The Hidden Retirement Problem No One Talks About
Written by Chris DeVito
The Hidden Retirement Problem No One Talks About: Giving Yourself Permission to Spend
One of the most common retirement challenges I see has nothing to do with market returns, tax brackets, or investment performance.
It's psychological.
Many retirees don't feel comfortable spending their own money—even when they can clearly afford to.
The Retirement Dilemma Most People Don't See Coming
For years, sometimes decades, pre-retirees are conditioned to do one thing, save.
Save for retirement. Save for college. Save for emergencies.
By the time retirement finally arrives, that habit is deeply ingrained. And for many people, it doesn't automatically shut off just because work stops.
I've seen retirees who delay buying a new car, skip vacations they've always dreamed about, hesitate to upgrade their lifestyle, and constantly worry about "running out." Not because they will run out, but because decades of saving have rewired how they relate to money.
When Guilt Becomes the Real Risk
Most retirees I work with have adult children. Many want to help them. Some feel a strong sense of responsibility to leave a meaningful inheritance.
That's admirable.
But here's where things get tricky, I've sat across from retirees who want to enjoy their retirement but feel guilty doing so. They worry that every dollar they spend is a dollar their kids won't receive someday.
Ironically, this can lead to a retirement that looks good on paper but feels constrained in real life.
Your Goals Evolve (And That's Normal)
Another overlooked reality: your mindset changes as you age.
Early in retirement, many people think: "I don't need to leave a huge inheritance. I just want to enjoy life."
Later, especially when grandkids enter the picture, that perspective often shifts: "I'd really like to help my family more if I can."
Neither mindset is wrong. But the uncertainty between them creates hesitation, and hesitation leads to under-spending.
The Power of a "Permission Slip"
One of the most effective solutions isn't about spreadsheets or projections, it's about structure.
Some families intentionally create a separate legacy bucket: assets they don't plan to touch during retirement. Knowing that something is already earmarked for heirs can dramatically reduce guilt around spending the rest.
For some, that might be dedicated legacy assets, strategically positioned permanent life insurance, or a clearly defined inheritance plan that doesn't depend on "whatever's left over."
The result? Retirees often feel immediate relief. They finally give themselves permission to enjoy the money they spent a lifetime earning.
Retirement Isn't Just About Not Running Out
Traditional retirement planning focuses almost entirely on avoiding failure, don't run out of money, don't overspend, don't make mistakes.
But great retirement planning also asks, “are you actually enjoying this phase of life?” Are you spending on what matters most to you? Are fear and guilt driving decisions more than clarity?
Because at the end of the day, retirement isn't just about preserving wealth, it's about using it intentionally and meaningfully.
The Final Verdict
If you've done the hard work, built the assets, planned carefully, and stayed disciplined, you deserve a retirement that feels abundant, not restrictive.
Sometimes the most valuable part of a financial plan isn't higher returns or better tax efficiency. It's something much simpler, peace of mind and permission to live the way you want.
If you want help thinking through how to balance enjoying retirement and supporting the people you care about, that conversation is often more important than any portfolio tweak. And it's one most people wait far too long to have.
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