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The Top 5 Money Regrets People Have Before They Die — And How To Avoid Them

Casandra Andrews  |  March 16, 2023

Want to live a life free of financial regret? A hospice physician shares the secrets to success and a fulfilling life. 

We all want to live lives that are as stress-free and regret-free as we possibly can. Feelings of regret can negatively impact our emotional and mental health, yet many Americans — 32% — experience financial regrets every year, according to a Forbes Advisor poll

But why do we feel regret, exactly? Sometimes we struggle with it because we don’t have the courage to take that giant leap we’ve been debating, like starting a business. Other times, it’s because we simply failed to consider all our options. 

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Hospice physician Jordan Grumet spent years of his life caring for the terminally ill, and in his new book “Taking Stock: A Hospice Doctor’s Advice on Financial Independence, Building Wealth, and Living a Regret-Free Life” he offers a first-hand account of what some terminal patients regretted most. Specifically, he analyzes those things they wish they’d accomplished for themselves and their families. 

So, what would we do if we could get really brave, set our fears aside, and figure out how to live a life with more purpose and fewer regrets? (Spoiler alert: No one wished they worked more weekends.) Here’s a look at the top five ways to find your purpose and live a life with no regrets. 

The Regret: You Never Pursued The Things You Wanted Most 

The Solution?  A ‘Life Review’ That Exposes Your Unfulfilled Passions 

Before you commit to spending less, saving more or making any other money moves, it’s important to spend time going over your personal accomplishments and the regrets you may have now. In the hospice setting, Grumet says, a structured series of questions is used to help patients look at their life, discuss what was important, and talk about their mistakes and successes. 

While this may seem intimidating, anyone can do this life review. “Imagine that you’re on your dying bed,” he says. “And you were just told you have a terminal illness. What do you always wish you had the energy, courage or time to do but you never pursued?” 

Admittedly, this is a thought-provoking question. “It’s not something you answer today or tomorrow; this is really something you sit with,” he explains. The idea is that by doing this kind of thought exercise, you allow yourself to think about your dreams and unfulfilled passions.

The Regret: You Feel Unfulfilled In Your Career 

The Solution? A Mindset Shift That Allows You To Find Your Sense of Purpose 

Many people, the physician says, have deep inner secrets that are important to them,  that they’ve never had the courage to talk about. If you don’t already feel a sense of purpose in your work or personal life, Grumet suggests doing some soul-searching until you gain a grasp on what yours could be. Then, you can work towards building a financial framework that supports that. 

“To me, that’s actually the real meaning of financial independence,” he says. “It’s not a number. It’s this idea that I can figure out what makes me feel good and purposeful in life and pursue that. And then use money to support that pursuit.” 

For some people, he notes, that could mean making lots of money. For others, it’s actually building their sense of purpose into their jobs, so that they don’t need as big of a number to start living the life they want to live. 

This is where shifting your mindset can come into play. For example, if someone who cleans patient rooms in a hospital was feeling unfulfilled in their career, they could shift their mindset to begin viewing their job as related to helping the sick and caring for those in need. In this way, they might find more purpose in their day-to-day life than someone who views themselves as simply a janitor. 

The Regret: You Never Took Risks To Try Something New 

The Solution? Do What Scares You, Then Repeat

This is where you may have to throw some spaghetti on the wall, so to speak. 

“Start saying ‘yes’ to things you normally say ‘no’ to,” Grumet says. “Get yourself out there, volunteer to join groups, meet new people, put yourself in situations that might feel uncomfortable, and see what sticks.”

Remember, it doesn’t have to be a perfect fit. “The point is a lot of us are wandering this world either working ourselves to death, or decompressing from work,” he explains. “And we’re not spending any of our real valuable time doing those things that are important to us.”

Grumet hopes more people will step outside of their busy lives and seek out opportunities that can help them find more purpose: “Even if it’s not your life journey, you can start filling some of that limited time you have with some of these more purposeful activities. [You’ll be] in a better place than when you started.”

The Regret: Money Is Your Main Motivating Factor 

The Solution? Make Money A Secondary Goal

Money can’t be your sole motivating factor when seeking a life with fewer regrets. Say you have a goal of saving $2 million for retirement. Once you reach that number, Grumet explains, you may find a sense of emptiness, because you got to your goal and you didn’t know where to go next, or you double your goal and chase an even higher net worth.

There’s also the issue of loss aversion. Sometimes, when people reach a money goal, instead of being delighted, they become terrified they could lose it all. “It leaves us a little empty when we make our goal pursuing wealth,” Grumet says. “Because while it sounds really good at the beginning, it usually doesn’t lead to real happiness, because it’s almost what I call a mirage — it looks very important and shiny.” 

The wealth itself, he notes, is not nearly as important as what it allows us to do.

The Regret: Never Talking About Your Estate Plan With Your Family 

The Solution? Prepare An Estate Plan, Then Have A Family Meeting 

Talking about death can be difficult. In Grumet’s line of work, he sees what happens when someone doesn’t have a plan in place detailing a person’s final wishes. An estate plan should include medical legal documents, plus legal and financial documents, he explains. 

“We’ve got to be unafraid to look at them now,” he says of making estate plans. These crucial conversations are needed in order to “provide dignity to our families – that they’re given the appropriate time to mourn for us, as opposed to scrambling to figure out our estate and our money, which happens to a lot of people.”

To get started, check out Hermoney’s complete estate planning checklist


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