May 8, 2026
Reader
The Emotional Side of Spending in Retirement — And Why We All Struggle With It Differently
I have a confession to make.
Even as retirement draws closer, even with a financial advisor who assures me we're in good shape, there is a voice in the back of my mind that whispers the same thing it always has: but what if you run out?
I call her my inner bag lady. And apparently, I'm not alone.
It started early. Growing up, money was tight. If I wanted something — and I mean something as simple as a pair of those coveted designer jeans every other girl seemed to have — I earned it myself. Babysitting. And yes, at fourteen, with a work permit, I was cleaning motel rooms. I learned young that security doesn't just appear. You work for it. You save for it. You protect it.
That lesson served me well for decades. My husband and I saved diligently, maxed out retirement contributions, made careful choices. And yet here I am, on the doorstep of the years we saved for, and I still find it hard to spend.
Our financial advisor — and we deliberately chose to work with a husband and wife team, specifically because of her — has heard my worries more times than she'd probably like to count. She is patient, reassuring, and brilliant. And still, that little voice persists.
Here's what she can't fully argue away — I was in banking during the 2000 technology crash. I watched 2008 unfold from the inside. Those aren't abstract historical events to me. They are visceral memories. And they live in my bones in a way that a strong market today simply cannot erase.
But here's the thing. Not everyone carries that same fear.
I have a friend who is happily remodeling her new house — and loving every minute of it. Her philosophy? We might as well spend it now. Another friend has made peace with a different truth: she doesn't feel the need to leave a large inheritance. Her kids are grown and capable, and she worked hard for this money. She intends to enjoy it.
And honestly? I admire them both.
Because what I've come to realize is that retirement spending isn't one conversation. It's two — and most of us are living somewhere on the spectrum between I'm afraid to touch it and life is short, let's remodel the house.
Neither extreme serves us particularly well. But understanding where you fall — and why — might be the most important financial work you do in this season of life.
If you're holding on too tight — like me:
The scarcity mindset that drove us to save was real and necessary. It was the right response to real circumstances. But retirement asks something different of us now. It asks us to trust — the plan we built, the advisor we chose, the life we worked toward. The goal was never just the number. It was the life. We saved so we could say yes — to the trip, the experience, the round of golf, the dinner that feels a little indulgent. Somewhere along the way, saving became the habit and spending became the fear. It's okay to gently reverse that.
If you're spending freely — and loving it:
There's real wisdom in your approach. You understand something important — that money unspent is just a number on a screen, and that experiences, joy, and comfort are worth something. But even the most liberated spender benefits from a plan. Spending intentionally — knowing what you're spending toward and why — means the money goes where it actually matters most to you, and where it brings you the greatest joy.
What we all need — regardless of which camp we're in:
A trusted advisor you genuinely connect with. A plan that reflects not just your finances, but your values. And the self-awareness to understand the story you've been telling yourself about money — because that story, more than any market condition, is often what's really driving your decisions.
I'm still working on loosening my grip. My inner bag lady still shows up, usually around market volatility, like now. But I'm learning to hear her out — and then gently remind her that we've come a long way from those motel rooms.
We saved for this. It's okay — it's more than okay — to live it.
What about you — do you hold on too tight, or have you given yourself full permission to spend? I'd love to hear where you fall on the spectrum.
Quote for the Day:
"A penny saved is a penny earned — but a life unlived is a tragedy.” — Benjamin Franklin
Recent Blog Posts:
Why Spending Money in Retirement Is Harder Than You Think (Full Post)
Hidden Medicare Costs in Retirement: What to Expect at 65
Treasury Inflation Protected Securities (TIPS) for Retirement
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Books I'm Reading
A Fun Book: The Last Call at the Savoy - Brisa Carlton
The Meaning of Your Life - Arthur C. Brooks
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Warmly,
Wendy
Founder OverSixtyInsights
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