‘I’ve Met Women Who Had 5 Million and Were Afraid to Spend $5,000’: Orman’s 5 Regrets That Haunt People to the Grave

“I’ve met women who had $5 million and were afraid to spend $5,000 on something that would bring them joy.” Suze Orman, the personal finance author and podcast host, said that on the October 1, 2026 episode of Suze Orman’s Women & Money. The episode is a Classic Suze School rerun, Living a Life of No Regrets, republished that day after it was originally produced earlier.

The timing is awkward. On September 2, 2026, Fortune ran the headline “Despite being a multimillionaire, Suze Orman says eating out is one of the biggest wastes of money.” A month later, the same adviser says fear of spending ranks among the regrets people die with.

The stakes for a careful saver are real. Hoard too hard and you can finish life with a large balance and a list of trips you never took.

Why Orman’s Deathbed Lesson Survives Her Own Frugality

Her advice is sound, and the contradiction is smaller than it looks. Orman says that after years of sitting with the dying and talking with widows, “nobody has ever said to me, ‘I wish I had made 2% more on my portfolio.'” What they do say: “I wish I had taken that trip. I wish I had said I love you more. I wish I hadn’t stayed so afraid.”

The financial mechanism that settles both views is the sustainable withdrawal rate. It represents the share of a portfolio you can spend each year without running out of money. A plan built on that rate tells you exactly how much spending your savings can support.

Recurring leaks, like frequent restaurant meals, quietly eat into that annual budget every month for decades. A deliberate, one-time purchase that fits inside the budget is different. A $5,000 trip barely registers against a $5 million balance under any reasonable withdrawal plan, so refusing it protects nothing.

Orman also has no patience for status spending. “Nobody is thinking about your handbag as much as you think they are,” she says. Her target is fear, which she calls the root: “Regret comes when fear runs your life instead of truth.”

Five Regrets Orman Hears From People at the End

1. Not investing earlier. “Time is the most valuable asset you will ever have, and you will never, ever get time back.” Compounding needs years to work, and a year spent waiting is a year of growth that can never be recovered.
2. Trusting the wrong person. A Hollywood friend in her 40s pulled 100% of the portfolio Orman advised after a second adviser asked “are you crazy?” about holding only stocks. He missed that she also held cash, CDs and Treasuries elsewhere.
3. Staying silent about money. “When you are silent about money, it creates dependency.” Orman says she has met women who stayed in marriages they knew were wrong for 20 years because they feared they couldn’t survive financially.
4. Spending to show off. She says that people “recognize your inner power before they admire your clothing.” Labels drain the same budget that could fund the trip people later regret skipping.
5. Waiting for someday. “Someday has to be the most expensive word in the English language.” Delay costs both compounding years and the healthy years when experiences are best to enjoy.

One Account Can Mislead You About Your Entire Plan

The Hollywood story reveals the variable that determines whether any money advice helps you: whether you judge a decision against your full balance sheet or one piece of it.

Viewed alone, an all-stock account looks reckless. Viewed alongside her cash, CDs and Treasuries, the allocation was sound. Her move came from a partial picture, which is exactly how bad advice wins.

Spending works the same way. A $5,000 purchase feels dangerous when you look at your checking balance. Measured against total assets and a written withdrawal plan, the answer usually becomes obvious in one direction or the other.

Four Questions Orman Wants Answered This Week

Orman asks listeners to write down answers to these and then take one action that week to reverse one regret:

1. “Where am I living smaller than I should be?” Compare one purchase you keep putting off against your annual withdrawal budget.
2. “Where am I staying silent?” List every account in your household, its balance and who controls it.
3. “What financial decision am I postponing because I’m scared?” If it is investing, set up one automatic contribution today.
4. “If I only had five years left, what would I fix today?” Put that item on your calendar with a date and a dollar amount.

Cut the recurring leaks, fund the moments that matter, and judge every money decision against your whole financial picture.

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