We often imagine retirement as the ultimate reward: No alarm clocks, no meetings, no bosses — just the freedom to do whatever we want.
Here’s the paradox: That very freedom can feel empty if it lacks direction.
I’ve seen it firsthand, not only in clients but in my own family.
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more – straight to your e-mail.
Profit and prosper with the best of expert advice – straight to your e-mail.
A teenager once told his retired grandfather, “You’re free — you don’t have to do anything.”
The grandfather chuckled and replied, “Last month, I tried that. Sat around, watched TV, slept in. Thought I’d feel free. Turns out, I felt useless.”
The Kiplinger Building Wealth program handpicks financial advisers and business owners from around the world to share retirement, estate planning and tax strategies to preserve and grow your wealth. These experts, who never pay for inclusion on the site, include professional wealth managers, fiduciary financial planners, CPAs and lawyers. Most of them have certifications including CFP®, ChFC®, IAR, AIF®, CDFA® and more, and their stellar records can be checked through the SEC or FINRA.
That conversation revealed a deeper truth: Freedom isn’t simply the absence of obligation — it’s the presence of purpose.
The myth of doing whatever you want
Culturally, we equate freedom with autonomy: no rules, no restrictions, no one telling us what to do. Teenagers crave it. So do many retirees.
However, unstructured freedom can feel less like liberation and more like freefall — a loss of orientation that can lead to dissatisfaction or even depression.
The philosopher Viktor Frankl wrote: “Freedom is in danger of degenerating into mere arbitrariness unless it is lived in terms of responsibleness.”
In other words, liberty without purpose doesn’t deepen our lives — it leaves us restless.
Consider retirees who fill their days with leisure: golf, travel and entertainment. There’s nothing wrong with these pursuits, but over time, many discover they’re not enough.
Humans are wired not only to consume but to create, contribute and connect. Without those elements, “freedom” can feel strangely hollow.
The trap of wants
We all have desires — some fleeting, some enduring. But not every want leads to growth or fulfillment. An alcoholic might want another drink; a bored retiree could want another vacation. These might offer temporary pleasure but can erode long-term satisfaction.
The real question isn’t “What do I want right now?” Instead, it’s “What do I want most? Am I willing to discipline my lesser wants in service of my greater ones?”
Aristotle’s ancient insight still rings true: “True freedom is the ability to act well, not merely to act.” That means aligning choices with higher values — what I call principle-based living.”
‘Should’ vs ‘ought’
One way to find that alignment is to distinguish between “should” and “ought.”
Should is external. It comes from societal expectations, peer pressure or long-held routines:
- “You should travel more.”
- “You should relax.”
- “You should take it easy.”
Ought is internal. It arises from your principles, your conscience, your sense of meaning:
- “I ought to mentor young professionals.”
- “I ought to volunteer at the food bank.”
- “I ought to write my family history.”
Retirement often strips away the “shoulds” tied to a career. That can feel liberating — but it also leaves a vacuum. Filling that space with “oughts” is where the richest form of freedom emerges.
Think of whistleblowers such as Frances Haugen, who risked career security to act on principle, or Fred Swaniker, who left a lucrative corporate career to found the African Leadership Academy.
These aren’t retirement stories, but they illustrate the power of choosing based on “ought” rather than “should.”
Retirement as a launchpad
Many people view retirement as an extended vacation. However, the most fulfilled retirees view it as a launchpad — a chance to reallocate their time and energy toward work that matters to them.
Looking for expert tips to grow and preserve your wealth? Sign up for Building Wealth, our free, twice-weekly newsletter.
Mark, a finance professional, retired at age 62. The first year was bliss: travel, golf, leisure. By year two, he felt adrift.
“I thought I wanted freedom,” he said, “but I didn’t know what to do with it.”
Contrast that with Sister Jean, the 100-year-old chaplain for Loyola Chicago’s basketball team, who continues to invest in relationships, encouragement and service. Her purpose didn’t retire when she did.
Journalist John Leland, after interviewing dozens of people over 85, found that the happiest were not those who focused solely on leisure, but those who stayed connected to people, to purpose, to something larger than themselves.
How to find your ‘ought’ in retirement
If you’re approaching retirement — or already there — ask yourself:
- What energizes me? Look for activities that leave you more engaged afterward, not drained.
- Who can I help? Service, mentorship and community involvement deepen meaning.
- What unfinished work matters to me? This could be creative, relational, or civic.
- What principles do I want to live by? Write them down. Let them guide your daily decisions.
The key is not to fill your calendar with busy activities, but to fill it with commitments that reflect your deepest values.
Freedom with direction
In the end, the teenager who slams the door shouting, “I just want to be free!” and the retiree who sighs, “Now I can do what I want,” are chasing the same thing: a life that matters.
The difference lies in understanding that freedom without purpose is just drifting. Freedom with purpose — grounded in “ought” — is where life becomes rich.
As author Frederick Buechner put it, “Your vocation is where your deep gladness meets the world’s deep need.” Retirement doesn’t end that search; if anything, it’s the perfect time to begin it in earnest.
As you navigate your retirement years, don’t just ask, “What do I want to do?” Ask, “What ought I to do?” Then choose it — not because you have to, but because you can. That’s the kind of freedom worth retiring into.
Dr. Richard Himmer is the author of Your Encore Years: The Psychology of Retirement and host of the podcast How Not to Retire. Learn more at hownottoretire.com.
