of Lifetime Income likes to say: “Woulda, coulda, shoulda. It’s time for will, can, did.”

WATCH Your Money Map: Check-Off Your Bucket List With Fun (but Meaningful) Goals

On June 28, 2023, Chris Farrell, Senior Economics Contributor at Marketplace joined Jean Chatzky for an episode titled, Check Off Your Retirement Bucket List. Episode Details: For many of us, retirement is about more than just relaxing — it’s about having the time, money, and freedom to accomplish dreams and goals that might have been decades in the making. That might mean traveling the world, starting a business, or spending quality time with friends and family. The big question — how can we afford it? Join host Jean Chatzky and Chris Farrell, senior economics contributor at Marketplace, as they unpack what today’s pre-retirees want to achieve in their later years, how they can make it happen financially, and what it looks like to find both purpose and a paycheck in retirement.

Take Two

Spending a solid two(ish) years focusing on the items on your bucket list is essential for many people, particularly Baby Boomers, Farrell explains.  Why?  Because for many who grew up at work in the years before the pandemic (when many of us lived to work rather than the other way around – and didn’t consider it a bad thing) it takes a long time to separate their job title from their identities, and the tasks they’ve been doing from their skill set.  Take that time.  It’s important to clear your mind and give yourself time to both pause and process.   “You can start to think about what is it that I might want to be doing, not what my organization thinks is an okay thing for me to be doing,” Farrell says.

Harness Your Idealistic 24-Year-Old “Experimental Mindset”

Most young adults just starting out, some right out of college, some not, know what a job is, Farrell says.  They’re a little less sure about what makes a career.  “All they know is they want to do something that makes a difference.”  A conversation with a 60-something-year-old, he explains, is often the very same thing.   “The only difference is that at 24, you think time is infinity.  At 65, you’re very aware that time is shorter.”  So, the challenge becomes: What’s the portfolio that’s going to provide you with purpose.   It may take what Farrell calls an “experimental mindset” to find the answer.  This is a hit-and-miss proposition.  Maybe you think, “I love animals.  I’ve always wanted to work for [an organization like the] humane society.”  But you try it out and you realize a lower- level job than you’re used to isn’t going to do it for you.  Or you don’t like the way it’s run.  But you realize the cause is important and you’ve met some new people who say: “Hey, maybe you want to go try this thing over here.”  Eventually you find it.

Don’t Skimp On The Paycheck Part

There’s a lot to be said for earning some money as you enter “retirement.” (Yes, it needs another name, Farrell acknowledges.  We’re working on that.)  Among the many benefits: You can delay taking Social Security, which results in an annual bump in benefits that’s tough to achieve in any other guaranteed way.  You may be able to put off beginning those distributions from your 401(k)s, IRAs or other retirement accounts, allowing that money to continue to grow.  There’s also the fact that when someone is paying you, they take you seriously, Farrell notes.  “I was talking to a former accountant,” he recounts.  “He was working for an organization where he was using his skills but making just $10 an hour.  When people met him, they were on time, they did their work.  When he volunteered, [in contrast] sometimes they didn’t show up.”

Hanging out a shingle or selling your services – perhaps the same skills and knowledge that you used in your original day job – as a consultant or gig, can be a good place to start.  You can try to tap into your network from your previous company – which Farrell calls most people’s “greatest asset” — or find work through a local business accelerator.  “The entrepreneurial ecosystem has really grown,” he notes.

Bottom line: As David Blanchett, Research Fellow in the Alliance’s Retirement Income Institute and Managing Director and Head of Retirement Research for PGIM DC solutions, often says: Retirement is the most expensive purchase most households will ever make.  You want to be sure that you’re not only set up to fund it – but to enjoy it for many years to come.


For ideas on having the financial freedom to check-off your bucket list, visit Protecting Your Bucket List or the Tools and Guides section of the Alliance website.

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