Many people say they can’t wait to retire. Yet when the time comes, many can’t take the plunge.
“Most people think when I say, ‘Hey, you’re in a position to retire,’ that people just do,” said Ari Taublieb, host of the Early Retirement podcast. “That doesn’t happen that often.” People often continue working another year for their team, to finish a project, or to simply enjoy the confidence that comes from attending work knowing “I don’t actually have to be here.”
Financial readiness rarely flips a switch. Knowing you can retire creates psychological freedom even while you keep working. The goal isn’t to rush retirement, but to eliminate the “I don’t know” phase. Taublieb compares it to getting an MRI for a soccer injury: even bad news brings relief because “now I know the truth. I have a plan.”
The overall economic environment stops some retirees in their tracks. University of Michigan consumer sentiment sits at around 49.8 in April, the lowest on record. That uncertainty can be hard to shake even if you’re sitting on a sizable nest egg.
Taublieb’s prescription is to stress-test the plan against multiple scenarios: “What if markets went down right when I retired? Or what if tax brackets change? Or what if my health changes? Or what if I live longer?” If conservative calculations show you have more than enough money to retire, believe the numbers.
The Cost of Delaying Retirement Could Be Health
Consider the Ohio caller Taublieb featured on a recent episode. He has more than enough ($3 million) to retire but feels trapped by the business he owns. His blocker is loyalty to 12 long-tenured employees, some with 15 to 20 years at the company. He has spent a year and a half trying to find a successor, prioritizing continuity over profit so “the guys continue working.” But his stress is so severe that he’s not sleeping, which is affecting his spouse and children as well.
Taublieb had a warning. “I’ve seen that get drawn out so much that by the time something occurs, it’s now your health.” Don’t let loyalty to a business compromise the retirement you’ve already earned financially, Taublieb said. Business owners can search for a Certified Exit Planning Advisor (CEPA) to structure a handoff that protects employees without trapping the owner indefinitely.
Others are able to retire but still can’t bring themselves to spend the money. Taublieb described a retired couple living comfortably on $7,000 to $8,000 a month, with enough saved to sustain that lifestyle for 40 years, “definitely 20 years past” expectation. But they have not taken a vacation by themselves in 20 years.
His thought experiment: “If I forced you to spend $200,000 a year, you will have to double it. And if you don’t … it goes to your least favorite political party.” Suddenly a list emerged: Jamaica, Europe, Alaska. As Taublieb put it, “The nicest and best people sometimes put themselves last.” The book “Die With Zero” is a useful framework for thinking about intentional spending while you can still enjoy it.
The Appetizer Rule: Practice Spending
Habits built over 30 years of saving do not unwind on day one of retirement. One client couple living on $100,000 a year balked at a $50,000 family trip to Australia. Taublieb’s prescription was to start small. Take the family to dinner and require that “everyone has to get an appetizer. It’s required. It’s going to feel weird the first time, but you have to get an app and you have to get an entree and a dessert.”
Two outcomes are possible. You discover lavish spending genuinely does not move you, or you build the comfort to fund bigger experiences later. Either is useful information. Use these small experiences to gradually increase your spending comfort. As Taublieb notes, the goal is protecting “the early years of retirement” from overspending on healthcare, home remodels, and family obligations while still experiencing life. The key is not dying with regrets about money you never enjoyed.
Run the “I don’t know” out of your plan, Taublieb advises. Build three scenarios on paper: a market drop in year one, a tax-bracket shift, and a longevity assumption stretched 10 years past your gut estimate. If the plan survives all three, the hesitation is psychological. Schedule the appetizer dinner. If you own a business, start the succession conversation now, before health makes it for you.
Achieving the right retirement number is step one. The harder work is giving yourself permission to use it.
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