Should I Retire Now…Or Keep Working?

Retirement isn’t simply about reaching a certain age or account balance.

If retirement has been on your mind lately, chances are you’ve asked yourself another important question:

“Should I retire now…or should I keep working?”

At first glance, it seems like a straightforward decision.  If you’ve saved enough money, you retire.  If you haven’t, you keep working.

Simple…right?

Not necessarily.

Over the past 23 years, I’ve had the privilege of helping individuals and families prepare for retirement, and one thing has become very clear:

Retirement is rarely just a financial decision.

Whether I’m meeting with someone from Delafield, Dousman, New Berlin, or Milwaukee, I continue to notice the same thing: retirement decisions are rarely just about the money. More often than not, they’re about confidence, purpose, and feeling ready for the next chapter of life.

For many years, when I would ask people when they’d like to retire, a somewhat sarcastic response I often heard was: “Tomorrow.”

Over time, I began asking the question a little differently.  Instead, I’d say, “If you could, when would you like to stop needing to work full-time? And be realistic.”

Most people would answer that question through the lens of whether they believed they had saved enough. But over the years, I noticed something interesting among clients who already had the financial ability to retire:

Many of them needed reassurance that it was actually “okay” to retire.

In some cases, they simply couldn’t picture themselves no longer going to work every day.  Beyond the numbers, the idea of waking up one morning and not needing to do that – a routine built over decades – felt almost unreal…from an emotional standpoint.

So, I found myself encouraging clients to recognize something they hadn’t yet recognized themselves – that they had earned the opportunity to retire and begin the next chapter of their lives, and that it IS okay.

Interesting, isn’t it?

While many people are eager to retire, I’ve found that being financially prepared and being emotionally prepared are often two very different things.

That’s why I believe the better question isn’t simply, “Can I retire?” 

The better question is, “Am I truly prepared for retirement?”

Those are two very different questions.

And sometimes, a few thoughtful planning decisions—and the confidence that comes from having a coordinated retirement plan—can make all the difference in helping someone feel emotionally prepared to take that next step.

Retirement Is More Than Leaving Your Job

For most of our working lives, the goal is fairly simple:

1. Go to work.
2. Earn a paycheck.
3. Save for retirement.
4. Repeat

Then Retirement changes everything…

Instead of asking how much to save, the questions become much more personal.

• Will I have dependable income (or will I be okay) for the rest of my life?
• Will my retirement savings support the lifestyle I envision?
• What happens if the market experiences a prolonged downturn?
• Have I thought through healthcare costs, inflation, taxes, or maybe even living too long?
• If something unexpected happens, will my plan be flexible enough to adapt?

Quite frankly, these are questions many people don’t even realize they should be asking, and that’s perfectly understandable.

There Isn’t One “Right” Retirement Age

People often ask me whether they should retire at 62…65…or wait until 70. 

Many think it’s an age thing or when their hair gets gray enough.  Some assume it’s time to retire simply because that’s when their parents did.

The truth is, there isn’t one answer that’s right for everyone.

I’ve seen people retire earlier than planned and enjoy wonderful retirements because they had a well-coordinated plan and lived a prudent financial life.  (In my experience, that’s one of the biggest drivers of retirement confidence, but we’ll save that for another discussion.)

I’ve also seen people continue working—not because they had to—but because they genuinely enjoyed what they did and they needed a purpose.  In so doing, their choice to continue producing income also allowed them to strengthen an already solid retirement plan.

Neither approach is automatically better. 

What matters is whether your decision fits your goals, your resources, and the retirement you hope to enjoy.

It’s About Making Informed Decisions

One of the biggest misconceptions about retirement is believing there’s one perfect answer.  There usually isn’t.

Retirement involves dozens of financial decisions, and each one affects the others.

That’s why I encourage people not to think of retirement as a single decision, but as a series of informed decisions that work together.  Retirement often becomes much less stressful when you’ve planned for the whole picture.  That means having a plan for where your retirement income will come from, which accounts you’ll draw from first, how those decisions affect taxes, how you’ll continue to grow and protect the nest egg you’ve worked all your life to build, and how you’ll prepare for life’s unexpected events along the way. 

Having a plan is where confidence begins.

Instead of asking, “Should I retire now?” 

Instead, you may want to ask:

“If I retired tomorrow, would I feel confident in the decisions I’ve made…or would I simply be hoping everything works out?”

There’s an important difference.

Continue Your Retirement Journey

If today’s article gave you a different perspective on retirement, we’d love to help you take the next step.

Watch our Complimentary Presentation, “The Retirement Confidence Roadmap”

OR

Schedule Your Complimentary Assessment

If you’d rather begin with a conversation, we’d be happy to answer your questions during a complimentary Introductory Conversation.