Ten years ago, I asked the question: Can I retire at all? Not how much do I need, but can I actually do it? Back then, we talked about kids, unexpected expenses, and the difference between surviving and saving.
Today, the question hasn’t changed. But the stakes? Way higher.
The Numbers Are Getting Worse
It’s not just about budgeting better anymore. It’s about the fact that even the most disciplined person is now playing a losing game.
- Inflation is eating the dollar alive. Prices haven’t just gone up, they’ve leapt forward, and wages haven’t kept up. Your money is worth less, and your future costs are worth more.
- Home ownership used to be part of the plan. Now, for many, it’s a fantasy. Prices are sky-high, and even those who own a home can’t count on selling it when they need to.
- Healthcare costs keep climbing. Retiring means aging, and aging means medical bills. A lot of them. Especially in the U.S.
- Social Security is under threat. Yes, you’re paying into it. No, you’re not guaranteed to get it back. Current projections say the trust fund could be depleted within a decade. That doesn’t mean it’s gone. It could mean reduced benefits, delayed retirement age, or higher taxes to keep it afloat.
So now we’re planning for retirement in a world where:
- Everything costs more,
- Nothing is guaranteed,
- And we’re told to “just save more” with money we don’t have.
You’re Not Lazy. The System Is Broken
Let’s be honest. For many people, retirement isn’t a matter of responsibility or discipline. They’re not spending recklessly or refusing to budget. They’re simply underpaid, overburdened, and living in a time where the math no longer works.
Want to save $6,000 a year like the old example? That’s $500 a month, not easy to do when rent alone is $2,000. And that assumes you’re healthy, don’t have student loans, and don’t face any big emergencies (like… life).
The Gig Illusion
Some turn to gig work to bridge the gap. But gig work rarely comes with retirement plans, benefits, or stability. It’s a hamster wheel. A trap disguised as flexibility. And it burns people out before they can even think long-term.
Entrepreneurship? Great in theory. Risky in practice. Most small businesses don’t survive long enough to fund a retirement. And even the ones that do often require the owner to work past 65 anyway.
Social Security: The Elephant in the Room
Let’s talk about it.
People have been paying into Social Security their whole lives. And yet, there’s a very real chance they’ll only get a fraction of what they were promised or get it later than expected.
It’s not their fault. The system is underfunded and aging. There are more retirees than ever, and fewer workers supporting the system. And while Congress could act to shore it up, solutions are politically messy. In the meantime, people are told to “prepare for less” as if they had anything left to prepare with.
So… Can You Retire?
That depends. Not on how smart you are. Not on how disciplined you are. But on where you live, how much you earn, and whether the economy (and government) decides to play fair.
Here’s the truth: More people today are doing everything right and still falling behind. That’s not personal failure — that’s systemic failure.
And that’s why the question remains the same, louder than ever:
Can I retire at all — or am I working until I die?
Worried?
If that question scares you, it should. Not because you failed, but because we’ve built a society where security is optional and survival is expensive.
You’re not crazy for feeling anxious. You’re paying attention.
