Retirement is one of life’s biggest transitions, but for many people, it’s not clear where the finish line actually is. You may have spent decades saving, investing, and working toward the goal of retiring—but how do you know when you’re truly ready?

At Suttle Crossland, we’ve helped many clients wrestle with this exact question. The answer is rarely just about how much money you have. Retirement readiness is about more than your account balance. It’s a mix of financial preparedness, lifestyle planning, and emotional clarity.

Let’s take a closer look at what really goes into knowing if you’re ready to retire—beyond the rules of thumb.

Understanding What Retirement Will Actually Cost

One of the most common mistakes people make is assuming they’ll automatically spend less in retirement. There’s a popular rule of thumb that says you’ll only need about 70% to 80% of your pre-retirement income. But in reality, your spending might not drop significantly—especially in the early years of retirement.

Many people spend more at first, not less. With more free time, it’s easy to say yes to travel, hobbies, or long-postponed home renovations. You might also have new costs that didn’t exist before—like buying health insurance before you qualify for Medicare, or covering more out-of-pocket medical expenses.

Creating a realistic retirement budget is key. This means thinking carefully about how your lifestyle will change, where you’ll live, how much support you’ll offer to family, and what your ideal days will look like. It’s not just about plugging numbers into a spreadsheet—it’s about envisioning how you actually want to spend your time, and then aligning your financial plan to support that vision.

Planning for a Longer Life Than You Might Expect

Another common misstep is underestimating how long retirement might last. With advances in healthcare and improvements in longevity, many people are spending 25 to 30 years—or more—in retirement. That’s a long time for your savings to last.

Outliving your money is a real risk, and it becomes more significant the longer you live. A sound retirement plan needs to account for longevity—not just in terms of covering your expenses, but also in maintaining your purchasing power over time.

Inflation is a slow, steady force that can erode your income if your plan doesn’t include investments that keep pace with rising costs. At the same time, you’ll want a plan that balances growth with stability. Having too much risk in your portfolio might lead to losses you can’t recover from. Too little risk, and you may struggle to keep up with inflation or generate the income you need.

A well-constructed plan should reflect your specific life expectancy, health history, family background, and risk tolerance. It should also be flexible enough to adapt as your needs change—because retirement isn’t static. It evolves.

Turning Your Savings Into Reliable Income

While working, income is relatively straightforward—it comes from your paycheck. But in retirement, that paycheck disappears. The question becomes: how do you turn your life savings into consistent income you can depend on?

Most people will draw income from a mix of sources—Social Security, investment accounts, pensions (if they’re lucky), and possibly annuities or part-time work. Each of these income sources behaves differently. Some are predictable, like Social Security, while others fluctuate with the market, like investment withdrawals.

The goal isn’t just to generate income, but to do so in a way that’s sustainable. You need to make sure you’re not withdrawing too much too quickly, which could deplete your portfolio. But you also don’t want to be so cautious that you limit your lifestyle unnecessarily.

One key part of this conversation is timing. Should you claim Social Security early, or wait to maximize your benefit? Should you draw from taxable accounts first, or your IRA? These decisions can have a big impact on how long your money lasts—and how much you pay in taxes along the way.

At Suttle Crossland, we build personalized income strategies that align with each client’s lifestyle, tax situation, and long-term goals. The result isn’t just a budget—it’s a paycheck replacement plan you can count on.

Factoring in Retirement Taxes

Retirement doesn’t mean you stop paying taxes. In fact, taxes often become more complicated in retirement than they were during your working years.

This surprises a lot of people. You may be withdrawing from pre-tax accounts like a 401(k) or traditional IRA, which are taxed as ordinary income. Add in Social Security, which can also be taxable depending on your income, and you may find yourself in a higher bracket than expected. If you have investments with capital gains or sell a second property, those events may also trigger taxes.

And once you hit a certain age—currently 73—you’ll be required to take minimum distributions (RMDs) from certain retirement accounts, even if you don’t need the money. Those RMDs can push you into a higher tax bracket, increase your Medicare premiums, or impact other parts of your financial plan.

This is where proactive planning can really shine. By thinking about taxes years in advance, you may be able to spread out withdrawals, perform partial Roth conversions, or strategically harvest gains to reduce your long-term tax liability.

Simply put, a good retirement plan doesn’t ignore taxes. It uses them as a tool to maximize your income and preserve your wealth over time.

Being Emotionally Ready to Leave Work

Even when the numbers work, not everyone feels ready to walk away from their career. Retirement isn’t just a financial decision—it’s a deeply personal one. You’re not just changing your schedule, you’re redefining your identity.

It’s common for people to struggle with the emotional side of retirement. Some miss the structure of the workday. Others feel a loss of purpose. Even couples who’ve been married for decades may find themselves navigating new dynamics now that both partners are home all the time.

That’s why emotional readiness matters just as much as financial readiness. Do you have a plan for how you’ll spend your time? Do you feel comfortable living off your savings? Do you know what will bring you joy and meaning in this next chapter?

Retirement can be incredibly fulfilling—but only if it’s built around a life you actually want to live. Planning for that life is just as important as planning for the money to support it.

Do You Have a Strategy for Managing Withdrawals?

Once you transition from earning a paycheck to relying on your investments for income, having a structured withdrawal strategy becomes essential. This isn’t just about pulling money out when you need it—it’s about doing so in a coordinated way that supports your lifestyle, limits tax exposure, and aligns with your long-term goals.

Without a plan, it’s easy to fall into reactive decisions—selling during market downturns, taking more than you intended, or triggering unnecessary taxes. A thoughtful withdrawal strategy helps you maintain clarity and consistency, even when the market or your personal needs shift.

There are several approaches to managing withdrawals, including methods that allocate funds across different time horizons, rules-based strategies that adjust with market performance, or customized plans tailored to income needs and legacy goals. The right approach depends on your preferences, your mix of account types, and the kind of flexibility you want in retirement.

Ultimately, this part of your plan helps answer the question: How do I translate my savings into the lifestyle I want—without undermining the future I’ve worked for?

So, Are You Actually Ready?

If you’re still wondering whether you’re ready to retire, you’re not alone. Most people don’t get a clear yes or no from their bank statements. What you really need is a plan—one that brings together the financial, emotional, and logistical parts of your life into one cohesive picture.

At Suttle Crossland Wealth Advisors, we believe retirement planning should feel like planning for your life, not just solving a math problem. We walk with clients through the process—from the early “what if” questions to the moment they give their two weeks’ notice—with the kind of clarity and care that helps them feel truly ready.

Let’s Talk About Your Next Chapter

Whether you’re five years from retirement or already in it and wondering if you’re on the right path, we’re here to help you build a plan that fits your life.

If you’d like to talk through your retirement readiness and what steps to take next, let’s start a conversation.