The Squeeze Didn’t Go Away: A Note to the Sandwich Generation, Five Summers Later

What a summer it is shaping up to be in the Armstrong household. This August, my wife and I will travel to Italy to celebrate the wedding of our oldest, Liam, and his beautiful bride, Gabi. It seems like only yesterday that I sat under clear blue skies in College Park and watched him graduate from the University of Maryland, full of optimism and bound for the working world. That was five summers ago. Now here we are, preparing to raise a glass to a brand new family under the Italian sun. And the part that stops me in my tracks, believe it or not, is not the passage of time. It is the addition. After raising our three, I suddenly find myself with another daughter. What a gift.

I tell you this because a wedding on the calendar makes a person take stock. And it has me thinking about the families I sit with every week, for whom time is moving in three directions at once: for their parents, for their children, and for themselves. They are helping an aging parent move out of the family home. They are writing the last of the tuition checks, or the first of the wedding checks. And in the back of their minds sits a question they rarely say out loud: what about us? What about our own retirement?

Five summers ago, I wrote about this squeeze on the sandwich generation, and I can tell you it did not go away. For many, the caregiving has deepened. Some families have said goodbye to a beloved parent in these years and learned that the caring does not simply end. It changes shape. It becomes settling affairs, honoring wishes, and looking after the parent who remains. Meanwhile, the kids who were in high school are now launching careers or standing at the altar. And here is the part that gets lost in all that full, beautiful chaos: you are also five years closer to your own retirement.

The families I meet in this stretch of life are some of the most generous people I know. They show up for their parents and their children, again and again, without hesitation. The one person they put at the back of the line is their future self. I cannot begin to tell you how many times I have heard a version of this from prospects: “Rob, I know our own planning is important, but between my mother’s care and the kids, I simply do not have the bandwidth. It keeps ending up on the back burner.”

If that sounds like you, please hear me on this. There are loans and scholarships for college. There are programs and resources for elder care. There are no loans for retirement. The airlines have it right. You must secure YOUR oxygen mask first and then assist others. It is the only way you remain able to keep helping the people you love.

So, what does that look like? It is not a product or a hunch. It is a number. Last month I wrote about what a true cash flow analysis reveals. If you retired tomorrow, what would you spend in year one? What would health insurance cost in the years before Medicare? When should Social Security begin? What might your portfolio look like in year ten, after a decade of real life? If you missed that piece, I would encourage you to read it. If You Retired Tomorrow, What Would Happen Next?

For sandwich generation families, that same analysis puts honest numbers on the competing demands. How much can we help Dad without derailing ourselves? Can we cover the wedding and still retire at 62? Believe it or not, most families discover they are in better shape than they feared. The rest find out while there is still ample time to adjust course. Either way, the fog lifts, and guessing gives way to knowing.

So as the toasts are raised and the dance floors fill this wedding season, won’t you take a quiet moment to consider your own path forward? If you are caring in both directions at once, this is a conversation worth having, and it is one we have walked through with many families over the past two decades. We would be honored to walk it with yours.

Authored by: Rob Armstrong

The Beatles - “Ob-La-Di, Ob-La-Da” (Remastered 2009)

Source: YouTube, provided by Universal Music Group

Songwriters: John Lennon / Paul McCartney

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