"They didn’t regret what they spent. They regretted what they waited too long to do."
I’m Megan Ramshaw, CFP®, lead advisor at MOKAN Wealth. After speaking with more than 250 disciplined, self-made 401(k) and IRA millionaires, one truth came up again and again. Regret in retirement is rarely about market moves or a purchase you wish you hadn’t made. It’s about time, clarity, and confidence. If you’re in your 50s or early 60s, have saved well, and want to spend without second-guessing your future, this is your field guide.
Here’s what you’ll find inside:
- Why waiting “one more year” can cost more than money
- The real reason smart savers struggle to spend
- Why your go-go years slip away faster than you think
- The single “enough” number that gives you confidence
- The health mistake too many retirees admit
- What the happiest retirees did sooner, not later
You’ve done the hard part. This is your permission to enjoy what you’ve earned.
Why Retirees Regret Waiting
The pattern is clear. Retirees do not look back and wish they had guessed the market better. They wish they had used their healthiest years more fully. In a New York Life survey, 50% of people who retired at 60 or older regretted waiting, and they wished they had retired about four years earlier.
These go-go years (roughly 60 to 72) are time-sensitive. Health shifts. Energy changes. Family needs evolve. If you plan to retire smarter, not just richer, you need a strategy that puts meaningful experiences earlier, then adjusts over time.
Regret #1: Waiting Too Long to Enjoy Life
What retirees said: “We played it safe for too long and missed the sweet spot.”
The early retirement window, often your ages 60 to 72, is prime time for travel, active hobbies, and big memories with the people you love. Many savers push off those years for the comfort of “one more year” of work, one more round of saving, one more proof point that it’s safe. Then health or family dynamics change, and the window narrows.
The data backs up what real families share. Half of those who retired at 60 or older wish they had pulled the plug earlier, by about four years. The cost is not just financial. It’s missing the season when your body can handle that long hike, when your parents are still able to join you, or your grandchildren still want to go.
“We played it safe for too long and missed the sweet spot.”
Build a Front-Loaded Spending Plan
A front-loaded plan helps you spend more when it matters most, then taper later as your lifestyle shifts.
- List your top 5 bucket-list experiences and relationships to prioritize in years 1 to 10.
- Budget 20 to 30 percent more for years 1 to 5, and tie those dollars to named experiences.
- Review your plan every year, and shift dollars as your health and interests evolve.
This doesn’t mean overspending. It means spending with purpose while you have the most freedom and energy.
Regret #2: Never Getting Clarity on Your “Enough” Number
What retirees said: “I could have retired earlier, but I didn’t know I could.”
The single biggest driver of overwork in your 50s and early 60s is fear. Not a lack of savings, a lack of certainty. A recent study shows nearly a quarter of pre-retirees are thinking about working longer, and over half of early retirees ages 45 to 60 are considering going back to work. Not because they want to, but because they’re unsure if the numbers support their life.
It’s a clarity problem, not a savings one.
If you do not know your “enough,” you default to more saving and less living. The result is lost time you cannot get back.
Find Your Work Optional Number
Your work optional number is the amount of assets and income where work becomes a choice, not a must. It accounts for taxes, healthcare, spending patterns, and market swings. At MOKAN Wealth, we guide clients through defining that number, then stress test it across real scenarios so you can make decisions with facts.
Benefits of knowing your number:
- Freedom from worry, since you know the floor that keeps your plan safe.
- Confidence to retire on time, or earlier, backed by a plan, not a hunch.
- A model tailored to your tax picture, spending needs, and goals.
Regret #3: Thinking You Had to Keep Saving Forever
What retirees said: “I was great at saving, terrible at spending.”
Saver habits are sticky. You have decades of saying no so your future self could say yes. The day after you retire, those habits do not flip. Many people keep the same tight belt, not because they need to, but because the habit is strong. It can cap your early retirement lifestyle for no good reason.
In a Medicare FAQ study, 86% of retirees said they wish they had spent more and lived more earlier, not saved more. That should reset your mental model. The common regret is not running out. It’s missing the chance to live fully while you still could.
The regret isn’t running out, it’s not living.
Create a Flexible Income Plan
A flexible plan gives you permission to enjoy life, knowing guardrails are in place.
- Set spending guardrails. Define a comfort range and a trigger to cut back if markets drop.
- Track joy, not just dollars. Review which expenses brought the most satisfaction.
- Rebalance yearly. Adjust your withdrawals, taxes, and portfolio risk to stay on track.
This structure replaces guilt with clarity. You keep control while making room for the parts of life that matter most.
Regret #4: Not Prioritizing Health Early Enough
What retirees said: “Now that I have the time, my body can’t keep up.”
Your freedom rests on your health. Your health is your retirement. Without it, trips get shorter, activities get limited, and that hard-earned flexibility fades. In a Medicare FAQ study of more than 500 retirees, a common regret had nothing to do with money. It was delaying exercise, skipping preventative care, or ignoring Medicare choices, then paying the price in mobility and freedom.
This includes physical habits and planning choices. If you delay strength work, cardio, or routine check-ups, you reduce your future range. If you ignore Medicare strategy, you risk gaps in coverage and higher costs later.
Health, mobility, and coverage are part of your retirement plan.
Start Small Habits for Big Gains
Your goal is consistent, simple habits you can keep.
- Walk 30 minutes a day, and add two days of strength work each week.
- Schedule annual check-ups, dental visits, and key screenings now.
- Review your Medicare coverage before open enrollment, and compare options.
Small steps compound. You protect the go-go years, extend your travel window, and move with more confidence.
Regret #5: Not Planning What to Do with Your Time
What retirees said: “I retired from work but had nothing to retire to.”
Retirement is not only an end. It is a shift into a life you design on purpose. The happiest retirees do not just relax. They engage. They build structure around learning, community, contribution, and fun. Without that, the first six months feel great, then boredom, loss of identity, or isolation can creep in.
It’s about starting a new purpose.
Design Your Purpose Plan
Lay out what a great week looks like before you leave your career.
- Join a club or community that meets regularly.
- Learn a skill you paused, like guitar, art, or a language.
- Volunteer with an organization that needs your experience.
A simple purpose plan goes a long way. It gives rhythm to your weeks and meaning to your days.
Regret #6: Waiting Too Long to Travel
“We put it off and then it was too late.”
Travel rarely gets easier with age. Long flights, stairs, heat, uneven streets, and jet lag take a larger toll later. If you’re healthy now and have the itch, plan the big trips in the first 10 years. Save short, local, or low-effort travel for later.
- Plan your year 1 to 3 “signature trips” and put deposits down.
- Budget for experiences, not just flights and hotels, so you actually do the thing.
If it fits your health and your plan, go sooner. It’s harder and less enjoyable later.
Key Lessons from 250+ Retirees
The regrets we hear most are about timing, not numbers. If you’re in your 50s or early 60s, this is your window, the period when health, wealth, and freedom tend to align.
Top insights to act on now:
- Use your go-go years. Spend more early on the experiences that matter.
- Get clarity on your work optional number. Confidence comes from a tested plan.
- Replace guilt with structure. A flexible income plan sets guardrails so you can enjoy life.
- Protect your health. Fitness, sleep, and preventative care belong in your plan.
- Plan your purpose. Decide what you’re retiring to, not just what you’re leaving.
- Travel sooner. Put the big trips in years 1 to 10 if your health allows.
Conclusion and Next Steps
You do not need another year at work to feel safe. You need a clear plan that tells you what is enough, when to spend, and how to protect what matters most. Use these lessons to retire smarter, spend with confidence, and avoid the regrets real retirees share. What’s one thing you refuse to wait too long to do?
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