Why Retiring Now Might Just Make Sense

Thinking about retirement? You’re not alone. Many people in their late 50s and early 60s start feeling the itch to slow down, step away from the daily grind, and start the next chapter of life. But how do you know when the timing is right?

While the economy and markets go through their usual ups and downs, the bigger picture for retirement has become more encouraging. If you’ve been saving, planning, and dreaming about freedom, now might be an ideal time to make it real.

Let’s explore why—and how to know if you're truly ready to make the leap.

Why Retirement Feels Right—Even If You’re Not Fully Ready Yet

For a lot of people, the desire to retire doesn’t start with a spreadsheet—it starts with a feeling:

You’re tired of the grind. You want your time back. You’re ready to focus more on your health, your family, your hobbies, and less on meetings, deadlines, or managing people. Work used to energize you—but now, it just drains you.

That emotional readiness is real—and it matters. But sometimes, your finances or your support system haven’t quite caught up yet.

Maybe you haven’t run the numbers in detail. Maybe your spouse isn’t on the same page.

Maybe you’re unsure what you’ll do all day when the routine of work disappears.

That’s where planning comes in. The goal isn’t to delay retirement until every star aligns— it’s to make sure you’re stepping into this new chapter with confidence, clarity, and a strong foundation.

There’s nothing wrong with feeling ready before every detail is buttoned up. In fact, that inner pull to leave work can be a healthy signal that it’s time to start making serious plans. With the right conversations and guidance, you can go from “I think I’m ready” to “I know I am.”

That’s also why it helps to work with someone who does this every day. A CERTIFIED FINANCIAL PLANNER™ who specializes in retirement can help you sort through the emotional side and the numbers—so you’re not just guessing, you’re making informed choices that give you the best shot at a successful, fulfilling retirement.

6 Signs You’re Ready to Retire

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1. You’re Excited About Life After Work

For many of us, work isn’t just a paycheck—it’s a big part of our identity. We've spent 30 or 40 years building a career, creating value, solving problems, and staying productive. So, stepping away from that isn’t easy.

But if you’ve started imagining what life looks like without the calendar full of Zoom calls or back-to-back client meetings—and you feel excited—that’s a powerful sign.

Retirees who thrive often say they weren’t just leaving something behind—they were moving toward something: more time with grandkids, more travel, or just a slower, more intentional pace of life.

If the idea of Mondays filled with hobbies, gardening, pickleball, or volunteering lights you up, you’re likely ready for the next chapter. If you’re unsure, that’s okay too. Use that

uncertainty as a prompt to explore and test out retirement rhythms while you’re still working.

“If you retire today, what does Monday look like?”

—Scott Bishop, Presidio Wealth Partners

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2. You're Making the Numbers Work

Retirement isn’t about hitting a magic number—it’s about making sure your income can support your lifestyle. And the sooner you understand what your lifestyle will cost, the

easier it is to make informed decisions.

Start by estimating your monthly spending in retirement. Think through:

• Housing (mortgage, taxes, maintenance)
• Utilities and insurance
• Health care and out-of-pocket medical costs
• Travel, hobbies, and giving
• Groceries, dining out, and entertainment
  

Then map out where the money will come from:

• Social Security
• Pension income (if any)
• IRA, 401(k), or other investment accounts
• Part-time work or rental income
• Cash savings or annuities

If there’s a gap between income and expenses, you have options. You might adjust your spending plan, work an extra year or two, or shift your investment strategy for better long- term results.

A good retirement plan includes smart withdrawal strategies, tax efficiency, and protection against inflation. It’s not about being perfect—it’s about creating a plan that’s flexible,

sustainable, and built around your life.

And you don’t have to figure it all out alone. A CERTIFIED FINANCIAL PLANNER™ can help you put the puzzle together so your money works not just on paper, but in real life.

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3. You Have a Purpose Outside of Work

One of the biggest predictors of retirement happiness? Knowing what you’ll do with your time.

After years of structured workdays, retirement can feel like a blank canvas—and for some, that’s freeing. For others, it’s overwhelming.

The happiest retirees tend to have a sense of purpose, whether that’s:

• Consulting or mentoring part-time
• Picking up a new hobby or revisiting an old one
• Volunteering in the community
• Spending more time with family and friends
• Traveling or taking classes

A WebMD survey found that nearly 1 in 3 retirees reported feeling depressed—more than among the general adult population. That doesn’t mean retirement causes depression— but it highlights how important meaning and connection are once the job title goes away.

“If you retire and don’t have a hobby or schedule, you can go into a depression.”

—Erika Wasserman, financial therapist

So before you make the leap, sketch out what a typical week might look like. It doesn’t have to be packed with activities—but having a rhythm helps.

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4. You’re Okay Watching Your Savings Go Down

You’ve spent years building up your nest egg. You’ve watched the balance grow with every paycheck and investment gain. So it’s completely normal to feel a little anxious about

seeing those numbers go the other way.

But that’s exactly what your retirement savings are for—to spend.

If the thought of withdrawing from your accounts makes you uneasy, try framing it differently: you're turning savings into income, using a plan that balances growth, income, and sustainability. You’re not just spending money—you’re using it wisely to live the life you’ve worked hard to create.

Still nervous? You might explore:

• A phased retirement
• A lower withdrawal rate
• Creating a guaranteed income stream with annuities
• Keeping part-time income for a few years

“If you’re not okay seeing your savings go down, ask yourself why. Maybe full retirement isn’t the right move just yet.”

—Erika Wasserman

There’s no shame in easing into retirement on your terms.

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5. You and Your Spouse Are on the Same Page

If you’re in a relationship, retirement is a team decision.

You’re not just changing your own schedule—you’re changing how you both live, spend, and relate to each other. More time together can be wonderful—or surprisingly challenging—especially if you haven’t talked through expectations.

Have honest conversations about things like:

• Your daily routines
• Household roles and responsibilities
• Travel or relocation plans
• Spending and budgeting in retirement
• How much time you each want together vs. apart

Some couples even try a “test run” by taking extended time off to see how the new rhythm feels.

The first few years of retirement can be a rough transition for couples. Talk it through together.

Clear communication now can lead to a much smoother transition—and a stronger partnership in this next phase.

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6. You’re Prioritizing Your Health

You can’t enjoy retirement without your health. And while none of us can control everything, there’s a lot we can do to stay well and active in our 60s, 70s, and beyond.

That means building a lifestyle that supports your well-being:

• Regular physical activity (even walking counts!)
• Healthy eating habits
• Social connections
• Routine checkups and screenings
• Managing stress and sleep

It also means being prepared on the financial side:

• Enrolling in Medicare on time
• Choosing between supplemental and Advantage plans
• Planning for dental, vision, and hearing costs
• Exploring long-term care coverage or alternatives
  

“Without health, there’s not much anyone can do—regardless of how much wealth they have.”

—Nilay Gandhi, Vanguard

Investing in your health is one of the best ways to protect your wealth—and your quality of life.

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Is It Time for Your Next Chapter?

Retirement isn’t a finish line—it’s a transition. Some people know exactly when they want to step away. Others ease in gradually. And some wait longer than expected because they want to feel completely ready.

But when your finances are in place, your days have meaning, and your heart is nudging you toward something new—that’s when you know.

And if you’re still not sure? That’s okay. We’re here to help.

Whether you’re looking to confirm your numbers, create a tax-efficient income plan, or just talk through what retirement might look like for you, we’re here to walk with you every step of the way.

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Let’s Talk About Your Retirement

Contact us to schedule a free, no-pressure consultation with our team. We’ll help you figure out if you’re truly ready—and if not, how to get there with confidence.

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