Let me guess. You’ve done a lot right.
You saved. You stayed invested. You didn’t panic when things got ugly. And now you’re somewhere in your 60s thinking, “I should be fine… right?”
That’s usually the moment when people get blindsided.
Not because they were reckless. But because a few quiet decisions along the way end up costing them more than any market downturn ever could.
Over the years, we’ve seen it happen more times than we can count.
The dangers of not being invested properly….
The first quiet decision shows up in conversations that sound like confidence… but aren’t. Someone tells me they’re “pretty conservative now,” and when we actually look under the hood, they’re still carrying way more risk than they realize. Not reckless risk. Just the kind that doesn’t feel like a problem until the timing is wrong. A couple heading into retirement in early 2022 felt fine… until they needed income from accounts that had just dropped. That’s not a market issue. That’s a sequencing issue. Big difference.
Then there’s the opposite mistake. Pulling back too far.
Over the years we’ve seen people who had moved almost everything to cash after retiring. They said they were done “playing the game.” I get it. But now inflation is quietly eating away at purchasing power, and they may be more anxious than they were before. Cash, or cash-equivalent investments, that may not be subject to market risk can feel good in the moment… until it creates a different kind of risk you didn’t see coming.
Social Security decisions? This is where I see a lot of permanent mistakes.
Not bad decisions. Just… uninformed ones. Filing early because a friend did. Or because “we’ll just invest it.” Or delaying without really thinking through life expectancy, taxes, or income needs. Once that switch is flipped, there’s not much room for do-overs. And for couples especially, one decision can ripple through the rest of their lives in ways they didn’t expect.
Taxes tend to sneak up on people too.
I’ve had people sit across from me feeling great about their savings… until we start mapping out withdrawals. Then they realize how much of that money isn’t entirely theirs yet. Required minimum distributions, IRMAA brackets, capital gains, all stacked on top of each other. It’s not that taxes are new. It’s that the way they show up in retirement is different. And if you don’t plan for how they interact with your investments ahead of time, you end up reacting instead of deciding.
Healthcare is another one that gets underestimated.
Not the big, scary events. Those are the things that people think about. It’s the slow drip. Premiums that rise faster than expected. Long-term care conversations that get pushed off because “we’ll deal with it later.” Later has a way of showing up at the worst possible time. And by then, options tend to shrink.
Spending is an interesting one. Most people think they’ll slow down in retirement.
Some do. A lot don’t. The first five to ten years can actually be the most expensive stretch. Travel, helping kids, fixing up the house, finally doing the things that were put off for decades. I’ve watched people go from careful savers to wondering, quietly, if they’re burning through more than they should. Not because they’re irresponsible. Because no one helped them connect spending to a real plan.
And then there’s the belief that diversification alone is a plan.
I hear it all the time. “We’re spread out. We’ve got a little bit of everything.” But when you press a little deeper, there’s no clear strategy for how income gets generated, which accounts get tapped first, or how decisions change if markets shift. Diversification is useful. But it’s not direction. And without direction, people end up making emotional decisions at exactly the wrong time.
The last one might be the most subtle.
Thinking you can figure it out as you go.
That works when you’re accumulating. You have time. Mistakes can be recovered from. But retirement is different. You don’t get those same second chances. I’ve seen very capable, intelligent people make decisions in their 60s that they would have approached completely differently in their 40s… simply because the margin for error changed.
Here’s the part most people don’t say out loud.
None of these mistakes feel like mistakes when you’re making them.
They feel reasonable. Logical. Even safe.
That’s what makes them dangerous.
What's Next?
If any of this sounds familiar, or even just makes you pause for a second, it might be worth taking a closer look at how your plan actually holds up under real-world conditions. Not a sales pitch. Just a conversation to pressure-test things and see if anything needs adjusting before small decisions turn into permanent ones. There’s no cost and absolutely no obligation. Schedule a phone or video call HERE.
Not quite ready to meet? I've created some guides you might find interesting. You can learn more and download them at the links below:
To your retirement,
Ben Harvey, RICP®
