• Average Retirement Age is 62
• The Story of Ronald Read
• Gallup: State of the Global Workplace
• The Rule of 55 
• The 72(t) Rule
• Healthcare Options Before Medicare
• Health Insurance Marketplace
• What Are Health Share Plans
• 40% of All Stocks Have Dropped 70% and Never Recovered

We’ve been told our whole lives that retirement happens at 65. Maybe 62 if you’re lucky. 

But in my experience, that traditional timeline isn’t always the reality. In fact, for many people, retirement may be much closer than they realize.

After nearly two decades of building retirement plans, I’ve noticed a recurring theme: most people overestimate how much they think they need and underestimate how financially and personally ready they already are. 

So today, I’m breaking down seven signs that could indicate you’re closer to early retirement than you might think. These aren’t about hitting some arbitrary savings target or chasing a so-called “magic number.”

Instead, they’re practical, real-world markers that can help you reframe your own timeline.

If even a few of these resonate with you, it may change the way you think about making work optional and enjoying the money you’ve worked so hard to save. 

7 Signs You’re Closer to Retirement Than You Think

Before we dive into the 7 signs, let me share a quick story that tackles one of the biggest misconceptions about retirement.

As many listeners know, I have three kids under the age of 8, and this summer I spent an afternoon hauling boxes of their old toys into the garage. I kept telling myself (and my wife), “One day we’ll find a use for these things, so we’d better hang onto them.” But all it really did was fill the space and block us from turning that third-car garage into the home gym we’ve always wanted.

Most people treat retirement the same way. They keep packing away more and more—convinced they’ll need every last dollar. But in reality, chasing that arbitrary number ends up crowding out what those savings are really for: your life, your family, your time.

The goal isn’t to stack more boxes in the corner. It’s to clear enough space so your money and your life can actually work together. That’s balance. And balance is exactly what these seven signs are all about. Each one helps to show that you may already be in better shape for retirement than you think.

So, let’s dive into the first sign, which is: You spend with intention and know your numbers.

Sign #1: You Spend With Intention and Know Your Numbers

One of the most famous examples of this principle is the story of Ronald Read. He was a janitor and gas station attendant in Vermont who lived a quiet, simple life. He drove a used car, chopped his own firewood, and tracked every dollar he spent. 

But when he passed away in 2014, people were shocked to learn he had built an $8 million estate. He didn’t have a huge salary or some hidden inheritance. He simply lived within his means, invested consistently, and let time and compounding do the heavy lifting. 

Now, the lesson here is not that you need to get a job as a janitor, live just like Ronald, or avoid spending lavishly on things that bring you joy. The takeaway is that building wealth is not just about how much you make—it’s also about how much you keep. And knowing exactly where your money is being spent is a key ingredient to ensuring you don’t outlive your nest egg.

That’s why I continue to argue that creating a system to track your expenses is more impactful than creating a budget. Budgets tend to feel rigid and often break down when real life throws curveballs and spending gets volatile. Tracking, on the other hand, provides you with awareness, flexibility, and confidence. In fact, research shows that people who track their spending experience lower stress, catch mistakes faster, and are able to course-correct more easily. As the old adage goes, you can’t improve what you don’t measure.

Knowing your numbers also ensures you (and/or your advisor) are using accurate assumptions in your retirement planning and, equally as important, that your spending aligns with your values. 

So, if you’ve built a solid nest egg and have a clear handle on your spending, you may already be much closer to retirement than you realize. And if you haven’t taken that first step of knowing your numbers, that’s the foundation everything else rests on.

Once those numbers are dialed in, the next big question is: how do you actually access your retirement savings? Which leads us to the second sign that you could retire earlier than you think—your nest egg is finally unlocked.

Sign #2: Your Nest Egg Is Finally Unlocked

Here’s a quick question for you: If you take money out of pre-tax retirement accounts before age 59 ½, what’s the penalty? Is it 5%, 10%, 20%, or, that’s a trick question, there is no penalty?

Now, I bet most of you answered 10%—and, if so, you’d be right. And if my daughter were here, she would let you pick out a sticker. But here’s where things get interesting: that penalty isn’t as rigid as it seems. With the right strategy, there are legitimate ways to access your funds early without getting hit by the IRS.

For example, the Rule of 55 allows penalty-free withdrawals from your employer 401 (k) if you leave your job at age 55 or older. IRAs don’t qualify, which is why you may want to hold off on rolling your 401 (k) into an IRA until you’ve gone through a comprehensive planning process. You may also want to consolidate more of your pre-tax savings into your company’s 401(k) before you officially leave, allowing you to take full advantage of this strategy.

There’s also rule 72(t), which lets you set up a steady stream of income from pre-tax retirement accounts before age 59 ½ without penalty. But because this rule is packed with tricky nuances, it’s critical to read the fine print or work with a professional before attempting to use it. Finally, while not the most ideal choice, Roth contributions can also be withdrawn at any time, penalty-free, if absolutely needed. 

The key takeaway here isn’t memorizing the fine print of every rule—it’s recognizing that you may have more options to access your nest egg than you realize. So, if you’ve built financial stability and understand which of these strategies apply to you, you may not need to wait until 59 ½ to start tapping into your retirement savings.

Now, unlocking your nest egg provides flexibility and freedom, but true peace of mind comes from knowing you can weather the unexpected storms ahead. Which leads us to Sign #3, Your Portfolio Has Multiple Lines of Defense.

Sign #3: Your Portfolio Has Multiple Lines of Defense

So, last year, we sat down with a new client—we’ll call her Diane. On paper, Diane looked ready to retire. Mortgage-free. Living within her means. Retirement accounts unlocked.

But there was one big problem: a large percentage of her wealth was tied up in her company stock. And right as she was planning to retire, the stock took a nosedive, dropping over 50%. Suddenly, her retirement wasn’t just delayed; it felt like it had been ripped out from under her.  By the way, this was not a small, high-risk stock—this was Intel, a large blue-chip company with a market cap of 137 billion dollars, highlighting that no single company is immune to catastrophic losses.

Not even a company like Amazon, which many forget, dropped 95% from its highs in the early 2000s. Or companies like Microsoft and Netflix, which have both experienced drawdowns of over 70%. And these are the lucky ones. According to JP Morgan, 40% of all companies in the US stock market have experienced a decline of 70% or more without ever recovering. 

Contrary to popular belief, early retirement doesn’t go to the person with the largest nest egg. It goes to the person with the most resilient plan. And resilience comes from diversification—both in your investments and your income. So, if you’ve got multiple streams to draw from—maybe it’s a pension, rental income, or a consulting gig—you’re in a far stronger position. Combine that with a properly diversified, tax-smart portfolio, and you’ve built yourself a retirement that’s not only possible, but sustainable.

So, if you gave a thumbs up to signs one and two—you know your numbers and your nest egg is unlocked—and now you’ve built a portfolio with real safety nets—then financially, you may be ready to retire earlier than you thought.

But I wouldn’t be doing my job here if I didn’t share that money is only half the equation. Because you could have the perfect financial plan and still feel anxious and unfulfilled if you’re not MENTALLY PREPARED. So let’s flip the script. If the financial side of your plan is strong, how do you know if you are personally ready? That’s what the next 3 signs will tell you, beginning with Sign #4: Health and Adventure Are on Your Side

Sign #4: Health and Adventure Are on Your Side

Here’s a question those popular online retirement calculators don’t ask: What’s the state of your health, and what do you want to do with it? If you’re active, energized, and sitting on a bucket list that makes you light up just thinking about it, that’s not just an interesting detail; that’s a critical signal.

Consider this: according to multiple studies, the average American retires at about age 62. Sounds reasonable, right? But by 75—just 13 short years later—statistics show that mobility and health challenges ramp up. At that point, the calendar begins to fill with more doctor visits than adventures.

Now flip the script: what if you retired at 55 instead? That’s potentially two full decades of peak health—20 years to take those bucket list hiking trips, launch that passion project, or chase your grandkids around without feeling winded.

And here’s something we can all easily lose sight of: unlike money, health doesn’t compound. You can always make (or even borrow) another dollar, but you can’t buy back a decade of feeling strong and adventurous. That’s why I put health and adventure on the same level as savings when talking about early retirement. If you’ve got both in your corner, that might be the clearest signal yet that waiting could cost you more than retiring early. 

But even the best health and the longest bucket list won’t matter much if your day-to-day reality is draining you. And that brings us to Sign #5—Your Job Takes More Than It Gives.

Sign #5: Your Job Takes More Than It Gives

Be honest with yourself: When was the last time you woke up on a Monday genuinely excited about the week ahead?

If you’re like most people, you probably had to think a little too hard about that. In fact, Gallup found that nearly 70% of workers feel unfulfilled in their jobs, a number that’s been slowly increasing since 2022. And yet, so many financially successful retirement savers keep pushing through. Yes, for some, it’s because they love what they do, but for many, it’s because they’re waiting to reach a “magic number” that will finally make them feel comfortable hanging it up.

Now, I’m not saying you should throw in the towel after one rough month or a stressful project. But if you’ve been dragging yourself into the office for a year or more, and not even a two-week vacation helps you reset, that’s no longer just burnout—that’s your body (and your mind) telling you it’s time for a change

The caveat is that this really only matters if you can also check off the next sign, sign #6. Because successfully walking away from a job that drains you is only possible if you have a clear vision for what you want the next chapter to look like.

Sign #6: You Have a Clear Vision for “What’s Next” In Your Life

Here’s a question I like to ask soon-to-be retirees: When you imagine waking up on your first Monday of retirement, what does your day look like?

Some people shrug and say, “I’ll probably sleep in, maybe play a little golf or go for a walk, and figure it out from there.” Others light up—they’ve already got trips booked, hobbies lined up, or projects they can’t wait to finally dive into.

If you fall in the first camp, I’ll give you a quick cautionary tale. Years ago, I was hired by a very wealthy executive after he had already retired. On paper, he was more than fine, but he said to me, “Taylor, I left the corporate grind as soon as I could, and now I don’t know what to do with myself.” Like many in his situation, he felt restless and unfulfilled, and it clearly showed in his health and happiness.

That’s the danger of retiring from something instead of retiring to something. A spreadsheet can tell you that you’re financially ready, but it can’t tell you what will get you out of bed every morning with energy and purpose.

Now, if you’re in that second camp—a community for you to share your passions with, a passport ready for more stamps, or grandkids who can’t wait for you to show up—then you’ve already done the hard part. You’re not just financially ready; you’re emotionally ready, too. And that brings us to the final sign—one you might not even realize you’ve already checked off, which is: You’re listening to this podcast right now.

Sign #7: You’re Here, Listening to This Podcast

Think about it. You could be anywhere right now—scrolling through social media, binging Netflix, or checking the news. But instead, you’re here, listening to an educational podcast about retirement.

That tells me something important: you are not average. You’re curious, you’re learning, and you’re intentional. And the research supports this—study after study shows that people with higher financial knowledge end up with more savings and better outcomes in retirement. Simply by being here, you’re stacking the deck in your favor.

And here’s the real takeaway: retirement doesn’t have to be a cliff you jump off—it’s not all or nothing. In other words, if you’ve been nodding along to these signs, you don’t have to wait for some magic date to test-drive retirement. What if you worked three days a week instead of five? Or, what if you only took on the projects you actually enjoy? Or what if you found a part-time consulting gig that gave you complete control over your calendar? That middle ground—semi-retirement or a phased retirement, whatever you want to call it—that middle ground can keep some income flowing and give you breathing room so you can figure out what retirement really looks like for you.

The beauty of this is that you get to experiment. Maybe you’ll discover that a few rounds of golf each week is enough, or that you love the freedom to say yes to your grandkids and no to office politics. Either way, you’re not stuck. You’re designing your future with intention.

Now, before we wrap up, let’s address one important concern that I’m flooded with questions about whenever I discuss early retirement, and that is health insurance before Medicare kicks in at age 65. Yes, it’s true—health coverage is a major factor in your retirement plan and retirement timing decision, and needs to be accounted for carefully. But too often, people let this single issue become a roadblock that delays their retirement unnecessarily. If stepping away from work in your 50s or early 60s is important to you, the real question isn’t if you can get health coverage—it’s how you’ll secure it and if your plan can absorb it. 

For some, the solution is straightforward: you have a spouse who continues to work and has access to an employer plan. For others, it may mean using COBRA, purchasing a policy through the health insurance marketplace at healthcare.gov, exploring private policies, or even looking into healthshare plans, sometimes referred to as medical cost-sharing programs. The point is, you have choices. Health insurance is a hurdle, yes, but it’s not an immovable wall. With smart, careful planning and a healthy plan, it can be managed—and it shouldn’t be the reason you delay the life you want.

So let’s bring this home. If you’ve checked off at least a few of these signs discussed today, you’re probably closer to early retirement than you realize. And remember, retirement isn’t about a perfect number; it’s about balance. Aligning your money with your values, your health with your ambitions, and your time with the people and experiences that matter most. If you’re unsure about your retirement timing, that’s where planning comes in, and my team and I would be grateful for the opportunity to help if professional guidance is needed. You can follow the link in the episode description right there in your podcast app to schedule a Free Retirement Strategy Session, where we will learn what matters most to you, answer your biggest questions, and show you how our unique planning process can help you achieve your retirement goals. 

Thank you, as always, for listening, and once again, to view the research and resources referenced in today’s episode, just head over to youstaywealthy.com/254.

Disclaimer

This podcast is for informational and entertainment purposes only, and should not be relied upon as a basis for investment decisions. This podcast is not engaged in rendering legal, financial, or other professional services.