I'm a CFP: 7 Things I'd Do Differently if I Were Retiring in 2027
If you’re planning to retire in 2027, the months leading up to your final paycheck could be some of the most important for getting your finances in order.
Rather than focusing on whether you’ve accumulated a large enough nest egg, Christopher Stroup, a certified financial planner (CFP) and owner of Silicon Beach Financial, said he would use this time to build a detailed plan for how his money will actually support him once he stops working.
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Build 1 to 2 Years of Portfolio Withdrawals Into a Cash Cushion
Stroup would focus on building a retirement plan he could live with, which would include mapping out “spending, income sources, taxes, healthcare costs and major one-time expenses,” he said. Then he’d stress-test the plan against different market and longevity scenarios.
He would also keep enough cash and short-term investments to cover roughly one to two years of the money he expects to withdraw from his portfolio, after accounting for reliable income such as Social Security or a pension.
This bucket, he said, “gives me flexibility to avoid selling volatile investments during a downturn while keeping the rest of the portfolio invested for longer-term growth.”
Match Your Investments to When You’ll Need the Money
Stroup would not necessarily get more conservative in his portfolio, but he would organize investments around his withdrawal timeline. That would create a pool for near-term expenses while retaining enough equities to support growth over a retirement that could potentially last 30 years.
“I’d also reduce unnecessary concentration risk, particularly if a large portion of my wealth came from employer stock.”
Stroup prefers to be able to look at retirement “year by year” than as one large time period.
Make Social Security Part of Your Income Strategy
Stroup wouldn’t automatically claim Social Security at retirement time. He would evaluate claiming age in the context of expected longevity, household cash-flow needs, taxes and spousal benefits.
There can be a significant financial difference between claiming early and waiting. For people born in 1960 or later, full retirement age is 67. Benefits can begin at 62 but can be reduced by as much as 30%, while delaying beyond full retirement age increases benefits until age 70.
Use Early Retirement as a Tax-Planning Window
The transition from a final working year into retirement creates opportunities to manage taxable income, as well. Stroup would examine Roth conversions, capital gains, charitable giving and retirement-account withdrawals together. “The goal would be to manage my lifetime tax liability rather than simply minimize taxes in one year.”
Give Healthcare Its Own Retirement Budget
Stroup would create a separate budget for Medicare premiums, out-of-pocket costs, supplemental insurance and potential long-term care expenses, while also considering how taxable retirement income could affect Medicare premiums.
Currently, the 2026 standard Medicare Part B premium is $202.90 per month, but higher-income beneficiaries can pay as much as $689.90 per month because of the income-related monthly adjustment amount (IRMAA). The Center for Medicare and Medicaid Services (CMS) has not yet announced final 2027 premiums, so those figures should be updated when available, but AARP reported they are expected to begin at $209.50.
Stroup said he’d also discuss long-term care “as a planning risk rather than assuming insurance will solve it" and that healthcare deserves its own line in the retirement plan.
Reduce Expenses That Lock You Into High Monthly Payments
Stroup wouldn’t necessarily enter retirement determined to be completely debt-free. Instead, he would target high-interest debt and other large, fixed obligations that could make the retirement budget harder to manage.
That distinction matters because using a large amount of retirement savings to eliminate a low-rate mortgage or other loan can have its own opportunity cost.
Plan Your Retirement Trajectory
Stroup said he’d spend more time planning what he’s retiring to, not just what he’s retiring from.
“I’d test the lifestyle financially before leaving work, including travel, family support, hobbies, and major purchases,” he said.
He feels that a strong retirement plan should answer two questions: "Can I afford this?" and "What do I want my money to make possible?"
This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal or tax advice.
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