I’m a Financial Planner: 6 Retirement Moves You’ll Regret If You Plan To Retire in 2026
Written by
Josephine Nesbit
Edited by
Jenna Klaverweiden
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Planning to retire in 2026? With retirement right around the corner, not all retirement moves will set you up for the financially stable, stress-free lifestyle you’re hoping for. Some decisions can shrink your savings or limit your flexibility once you’re out of the workforce.
According to finance experts, here are retirement moves you’ll regret if you plan to retire in 2026.
1. Not Switching to a Profit Maximization Strategy
If you’re a business owner and looking to retire in 2026, Paul Cheetham, CEO and founder of Vanla Group, a boutique mergers and acquisitions firm specializing in small to midsize business transactions, suggested speaking with a tax advisor and switching your strategy from tax minimization to a profit maximization strategy.
“This is a foreign concept to a lot of tax professionals who believe they’re helping you out by saving you money on taxes,” Cheetham wrote in an email. “However, when you go to sell, the buyer will use a bank to finance the transaction and their credit department will rely heavily on the tax returns of the business for debt servicing calculations.”
And by paying slightly more taxes now, Cheetham explained that you would be significantly increasing the valuation of your company in 2026.
2. Selling Assets To ‘Play It Safe’
“We often see long-term investors selling assets to ‘play it safe,’ and that passive attrition of a retirement runway can be a silent killer,” Erik Croak, CFP, accredited wealth management advisor and president of Croak Capital, an Ohio-based fiduciary financial firm, wrote in an email.
For example, someone with $500,000 in a 60/40 portfolio assumes short-term risk reduction means cash or certificates of deposit, Croak explained, so they move those assets out of the market. “The issue is once those assets are out, they are no longer growing,” he said.
Moving too early to “protect” also allows inflation to slowly erode its purchasing power with no return growth. “In five years, they will look back on that decision with regret as they struggle to generate income that has not kept up,” he added.
3. Underestimating Healthcare Costs and Timing
Underestimating your healthcare costs and timing could also derail your retirement plans for 2026.
“COBRA does not last forever, and Medicare eligibility starts at age 65. So retiring at 62 means three years until you can lock in that government health insurance option,” Croak explained.
Until you qualify for Medicare, you’ll need private coverage. “I suspect we should plan for $1,000-$1,500 per month, per person for premiums alone,” he explained.
There are also out-of-pocket costs to consider. “When you do the math, it can run through $50K before Medicare coverage even starts,” Croak estimated. “Guess what, that doesn’t appear in your early retirement calculators.”
4. Not Paying Attention to Tax Timing
Tax timing can fall apart faster than most people plan. According to Croak, retirees who take the “wait and see” approach on required minimum distributions (RMDs) often miss the short time frame where there is a window to use Roth conversions and income spreading to drive lifetime tax savings.
“By the way, there is this blind spot with capital gains harvesting as well,” he added. “I find that many just push that decision down the road with the lazy assumption that their tax rate will be lower in retirement when the market is ‘helping’ them … only to end up with a higher effective tax rate when RMDs, Social Security and investment drawdowns push them into a higher bracket.”
5. Relying On Generic Rules of Thumb
Relying on a generic rule of thumb can also hold you back in retirement.
“I suspect those rules are more harmful than helpful when real money is on the line,” Croak said. “Anybody who is relying on ‘4 percent’ withdrawal math or cookie-cutter glide paths is likely underestimating just how different their household dynamics, tax profile or market exposure could be from the rest of the crowd.”
6. Retiring Too Soon
Even the best laid plans will fall apart if you quit before finishing long-term income planning.
“Retiring with a 401(k) balance but no withdrawal plan, no tax diversification strategy and no pre-determined glidepath is like jumping out of an airplane before your parachute has been unpacked yet,” Croak said. “It could all go well, sure, but the person with $1.5 million across pretax, Roth and brokerage can easily retire efficiently or lose $15,000 per year to bad sequencing.”
According to Croak, it’s not the size of the nest egg that matters, but the withdrawal strategy. “And it needs to be written down (and signed) before your last day on the job,” he explained.
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