The sandwich generation’s timing problem

Editor’s note: This article first appeared in Money Matters, a newsletter from Britannica Money, on May 27, 2026.

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Midlife is when the bills don’t take turns.

© luckybusiness, Krakenimages.com/stock.adobe.com; Photo illustration Encyclopædia Britannica, Inc.

One of the luckiest breaks I ever got—totally underappreciated at the time—was marrying into a family of “savers” (one of the five archetypes in our Money Personality quiz). That came in handy when, as a 40-something, I found myself at a career crossroads at the same time I was dealing with the pressures of the sandwich generation—that stretch in midlife when you’re helping kids get launched while starting to support aging parents.

It’s a strange phase financially. You’re supposed to be hitting your stride—peak earning and peak saving years—but the demands don’t show up one at a time. They overlap. And the years that look like they should propel you forward can end up feeling more like you’re just holding your ground. What I didn’t fully appreciate at the time is how many of the most basic investing ideas carry over to everyday money decisions. Not perfectly, but close enough to be useful—even in the middle of the proverbial sandwich.

Retirement planners talk about sequence of returns risk. It sounds technical, but the idea is simple: If you’ve invested for retirement but the market drops right when you start withdrawing, you can do lasting damage to your portfolio, even if returns average out over time. Two people can earn the same long-term return and end up in very different places, depending on the order in which the good and bad years show up.

There’s a real-life version of that, too. I’ll call it sequence of expense risk. It’s not just how much you spend over time, but when the big expenses hit. If your kids’ peak needs line up with your parents’ increasing needs—right when your own income isn’t as flexible as it used to be—you’re taking hits from both sides at once. Spread those same expenses out over time, and they’re manageable. Stack them together, and the years that should move you forward can turn into years where you’re just trying not to fall behind.

If you invest in bonds or other fixed-income securities, you may have heard of the barbell strategy. Barbell investors don’t put everything in one bucket; they balance stability on one end with growth on the other, so they’re not relying on any single outcome to carry the whole plan.

You can think about a lifetime of saving the same way.

On one end, you push hard early. You save aggressively, let compounding do its thing, and build a lead while you have the flexibility to do it. On the other end—after the kids are launched and the big expenses start to fade—you lean back into saving again, perhaps using catch-up contributions to help you hit your retirement savings target.

The middle looks different. It’s not about maximizing. It’s about absorbing—holding the line while the pressures from both sides are at their peak.

None of this is theoretical. Wherever you are on life’s arc—heading into the squeeze, in the middle of it, or coming out the other side—the timing still matters. You can’t control when life’s big expenses will show up, but you can decide how prepared you are when they do, and what kind of pressure you pass along to the next generation.

The middle can feel like a panini press—pressure and heat from both sides, all at once. But that stretch doesn’t define the outcome. It’s just one part of a longer plan. Assume the timing won’t be ideal—and plan anyway.