Feeling Too Guilty to Spend in Retirement? You Really Need to Get Over That

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You've spent years making careful, disciplined financial decisions. You've built a retirement plan, stuck to it and reached a point where you're no longer wondering if you have enough. But you're struggling with how to enjoy it.

That's more common than you might think. I meet a lot of people who are financially free but emotionally stuck. The plan says they're more than ready, but they can't bring themselves to spend.

The reasons people don't spend — even when they can

In my experience, the numbers aren't what hold people back. Some people live far below their means even when they have more than they'll ever need.

Others feel guilty about enjoying what they've earned, or worry about whether they've saved "enough" for their kids.

Much of this stems from early experiences with money. Some people were raised in families where every dollar had to stretch, and that mindset never really left them.

Others had parents or grandparents who lived through economic hardship, and those values were passed down to them.

Parents also link big spending decisions to how their children are doing. As the saying goes, we are only as happy as our saddest child, which makes it easy to postpone joy when a child is struggling.

I've worked with clients who tell me, "I just like seeing the balance grow." They find comfort in the control. For some, the bar keeps moving: $5 million to $10 million, then $10 million to $20 million. It turns into a scoreboard instead of a tool. When is enough enough? If the goalpost keeps moving, it never is.

If we're not careful, the life you spent years preparing for can pass you by.

What are you saving it for?

There's a saying I often share: If you don't fly first class, your kids will.

You may be saving for their future, but if you're not enjoying the life you've built, they will — either through an inheritance or by watching you underspend year after year. That last part matters.

You're not only saving for your kids; you're also teaching them how to live. If you never give yourself permission to enjoy money thoughtfully, you may be signaling that they shouldn't either.

Many parents feel a strong sense of commitment to leaving a lasting legacy.

Yet, in countless conversations, adult children say, "We're not expecting anything. We just want you to enjoy life."

A short family conversation, even a 15‑minute call, can reset assumptions. Hearing "we're okay" directly from your adult children often relieves the guilt that keeps people from enjoying what they've built.

Other turning points for some can be encouragement from a spouse or seeing a peer take a leap and find joy. If none of these is enough today, that's ok. Readiness is a process.

Permission can change everything

Often, the most important thing I offer as an adviser is permission: a clear, data‑backed "you can do this."

Permission to travel. To upgrade the car. To say yes to the experience instead of defaulting to "maybe someday."

When clients see that their plan supports what they want and won't jeopardize their future, something shifts. They stop asking, "Should I?" and start asking, "Why not now?"

They almost never regret it. More often, they say, "I wish I'd done this sooner."

Living well is part of the plan

A good financial plan protects your future and honors your present.

You worked hard for your security. If the plan says you're on solid footing, spending with intention is responsible. It's what the planning was for.

Consider writing a short note from your future self thanking you for the decision you're weighing, describing the memory you made and who you shared it with. It's a simple prompt that can help move you from hesitation to action.

The goal isn't to leave behind the largest account balance. It's to live a life that feels full and aligned with what matters most.

And if you don't fly first class, your kids probably will.

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.