Real-life retirement lessons from people who have chosen (or faced) radical, inspiring and unexpected journeys

Most retirement advice assumes that everyone wants the same things: stop working at age 65, cut back on spending, maybe travel a little, and hope that your money lasts.

But real life is not like that.

People retire early, retire late, abroad, at home, with passion projects, with heartbreak, with courage, with second chances, with dreams that are completely different from the “traditional” model. Every path teaches something about the power of money, yes, but it also teaches something about purpose, identity, resilience, and freedom.

Here are 12 real-world retirement journeys and their hidden lessons. Think of it not as a map, but as a reminder: Your retirement can and should be like you.

1. RV Nomads: Retirement is a road trip, not a destination

After working at a desk for many years, Jim and his wife bought a 30-foot RV, sold most of their possessions, and spent the first three years of their retirement exploring national parks. They're not trying to “retire on the cheap,” in fact, living in their RV is quite expensive. However, the couple wanted to have an adventure while still in good health.

Money Lessons: Housing is the biggest lever in retirement planning, and it's important to have a long-term plan for deciding what to expect when you settle down. RVing may just be a relaxing phase of retirement. It’s also important to plan for slow and stagnant years.

Life Lessons: You don't have to “settle”. Movement can be clear, and less often means more life.

What they will tell you: “Try living a little for 30 days before retiring to your RV. If you love it, you've opened a door that most people never consider.”

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• Nomadland is an award-winning film about an RV driver who finds himself in financial ruin.
• Even more interestingly, if you use social media, you may want to join various Facebook and Reddit groups to learn more about retirement living. Do a search and try different communities until you find one that fits your needs.
• Use the Boldin Planner to ensure your retirement plan simulates housing and medical expenses later in life.

2. Foreign retirees: new life – new language, new budget, new friends

Stacey moved to Portugal for the climate, culture and healthcare and found her cost of living dropped by almost 40%.

Money Lessons: Retiring abroad can save you more money than almost any other strategy, but it requires advance planning for taxes, visas and health care.

Life Lessons: Reinvention is possible at any age. Community builds faster when you take small risks, like joining a language group or talking to strangers in a café.

What they will tell you: “Visit in different seasons. If it feels good year-round, you may have found your new home.”

“Missing family members are a real problem.”

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• Find out how to retire abroad and the best places to retire abroad.

3. Very early retirees (FIRE): freedom before age 45

Sam saved money aggressively, lived lean, and left the company at age 43. Now he writes in the morning and coaches youth soccer in the afternoon.

Money Lessons: Extreme early retirement is math + mentality. Savings rate is more important than investment choices.

Life Lessons: If you give up on something instead of moving towards something, you will feel lost. Purpose needs to be part of the plan.

What they will tell you: “Start experimenting with your 'off-duty identity' years before you stop working.”

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Check out 18 Great Lessons from FIRE Influencers and our podcast with Scott Reickens, author of Playing with Fire.

4. 80-year-old worker: Retire on your own terms

Mary never stopped working, partly because she loved it, but the money was also useful. At 80, she still works part-time in consulting and says it keeps her sharp and socially competent.

Money Lessons: Working longer hours isn’t just about income; It reduces portfolio withdrawals and preserves Social Security benefits. Once Social Security kicks in, part-time work can boost your income to pre-retirement levels or beyond, improving your quality of life and ability to spend stress-free.

Life Lessons: There's joy in working when it's on your schedule and not someone else's.

What they will tell you: “Don't let anyone tell you when to retire. Choose the path that allows you to stay active, curious, and have enough money to play.”

5. Semi-retirees: Not done yet, just different

After retiring at age 62, Bob found a part-time job at a garden nursery simply because he was bored at home and liked plants.

Money Lessons: While Bob works for lifestyle reasons, many people find a part-time job to help pay for medical expenses, especially if they retire before reaching Medicare eligibility.

Life Lessons: A life of pure leisure isn’t for everyone, and research shows that having a plan, goals, and the social and intellectual engagement that comes with work can keep you younger and healthier!

What they will tell you: “It's best to have a rhythm in retirement. Organize your life around the things that energize you.”

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Discover the best part-time jobs for retirees and 5 tips for a second career after retirement.

6. Retirees facing divorce

She retired at 64 and six months later found out she was divorced after 30 years of marriage.

Money Lessons: Divorce after retirement is financially complex. You'll need to figure out Social Security spousal benefits, housing costs, and asset division early on.

Life Lessons: You can start over at any age. Community is important. ask for help.

What they will tell you: “Put your own financial plan on paper. Seeing it in black and white is empowering.”

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In this situation, many people feel the need to work with a financial advisor, and Boldin Advisors can help. Learn more about divorce after age 50.

7. Retired Caregivers: Retire Early, Not Voluntarily

Kelly quit her job at age 61 to care for her mother after she suffered a stroke.

Money Lessons: Caregiving impacts income, benefits, and emotional bandwidth. Emergency funds and insurance are not luxuries, they are lifelines.

Life Lessons: Plans change. The most important thing is to have a foundation that is flexible enough to bend.

What they will tell you: “I'm still picking up the pieces. I don't feel like I have a choice, but I hope my actions weren't motivated by pure emotion and I'd better think about the financial implications.”

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Caring for an aging parent is often described as a heartbreaking honor. It can also feel scary and hopeless. Getting support is important. The American Association of Retired Persons (AARP) provides a guide to finding a support group.

And, before taking a financial hit, make sure your own future is secure. Explore your options with the Boldin Planner.

8. Continuous retirees

Gillian regularly retires. She is only 40 years old and has already “retired” (taken leave of absence) more than a dozen times. She has traveled the United States in a camper van, lived abroad, and visited over 27 countries.

Money Lessons: Short retirements and vacations don't necessarily mean you're behind on income and savings. When Jillian retired one time, she renovated a house and ended up adding $300,000 to her wealth.

Life Lessons: Life is very long, why not spread out your leisure time and concentrate it at the end of your life?

What they will tell you: “A lot of retirements don't come easily. It takes a little courage and gumption to go out and do something cool.”

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Check out Jillian’s book Retire Often and listen to her talk about mini-retirements on the Boulding Podcast.

9. True early savers

Brie saved $100,000 in high school. I know it sounds crazy, but instead of playing sports and participating in extracurricular activities, she worked hard, was very frugal, and saved every penny she earned. At 18, she was already on the path to financial independence before she even truly had her own legal independence.

Money Lessons: Saving early and consistently lets compound interest do most of the heavy lifting. When you give your money enough time to grow, building real wealth becomes more achievable.

Life Lessons: Starting early isn’t just about the money, it’s about building confidence, choice and a sense of control over your future. When you learn to delay gratification and make intentional choices at a young age, you lay the foundation for every decision you make later. But it also reminds us that there is no single “right” path: discipline is powerful, but so is balance.

What they will tell you: “Start sooner than you think, even if it's only $25 a week. You don't need to copy my intensity. Just develop a habit you can maintain, because it's the habit, not the amount of money, that changes your life.”

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Learn the amazing power of compound interest to change your life.

10. Late Savers: Start at 50

Dave didn't start saving seriously until he was 50 years old. By prioritizing catch-up contributions, working a few more years, and adjusting his spending appropriately, he retired very comfortably at age 64.

Money Lessons: It's never too late to improve your plan. The impact of small, consistent choices is more complex than one might imagine at any stage of life.

Life Lessons: Shame on being a bad financial advisor. No matter where you are, this is the right place to start.

What they will tell you: “Don't procrastinate on financial transparency. Knowing your numbers reduces fear.”

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Learn more about catch-up contributions.

11. Health Shock Survivor

She retired at age 63 and faced a major health event at age 64. Because of her thoughtful planning, she had enough insurance and cash flow to focus on treatment.

Money Lessons: Good planning cannot prevent crises, but it can prevent them from turning into financial disasters.

Life Lessons: Health is wealth. Invest it with your investment portfolio.

What they will tell you: “Take into account the unpredictable. It's part of the plan, not a failure of the plan.”

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Learn about some unexpected skills (like resilience) needed to be a successful retiree.

12. Blended Family Retirees

He has adult stepchildren and children of his own. Estate planning is essential to avoid future confusion or conflict.

Money Lessons: Everyone needs a solid estate plan, but blended families have unique needs. Wills, beneficiaries, Social Security assignments and clear communication are more important than most.

Life Lessons: Clarity is love. Don't keep your family guessing.

What they will tell you: “Talk about inheritance early on. Not because you have to, but because it keeps everyone connected.”

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Talking to your heirs (and your own parents) about money is crucial. Learn how to pass on financial value, average an estate, and get tips for discussing finances with loved ones.

Big Fact: There’s no standard playbook for retirement

These stories prove something simple yet profound:

Retirement is not a number. This is not an age. This is not portfolio value. Retirement is a design choice. Then you can design it.

• The most powerful plans are flexible.
• The happiest retirees stay curious.
• The most resilient people know that control comes from clarity, not certainty.

At Boulding, our work is rooted in the belief that: You can run every “what if,” explore every path, and create a plan that works for the life you want—today and decades from now.

Start your personalized plan today.

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