“It’s a traumatic event for many that after 40 years of working, that this Friday I’m not getting a paycheck,” Ray Ferrara, executive chair at ProVise Management Group Inc. in Clearwater, Fla. “We have to help them realize that their paycheck now comes in the form of Social Security and their savings and investments.”

“It’s a difficult thing for many people. We have to give people permission to spend their money,” Ferrara said. “Clients don’t outlive their money unless it’s a health event or a family crisis. It’s really about lifestyles changing and we all like our lifestyle.”

As a financial planner, Ferrara often has to tell clients: “You have permission. It’s OK to spend $30,000 to go on a 30-day cruise around the world. Nobody knows how many tomorrows we have,” said Ferrara, who owns a boat named “Someday is Today.” “It’s OK to spend that little extra to have a little extra fun.”

Ferrara urges retirees to check in with their financial advisers regularly to make sure they are on track, especially after 2022’s turbulent markets.

The spending doesn’t have to be big or outlandish. It can be about bringing small doses of joy into your life.

Nancy Schlossberg, a retirement speaker and author, once went to a dinner party on her birthday. She didn’t tell anyone about the occasion, but she brought a small bottle of blowing bubbles for each guest and invited them to blow bubbles with her around the home’s outdoor turtle pond.

“It was ridiculous. It was fabulous,” said Schlossberg, author of the book “Too Young to be Old: Love, Learn, Work and Play as You Age.”  

“You can do things that aren’t expensive. I, myself, need to spend more time playing. I’ve always been working. I’ve always been serious,” said Schlossberg. “Bring pleasure into every day, not just for a big birthday or a big celebration.”

Schlossberg, 93, said she has very few regrets in her life, but one is not taking her family to the Galápagos Islands when she was a bit younger. “It’s foolish and I’m sorry I put it off. But the time I got around to it, it was just a little much of a trip at 93. Even eight years ago I could have done it more easily.”

“There’s no point to waiting. It doesn’t need to be expensive. Think about what would give you pleasure and build it into your year. Don’t delay,” Schlossberg said. “What are you waiting for? An illness? Seize the moment. Carpe diem.”

Robert Laura, founder of RetirementProject.org and Retirement Coaches Association, said one of the biggest flaws of traditional retirement planning is the notion that you have 20, 30, or even 40 years in retirement to do whatever you want, whenever you want. 

“Reality is, the only guarantee that comes with retirement is that at some point you will die. Now, on the surface, that sounds like a very negative way to look at and approach life in retirement. However, what if new, existing, or soon-to-be retirees use it to examine what they would regret if their retirement only lasted one year, five years or 10?” Laura said.

You have to develop a plan and take specific steps to identify a goal or target and start moving toward it, Laura said.

“There is a major difference between good intentions and being intentional. You may have the best intentions of taking a big family vacation, doing something special with the grandkids, or helping out on a mission trip or a natural disaster, but thinking about it won’t be enough,” Laura said.

Joe Casey, managing partner of Retirement Wisdom in Princeton, N.J., and author of “Win the Retirement Game: How to Outsmart the 9 Forces Trying to Steal Your Joy,” recommends making a list of things that give you delight, and the things and circumstances that take joy away.

“It’s important to get to really know what gives you joy and get to know what steals it from you,” said Casey. “Thirty years of going into an office every day can dull your sense of joy.” 

“Fun and joy often don’t involve money. It’s like that old saying ‘The best things in life are free.’ There’s truth to that,” Casey said. “That’s just an excuse that it takes time and money to be happy.”

Casey said the more gratitude you feel, the more likely you are to feel joy. “They used to say ‘Count your blessings’ and they knew what they were talking about,” Casey said.