Retirement Redefined

Achieve Financial Freedom and

A Better Work/Life Balance

Here's what I can offer :

  • Clarity:

    A clear path to financial freedom tailored for you.

  • Work/life balance strategies:

    Create more time for family, travel, and personal passions.

  • Confidence:

    The tools to make informed financial decisions with ease.

  • Efficiency:

    Simplified, actionable steps to build wealth without unnecessary complexity.

  • Freedom:

    A roadmap to design a life aligned with your goals and values.

On-demand Learning

Educational webcasts that inspire smarter choices.

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Masterclasses

Strategies to preserve wealth, navigate taxes, and retire on your terms.

Confident midlife professional walking along a peaceful path, symbolizing a thoughtful, intentional transition into retirement—not a sudden leap

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

July 28, 20255 min read

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

Watch the video here!

Are You Ready to Retire… or Just Ready to Escape?

Let's be honest—sometimes, it feels like the only thing standing between you and peace of mind is your Outlook calendar. Another meeting, another fire to put out, and you start daydreaming about beaches and zero unread emails.

But here’s the thing: retirement isn’t a vacation. It’s not just a reward for all your years of hard work. It’s a massive shift in your lifestyle, your finances, and your identity.

And smart professionals? They don't just leap. They test-drive their future before they make it permanent.


Why This Matters Now More Than Ever

If you're a high-earning professional, odds are you've been in go-mode for decades. Planning, building, leading, solving. You've mastered efficiency, built wealth, and earned respect. But stepping away? That's a different muscle—and it's one most people don't flex until it's too late.

Retirement isn't just about the money. It's about alignment. Do your finances, goals, and day-to-day life actually match the vision you have for your future?


Let's Bust a Big Myth

"Just save enough and you'll be fine."

Sure, having enough saved matters. But what if your definition of "enough" doesn’t cover what brings you joy? What if you find yourself financially secure but emotionally unfulfilled?

Here’s where it gets real:

  • You could retire with money but feel restless.

  • You might have freedom but lack purpose.

  • You might walk away from your job only to miss the challenge, the structure, and even the small stuff like morning coffee banter.

Retirement shouldn't feel like hitting the brakes. It should feel like changing gears.


What Exactly Is a Retirement Test Drive?

It's simple: you try out retirement while you're still working—just in a controlled, lower-stakes way.

Think of it like running a beta version of your post-work life. No pressure, just insight.

Try any of these:

  • Take a sabbatical or mini-retirement: Step away for a few weeks and live like you're retired.

  • Shift to a 3- or 4-day workweek: Test how it feels to work less without unplugging completely.

  • Follow your retirement budget for a month: Can you live well within that structure?

  • Plan your weeks with zero meetings: What fills the space? Netflix... or maybe something deeper?

This isn't theory—it's practice. And the results can be surprisingly revealing.


Who Benefits the Most from a Test Drive?

This isn’t just for people on the cusp of retirement. It’s for anyone who wants to make smart, informed decisions.

Especially:

  • Professionals 5–10 years out from retirement

  • Entrepreneurs thinking about selling or stepping back

  • Leaders whose identity is deeply tied to their role

  • Couples who aren't quite on the same timeline

If you’re even thinking about retiring, a trial run makes sense.


How to Run Your Retirement Test Drive

You don’t need a six-month sabbatical or a massive spreadsheet. You just need intention. Here’s how to keep it simple:

1. Decide what you’re testing

Is it the lifestyle? The income? The emotional shift? Pick one (or a few) and write it down.

2. Choose your timeline

Even a two-week test can surface surprising insights. You don’t need months.

3. Block your schedule

No fake meetings. No "just one quick email." Simulate the space you’d have in retirement.

4. Take notes

What feels good? What feels off? What would you change?

5. Review your financial plan

Does your real-life trial match what your money can support? If not, tweak it now, not later.

This isn’t about checking boxes. It’s about building clarity.


The Emotional Side: More Than Just Free Time

Let’s not pretend retirement is just about money. Work gives us structure, identity, and sometimes even community. Losing that overnight? It can be jarring.

A test drive helps you figure out:

  • What do I enjoy doing when I’m not working?

  • Where do I get purpose if not from my title?

  • Am I ready to slow down, or do I just need a better rhythm?

These questions matter just as much as your account balance.


Real Talk: FAQs Answered

Q: Won’t this make it harder to go back to full-time work?
A: Not at all—if anything, it gives you leverage. Phased retirement and flexible work are on the rise. You’re in the driver’s seat.

Q: What if I can't afford time off?
A: That’s fair. Try weekend or holiday simulations. Or block evenings and treat them like "retirement hours."

Q: My partner and I aren’t on the same page.
A: That’s normal. Try overlapping your test runs or doing one solo. Compare notes later—you might be surprised.


Why More Professionals Are Doing This Now

Because time is valuable. So is freedom. And the last thing you want is to spend your retirement figuring out what you should have done before you got there.

A test drive lets you:

  • Make course corrections early

  • Clarify your values

  • Build a plan based on experience, not assumptions

It’s not about being perfect. It’s about being prepared.


Bottom Line: Better Questions Lead to Better Outcomes

If you take one thing from this, let it be this: Don’t wait until your last day at work to figure out your first day of retirement.

Ask yourself:

  • What do I want my life to feel like?

  • How will I spend my time when work isn’t the center?

  • What’s my rhythm when I’m not on someone else’s clock?

Then test it. Try it. Live it. Adjust it.


Wrap-Up: Let’s Make This Real

Quick recap:

  • Retirement isn’t just a financial decision. It’s a life decision.

  • Test-driving gives you insight without the commitment.

  • You don’t need months—you just need intention.

Try one small strategy this month:

  • Block off a day as if you were retired.

  • Stick to your retirement budget for a week.

  • Journal your thoughts about life without work.

Then come back and reflect: What worked? What didn’t?

The goal here isn’t to have all the answers. It’s to ask smarter questions—and feel empowered by the journey.

Want help designing your retirement test run? Let’s talk. One conversation could change the entire trajectory of your next chapter. Schedule Your Appointment Now

Retirement test drivePreparing for retirementTrial retirementHow to retire smarterRetirement planning for professionals
Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Rob Leiphart, CFP®

Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Back to Blog
Confident midlife professional walking along a peaceful path, symbolizing a thoughtful, intentional transition into retirement—not a sudden leap

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

July 28, 20255 min read

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

Watch the video here!

Are You Ready to Retire… or Just Ready to Escape?

Let's be honest—sometimes, it feels like the only thing standing between you and peace of mind is your Outlook calendar. Another meeting, another fire to put out, and you start daydreaming about beaches and zero unread emails.

But here’s the thing: retirement isn’t a vacation. It’s not just a reward for all your years of hard work. It’s a massive shift in your lifestyle, your finances, and your identity.

And smart professionals? They don't just leap. They test-drive their future before they make it permanent.


Why This Matters Now More Than Ever

If you're a high-earning professional, odds are you've been in go-mode for decades. Planning, building, leading, solving. You've mastered efficiency, built wealth, and earned respect. But stepping away? That's a different muscle—and it's one most people don't flex until it's too late.

Retirement isn't just about the money. It's about alignment. Do your finances, goals, and day-to-day life actually match the vision you have for your future?


Let's Bust a Big Myth

"Just save enough and you'll be fine."

Sure, having enough saved matters. But what if your definition of "enough" doesn’t cover what brings you joy? What if you find yourself financially secure but emotionally unfulfilled?

Here’s where it gets real:

  • You could retire with money but feel restless.

  • You might have freedom but lack purpose.

  • You might walk away from your job only to miss the challenge, the structure, and even the small stuff like morning coffee banter.

Retirement shouldn't feel like hitting the brakes. It should feel like changing gears.


What Exactly Is a Retirement Test Drive?

It's simple: you try out retirement while you're still working—just in a controlled, lower-stakes way.

Think of it like running a beta version of your post-work life. No pressure, just insight.

Try any of these:

  • Take a sabbatical or mini-retirement: Step away for a few weeks and live like you're retired.

  • Shift to a 3- or 4-day workweek: Test how it feels to work less without unplugging completely.

  • Follow your retirement budget for a month: Can you live well within that structure?

  • Plan your weeks with zero meetings: What fills the space? Netflix... or maybe something deeper?

This isn't theory—it's practice. And the results can be surprisingly revealing.


Who Benefits the Most from a Test Drive?

This isn’t just for people on the cusp of retirement. It’s for anyone who wants to make smart, informed decisions.

Especially:

  • Professionals 5–10 years out from retirement

  • Entrepreneurs thinking about selling or stepping back

  • Leaders whose identity is deeply tied to their role

  • Couples who aren't quite on the same timeline

If you’re even thinking about retiring, a trial run makes sense.


How to Run Your Retirement Test Drive

You don’t need a six-month sabbatical or a massive spreadsheet. You just need intention. Here’s how to keep it simple:

1. Decide what you’re testing

Is it the lifestyle? The income? The emotional shift? Pick one (or a few) and write it down.

2. Choose your timeline

Even a two-week test can surface surprising insights. You don’t need months.

3. Block your schedule

No fake meetings. No "just one quick email." Simulate the space you’d have in retirement.

4. Take notes

What feels good? What feels off? What would you change?

5. Review your financial plan

Does your real-life trial match what your money can support? If not, tweak it now, not later.

This isn’t about checking boxes. It’s about building clarity.


The Emotional Side: More Than Just Free Time

Let’s not pretend retirement is just about money. Work gives us structure, identity, and sometimes even community. Losing that overnight? It can be jarring.

A test drive helps you figure out:

  • What do I enjoy doing when I’m not working?

  • Where do I get purpose if not from my title?

  • Am I ready to slow down, or do I just need a better rhythm?

These questions matter just as much as your account balance.


Real Talk: FAQs Answered

Q: Won’t this make it harder to go back to full-time work?
A: Not at all—if anything, it gives you leverage. Phased retirement and flexible work are on the rise. You’re in the driver’s seat.

Q: What if I can't afford time off?
A: That’s fair. Try weekend or holiday simulations. Or block evenings and treat them like "retirement hours."

Q: My partner and I aren’t on the same page.
A: That’s normal. Try overlapping your test runs or doing one solo. Compare notes later—you might be surprised.


Why More Professionals Are Doing This Now

Because time is valuable. So is freedom. And the last thing you want is to spend your retirement figuring out what you should have done before you got there.

A test drive lets you:

  • Make course corrections early

  • Clarify your values

  • Build a plan based on experience, not assumptions

It’s not about being perfect. It’s about being prepared.


Bottom Line: Better Questions Lead to Better Outcomes

If you take one thing from this, let it be this: Don’t wait until your last day at work to figure out your first day of retirement.

Ask yourself:

  • What do I want my life to feel like?

  • How will I spend my time when work isn’t the center?

  • What’s my rhythm when I’m not on someone else’s clock?

Then test it. Try it. Live it. Adjust it.


Wrap-Up: Let’s Make This Real

Quick recap:

  • Retirement isn’t just a financial decision. It’s a life decision.

  • Test-driving gives you insight without the commitment.

  • You don’t need months—you just need intention.

Try one small strategy this month:

  • Block off a day as if you were retired.

  • Stick to your retirement budget for a week.

  • Journal your thoughts about life without work.

Then come back and reflect: What worked? What didn’t?

The goal here isn’t to have all the answers. It’s to ask smarter questions—and feel empowered by the journey.

Want help designing your retirement test run? Let’s talk. One conversation could change the entire trajectory of your next chapter. Schedule Your Appointment Now

Retirement test drivePreparing for retirementTrial retirementHow to retire smarterRetirement planning for professionals
Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Rob Leiphart, CFP®

Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Back to Blog
Confident midlife professional walking along a peaceful path, symbolizing a thoughtful, intentional transition into retirement—not a sudden leap

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

July 28, 20255 min read

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

Watch the video here!

Are You Ready to Retire… or Just Ready to Escape?

Let's be honest—sometimes, it feels like the only thing standing between you and peace of mind is your Outlook calendar. Another meeting, another fire to put out, and you start daydreaming about beaches and zero unread emails.

But here’s the thing: retirement isn’t a vacation. It’s not just a reward for all your years of hard work. It’s a massive shift in your lifestyle, your finances, and your identity.

And smart professionals? They don't just leap. They test-drive their future before they make it permanent.


Why This Matters Now More Than Ever

If you're a high-earning professional, odds are you've been in go-mode for decades. Planning, building, leading, solving. You've mastered efficiency, built wealth, and earned respect. But stepping away? That's a different muscle—and it's one most people don't flex until it's too late.

Retirement isn't just about the money. It's about alignment. Do your finances, goals, and day-to-day life actually match the vision you have for your future?


Let's Bust a Big Myth

"Just save enough and you'll be fine."

Sure, having enough saved matters. But what if your definition of "enough" doesn’t cover what brings you joy? What if you find yourself financially secure but emotionally unfulfilled?

Here’s where it gets real:

  • You could retire with money but feel restless.

  • You might have freedom but lack purpose.

  • You might walk away from your job only to miss the challenge, the structure, and even the small stuff like morning coffee banter.

Retirement shouldn't feel like hitting the brakes. It should feel like changing gears.


What Exactly Is a Retirement Test Drive?

It's simple: you try out retirement while you're still working—just in a controlled, lower-stakes way.

Think of it like running a beta version of your post-work life. No pressure, just insight.

Try any of these:

  • Take a sabbatical or mini-retirement: Step away for a few weeks and live like you're retired.

  • Shift to a 3- or 4-day workweek: Test how it feels to work less without unplugging completely.

  • Follow your retirement budget for a month: Can you live well within that structure?

  • Plan your weeks with zero meetings: What fills the space? Netflix... or maybe something deeper?

This isn't theory—it's practice. And the results can be surprisingly revealing.


Who Benefits the Most from a Test Drive?

This isn’t just for people on the cusp of retirement. It’s for anyone who wants to make smart, informed decisions.

Especially:

  • Professionals 5–10 years out from retirement

  • Entrepreneurs thinking about selling or stepping back

  • Leaders whose identity is deeply tied to their role

  • Couples who aren't quite on the same timeline

If you’re even thinking about retiring, a trial run makes sense.


How to Run Your Retirement Test Drive

You don’t need a six-month sabbatical or a massive spreadsheet. You just need intention. Here’s how to keep it simple:

1. Decide what you’re testing

Is it the lifestyle? The income? The emotional shift? Pick one (or a few) and write it down.

2. Choose your timeline

Even a two-week test can surface surprising insights. You don’t need months.

3. Block your schedule

No fake meetings. No "just one quick email." Simulate the space you’d have in retirement.

4. Take notes

What feels good? What feels off? What would you change?

5. Review your financial plan

Does your real-life trial match what your money can support? If not, tweak it now, not later.

This isn’t about checking boxes. It’s about building clarity.


The Emotional Side: More Than Just Free Time

Let’s not pretend retirement is just about money. Work gives us structure, identity, and sometimes even community. Losing that overnight? It can be jarring.

A test drive helps you figure out:

  • What do I enjoy doing when I’m not working?

  • Where do I get purpose if not from my title?

  • Am I ready to slow down, or do I just need a better rhythm?

These questions matter just as much as your account balance.


Real Talk: FAQs Answered

Q: Won’t this make it harder to go back to full-time work?
A: Not at all—if anything, it gives you leverage. Phased retirement and flexible work are on the rise. You’re in the driver’s seat.

Q: What if I can't afford time off?
A: That’s fair. Try weekend or holiday simulations. Or block evenings and treat them like "retirement hours."

Q: My partner and I aren’t on the same page.
A: That’s normal. Try overlapping your test runs or doing one solo. Compare notes later—you might be surprised.


Why More Professionals Are Doing This Now

Because time is valuable. So is freedom. And the last thing you want is to spend your retirement figuring out what you should have done before you got there.

A test drive lets you:

  • Make course corrections early

  • Clarify your values

  • Build a plan based on experience, not assumptions

It’s not about being perfect. It’s about being prepared.


Bottom Line: Better Questions Lead to Better Outcomes

If you take one thing from this, let it be this: Don’t wait until your last day at work to figure out your first day of retirement.

Ask yourself:

  • What do I want my life to feel like?

  • How will I spend my time when work isn’t the center?

  • What’s my rhythm when I’m not on someone else’s clock?

Then test it. Try it. Live it. Adjust it.


Wrap-Up: Let’s Make This Real

Quick recap:

  • Retirement isn’t just a financial decision. It’s a life decision.

  • Test-driving gives you insight without the commitment.

  • You don’t need months—you just need intention.

Try one small strategy this month:

  • Block off a day as if you were retired.

  • Stick to your retirement budget for a week.

  • Journal your thoughts about life without work.

Then come back and reflect: What worked? What didn’t?

The goal here isn’t to have all the answers. It’s to ask smarter questions—and feel empowered by the journey.

Want help designing your retirement test run? Let’s talk. One conversation could change the entire trajectory of your next chapter. Schedule Your Appointment Now

Retirement test drivePreparing for retirementTrial retirementHow to retire smarterRetirement planning for professionals
Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Rob Leiphart, CFP®

Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Back to Blog
Confident midlife professional walking along a peaceful path, symbolizing a thoughtful, intentional transition into retirement—not a sudden leap

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

July 28, 20255 min read

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

Watch the video here!

Are You Ready to Retire… or Just Ready to Escape?

Let's be honest—sometimes, it feels like the only thing standing between you and peace of mind is your Outlook calendar. Another meeting, another fire to put out, and you start daydreaming about beaches and zero unread emails.

But here’s the thing: retirement isn’t a vacation. It’s not just a reward for all your years of hard work. It’s a massive shift in your lifestyle, your finances, and your identity.

And smart professionals? They don't just leap. They test-drive their future before they make it permanent.


Why This Matters Now More Than Ever

If you're a high-earning professional, odds are you've been in go-mode for decades. Planning, building, leading, solving. You've mastered efficiency, built wealth, and earned respect. But stepping away? That's a different muscle—and it's one most people don't flex until it's too late.

Retirement isn't just about the money. It's about alignment. Do your finances, goals, and day-to-day life actually match the vision you have for your future?


Let's Bust a Big Myth

"Just save enough and you'll be fine."

Sure, having enough saved matters. But what if your definition of "enough" doesn’t cover what brings you joy? What if you find yourself financially secure but emotionally unfulfilled?

Here’s where it gets real:

  • You could retire with money but feel restless.

  • You might have freedom but lack purpose.

  • You might walk away from your job only to miss the challenge, the structure, and even the small stuff like morning coffee banter.

Retirement shouldn't feel like hitting the brakes. It should feel like changing gears.


What Exactly Is a Retirement Test Drive?

It's simple: you try out retirement while you're still working—just in a controlled, lower-stakes way.

Think of it like running a beta version of your post-work life. No pressure, just insight.

Try any of these:

  • Take a sabbatical or mini-retirement: Step away for a few weeks and live like you're retired.

  • Shift to a 3- or 4-day workweek: Test how it feels to work less without unplugging completely.

  • Follow your retirement budget for a month: Can you live well within that structure?

  • Plan your weeks with zero meetings: What fills the space? Netflix... or maybe something deeper?

This isn't theory—it's practice. And the results can be surprisingly revealing.


Who Benefits the Most from a Test Drive?

This isn’t just for people on the cusp of retirement. It’s for anyone who wants to make smart, informed decisions.

Especially:

  • Professionals 5–10 years out from retirement

  • Entrepreneurs thinking about selling or stepping back

  • Leaders whose identity is deeply tied to their role

  • Couples who aren't quite on the same timeline

If you’re even thinking about retiring, a trial run makes sense.


How to Run Your Retirement Test Drive

You don’t need a six-month sabbatical or a massive spreadsheet. You just need intention. Here’s how to keep it simple:

1. Decide what you’re testing

Is it the lifestyle? The income? The emotional shift? Pick one (or a few) and write it down.

2. Choose your timeline

Even a two-week test can surface surprising insights. You don’t need months.

3. Block your schedule

No fake meetings. No "just one quick email." Simulate the space you’d have in retirement.

4. Take notes

What feels good? What feels off? What would you change?

5. Review your financial plan

Does your real-life trial match what your money can support? If not, tweak it now, not later.

This isn’t about checking boxes. It’s about building clarity.


The Emotional Side: More Than Just Free Time

Let’s not pretend retirement is just about money. Work gives us structure, identity, and sometimes even community. Losing that overnight? It can be jarring.

A test drive helps you figure out:

  • What do I enjoy doing when I’m not working?

  • Where do I get purpose if not from my title?

  • Am I ready to slow down, or do I just need a better rhythm?

These questions matter just as much as your account balance.


Real Talk: FAQs Answered

Q: Won’t this make it harder to go back to full-time work?
A: Not at all—if anything, it gives you leverage. Phased retirement and flexible work are on the rise. You’re in the driver’s seat.

Q: What if I can't afford time off?
A: That’s fair. Try weekend or holiday simulations. Or block evenings and treat them like "retirement hours."

Q: My partner and I aren’t on the same page.
A: That’s normal. Try overlapping your test runs or doing one solo. Compare notes later—you might be surprised.


Why More Professionals Are Doing This Now

Because time is valuable. So is freedom. And the last thing you want is to spend your retirement figuring out what you should have done before you got there.

A test drive lets you:

  • Make course corrections early

  • Clarify your values

  • Build a plan based on experience, not assumptions

It’s not about being perfect. It’s about being prepared.


Bottom Line: Better Questions Lead to Better Outcomes

If you take one thing from this, let it be this: Don’t wait until your last day at work to figure out your first day of retirement.

Ask yourself:

  • What do I want my life to feel like?

  • How will I spend my time when work isn’t the center?

  • What’s my rhythm when I’m not on someone else’s clock?

Then test it. Try it. Live it. Adjust it.


Wrap-Up: Let’s Make This Real

Quick recap:

  • Retirement isn’t just a financial decision. It’s a life decision.

  • Test-driving gives you insight without the commitment.

  • You don’t need months—you just need intention.

Try one small strategy this month:

  • Block off a day as if you were retired.

  • Stick to your retirement budget for a week.

  • Journal your thoughts about life without work.

Then come back and reflect: What worked? What didn’t?

The goal here isn’t to have all the answers. It’s to ask smarter questions—and feel empowered by the journey.

Want help designing your retirement test run? Let’s talk. One conversation could change the entire trajectory of your next chapter. Schedule Your Appointment Now

Retirement test drivePreparing for retirementTrial retirementHow to retire smarterRetirement planning for professionals
Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Rob Leiphart, CFP®

Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Back to Blog

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4 Corporate Drive, Suite 482 Shelton, CT 06484

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+1 203-220-6474

Monday - Friday | 8:30AM - 5:00 PM

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Access expert guidance, comprehensive analysis, and actionable steps to safeguard your wealth.

Confident midlife professional walking along a peaceful path, symbolizing a thoughtful, intentional transition into retirement—not a sudden leap

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

July 28, 20255 min read

Retirement Isn't a Cliff—It's a Curve: Why Smart Professionals Test-Drive Before They Exit

Watch the video here!

Are You Ready to Retire… or Just Ready to Escape?

Let's be honest—sometimes, it feels like the only thing standing between you and peace of mind is your Outlook calendar. Another meeting, another fire to put out, and you start daydreaming about beaches and zero unread emails.

But here’s the thing: retirement isn’t a vacation. It’s not just a reward for all your years of hard work. It’s a massive shift in your lifestyle, your finances, and your identity.

And smart professionals? They don't just leap. They test-drive their future before they make it permanent.


Why This Matters Now More Than Ever

If you're a high-earning professional, odds are you've been in go-mode for decades. Planning, building, leading, solving. You've mastered efficiency, built wealth, and earned respect. But stepping away? That's a different muscle—and it's one most people don't flex until it's too late.

Retirement isn't just about the money. It's about alignment. Do your finances, goals, and day-to-day life actually match the vision you have for your future?


Let's Bust a Big Myth

"Just save enough and you'll be fine."

Sure, having enough saved matters. But what if your definition of "enough" doesn’t cover what brings you joy? What if you find yourself financially secure but emotionally unfulfilled?

Here’s where it gets real:

  • You could retire with money but feel restless.

  • You might have freedom but lack purpose.

  • You might walk away from your job only to miss the challenge, the structure, and even the small stuff like morning coffee banter.

Retirement shouldn't feel like hitting the brakes. It should feel like changing gears.


What Exactly Is a Retirement Test Drive?

It's simple: you try out retirement while you're still working—just in a controlled, lower-stakes way.

Think of it like running a beta version of your post-work life. No pressure, just insight.

Try any of these:

  • Take a sabbatical or mini-retirement: Step away for a few weeks and live like you're retired.

  • Shift to a 3- or 4-day workweek: Test how it feels to work less without unplugging completely.

  • Follow your retirement budget for a month: Can you live well within that structure?

  • Plan your weeks with zero meetings: What fills the space? Netflix... or maybe something deeper?

This isn't theory—it's practice. And the results can be surprisingly revealing.


Who Benefits the Most from a Test Drive?

This isn’t just for people on the cusp of retirement. It’s for anyone who wants to make smart, informed decisions.

Especially:

  • Professionals 5–10 years out from retirement

  • Entrepreneurs thinking about selling or stepping back

  • Leaders whose identity is deeply tied to their role

  • Couples who aren't quite on the same timeline

If you’re even thinking about retiring, a trial run makes sense.


How to Run Your Retirement Test Drive

You don’t need a six-month sabbatical or a massive spreadsheet. You just need intention. Here’s how to keep it simple:

1. Decide what you’re testing

Is it the lifestyle? The income? The emotional shift? Pick one (or a few) and write it down.

2. Choose your timeline

Even a two-week test can surface surprising insights. You don’t need months.

3. Block your schedule

No fake meetings. No "just one quick email." Simulate the space you’d have in retirement.

4. Take notes

What feels good? What feels off? What would you change?

5. Review your financial plan

Does your real-life trial match what your money can support? If not, tweak it now, not later.

This isn’t about checking boxes. It’s about building clarity.


The Emotional Side: More Than Just Free Time

Let’s not pretend retirement is just about money. Work gives us structure, identity, and sometimes even community. Losing that overnight? It can be jarring.

A test drive helps you figure out:

  • What do I enjoy doing when I’m not working?

  • Where do I get purpose if not from my title?

  • Am I ready to slow down, or do I just need a better rhythm?

These questions matter just as much as your account balance.


Real Talk: FAQs Answered

Q: Won’t this make it harder to go back to full-time work?
A: Not at all—if anything, it gives you leverage. Phased retirement and flexible work are on the rise. You’re in the driver’s seat.

Q: What if I can't afford time off?
A: That’s fair. Try weekend or holiday simulations. Or block evenings and treat them like "retirement hours."

Q: My partner and I aren’t on the same page.
A: That’s normal. Try overlapping your test runs or doing one solo. Compare notes later—you might be surprised.


Why More Professionals Are Doing This Now

Because time is valuable. So is freedom. And the last thing you want is to spend your retirement figuring out what you should have done before you got there.

A test drive lets you:

  • Make course corrections early

  • Clarify your values

  • Build a plan based on experience, not assumptions

It’s not about being perfect. It’s about being prepared.


Bottom Line: Better Questions Lead to Better Outcomes

If you take one thing from this, let it be this: Don’t wait until your last day at work to figure out your first day of retirement.

Ask yourself:

  • What do I want my life to feel like?

  • How will I spend my time when work isn’t the center?

  • What’s my rhythm when I’m not on someone else’s clock?

Then test it. Try it. Live it. Adjust it.


Wrap-Up: Let’s Make This Real

Quick recap:

  • Retirement isn’t just a financial decision. It’s a life decision.

  • Test-driving gives you insight without the commitment.

  • You don’t need months—you just need intention.

Try one small strategy this month:

  • Block off a day as if you were retired.

  • Stick to your retirement budget for a week.

  • Journal your thoughts about life without work.

Then come back and reflect: What worked? What didn’t?

The goal here isn’t to have all the answers. It’s to ask smarter questions—and feel empowered by the journey.

Want help designing your retirement test run? Let’s talk. One conversation could change the entire trajectory of your next chapter. Schedule Your Appointment Now

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Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

Rob Leiphart, CFP®

Public Speaker | Writer | Educator | Family Advocate | Volunteer | Certified Financial Planner TM practitioner

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DISCLAIMER:


The content is developed from sources believed to be providing accurate information. This material is not intended as investment, tax, or legal advice, it is for educational and informational purposes only. Please consult legal, investment, or tax professionals for specific information regarding your individual situation. Please visit rbcapitalmanagement.com for all information and disclosures relating to investment advisory services. Investment advice is not offered or solicited through this website. This material was developed and produced by Rob Leiphart, CFP® to provide information and education on topics that may be of interest to you.