The Real Reason You Don’t Feel Ready for Retirement

12 May 2026 · 16 min · 6 chapters

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In short

Why retirement feels out of reach for Gen X women/couples in their mid-40s to late-40s (“messy middle”), and how to close three “hidden gaps” that cause stalling: no retirement vision, no trusted retirement number, and no system linking today’s cash flow to retirement.

Guest backgrounds

No guests mentioned; episode is hosted by Dailene Higgins (money coach and retirement strategist).

Key claims

Waiting until life calms down can be too late; generic retirement calculators create discouragement; retirement success comes from everyday decisions and a cash-flow system that builds consistency and reduces fear of “doing wrong.”

Notable examples

“Normal day” in retirement vs travel days; asking whether current spending reflects future values; using a “success indicator” in her Retirement Ready workshop; promoting a June 2–4 “accelerate your retirement” challenge to create a retirement number.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Understanding the Messy Middle

0:51 to 2:26

Exploring why retirement feels distant and the challenges in the 'messy middle' phase of life.

“So why does retirement feel so far out of reach?”

Identifying the Feeling of Being Stuck

2:26 to 3:52

Questions to reflect on feelings surrounding retirement readiness.

“And if you wait till it feels like it's calmed down or you can take some more or whatever it is, whatever feeling you're hoping for, it might be too late.”

Gap 1: Lack of a Clear Retirement Vision

3:52 to 6:06

Discussing the importance of having a clear vision for retirement.

“quickly, we've got to make sure we do it well.”

Gap 2: Understanding Your Retirement Number

6:06 to 11:40

The significance of knowing your retirement number and how to find it.

“The reflective question for this gap, what does a normal day in your retirement actually look like?”

Gap 3: Connecting Today to Retirement

11:40 to 14:02

The necessity of having a system that links your current actions to your retirement goals.

“So as you think about those three gaps, right?”

Connecting Present Actions to Future Retirement

14:02 to 14:42

Learn how recognizing current expenses can enhance your retirement readiness.

“So what expense is supporting your future and or is a part of your future?”
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Transcript

Automatic transcript. May contain errors.

0:06Welcome to the Wealthy After 40 podcast, the show for Gen X women and couples who are ready to ditch financial stress and feel confident about retirement. I'm your host, Dailene Higgins, money coach and retirement strategist to help you gain clarity and confidence with your money by creating a spending plan that aligns with your financial goals and dreams so you can spend intentionally, save consistently, and feel at peace about your future. Join me every week to understand your money, simplify your decisions, and take intentional steps toward the life you want.

0:50Welcome to today's episode. So why does retirement feel so far out of reach? As I talk with individuals, whether they're going to work with me or not, and they are in their mid 40s, maybe even almost 50, I hear so many times, it's too soon for me. I'll think about it later. I'm not going to worry about this right now. I'm saving. It'll be good. I'll worry about it later. I've got time. That blanket statement. And while I understand this to some extent, you're stuck in this phase of life that I have now termed the messy middle. You're in the middle of your career plugging along, whether you hate it or love it, trying to make those advances be good, all of those things.

1:42You're raising your kids, prepping them for college, maybe experiencing empty nest. You're paying all of your bills and enjoying life. There doesn't seem to be anything that's jumping out at you that's saying, hey, focus on me. And so you just go along because you think, wow, could I start planning for retirement? I've already got so much on my plate. And we do in this phase, been there, done that, have a lot going on. And many times, I think the reason why retirement feels so far out of reach is that we don't ever think about what is on the other side of that messy middle. And if you wait till it feels like it's calmed down or you can take some more or whatever it is, whatever feeling you're hoping for, it might be too late.

2:41So I want you to ask yourself the following question. Why does it feel like retirement is so much further down the road? And why do I feel like I'm not ready to take action? Again, why does it feel like retirement is so far out of reach? And why do I feel like I'm not ready to take action? As you define that feeling as what is keeping you stuck. So recognizing what it is, make sure you reflect on that, solidify that, understand that. And as we talk about the next part of this episode, I want you to think about feelings. As we work through, we're going to define three hidden gaps. These gaps are part of why you're stalling and not taking action.

3:42This feeling that you've identified, how can you shift that feeling to help close at least one of these gaps. Because around here, we're not about doing everything quickly, we've got to make sure we do it well. So choosing one of these gaps to close, and I'll give you more direction at the end, is where I want you to start. So the first hidden gap is you don't have a clear picture of retirement. We talked about that in the last episode about retirement vision. And so not having a picture, a vision, whatever you want to call it, dream. There are three things that can help you start creating a picture for yourself.

4:32When do you want to retire? What is life going to look like in retirement? and what do you want to protect and prioritize? Now, if you've been a podcast listener for a while, that protect and prioritize is the biggest thing I request I get from my clients. I don't want to give up my current lifestyle. But if you don't create a clear picture and you don't understand that piece, what you want to protect or prioritize, that fear is going to still keep you from wanting to plan for retirement. But if you think that it's something I can gain and hold on to with the action of retirement planning, then it closes this gap.

5:20It changes that feeling that you've defined. But as long as you just think, oh, retirement's down the road, or I have time, I haven't thought about it, retirement is going to stay abstract. It's going to stay not defined. You're not going to be excited. And if your brain can't see it, it can't plan for it. Because you're not sure what mark you're trying to hit, what you're trying to build, all of those things. So I want you to start thinking about those three things, when you want to retire, what life will actually look like, and what is it that you want to protect or prioritize in that retirement.

6:07The reflective question for this gap, what does a normal day in your retirement actually look like? Remember last episode, we talked about traveling and that's not a normal day. You're going to have more normal days than travel days. So really start thinking about that. But what are you looking forward to? How does that start painting that picture so that your brain can see it and you can start planning for it? All right, gap number two, you don't know your number, your retirement number, or you don't trust it. The problem here, and we've talked about it, is you're relying on generic calculators.

6:57and maybe you've googled how much do I need to save for retirement and then you're like wow I'm not even close you feel worse so you want to retract but relying on those generic numbers is not going to create what you want there is no connection between your lifestyle and those numbers. And so you are completely in the dark about, am I on track or what do I need to shift to get there? Now you don't need perfect numbers, you just need relevant numbers. And I can help you define this retirement number in many different areas. This is something I will be covering in that three-day challenge inside of my Facebook group.

7:47This is something I can walk you through if you want a personalization walkthrough, the roadmap to retirement call, and help you define what that number is going to be. It's also something I cover in my workshop, but that's not happening for a few months. So I'd love for you to attend the challenge or book a call. And having this number can provide you so much clarity. the reflective question here is do you know what you actually need or are you guessing and i'm sorry but those generic calculators those standard numbers thrown out there are a guess and as i've always said the further you are along 40s 50s we know what health is like we know what we love we know what we want to spend we know these things that getting that number is so much easier for us than, for example, a 20-year-old.

8:43If a 25-year-old came to me, I'm like, you're just going to have to go by the standard answer because that's a better crapshoot than trying to define what your expenses are going to be down the road. But as a 40-year-old, 50-year-old, I'm pretty sure you know what your expenses are going to be in your 60s. Yes, there's some things we don't know, but we're pretty close. We're pretty close. All right, so the third gap, third and final gap, is you don't have a system that is connecting today to retirement. There's a disconnect. Again, we're talking about it feels out of reach because, yes, you might be saving, you're paying all your bills, doing all the things, but you don't have a system that is messaging you, for lack of a better word, and telling you, okay, you're doing the right things.

9:36You're prioritizing your debt or you're prioritizing your saving and your lifestyle. And a system is going to help support your consistency in working through paying off debt, your consistency in being able to save for retirement. And so you can maintain that lifestyle. So it is really important to have a system that is going to help you intentionally plan your cash flow. Again, cash flow is money coming in and money going to all of the places it needs. It's not just spending. We've got to send some to savings. And within savings, there's a couple of different levels. I'm going to talk about that again in the future.

10:19I've talked about it before, but there's different levels of savings. But having a system that that ultimately also gives you some gaps and says, this is where you need to direct your money. And then being able to do so and being consistent. That's why I believe getting started sooner than later is that consistency piece is easier. There's less of a demand on your money. There's not a time crunch. You've allowed yourself space to grow, space to explore. And it really is helpful because retirement isn't built in big moments. It's not about finding that one stock. It's not about finding that one package that's going to make retirement happy or happen, excuse me.

11:05It's built in your everyday decisions and directing those decisions into your future is what's key. So the reflective question in this gap is, if I looked at your spending today, could I see your future in it? Are you spending things that I would be like, yep, this is what she's going to continue to do. This is what she values. This is what's supporting her. These expenses right here are her lifestyle. So as you think about those three gaps, right? It's not just about, okay, I've got to go out and do the things. It's believing you can do those things, right? It's getting rid of the, oh, I'm going to do something wrong.

11:54If you have a system, your system is going to show you if it's working or not working, right? In my retirement ready workshop, I have individuals choose a success indicator, right? There's things that we're going to make sure that things are working and things are happening so we can eliminate this fear of doing wrong. And that's key. You might be waiting for the right time, but there is no right time. This is the best time. And if you're thinking it's too late, why are you going to wait another day? Am I too late? Am I going to be able to make a difference? Yes. Every good decision from now till you need to retire is going to get you where you need.

12:41Because retirement doesn't become possible when you have more money. It becomes possible when you have a plan that works to create the life that you want. We've got to remember that's all retirement is our life continuing after we're working. Or as you're shifting, you might be wanting to work and do something different. You might want to be pivoting. You might want to be doing something different. It doesn't have to be like all of those generations before us. It doesn't have to be like what you've seen others do. So really, it's possible when you have a plan and you know what you want to create.

13:21So instead of trying to fix everything, we talked about three gaps. You might have one that's a big gap. Go back to it. Listen to it. I gave some action steps with each of those. But overall, I would love for you to look at your current spending and ask, is this expense go through each one supporting my future or would it be a part of my future that simple filter is going to create so much awareness about your spending and there are some expenses that you have to have now that won't go into the future but they are they are exactly supporting that. So what expense is supporting your future and or is a part of your future?

14:09Look at your expenses, build up your awareness, see how those come together. So retirement doesn't fill out of reach because it is. It fills out of reach because you have not made any connection. You've not started connecting those dots. You're not recognizing that what you're doing now actually benefits and reflects on the future. And being able to do now better helps us be more successful in retirement. Now, this discussion about all of these things and these steps that we can do will continue in my Retirement Ready Hub for Gen Xers Facebook community. I hope you'll join me over there. Link is down in the show notes or just Google retirement ready hub.

14:57And remember, I've got the three day accelerate your retirement three steps to get you started happening June 2nd to June 4th. We're going to create that number. We talked about one of these gaps in here, but it'll also help you start closing some of these gaps just naturally. So I hope you'll join me there and I will see you guys next week.

15:24Thank you for spending this time with me. If you're not already following the show, be sure to hit subscribe so you don't miss what's coming next. And I'd love to stay connected with you between episodes. So come join me inside my Facebook community, Retirement Ready Hub for GenXers. It's where we're having real conversations about money, sharing wins, working through challenges, and building a clear path toward retirement. And remember, retirement isn't just a dream it's a plan and you get to make it possible

From the publisher

What is your biggest challenge/problem with money?

[Ep 187]

If you’ve ever wondered why retirement still feels so far away and know you should be thinking about it, this episode is for you.

Today I’m talking about the real reason so many people don’t feel ready for retirement and why waiting until “later” to figure it out may be the very thing keeping you stuck.

By the end of this episode, you’ll understand the three hidden gaps that make retirement feel overwhelming and out of reach, so you can start creating clarity, confidence, and a realistic path toward the future you actually want.


In this episode you’ll learn:

✅ Why retirement still feels far away for so many people in their 40s and 50s

✅ The biggest mistake people make when planning for retirement

✅ How to start connecting your current spending and financial decisions to your future retirement goals

✅ A simple way to start creating clarity and confidence around retirement planning


Episode Highlights

00:00 Why Retirement Feels Far

00:32 Stuck in the Messy Middle

01:52 Name the Feeling Block

03:16 Gap One Retirement Vision

05:49 Gap Two Know Your Number

08:14 Gap Three Build a System

12:32 One Gap One Next Step


Join the Accelerate Your Retirement Challenge HERE. Challenge starts June 2, 2026!


Are you ready to stop hoping it all works out and start creating a clear plan for your retirement?

Message me on Instagram for details, or book your Roadmap to Retirement Call today!

Looking for more connection?! Join the Retirement Ready Hub for GenXers Facebook group and join others on the same journey.

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