“Retirement” used to mean one thing: you stop working, collect a pension, and live quietly off your savings. But today, retirement looks different—and better.

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According to Transamerica’s latest research, 43% of retirees dive into hobbies, 36% travel, 19% care for grandchildren, and 16% volunteer. These aren’t just pastimes—they’re passions, callings, and new beginnings.

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As a financial advisor who’s walked alongside hundreds of retirees, I’ve seen firsthand that the happiest clients don’t simply retire from something—they retire to something. They don’t view this phase as an ending. They see it as a redesign—a new chapter to live with purpose, freedom, and joy.

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So, as you think about your own next chapter, let’s explore how you can make it your best yet—emotionally, practically, and financially.

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The Emotional Shift: From “Worker” to “Explorer”

For decades, your career likely defined your schedule, purpose, and even identity. Retirement, in that sense, is more than a financial event—it’s an emotional transition.

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Suddenly, you wake up with time on your hands and the freedom to choose what comes next. That can feel both exhilarating and unsettling.

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Tip #1: Give yourself permission to experiment.

Don’t rush to fill every hour or define your new routine immediately. Think of the first year of retirement as a “gap year” for grown-ups. Explore what feels fulfilling—gardening, painting, traveling, mentoring, or maybe launching that side venture you’ve always imagined.

One client of mine, Linda, spent 35 years in corporate marketing. She retired with a plan to “do nothing” for six months. By month four, she’d rediscovered her love of photography and started selling prints at local art fairs. Today, she calls herself “semi-retired”—but really, she’s fully 

alive.

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Lesson: Your identity isn’t what you used to do. It’s what you choose to create now.

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Designing a Purpose-Driven Retirement

Money alone doesn’t create happiness in retirement—meaning does.

Ask yourself:

• What brings me joy and energy?
• What impact do I still want to make?
• What experiences have I postponed until “someday”?

Here’s what I often tell clients: Retirement isn’t the end of your story; it’s your encore. And like any good encore, it deserves planning.

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The 4 Pillars of a Fulfilling Retirement

1. Connection – Staying socially active through family, friends, or community. Isolation is one of the biggest threats to mental health in retirement. Join clubs, attend workshops, or even volunteer.
2. Purpose – Whether that’s caring for grandkids, mentoring, or starting a small business, having a reason to get up in the morning matters more than any paycheck.
3. Growth – Learning doesn’t stop when work does. Take classes, learn a language, or travel somewhere that expands your perspective.
4. Freedom – The ability to say “yes” to what you love and “no” to what you don’t—made possible through smart financial planning.

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When your retirement aligns with these four pillars, life after work doesn’t feel like “less.” It feels like more.

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The Financial Foundation: Freedom Through Planning

Let’s talk about the practical side—the finances that make all of this possible.

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Many retirees fear running out of money more than they fear death. That’s not an exaggeration—it’s a common survey finding. But fear often comes from uncertainty, not reality. With the right plan, you can replace worry with confidence.

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Step 1: Define Your “Freedom Number”

Your Freedom Number is the amount of monthly income you need to live comfortably and pursue your goals—without worrying about every market dip or grocery bill.

Start by estimating:

• Essential expenses (housing, healthcare, utilities, groceries)
• Lifestyle expenses (travel, hobbies, gifts)
• Legacy goals (charitable giving, helping family, estate plans)

Once you know your number, your advisor can help align your income sources—Social Security, pensions, investment withdrawals, and annuities—to create stability and predictability.

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Step 2: Plan for Longevity and Healthcare

People are living longer—often much longer—than previous generations. A 65-year-old couple today has a 50% chance that one of them will live past 90. That’s potentially 25+ years of retirement to fund.

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Healthcare is another key factor. Even with Medicare, out-of-pocket costs can average $300,000 over a lifetime. A sound financial plan builds this in from the start—whether through Health Savings Accounts (HSAs), supplemental insurance, or long-term care coverage.

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Step 3: Manage Risk Intelligently

As you move from accumulation to preservation, the goal shifts. It’s no longer about chasing returns—it’s about creating sustainable income.

Strategies may include:

• Diversifying income sources (dividends, bonds, annuities, real estate)
• Keeping a year or two of expenses in cash or short-term bonds to weather market downturns
• Using a “bucket strategy” to align investments with time horizons

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The best financial plans are living documents—adjustable as markets, goals, and life itself evolve.

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The New Retirement Lifestyle: Adventure, Legacy, and Balance

So, what does life after work actually look like when it’s done well?

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Hobbies: Rediscovering Play

43% of retirees dive into hobbies, according to Transamerica. That’s not surprising—hobbies provide structure, purpose, and joy.

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Think of John, a retired engineer who took up woodworking. What started as a hobby turned into a small Etsy shop selling handcrafted furniture. “I’m not doing it for money,” he told me. “I’m doing it because it keeps my hands and my mind busy.”

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Whether it’s painting, hiking, gardening, or music—hobbies aren’t “extra.” They’re essential for mental health and happiness.

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Travel: Living the Bucket List

36% of retirees say travel is their top dream—and for good reason. You’ve spent years saving and planning; now’s the time to see the world.

That might mean international adventures, RV trips across America, or simply visiting national parks. The key is intentional travel planning. Work with your advisor to balance these experiences with your long-term income plan so you can say “yes” to adventure without stress.

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Family: Passing Down Time and Wisdom

19% of retirees say caring for grandkids is central to their lives. That’s a beautiful way to stay connected, but it can also have financial implications.

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If you’re helping with childcare or education, consider tools like 529 plans or trusts to structure your support efficiently. Remember, generosity should enhance—not endanger—your retirement security.

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Volunteering: The Gift of Purpose

16% of retirees volunteer—and many say it’s the most fulfilling part of their week. Whether it’s mentoring at a local school, helping at a food bank, or sharing professional expertise, volunteering provides a sense of meaning money can’t buy.

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Some even blend purpose and travel through “voluntourism,” combining service with exploration—a true win-win.

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Financial Freedom: Balancing Security and Spontaneity

The best retirements strike a balance between two things: security and spontaneity.

Security gives you peace of mind—knowing the bills are paid, your healthcare is covered, and your money will last.

Spontaneity gives you joy—saying “yes” to that spur-of-the-moment road trip or enrolling in that pottery class without guilt.

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A strong financial plan supports both. For example:

• Use guaranteed income (Social Security, pensions, annuities) to cover essentials.
• Use flexible assets (brokerage accounts, Roth IRAs) for travel, hobbies, and opportunities.
• Revisit your plan annually to keep it aligned with your evolving life goals.

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As I tell my clients: The goal isn’t to die with the biggest balance sheet—it’s to live with the richest experiences.

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A Real-Life Example: The Millers’ Next Chapter

When Tom and Susan Miller, both 67, retired from teaching, they wanted three things:

1. To travel around the U.S. in their camper.
2. To help fund their granddaughter’s college.
3. To volunteer at local literacy programs.

We built a plan that turned their dream into a blueprint:

• Their pensions and Social Security covered 80% of fixed expenses.
• A modest annuity provided guaranteed income for healthcare costs.
• Their Roth IRA became their “fun fund” for travel and spontaneous adventures.

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Now, every spring they spend two months on the road. They call it their “Learning Tour”—visiting historical sites and reading about each destination as they go. They’re still teachers, just in a different classroom.

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Your Next Step: Dream with Intention

If you’re nearing or already in retirement, take a moment to reflect: What dream have you put off until “someday”?

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Maybe it’s learning the piano, writing your memoir, starting a nonprofit, or simply having more time for the people and causes you love.

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Your next chapter doesn’t have to be defined by limitation—it can be defined by liberation. But it starts with intention, and it’s sustained by preparation.

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That’s where a financial advisor can help—turning your what ifs into how to’s.

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Final Thought

“Retire from work, not from life.”

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You’ve spent decades earning, saving, and contributing. Now it’s time to live—on your terms.

Retirement isn’t an exit; it’s an entrance—into a life rich with possibility, purpose, and peace of mind.

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So, what’s one dream you’re ready to chase?

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