Early Retirement Reality Check: Six Months of Freedom, Fear, and Costco Runs

As the six-month mark of my early retirement approaches, I’ve started looking back at how it’s gone so far. Before I retired, I pictured waking up late, spontaneous adventures, and maybe a new hobby or two. And while some of that has happened, the reality has been a little less “vacation mode” and a little more “figure out how to make retirement enjoyable” mode.

Many people assume retirement is like flipping a switch—you leave your job on Friday and wake up Monday in permanent vacation mode. And that’s true… for about three weeks. Then it hits you: the vacation doesn’t end, and there’s no return to “normal” life. It’s both freeing and mildly terrifying.

The life that used to revolve around work—deadlines, routines, and that boss who called you on the weekend for a project—is gone. What’s left is a blank slate, which sounds great until you realize you actually have to fill it. Turns out, going from full-time employee to full-time retiree comes with its own kind of culture shock.

CRAVING ROUTINE

It’s liberating to have the freedom to do whatever I want, whenever I want; however, I realized early on that I missed having structure.

When I was working, my days were predictable: wake up, commute, work, eat, repeat. Once that vanished, things felt a little unmoored. So my wife and I created a new morning routine: dog walk, breakfast with the news, and a bit of yoga. Nothing fancy, but it gives the day some shape.

After 25 years of living by a schedule, going completely freeform is harder than it sounds. This new routine feels like a nicotine patch—something to help wean off a lifetime of structure without quitting cold turkey.

LOSING TRACK OF WHAT DAY IT IS

One of the stranger side effects of retirement is having no idea what day it is. When I was working, every day had a personality: Monday was dreadful; Wednesday was hump day; Saturday and Sunday were salvation. Now, they all blend together in one long weekend.

At first, it wasn’t a big deal. Then I started to miss important dates like birthdays, and I wondered if I was losing it.

Now, the calendar on my phone has turned into my lifeline. I even have a wall calendar and a planner—basically, I’ve become my own personal assistant. Scheduling one or two bigger outings each month helps, too. When you’ve got a concert or trip to look forward to, the rest of the days don’t blur together quite as much.

SPENDING THE MAJORITY OF TIME AT HOME

Everyone imagines retirement as constant travel and adventure. But guess what? Traveling all the time is expensive and exhausting. After a couple of days out and about, I start craving the couch again.

I never anticipated how much time we’d be spending at home. We’ve found ourselves spending most days at home—and honestly, it’s not bad. Until it is. After 2–3 days of barely leaving the house, even a Costco run feels like an exotic getaway.

Being home all the time also means spending a lot more time with my wife. A friend warned me before I retired, “I hope you get along with your wife because you’re going to be spending all your waking hours together!” She wasn’t kidding.

Fortunately, we both have our own hobbies and friends, and lately we’ve started taking solo adventures. The rule: each of us goes somewhere new alone—restaurant, park, whatever—and reports back. It keeps things fresh and gives us a break from…each other.

Don’t get me wrong; I love my wife, but even the best relationships benefit from a little breathing room. Turns out that nine-hour workday apart was doing more for marital harmony than I realized.

LEARNING TO SPEND MONEY

Of all the adjustments, this one’s been the toughest. I’ve run the numbers every which way, and they all say the same thing: we’re fine. We could even spend more and still be okay. But after decades of saving, it’s hard to flip that mental switch.

We still find ourselves hesitating over purchases, cutting back if we “overspent” in a month, and second-guessing anything that isn’t essential. On paper, that looks responsible. In reality, it sometimes means missing out on things we worked years to afford.

On the surface, this may seem responsible. After all, many unexpected things could happen in the future. But there are consequences to underspending—missed opportunities and sacrificed quality of living.

My dad’s a perfect example—still sleeping on the same mattress from the ‘90s despite back pain, because a new one’s “too expensive.” My grandma was the same way—she promised herself she'd travel after retiring, but she never did. She couldn’t bring herself to spend the money.

I’ve learned that struggling to spend isn’t uncommon among retirees. Many retirees actually die with more money—sometimes millions more—than they started with. Not because they ran out, but because they were too afraid to enjoy it.

And I get it. Even now, with the math emphatically screaming “you’re fine,” there’s still a little voice asking, “Are you sure?”

WRAPPING IT UP

Looking back, these first six months have been both an adjustment. I’ve realized that work doesn’t end in retirement—it just changes job titles. Now I’m in charge of scheduling activities, researching new Trader Joe’s snacks, and convincing myself it’s okay to spend money I literally saved for this exact purpose.

Retirement takes effort. The kind that doesn’t come with performance reviews or paychecks, but still manages to feel like a full-time gig. It’s the ongoing work of keeping life interesting, keeping your mind busy, and occasionally keeping your spouse from suggesting another “joint project.”

Six months in, I’m learning that freedom isn’t about doing nothing—it’s about doing what you want, and pretending it was the plan all along.

See you at the finish line!

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Disclaimer: I’m not a licensed financial professional. This blog shares my personal experiences and opinions around money, investing, and early retirement. It’s for informational and educational purposes only—not financial, legal, or tax advice. Always do your own research or consult with a qualified professional before making any financial decisions.