What are 5 regrets of Americans who called it quits too early by retiring?

[00:00:00] Ralph Estep, Jr.: Have you ever wondered if you retired too early, or maybe you're thinking about when's the right time to retire? Imagine this: you worked hard your entire life, you saved diligently, and you finally reached that magical retirement age. You hand in that resignation letter with a mix of excitement and some trepidation. You don't know exactly what's coming next, but fast forward a few years, and you're faced with a harsh reality: your nest egg is dwindling faster.

[00:00:29] Ralph Estep, Jr.: than you expected, your days lack purpose, and you're considering the unthinkable—going back to work. Well, this scenario is more common than you might think, and today we're going to dive deep into why this happens and how you can prevent it from happening to you. So today we're going to explore the five biggest regrets of Americans who called it quits before they were truly ready. This is going to be a good episode.

[00:00:51] Ralph Estep Jr.: So stay tuned to learn how you can avoid these common pitfalls and create a retirement that is both financially secure and, more importantly, spiritually fulfilling. Now, before we get started on today's show, let me talk to you briefly about yesterday's show. Yesterday we had a great discussion about the best money lessons to teach your kids.

[00:01:14] Ralph Estep Jr.: I highly recommend, if you missed it, to go back and check it out because we covered some crucial financial principles that can set your children up for a lifetime of financial success. As always, you can find new episodes at askralph.com. Well, we got a fantastic message from Jackie, and here's what Jackie said:

[00:01:34] Ralph Estep Jr.: She said, "Hey Ralph, I've been a loyal listener of your show for the past year, and it's truly changed my perspective on finances and faith. I'm writing because I'm approaching retirement age, and I am excited about the prospect of leaving the nine-to-five grind, but I'm also terrified of making a mistake. I've heard stories of people retiring too early and regretting it. Can you share some insights on this?

[00:01:56] Ralph Estep Jr.: You know, how do I know if I'm really ready to retire, both financially and spiritually? Thank you for all you do." Well Jackie, that is a powerful question, and it's one that I'm going to give you an answer to. And again, I want to say thank you for your question, and thank you for the kind words you said.

[00:02:12] Ralph Estep Jr.: You know, it's an incredibly timely discussion. As I get older—I just turned 52—and now I'm thinking about these things that are going on, so it's close to my heart. And I've worked with many clients, I mean many clients, who are in that same dilemma. So I'm excited to share some of those experiences with you today. Well, welcome to the show.

[00:02:32] Ralph Estep Jr.: I am thrilled you're joining me on this journey of finances and faith. I truly appreciate you taking your time. I know that you've got a limited amount of time, and you're spending it with me. I want to explore today a topic that is crucial, I mean crucial, for anyone that's approaching that retirement age. Now, before we get started, I want to share a Bible verse that I believe is particularly relevant to our topic today.

[00:02:56] Ralph Estep Jr.: And it comes from the book of Proverbs. Yes, we get a lot of them from Proverbs because there were some great things in there. This particular one's from 21:5. And I've used this before, but it hits exactly what we're talking about. And it says this: "The plans of the diligent lead to profit as surely as haste leads to poverty." That's a powerful verse, but it reminds us of the importance of careful planning.

[00:03:20] Ralph Estep Jr.: It reminds us of the importance of patience in our financial life, especially when it comes to major decisions like retirement. Well, let's get into the heart of today's topic, and that's the five regrets of Americans who retired too early. I want to start by telling you a story that really brings this issue to life.

[00:03:41] Ralph Estep Jr.: Now, I had this client a few years ago, and I'll call him George. Now, George was a hard-working dude. He was a successful small business owner, and he'd been running his company for 30 years. So he's 62, he's feeling burnt out, and the idea of retirement, man, it was like a siren's call—it beckoned him. You know, he saw his days being filled with golf, being able to travel with his wife, and just spending time relaxing. So George came in to me for advice, and yes, I do offer retirement planning advice.

[00:04:11] Ralph Estep Jr.: I don't do investment decisions, but I can help you make the decision about when to retire and what that should look like. So George came in, we sat down, we looked at his finances, and truth be told, on paper, everything seemed to be in order. He had really diligently put money into his retirement, put into what was called a self-directed 401(k).

[00:04:29] Ralph Estep Jr.: His house was almost paid off—in fact, I think it was like within a year or a year and a half of being paid off. He had, listen to me, built this decent emergency fund. So based on the standard calculations, it looked like George was ready to go and could retire comfortably. So guess what George did? He took the plunge. He sold his business, and he threw himself a big retirement party.

[00:04:50] Ralph Estep Jr.: I was there—it was a massive party—and it was cool seeing all the people that he had impacted through his life. And George embarked on this new time of journey, this new life of leisure that he had. And for the first few months, everything he dreamed of was great. He played golf three times a week, got to take a cruise with his wife—

[00:05:08] Ralph Estep, Jr.: he was never able to do that because he was running his business—and he caught up on all those books he'd been meaning to read. Hopefully, you've read my books. But then something started to change. George shared with me, he said, "Ralph, I'm feeling restless." And George was missing the challenges of running his business.

[00:05:23] Ralph Estep Jr.: He missed that sense of purpose that it gave him. And to make matters even worse, George started to notice that his retirement savings weren't stretching quite as far as he had hoped. So picture this: two years into retirement, George came back to see me. He says, "Ralph, I need to sit down with you. I need to talk about what's going on." He was actually considering going back to work, but he was worried about how it would affect his Social Security benefits and his overall financial picture. He truly, he felt lost.

[00:05:49] Ralph Estep Jr.: He was confused, and frankly, I think he was a bit embarrassed too, because he thought he had made the right decision. But now, all of a sudden, he feels like he doesn't have a purpose. You know, he feels like he needs something to do. And unfortunately, George's story is not unique. It touches on several of the most common regrets I've seen among people who retire too early.

[00:06:10] Ralph Estep Jr.: So let me break those down for you. The first one—I see this all the time—and it's financial strain. Many people underestimate just how much money they're going to need in retirement. A lot of times, it's because of things like inflation. Like right now, we are in a period of inflation. If you go to the grocery store, stuff that cost something a year ago is more than it was six months ago.

[00:06:32] Ralph Estep Jr.: It just continues to go up. Another big one under this financial strain are these unexpected medical expenses. And that's just a fact of life because the truth is, the simple fact is, you might live longer than you anticipate. You're going to have those medical expenses, but you're going to have to spread that income over a longer period of time, which is great that you're alive, but that can lead to a lot of stress, and it forces you to make some difficult financial decisions. Let's talk about George. George realized his savings were going down quickly, and it scared him quite frankly.

[00:07:03] Ralph Estep Jr.: It really worried him. The second thing: loss of purpose. This one is enormous. People don't realize work provides more than just a paycheck. In many ways, our work is our sense of identity. It gives us purpose. It's our social connection. And I will tell you, many of my retiree clients struggle with feeling adrift or useless.

[00:07:26] Ralph Estep Jr.: I know that's a harsh word to use, but that's what they've told me since they left the workforce. George shared this with me firsthand. He said, "Ralph, I feel useless. I feel like I don't have any purpose. Yeah, I'm enjoying playing golf, I'm enjoying doing things with my wife, but man, I don't feel like I've got that connection."

[00:07:44] Ralph Estep Jr.: "I don't have that purpose, that sense of identity." Which leads me to the third thing, and that's boredom.

[00:07:51] Ralph Estep Jr.: Which leads me to the third thing, and that's just pure boredom. While the idea of endless free time sounds great, the reality is many of my retiree clients find themselves bored and under-stimulated. They miss those mental challenges and social interactions that work provided. Listen, in George's case, he did not like being idle. Even if he was able to play more golf, he needed those social interactions with his customers and suppliers.

[00:08:21] Ralph Estep Jr.: That's what fueled him, and he didn't have that anymore. He just felt lost and hopeless. Another thing a lot of people don't want to talk about, and that's number four, is strained relationships. And I'm not a relationship counselor, but I have seen this time and time again with my clients. This is the unfortunate truth: spending 24 hours a day, seven days a week with a spouse or partner can be challenging, especially if you're not used to it. If you've always worked in your own business—and trust me, if you're a small business person, you're probably working crazy hours—you don't think about that.

[00:08:58] Ralph Estep Jr.: All of a sudden, that changes, and you're home all the time. Many couples find that retirement puts an unexpected strain on their relationships. Now, George shared with me candidly that he felt like he and his wife were really struggling with this, and I've had many clients in the same situation. And here's the thing I'm going to say about that:

[00:09:17] Ralph Estep Jr.: You've got to plan for this. You've got to discuss that emptiness with your partner and start talking about what do we do when the kids leave? And this isn’t necessarily a retirement thing. I was talking to somebody this morning—this could be when your kids leave the nest, this could be when you change careers—you've got to have those discussions and talk about what that looks like.

[00:09:36] Ralph Estep Jr.: And number five, and this one is the tough one, and George kind of had a little bit of this, and that's difficulty re-entering the workforce. If you find yourself in that financial necessity or you're bored and you get driven back to work, you want to go back to work, unfortunately, you might find the job market has changed. The truth is, if you look around, technology moves fast, and skills can become outdated quickly. And here's the thing George said to me. He says, "Ralph, dude, I do not want to be one of those greeters at Walmart."

[00:10:06] Ralph Estep Jr.: He wanted to get back involved. He wanted to do things, but he said, "Ralph, I don't want to be standing on my feet or sitting on a stool and telling everybody as they come in the door, 'Hey, welcome to Walmart.'" Now you might be wondering, "Ralph, all this sounds pretty grim. Are you saying you shouldn't retire?" And I don't mean to be negative.

[00:10:19] Ralph Estep Jr.: I'm not saying that at all. The truth is retirement can be a wonderful phase of life, but it requires careful planning, both financially and spiritually. You might be asking, "Ralph, how can we avoid these regrets?" Here are some actionable steps that you can take. First thing you need to do: you need to sit down and do a thorough financial assessment. Don't just rely on those rules of thumb or those online calculators—there are a bunch of those out there. You might be looking at it and thinking, "Well, I'm 62 years old,

[00:10:47] Ralph Estep, Jr.: I'm going to collect my Social Security and do this and that." Well, you're missing out on some things. So you’ve got to sit down with a financial advisor who understands both your financial situation—and I’m going to plug myself here a little bit—but also your faith-based values because retirement is not just about your savings, but your expected expenses.

[00:11:08] Ralph Estep Jr.: It's those healthcare costs. And you want to make sure that your spending is going to align with your values. So that's number one: do a thorough financial assessment. Number two—and I'm going to stress this one—consider a phased retirement. It's not an all-or-nothing thing. Instead of going from full-time work to full-time retirement overnight, you could consider scaling back gradually. That way you can adjust both financially and emotionally.

[00:11:30] Ralph Estep Jr.: I've had clients that have done this, kind of what I call semi-retirement, and they phased themselves out over time. They found it to be really rewarding because they still had those connections, they still had that drive, but they didn't have to be so responsible for the day-to-day things. Third thing: you've got to develop a retirement purpose.

[00:11:48] Ralph Estep Jr.: You can't just decide, "Well, I'm going to retire," and not have a purpose. Before you retire, spend some quality time thinking about what you want this phase of your life to look like. You've got to ask yourself tough questions, like, "How do I serve God in my community? What goals do I want to accomplish?" You know, having a clear sense of purpose can make retirement much more fulfilling. This is a great time to share what you've learned over your career.

[00:12:11] Ralph Estep Jr.: Maybe you want to give back. Maybe you want to be a community mentor. Maybe you want to work with people in the same industry. Maybe you want to volunteer at your church. Maybe you want to become a missionary, but you've got to have that plan. You've got to know what that looks like before you even decide to retire.

[00:12:27] Ralph Estep Jr.: Number four: stay engaged. You've got to look for ways to stay mentally and socially active. Maybe that's through volunteering, and as we talked about, maybe it's taking classes or even starting a small business or a consulting practice. I have many clients who do this, and they find it extremely rewarding. You've just got to stay engaged.

[00:12:47] Ralph Estep Jr.: You want to stay involved in things because I've had so many clients who've retired and then their idea is to sit on the couch and watch what's next on TV. And to be frank with you, they don't last long. They don't have that fulfillment, and they get really, really negative. I'm not trying to be negative, but they get that way.

[00:13:05] Ralph Estep Jr.: So number five—and this one's important as well—maintain your skills. Even if you don't plan to work, you can keep your skills sharp. That will give you more options down the road. One of the great things we have here in Delaware, the University of Delaware has this thing called the Academy of Lifelong Learning.

[00:13:21] Ralph Estep Jr.: And as I understand it, you can basically go take college classes for free once you get to be a certain age. That can give you that skill set, and maybe it's just a matter of being engaged, a matter of having some social connections with people around you. This is also a great time to strengthen your relationships. If you are intentional about it, you can invest time in your marriage, invest time with your family, go do those things you never were able to do because you were always working. Grow those friendships. But the thing you're going to need to realize is you're going to have to do that before and during retirement. You can't just decide, "Okay, I'm going to retire."

[00:13:59] Ralph Estep Jr.: And then, next week, I'm going to have this social calendar full of stuff. It's not going to happen like that. You've got to invest that time before and after retirement because the truth is, if you've heard me say it once, you've heard me say it ten times: strong relationships are key to a happy retirement. The clients that I have who have happy retirements are the people who are involved.

[00:14:19] Ralph Estep Jr.: They're doing things with their senior center, they're involved in a community, they're doing something with their church. And last but not least, and I'm a big guy, but here's the deal: you've got to stay physically active. Maintain that regular exercise, keep that healthy diet because guess what? It's going to help you stay fit, but bigger than that, it will help you save on those healthcare costs in retirement because the truth is, I've seen way too many clients just fall apart after retirement. You know, and to be honest with you, I've told my wife this many times, I've told my boys the same thing: I'm planning to work until the day I die.

[00:14:54] Ralph Estep Jr.: Now, that might not work as hard as I work every day, but I'm planning to stay involved and going to stay connected. You know, I've already kind of planned for retirement. My house—I've got a first-floor master bedroom, my office here on the farm—I can walk to it if I needed to, if I couldn't drive, but I've planned for those things.

[00:15:11] Ralph Estep Jr.: And I'm planning to stay engaged. I'm planning to work. Like, my uncle passed away about two years ago, and my uncle was a Colonel from the army. And one thing he said to me was when he retired—he did like 33 years in the military—he says, "Ralph, I'm going to stay engaged." And he worked, he ran a small business.

[00:15:27] Ralph Estep Jr.: I got what we call a side gig. And even once he was done with that, he spent days doing his Sudoku every day, he would do the New York Times crossword puzzle because what he said to me many times is, "Ralph, I’ve got to keep the mind sharp. The body is going to fall apart; that's just the nature of what it is." But he said, "Ralph, it's all about keeping that mind sharp."

[00:15:45] Ralph Estep Jr.: And he lived to be, I want to say, like 87 or 88 years old. And remember this: retirement isn't just about having enough money. I think I've stressed that today. It's about creating a life that's meaningful, a life that's purposeful, and a life that's aligned with your values. The truth is, as Christians, we're called to be stewards of our resources.

[00:16:04] Ralph Estep Jr.: And that includes our time and our talents, as well as our money. So let's go back to George. Well, George was upset, but he decided he was going to figure out a solution. So he came in, we sat down, and guess what George did? He started a small consulting business. This allowed him to work part-time doing what he loved.

[00:16:22] Ralph Estep Jr.: It helped him provide additional income, so he wasn't feeling like his money was going away. It provided mental stimulation, and it gave him a sense of purpose. And the cool thing was, he didn't have the stress of meeting payroll, he didn't have the stress of worrying about building a business. He wasn't running that full-time business. And so, we were able to take that, we adjusted his financial plan to account for that additional income, and we ensured that he was still maximizing his Social Security benefits. So the key takeaway here is that retirement doesn't have to be an all-or-nothing proposition.

[00:16:52] Ralph Estep Jr.: It's not a decision of "Do I retire or not retire?" Because there are many ways to create a fulfilling post-career life that balances financial security, personal fulfillment, and most importantly, spiritual growth. So let me wrap up by reminding you of a few things. Number one: many people who retired too early regretted it due to financial strain, loss of purpose, boredom, relationship challenges, and difficulty re-entering the workforce. The second thing: I want to stress this—

[00:17:20] Ralph Estep Jr.: It all comes down to careful planning, both financially and spiritually. It's crucial for a successful retirement. And as I've said—you've probably heard it three times already—number three: consider a phased approach to retirement. And stay open to those hybrid options that allow you to remain engaged and still provide for some financial security. Develop a clear sense of purpose for your retirement years that aligns with your faith and values.

[00:17:43] Ralph Estep Jr.: If you don't have a purpose, your retirement is not going to be great. It's going to suck, to be blunt. And I've had many clients use that word. They said, "Ralph, this sucks. I enjoyed working. I enjoyed the things I do, and I feel like I'm useless. I feel like I've got nothing going on." But if you develop a sense of purpose that aligns with your faith,

[00:18:02] Ralph Estep Jr.: You can keep that. And lastly, but not—I'm not going to downplay this one—but stay physically, mentally, and socially active in retirement. And you’ve got to think along these lines. This is the truth: retirement is not the end of your journey. It's just the beginning of a new chapter. So with proper planning and a focus on what truly matters, it can be one of the most rewarding periods of your life. I know I sound a little bit negative today, but I've had so many clients who have enjoyed retirement. It gave them the opportunity to do things they haven't been able to do. Well, thank you for joining me today on this episode. I hope it's given you some food for thought as you consider your own retirement plans. Now tomorrow I'm going to be discussing a Spiritual Sunday topic, and that's how do I work at cultivating Christian community?

[00:18:48] Ralph Estep Jr.: This is a crucial aspect that can have a profound impact on our financial decisions as well. So make sure you tune in tomorrow. Now maybe today's episode has made you realize that you need some help planning for your financial future. Well, I would encourage you to schedule an appointment with me. So for a $150 consultation fee, I will work with you to improve your personal finances.

[00:19:07] Ralph Estep Jr.: I can help you look at your business finances. Maybe you need help growing your business, all with the goal to help you achieve all your financial goals. To schedule with me, just go to askralphpodcast.com/store. You can schedule right there. We'll put together a personalized planning session. But you need to do it.

[00:19:24] Ralph Estep Jr.: So go to that website and do it right now. Remember this: my passion is to help you achieve financial success. I want you to live out your dreams. Your dreams might not be the same as mine, and your dreams are not the same as my other clients' dreams, but I want to help you live out those dreams. I want you to grow in your faith. And I know if we work together, we can master your finances from a Christian perspective, which will open doors for you to be able to focus on your purpose. When you are able to handle those financial, lower-level needs, you'll be able to find that self-actualization and actually get to your purpose. So I know I've gone a little long today, but I want you to remember this: stay financially savvy, and God bless you.