Sometimes, I look back on my early days of retirement and chuckle at how I thought I had it all under control. 

I remember parading around with a big smile, telling everyone how excited I was to finally have “all the time in the world.” Deep down, though, I felt a bit adrift. Life had suddenly opened up, but it wasn’t the breezy, carefree picture I’d imagined.

I’ve spent a good chunk of my sixties observing fellow retirees—both in my local community and among old friends—and I’ve noticed something curious: it can be surprisingly easy for us to hide that vague sense of being lost. 

We mask it in subtle ways, often because we’re too proud or stubborn to admit to anyone, including ourselves, that we feel aimless. After all, who wants to look ungrateful when we’ve been told for decades that retirement is the “golden phase”?

In my own journey of learning and adapting (and believe me, I’m still learning every day), I’ve identified five subtle behaviors that some retirees slip into when they’re feeling lost but don’t want to admit it. 

Let’s talk about each of them—one retiree to another.

1. Over-filling the schedule with “busy work”

I’m not talking about meaningful, purposeful activities here, but rather doing a million and one things just to avoid that nagging sense of emptiness. 

I’ve met retirees who suddenly become the busiest people on earth: they sign up for every workshop, volunteer in six different organizations, and spend hours reorganizing their garage for the tenth time that year.

A close buddy of mine (I’ll call him Gary) took this approach soon after leaving his job. He’d always been a stellar manager at the office—used to a packed calendar. In retirement, he was terrified by the absence of deadlines. His solution? He created self-imposed deadlines for everything under the sun. He’d say, “I’ve got to repaint the fence by Tuesday or else!” But when Tuesday came, nobody was really waiting for that freshly painted fence except him.

There’s nothing wrong with having projects. In fact, I’ve often mentioned in a previous post that staying active is crucial for our mental and physical well-being. But when being busy becomes a cover-up for deeper anxieties—like feeling unimportant or unsure of what’s next—we can end up exhausting ourselves instead of finding healthy fulfillment.

If you suspect you’re guilty of this, I’d encourage you to pause and ask: am I actually enjoying these tasks, or am I frantically trying to fill every spare moment so I don’t have to face a deeper question: “What do I really want out of this stage of life?”

2. Avoiding new challenges due to fear of “looking silly”

A friend of mine once invited me to join a digital photography class with her. Now, I’m someone who prefers a good old paperback to any fancy new gadget, so you can imagine my hesitation. I nearly said no, mostly because I didn’t want to be the slowpoke in the class who had to keep asking for help. Who wants to feel incompetent at this age, right?

That’s when I caught myself. I realized part of me was afraid of venturing into unknown territory—not because I didn’t have time, but because I didn’t want to look inexperienced. And I’ve seen this same fear in others, too. We tell ourselves we “prefer the old way” or that we “don’t need the new stuff.” Sometimes that’s true, but sometimes it’s a subtle cover for insecurity.

Winston Churchill famously said, “To improve is to change; to be perfect is to change often.” While I wouldn’t go so far as to say any of us should strive for perfection, I do think there’s something to be said about staying open to change. 

Retirement is the perfect time to learn new things—be it a language, a hobby, or even something as everyday as using a smartphone app to video chat with grandkids. By deliberately stepping into situations where we might fumble at first, we keep our minds agile and our spirits alive.

3. Deflecting when others express concern

Have you ever noticed how some retirees quickly change the subject when anyone asks how they’re really doing? 

Maybe a neighbor says, “How are you holding up?” and the response is a hasty, “Oh, I’m fine. By the way, how’s your daughter doing in college?” before they slip away.

I did this myself in the first year or so of my retirement. My kids would ask, “Dad, are you sure you’re not bored or lonely?” And I’d brush it off with, “Nah, I’m doing just great. Actually, how’s your new job going?”

Why do we do this? Often it’s because admitting to feeling lost, lonely, or directionless can make us feel weak or ungrateful. We might reason, “I should be enjoying this time. Plenty of people would love to retire at my age.” But that thought process doesn’t address the emotional reality—and deflecting doesn’t solve anything, either.

As a retired friend once told me, “It’s okay to admit you’re on shaky ground. The real strength comes in acknowledging it.” And she was right. Once I opened up, even just a little, I found that people were more than willing to empathize or offer suggestions. Being honest can lead to supportive conversations and connections, which might just be the springboard to a fresh sense of purpose.

4. Romanticizing the past instead of planning for the future

This is a big one. I’ve noticed how easy it is for retirees—including me, at times—to slip into constant “Remember when…” conversations. 

I’ve got a dear neighbor who loves to talk about his old corporate job—how he thrived under the pressure, led a top-performing team, you name it. 

If you ask him about his plans for the upcoming months, though, he’s usually at a loss. He shrugs and says, “Well, we’ll see.” It’s almost like the future is an empty page he’s afraid to write on, so he flips back to the chapters he already knows by heart.

There’s nothing wrong with being proud of your past. But if we dwell there too often—using it as an escape rather than a platform for growth—we might be missing out on the potential beauty of what lies ahead. 

If we want to keep forging new connections and finding joy, we have to risk stepping out of the shadows of our former life, uncertain though it may be.

5. Brushing off the importance of emotional health

Before I retired, I confess I was one of those folks who didn’t give much thought to counseling or support groups. 

“I’m a practical guy,” I used to say. “If I have a problem, I handle it.” But the truth is, emotional well-being can get complicated after you retire, particularly if your job was a big part of your identity.

I’ve seen peers get snippy or withdrawn, only to wave it off with a casual, “I’m just a grumpy old man (or woman).” Underneath that grumpiness, there might be a cocktail of emotions: feeling irrelevant, frustrated by bodily aches, or just unsettled by the vast open space that retirement brings. The subtle behavior is acting like everything’s fine—or that all the minor irritations are just part of “growing old.” 

However, if we never admit we’re struggling—if we brush off every concern and label ourselves “tough”—we risk missing out on the support that could help us rediscover our purpose.

Final thoughts

Being “lost” doesn’t always look dramatic; often, it comes masked in these quiet little habits that end up keeping us in a rut.

If you see a bit of yourself in any of these subtle behaviors, don’t fret. The first step to finding clarity is acknowledging that maybe you do feel a bit lost.

My guess is that once you open that door, you’ll find a path—however winding—that leads to a richer, more purposeful phase of life. 

Here’s to redesigning the next chapter of your retirement story.