This is Why Financially Ready People Struggle to Retire - Root Financial

This is Why Financially Ready People Struggle to Retire

Couple enjoys a happy retirement

Many people assume it’s a math problem when it comes to retirement. And sure—money matters. But if you’ve ever found yourself thinking “just one more year, just one more bonus,” you might already be stuck in a loop where financial optimization comes at the cost of everything else.

We see it all the time. Clients who are financially ready—portfolio in good shape, goals aligned—but emotionally hesitant to make the leap. Why? Because retirement isn’t just a financial decision. It’s a deeply personal one.

Let’s explore five types of wealth you may be overlooking—and why understanding them might just be the key to deciding when it’s time to retire.

1. Time Wealth: The One Currency You Can’t Rebuild

One client we worked with had built a highly successful career. He had saved consistently, invested wisely, and hit every benchmark on the traditional financial scorecard. Objectively, he could retire today.

But every year he stayed, his numbers improved. More stock vesting. A larger Social Security benefit. A bigger 401(k). The math kept nudging him to delay retirement.

And yet—he kept asking: “Why do I still feel stuck?”

The answer? He was focused on financial wealth but not considering time wealth.

Here’s the truth: money is renewable. Time is not. You can always make more money, but you can’t make more time. And when we talk about time wealth, we’re not just talking about years. We’re talking about seasons with your grandkids. Family vacations before everyone’s scattered. Holidays with aging parents.

There’s a concept called the “Time Billionaire”—someone with a billion seconds left to live (about 32 years). At 60 or 65, you may still be a time billionaire. But time passes quickly, and the wealthiest people in the world would trade their fortunes to reclaim it.

So ask yourself: What are you willing to give up to get more time back?

2. Health Wealth: The Body That Lets You Enjoy It All

A healthy person thinks of a thousand things. A sick person thinks of just one.

Physical health is easy to take for granted when you’re in your 50s or early 60s and still firing on all cylinders. But the effects of long hours, chronic stress, poor sleep, and lack of movement compound over time.

Our client’s demanding job was affecting his ability to exercise, recover, and even breathe easy. And while his balance sheet kept improving, his body was breaking down.

You don’t get a second chance at your healthiest years. And once your health begins to decline—particularly with chronic conditions—it may limit what you can actually do with your time and money.

So here’s the question: Are you trading vitality for another vesting schedule?

If your job is eroding your physical well-being and you’re financially ready to step away, it might be time to prioritize the wealth that lets you actually live the life you’ve built.

3. Social Wealth: Relationships Can’t Be Rushed

Money can grow fast. Relationships can’t.

One of the most overlooked parts of retirement planning is social wealth—your community, your connections, and your sense of belonging.

You can’t create deep friendships overnight. And if work has consumed most of your time for the past few decades, you may be approaching retirement without the social network you need to enjoy it.

We often see this in clients: they’re afraid of what comes next, not because of the finances, but because of the absence of structure and connection. Retirement without community can feel isolating—even if the numbers add up.

Investing in your social life—family, friends, community—requires time and presence. You can’t do it well if every week is a race to meet deadlines.

So ask yourself: Are you building social wealth that will support you for the next chapter?

4. Mental Wealth: Peace of Mind Has Value, Too

Financially, our client was thriving. Mentally, he was drained.

His job brought high rewards—and high stress. The weight of constant responsibility, tight deadlines, and burnout was taking a toll on his emotional and mental health.

He found himself losing sleep, feeling anxious, and constantly “on.” That kind of pressure isn’t just exhausting—it chips away at your quality of life.

The irony? He was working to secure a better future… but losing his ability to enjoy the present.

If your mind is always on high alert, it’s hard to be present with your family, focused on your health, or even appreciate what you’ve achieved.

Mental wealth means peace of mind, clarity, and space to breathe. And for many, retirement isn’t just an escape from work—it’s the pathway to healing and joy.

Ask yourself: What would change if I had more mental space and less stress?

5. Financial Wealth: When “More” Becomes a Trap

Let’s be clear: financial readiness is part of the equation.

Our client was financially ready. He had a sustainable withdrawal strategy, tax planning in place, and enough savings to fund the life he wanted.

But because his portfolio kept growing, it was hard to stop. He had optimized his finances so well that even better always felt just one year away.

That’s the trap.

If your mindset is “just one more year,” you may never feel quite ready. The truth is, you might already be there.

Financial wealth is essential. But it’s not the only thing. It’s meant to support a life of purpose—not delay it.

So instead of asking “Could I do better if I worked longer?” ask:

  • “Will this extra year give me more freedom—or take something irreplaceable away?”
  • “Are my finances serving my life—or becoming my life?”

The goal isn’t to stop optimizing—it’s to recognize when continuing to optimize is causing everything else to fall behind.

A Better Scorecard for Retirement

At Root Financial, we believe that a strong financial plan supports a life well lived. But “life well lived” means more than account balances and investment returns.

It means:

  • Having the time to chase what matters most
  • Having the health to enjoy it
  • Having the people around you to share it
  • Having the peace of mind to appreciate it

So if you’ve already done the work, if you’ve already built the financial side… maybe it’s time to look at the other kinds of wealth you’ve built—or let slide.

Because retirement isn’t just about leaving work. It’s about returning to what matters.

Curious What Your Five Types of Wealth Look Like?

At Root, we help clients align their finances with a richer definition of success. If you’re wondering whether it’s time to retire (or just want a second opinion) we’d be honored to help. Schedule a call with our team today or check out the step-by-step roadmap I use for retirement.


The information presented is for educational and informational purposes only and should not be construed as personalized investment or financial advice. The content discusses general retirement planning strategies and is not intended to recommend any specific course of action for any individual.

Examples provided are hypothetical and for illustrative purposes only. They do not reflect any specific client situation and should not be relied upon for investment decision-making. Past performance of investments is not indicative of future results. All investing involves risk, including the potential loss of principal.

Root Financial Partners, LLC provides tax planning as part of its financial planning services. However, we do not provide tax preparation services, represent clients before the IRS, or offer legal advice.

Clients should consult their CPA or attorney before implementing any tax or legal strategies discussed. Nothing in this content should be interpreted as a recommendation to take a specific tax position or legal action.

This content may include discussions around advanced financial planning strategies such as Roth conversions, backdoor Roth IRAs, tax loss harvesting, charitable giving, estate planning tactics. These concepts are general in nature and are not personalized advice. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.

Suitability for these strategies depends on your individual tax situation, income, age, investment profile, estate plan, and other factors. Actions related to these strategies may trigger tax consequences or legal implications. Always consult with your CPA or attorney to assess suitability based on your personal financial circumstances.