As advisors with more than 40 years in the industry, we’ve learned that financial plans are just as much about overcoming mental obstacles as they are about tax strategies or investment portfolios.
One of the biggest challenges is finding the line between saving/investing and spending as your wealth grows.
We see this surprisingly often among high‑net‑worth clients who have more than enough financial capacity to enjoy life but still feel a sense of guilt, fear, or uncertainty when it comes to spending, especially in retirement.
This isn’t unusual or irrational. It’s simply human nature.
We see it in retired clients with eight‑figure portfolios who stress over buying a $3,000 refrigerator. In 55‑year‑olds whose plans indicate they're well positioned for retirement who delay a long‑desired kitchen update. In people who have more than enough to support their own retirement and their childrens', yet can’t quite click the booking link on that big AirBNB for the family trip.
These spending hang-ups come in all shapes and sizes, but they have something in common: it’s rarely because something is actually unaffordable on paper. It’s because the purchase may not feel necessary.
Despite having the financial freedom to enjoy life, many struggle to grant themselves permission to do so. Let’s talk about why.
Where This Anxiety Comes From
A few themes show up again and again:
1. A Lifetime of Saving Is Hard to “Turn Off.”
Many high-net-worth individuals didn’t grow up wealthy. Even when their balance sheet says one thing, their identity says another. Going from “I save whenever I can” to “I can splurge a bit and still be on track” takes emotional rewiring.
2. The Fear of "What If?"
Even clients who have already succeeded worry about unknown future risks. Market downturns. Health events. Longevity. They wonder:
“What if spending today limits my options later?”
3. Behavioral Finance Biases at Play
This topic intersects with well‑documented behavioral tendencies:
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Loss aversion: Spending feels like losing money, even when it’s planned for.
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Mental accounting: Clients categorize purchases by “need” vs. “want,” even when both are easily affordable.
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Decision fatigue: Even relatively small purchases can feel momentous when you’re used to optimizing every financial move.
And then there’s the big one…
4. The Emotional Cost of Stressing Over Purchases
It’s like wanting a cookie and instead eating a banana… then almonds… then chocolate chips… trying to avoid the cookie.
You could have just had the cookie.
The emotional toll of agonizing over responsible, affordable purchases is real, and often far greater than the cost itself.
How to Recognize If This is Happening to You
Ask yourself:
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Do I hesitate on purchases even when I know I can afford them?
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Do I feel guilty spending on “wants,” even if my plan accounts for discretionary enjoyment?
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Do I constantly run numbers (formally or mentally) before making even low‑impact decisions?
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Do I skip experiences that I know would bring me joy?
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Do I think more about preserving wealth than enjoying it?
If any of these resonate, you’re far from alone.
How to Break the Cycle—Without Breaking Your Plan
Here are some strategies we coach clients through:
1. Use Your Financial Plan as a Permission Slip
A well‑built plan doesn’t just tell you what you need to do. It shows you what you can comfortably do. Seeing the long‑term projections, probabilities of success, and impact of discretionary spending in black‑and‑white can be incredibly freeing.
Tying back to the “what if” fear listed above, understand that when you discuss your plan and the probability of success with us, you’re looking at the result of 1,000 market outcomes applied to your plan. If you factor in the purchase and there is little or no change to the probability of success, that says a lot.
2. Reframe "Wants" as Part of Your Purpose
If your wealth doesn’t enhance your life, support your joy, or strengthen your relationships… what’s it for? This doesn’t mean you need to run to the nearest luxury department store and go on a spree, but achieving success requires some introspection on evaluating what you’re willing to splurge on now that you can.
3. Prioritize Experiences
Behavioral finance research tends to point to the idea that experiences deliver more lasting happiness than material goods because they include:
- Anticipation
- The experience itself
- The memories afterward
And unlike a new kitchen or a handbag, the value of an experience doesn’t go down over time.
4. Consider the Cost of Your Time and Mental Energy
If you spend weeks stressing about a purchase that has virtually no impact on your plan, that stress is the cost. Don’t fall into the trap of undervaluing your time and peace of mind.
5. Talk Through Decisions with Your Advisor
We’ve helped many families build the confidence to spend joyfully and intentionally. A conversation can make it easier to recognize when the fear is emotional, not financial. We happily do some live planning with clients evaluating purchases big and small so you can start on the path from being skeptical to genuinely fulfilled.
Want to Dive Deeper?
We've covered these themes in a couple of our Plancorp Perspective podcast episodes, which pair well with this discussion:
Can Money Buy You Happiness?
Explore the shift from saving to spending, balancing now vs. later, and stories from clients navigating that transition.
The Financial & Emotional Transition Into Retirement
A deeper look at what happens when the paycheck stops — and how identity, money, and emotions intersect.
Disclaimer: Examples discussed are hypothetical and for illustrative purposes only and do not reflect the experience of any specific client
