7 Things People Who Are Miserable in Retirement All Have in Common – Money Wasn't the Problem

Tech wipeout stretches to third day as Google's massive AI spending spooks investors

The quick scan: US stocks took sizable hits again on Thursday in a fruitless search for a reprieve from a building tech sell-off as investors awaited Amazon earnings, assessed Alphabet's big AI spending plans, and digested jobs data that signaled fresh weakness in the labor market. All three major indices fell over 1% as the tech carnage showed no signs of stopping.

S&P 500: -1.23% to 6,798.40 – Extended losses for a third straight session as tech weakness overwhelmed the broader market, with the index falling 84 points and pulling further away from recent record highs
Dow Jones: -1.20% to 48,908.72 – Decreased 593 points, led by Microsoft (-5.01%), Salesforce (-4.75%), and Amazon (-4.56%), marking a rare day when even the defensive blue-chip index couldn't escape the tech-driven selloff
NASDAQ: -1.59% to 22,540.59 – Led the decline lower for a third consecutive day, hammered by Alphabet after the company flagged AI-related capital spending of up to $185 billion for 2026, reviving doubts over how quickly heavy AI investment will translate into earnings, while Qualcomm tumbled 8.4% on cautious outlook.

What's driving it: The market is in the midst of a trillion-dollar tech wipeout as Alphabet's announcement of up to $185 billion in AI spending raised serious questions about return on investment. Labor market data added to concerns with weekly jobless claims rising more than expected, job openings sinking to their lowest level since 2020, and January marking the worst month for layoff announcements since 2009. Silver plunged 17% erasing its two-day recovery, bitcoin continued sliding, and investors braced for Amazon's earnings after the close.

Bottom line: Thursday's relentless selloff – the third straight day of tech carnage – shows that even the Dow can't hide when the sector rotation becomes a stampede. Google's announcement that it will spend up to $185 billion on AI infrastructure crystallized investors' growing fear: what if this massive spending never translates into proportional earnings? For L-Plate retirees, this is a stark reminder that "growth at any price" eventually meets price discovery. The jobless claims data (worst January for layoffs since 2009) adds another layer of concern – if the labor market weakens while companies burn cash on AI, where exactly will the earnings growth come from? Diversification beyond mega-cap tech isn't just prudent anymore; it's essential.

The Retirement Nobody Warns You About

The scoop: Retirement was supposed to be the golden years, right? After decades of grinding away at work, counting down to that magical day when you could finally relax, travel, and enjoy life without deadlines or demanding bosses.

Yet here's what nobody talks about: Some of the most miserable people are those who seemingly "have it all" in retirement – healthy savings accounts, beautiful homes, and all the time in the world.

After interviewing over 200 people about life transitions, including many retirees, journalist Sarah Mitchell has noticed striking patterns among those who find retirement more prison than paradise. Financial security wasn't their problem. The real issues were deeper, more fundamental, and often invisible until it was too late.

Here are the seven things miserable retirees have in common.

They never developed an identity beyond their job title. "What do you do?" becomes "What did you used to do?" and suddenly, the conversation feels hollow. The most miserable retirees still introduce themselves as "former VP of Sales" or "retired teacher" because they never figured out who they were without that professional label.

Mitchell watched her own father wrestle with this exact issue when he retired after thirty years in sales management. He'd spent so long being "the sales guy" that he couldn't imagine being anything else. The business cards were gone, but he kept trying to squeeze his identity into that old professional box.

Wholeness comes from discovering yourself outside professional roles, something that takes real work when you've spent forty years defining yourself by your position.

They treat retirement like an endless weekend. Remember how amazing long weekends felt when you were working? Three whole days to do whatever you wanted. Now imagine that feeling stretched over months and years. It gets old fast.

The unhappiest retirees approach retirement like it's one big vacation. They sleep in every day, watch endless TV, and wonder why they feel so empty. Without structure or purpose, days blur together into a meaningless haze. One retiree told Mitchell he couldn't remember if it was Tuesday or Thursday anymore because every day felt exactly the same.

They waited too long to build relationships outside work. How many of your closest friends are work colleagues? If you're like most people, probably quite a few. But what happens when you retire and those daily coffee breaks and lunch conversations disappear?

The loneliest retirees are those who realized too late that their entire social network revolved around the office. Without the forced proximity of work, those relationships often fade. One woman interviewed said she went from having dozens of daily interactions to sometimes not speaking to anyone for days. She had money for fancy dinners but nobody to share them with.

Building genuine friendships takes time and effort, especially when you're not thrown together by circumstance anymore. The retirees who struggle most are those who assumed their work friendships would automatically transition into retirement friendships. Spoiler alert: They usually don't.

They believed retirement would magically fix their problems. "Once I retire, I'll finally get in shape." "When I don't have work stress, my marriage will improve." "I'll be so much happier when I don't have to deal with my boss."

Sound familiar? The most disappointed retirees are those who thought retirement was a cure-all for life's problems. But here's the thing: If you're unhappy, out of shape, or struggling in your relationships while working, retirement won't magically fix those issues. In fact, without the distraction of work, these problems often become more pronounced.

What you think retirement "should" look like literally determines your experience. If you're expecting retirement to solve all your problems, you're setting yourself up for disappointment.

They never learned to be comfortable with themselves. Work provides a convenient escape from having to sit with your own thoughts. Meetings, deadlines, and projects keep your mind occupied from 9 to 5 (or longer). But what happens when that noise stops?

The most restless retirees are those who never learned to be alone with themselves. They fill every moment with activities – golf, volunteering, traveling – not because they enjoy these things, but because silence feels unbearable. One man told Mitchell he joined three different clubs in his first month of retirement, not out of interest but out of desperation to stay busy.

Your emotions during transition are wise guides. That uncertainty and fear about retiring contains valuable information when you stop resisting it. Instead of running from these feelings, the happiest retirees learn to sit with them and understand what they're really saying.

They let others define their retirement. "You should travel!" "Golf is perfect for retirees!" "Have you thought about volunteering?"

The most frustrated retirees are those living someone else's vision of retirement. They're playing golf because that's what retirees "should" do, not because they enjoy it. They're traveling because everyone says they should "see the world," even though they'd rather stay home with a good book.

Fulfillment comes from authentic self-expression and designing a life around your actual values, not society's retirement checklist. Purpose isn't found in retirement activities – it's found in knowing yourself well enough to choose activities that genuinely matter to you.

They view retirement as an ending rather than a beginning. The word "retirement" itself suggests withdrawal, retreat, conclusion. The most depressed retirees are those who see it as the beginning of the end, a slow decline toward irrelevance.

But what if retirement isn't an ending at all? What if it's actually a beginning for reinvention and possibility? Your "retirement years" narrative is inherited programming that doesn't have to define your experience.

The happiest retirees don't even use the word retirement. They talk about their "next chapter" or "second act." They see it as an opportunity to explore parts of themselves that work never allowed time for.

After all these interviews and observations, including watching her own father navigate retirement, Mitchell learned that financial security is just the foundation. The real work of retirement is internal – figuring out who you are when you're not defined by your job, learning to create your own structure and meaning, and being brave enough to design a life that's authentically yours.

If you're approaching retirement or already there and struggling, know that it's not about finding the perfect retirement activity or having more money in the bank. It's about the deeper work of understanding yourself and what you truly want from this phase of life.

Because when you strip away the job title and the daily grind, what's left is just you. And that can be either terrifying or liberating, depending on how prepared you are to meet yourself.

Actionable Takeaways for L-Plate Retirees:

• Start developing an identity beyond your job title now: If you're still working, begin exploring who you are outside your professional role – interests, values, characteristics that have nothing to do with your career – because "former VP" won't sustain you emotionally for decades.

• Create structure even without external obligations: Treating retirement like an endless weekend leads to emptiness and meaninglessness – design routines, commitments, and rhythms that give your days shape and purpose, even when nobody's requiring it of you.

• Invest in non-work friendships before you retire: Waiting until retirement to build genuine relationships is too late – your work colleagues rarely transition into retirement friends, so cultivate connections outside the office while you still have the energy and opportunity.

• Understand that retirement won't fix your existing problems: If you're unhappy, out of shape, or struggling in relationships now, retirement will amplify rather than solve these issues – address them while you're still working, not after.

• Practice being comfortable alone with yourself: Learn to sit with your own thoughts and feelings without constant distraction – the silence of retirement will feel unbearable if you've spent your entire working life running from introspection.

• Design your retirement around your values, not others' expectations: Playing golf, traveling, or volunteering because "that's what retirees do" leads to frustration – fulfillment comes from authentic self-expression aligned with your actual interests and values, not society's checklist.

Your Turn:
When you think about who you are without your job title, do you have a clear answer, or does the question make you uncomfortable because your identity is still wrapped up in your professional role?
Are you already building genuine friendships outside work, or have you been postponing this emotional labor until "after I retire" when it will be exponentially harder?
What problems are you secretly hoping retirement will magically fix – and what would happen if you acknowledged that these issues need addressing now, not later?

👉 Hit reply and share your thoughts – your answers could inspire fellow readers in future issues.

If this newsletter helped you see that financial preparation is only half the battle – and that the real work of retirement is internal, psychological, and deeply personal –consider supporting L-Plate Retiree on Ko-fi. Your support helps me tackle the retirement topics everyone avoids.