Why Traditional Retirement Planning Falls Short—and What to Do Instead
The traditional method of retirement planning is outdated. It prioritizes the fear of running out of money over the joy of using it to create meaningful experiences and lasting memories. Too often, conventional planning focuses heavily on numbers, overlooking that money is simply a tool—a means to support a life well-lived.
While spreadsheets and withdrawal rates might seem comforting at the beginning of retirement, this overly cautious approach can lead to unintended consequences later in life. In this piece, I’ll explain the shortcomings of traditional retirement planning and introduce a more human-centered approach—Guided Planning—that helps align your money with the kind of retirement you actually want to live.
The Real Risk: Running Out of Time
Some of the most common regrets of the dying include:
- Living according to others’ expectations instead of their own,
- Prioritizing work over relationships,
- Not sharing their feelings with loved ones.
Here’s one you rarely hear: “I wish I had saved more and spent less.”
Dying with too much money can, ironically, be riskier than dying with too little—because it often means you never gave yourself permission to spend on what matters. Traditional planning rarely accounts for the true value of time, or the importance of using your healthiest, most capable years to create memories that last.
Time, unlike money, is a non-renewable resource. You can’t save it for later. And running out of time before you run out of money is a far more common—and painful—problem than most planners talk about.
Healthspan vs. Lifespan
A critical component of modern retirement planning is understanding the difference between lifespan and healthspan.
- Lifespan is how long you are expected to live.
- Healthspan is how long you are likely to remain healthy and active enough to do what brings you joy.
Both diminish over time, and both are shaped by factors like lifestyle, family history, and occupation. All else being equal, a 50-year-old is usually healthier than a 70-year-old—and the experiences available at those ages are different, too.
If you wait until 70 to do what you could have enjoyed at 50—whether it’s skiing, traveling, hiking, or simply making memories with family—the experience may not be the same. While many people adapt and find joy in new ways, those who seize opportunities earlier in life build a rich bank of memories to revisit and share forever.
The Currency of Memory
As we age, life becomes less about acquiring and more about remembering. We become mosaics of the memories we’ve made. Ask anyone who has faced a disaster what they save first—photos, heirlooms, videos. These things aren’t valuable because they cost money; they’re priceless because they hold meaning. They remind us of who we are, what we’ve done, and who we’ve loved.
Retirement planning, at its best, should help you accumulate not just assets—but moments worth remembering.
Designing Your Retirement Around What Matters Most
A meaningful retirement plan should ask:
- How do you want to spend your time?
- What kind of memories do you want to create?
- What experiences do you want to share with the people you care about?
Everyone’s retirement will look different. Some may want luxury travel; others may prioritize time with grandkids, volunteer work, or creative pursuits. What matters is that your plan reflects your tastes, values, and desires—not someone else’s assumptions.
Guided Planning helps you build a retirement around how you want to feel—not just what you can afford. It blends financial realism with emotional clarity. It starts by exploring what a fulfilling life looks like to you, and then aligns your resources to make it possible. From there, it offers a roadmap—balancing facts and feelings—to track progress and adjust as life changes.
A Better Way to Plan
Traditional retirement advice can leave you overly cautious, with a life half-lived. Guided Planning invites you to think differently: to plan for joy, not just survival.
Because in the end, the goal isn’t just to have money left over—it’s to have stories worth telling, pictures worth saving, and a life that felt like your own.