How to Know If You're Really Ready to Retire

For many people, deciding when to retire is more complex than deciding whether to retire. You’ve worked hard, saved diligently, and built a foundation for the next season of life — but how do you know if you’re truly ready to take that step?

As a fiduciary financial planner, I’ve learned that “readiness” isn’t just about the numbers on a spreadsheet. It’s a mix of financial confidence, emotional preparedness, and a sense of purpose for what comes next.

If you’ve been wondering whether the timing is right, here are a few ways to think it through.

1. Financial Readiness: Can Your Plan Support Your Lifestyle?

This is where most people start — and rightly so. Do you have a clear picture of what your retirement lifestyle will cost, and how your income will support it?

That includes knowing how much will come from Social Security, pensions, and investment withdrawals — and how those income sources fit together.

I worked with a couple who had done an excellent job saving, but weren’t sure how to begin drawing down their assets. Once we created a withdrawal strategy and coordinated their income for tax efficiency, they said they finally felt like they could retire with confidence instead of hesitation.

Having a written retirement plan can make that difference —not because it predicts the future, but because it gives you a framework to make decisions as life unfolds.

2. Emotional Readiness: Are You Prepared for the Change in Roles?

Retirement isn’t just a financial shift; it’s an emotion alone. Many people are surprised to discover how much their sense of purpose was tied to their work — the structure, the relationships, even the daily rhythm.

That transition can be rewarding, but it can also take some getting used to.

As a financial advisor, I’ve seen that retirees who thrive often spend time thinking about what they’re retiring to, not just what they’re retiring from. Whether it’s volunteering, mentoring, travel, or new hobbies, having something meaningful to focus on can help make this stage feel vibrant and fulfilling.

3. Relational Readiness: Have You Talked About What This Looks Like Together?

If you’re married and share finances with your spouse, retirement is a team decision. It’s common for couples to have slightly different visions for what the next season will look like — how to spend time, where to live, or how much to spend.

Having open, ongoing conversations about your goals, expectations, and comfort levels helps ensure you’re both heading in the same direction.

A well-crafted retirement plan can support both perspectives, aligning your shared resources with each person’s priorities.

4. Practical Readiness: Have You Covered the Details?

The logistical side of retirement planning is often overlooked until the last minute. But small details can make a big difference.

Things like:

• Health insurance coverage if you retire before age 65.
• Timing your Social Security or pension benefits.
• Required Minimum Distributions (RMDs) once you reach your seventies.
• Updating wills, powers of attorney, and beneficiary designations.

These aren’t the most exciting parts of retirement planning, but addressing them early helps reduce stress later — and gives you more flexibility to enjoy your time as you choose.

5. Purpose Readiness: What Comes Next?

The most fulfilled retirees I’ve worked with are those who view retirement not as an end, but as a new beginning. They see it as a chance to invest their time and energy in the people and causes that matter most.

Your financial plan should support that. It’s not just about sustaining your lifestyle; it’s about aligning your money with your values so you can live out your purpose with freedom and contentment.

Bringing It All Together

Being ready to retire means having both the means and the mindset to take that next step with confidence. It’s understanding that retirement planning is about preparedness, not prediction — and that your plan should grow and adjust as life does.

If you’re approaching retirement and want to know whether your plan truly supports the life you envision, it might be time for a thoughtful conversation.

‍Retirement isn’t a finish line — it’s a transition.

‍Schedule a short Discovery Call with Stillwater Financial Planning to explore how a planning-first, fee-only approach can help you enter this next season with confidence and clarity.

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Disclaimer: This is not an offer to buy or sell securities. No investment process is free of risk and there is no guarantee that the investment process described herein will be profitable. Investors may lose all of their investments. Past performance is not indicative of current or future performance and is not a guarantee.

Investment advice offered through IHT Wealth Management, a registered investment advisor