Let’s be honest—if you’re within five years of retirement, it probably feels equal parts exciting and terrifying. You’ve spent decades saving, working, and planning. But now, the finish line is in sight—and what you do right now can make a massive difference in how smooth that transition actually feels.
This isn’t about wild financial overhauls or scary spreadsheets. It’s about small, smart steps that will help you go from “saving mode” to “spending mode” without panic. Whether you plan to retire early or work until 67, these five tips will help you enter retirement with more confidence—and fewer regrets.
Let’s dive in.
1. Figure Out What You Really Spend
Yeah, we know—budgeting sounds painful. But here’s the deal: if you don’t know your current expenses, how will you know if your retirement savings can support your lifestyle?
Instead of tracking every coffee or gas receipt, try this: look at your total bank withdrawals over the last 24 months, divide by 24, and boom—you’ve got your average monthly spending. It’s not perfect, but it’s a solid ballpark.
This one number can make or break your retirement plan. And most retirees want one thing above all else: to maintain their current lifestyle, not downgrade it.
2. Get Real About Health Care Costs
Health care in retirement is a wild card. If you’re retiring before 65, you’ll need a plan to cover costs until Medicare kicks in. And even with Medicare, premiums (especially Parts B and D) can be surprisingly high if you’ve saved a lot and have a high taxable income.
Translation? That big nest egg might actually cost you more in health premiums.
Talk to a planner or run a retirement projection. It doesn’t have to be perfect—but knowing what to expect helps avoid surprises, especially those that mess with your budget in year one.
3. Tackle Home Repairs Now, Not Later
Have a leaky roof, outdated kitchen, or a list of “someday” projects? Here’s a tip: do them before you retire.
Why? Because once you’re on a fixed income, big-ticket renovations can throw your entire plan off balance. Plus, if the market dips right after you retire, pulling money out of your portfolio to fix a water heater is the worst-case scenario.
Use your current paycheck to handle these now—and enjoy retirement without hammering in the background.
Related: 5 Smart Ways to Use Your Life Insurance While You’re Still Alive
4. Take That Big Trip While You’re Still Working
Waiting to travel until you’re fully retired? You might want to rethink that. Retirees in their 70s often say their biggest regret is not traveling more when they could.
Big vacations hit different when they’re backed by a paycheck. Whether it’s Europe, a cross-country road trip, or just a week at a dream resort, go now while your energy (and income) are still strong.
Besides, unused vacation days? They’re worthless once you leave your job. Use them.
5. Create Your “Model Week
Retirement is about more than money—it’s about how you’ll spend your days. Many people plan financially for retirement but forget to plan their time. Then they retire, lose structure, and feel lost.
Start thinking about what a “great week” in retirement looks like. Time with family? Volunteering? Golf? A part-time side gig?
Having a routine helps protect your mental and emotional health in retirement—and makes the transition feel less like a cliff and more like a bridge.
Bottom Line
If retirement is just a few years away, this is your moment to fine-tune your plan—not overhaul it. A few focused decisions now can help you avoid regret, reduce stress, and retire with confidence.
Start with one step. Tweak your spending, plan your health care, patch the roof, take the trip, or schedule your week. You’ve earned this. Now make sure you enjoy it.
This article was written by Loretta James. AI tools were used lightly for grammar and formatting, but the ideas, words, and edits are all mine.
