Why Retirement Feels so Uncomfortable

This one comes straight from the heart, shaped by both my own experiences and years of conversations with clients, friends, and family. No matter what season of life you’re in, I think this will resonate with you.

Retirement.

That one word alone stirs up so many emotions depending on where you are in life.

For some, it feels like it’s ages away, like something you don’t need to think about yet or as if it’s this far off future problem or concern. 

For others, you might be standing right on the doorstep of it checking your numbers, second guessing your life’s financial decisions from the past and the ones to come in the future, wondering if you can really afford to step away from the paycheck you’ve relied on for decades. 

And then some of you reading this might already be in it. Living retirement right now, still adjusting to this strange new stage of life.  

Wherever you are on this spectrum, you’re definitely not alone. After years of working with clients (past and present), watching my own parents retire, talking with friends’ parents, neighbors, etc. I can tell you this:

 Retirement is one of the weirdest financial phenomena out there.

Think about it. 

You spend 30+ years, oftentimes much more, working your tail off. Saving consistently through every season. Contributing to your retirement accounts. 

Watching that balance slowly, steadily grow. You’ve been told your whole life: “Work hard, save, invest, and one day, you’ll retire.” 

So you do it. You put in the hours, you climb the ladder, you raise the kids, care for aging parents, you juggle all the things, and you keep stashing money away, often sacrificing in the short term for that long term goal. 

And then one day…you hit the finish line. The moment you’ve supposedly been waiting for. 

But here’s the thing that really throws people for a loop…Now you’re supposed to stop earning money and start spending it.

Wait…what?

After decades of watching my accounts grow and reminding myself, “don’t touch it, just keep saving,” now I’m expected to flip a switch and start withdrawing? It feels so counterintuitive. Something feels so…wrong…about it for so many. 

And here’s the surprising part:

I’ve spoken with people who have $500,000, $5 million, or more. Across the board, their fears sound exactly the same:

• “Am I going to be okay?”

• “Will this money last?”

• “Can I afford the lifestyle I want?”

• “Will there be enough left for my family?”
  

Money doesn’t magically erase fear. Because retirement isn’t just about the math, it’s about the mindset. It’s about identity, purpose, safety and flexibility.

The Emotional Side of Retirement Planning

For decades, you’ve been building. Saving. Investing. Delaying gratification.

And then suddenly, the rules change. Instead of accumulating, you’re expected to start drawing down.

That shift can feel overwhelming, even paralyzing. 

For a lot of people, the transition from steady income to living off their life’s savings feels like a major shift, and truly, it typically requires a whole new mindset around money.

No wonder people hesitate to spend it. 

From the outside, when you’re younger, it almost seems silly, right?  

You look at your parents, or maybe a neighbor, or someone you know who’s retired and think:  

“This is what you’ve worked for! Go enjoy it. Go travel. Go garden. Spend time with your grandkids. Buy the boat. Take the trip. You’ve earned it.”  

But when you’re the one living it, the reality feels different.  

I’ve seen retirees hide behind their money as an excuse to not retire saying things like “I just don’t know if I have enough yet”…even when they have more than enough. 

I’ve seen people work years longer than they needed to, not because of financial necessity, but because of fear – fear that holds so many layers outside of finances. 

And I’ve also seen the opposite: people who stepped confidently into retirement, knowing their plan was solid, and then spent years second guessing every withdrawal, feeling guilty every time they transferred money out of their accounts. 

So, here’s the thing, money is emotional. It’s rarely ever just about the numbers. And retirement magnifies those emotions like nothing else I’ve ever seen. 

So Where Does That Leave Us?

For starters, retirement isn’t something you wait to figure out once you’re already there.   

The earlier you start preparing, not just financially, but mentally, the easier the transition becomes.  

It’s not only about having the right numbers in place, it’s about…

• Knowing what life will look like without a steady stream of income

• How you’ll use your time

• How you’ll feel about drawing from the savings you’ve spent decades building

That’s why my work isn’t just about answering “do I have enough?” It’s also about helping you navigate the emotions, financial systems, routines, and identity shifts that come with this stage of life. 

Because when your financial plan and your peace of mind line up, retirement stops feeling overwhelming and starts feeling like freedom…as it should. 

So let’s talk about what you can do right now, the common struggles people face, and why so many end up feeling the way they do in retirement.

Whether you’re 30, 40, 50, or 65, there’s one thing that changes everything: 

Having a Plan

When you get clear on what you actually want your money to accomplish, not just “someday,” but right now, you begin to understand the natural give and take of money. 

It’s not just saving every last dollar and hope it’s enough one day. It’s to plan, prepare, and use your money for impact.

How to Start Shifting Into Intentional Planning

Here are a few steps that make all the difference:

Get in tune with your goals. Write down what the life you’re building for actually looks like? Is it travel? More time with family? Starting a business? Supporting causes you care about? 

Know your financial needs and numbers. Not the vague “I’ll need a lot” idea floating in your head, but the actual numbers that support your lifestyle today and tomorrow. And you might wonder how to do that, but there are frameworks to use that will help guide you through this. 

 (This one matters a lot to me) Practice using your money with intention. If you want to be generous in retirement, start giving now. If travel matters, make room for it today. Habits you build now are the ones you’ll carry into retirement. Using your money with intention is a muscle, and like any muscle, it only gets stronger the more you practice.

Because here’s where people get surprised…money habits don’t magically change once you hit retirement. They follow you.   

Which means the best way to prepare for the future you want is to start living those values and priorities out today, with intention.   

We’re Not Guaranteed Tomorrow

I’ve seen firsthand how fragile life can be. My dad passed away right after retirement, and my brother’s life was cut short way too soon at age 29. Those losses completely shifted how I look at money. 

It doesn’t mean I go wild and ignore savings. But it also doesn’t mean I’m saving every last dollar to cross my fingers and hope I’ll see the benefit of it one day, nor does it mean I’m randomly tossing money into accounts, hoping it’s “enough” one day and not having any insight into whether I’m overdoing it without realizing. 

It’s about being intentional, preparing, planning, and using money in a way that creates impact both now and later. 

Because at the end of the day, the point of saving and investing isn’t just to watch numbers on a screen…IT’S TO LIVE.

The Takeaway: Financial Security in Every Season

Yes, retirement is weird. It’s emotional. It’s a huge shift. But it’s not the finish line, it’s just a new chapter.

The sooner you start planning and living intentionally with your money, the more freedom you create in every season of life. 

Retirement might come earlier than expected, or later by choice, not out of fear or necessity. That’s real freedom. 

You don’t have to wait for some far off “someday” to prepare. Start now by shifting your relationship with money: away from fear and scarcity, and toward intention, confidence, and impact. 

Retirement isn’t the end of the story, it’s just a new chapter. When your numbers align with your peace of mind, it stops feeling scary and starts feeling like freedom, as it should. 

Even better, retirement won’t be the only thing you’ve worked your whole life for, you’ll already be living a life you enjoy. And that’s the kind of financial freedom I want for you.

The truth is, you don’t have to navigate these decisions on your own or torture yourself with “what-ifs.” This is exactly what I help my clients with every day: turning financial questions into a clear, intentional plan that supports the life they actually want.

If you’re ready to stop second guessing and start planning with confidence, I’d love to walk you through what that can look like for you. You can book a free clarity call here and we’ll take the first step together.