Six Financial Actions to Take the Year Before You Retire, From a Financial Planner
Having your income, health care and tax plans in place before you exit the day job can make it more likely that you'll have a happy retirement.
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.
You are now subscribed
Your newsletter sign-up was successful
Want to add more newsletters?
Delivered daily
Kiplinger Today
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more delivered daily. Smart money moves start here.
Sent five days a week
Kiplinger A Step Ahead
Get practical help to make better financial decisions in your everyday life, from spending to savings on top deals.
Delivered daily
Kiplinger Closing Bell
Get today's biggest financial and investing headlines delivered to your inbox every day the U.S. stock market is open.
Sent twice a week
Kiplinger Adviser Intel
Financial pros across the country share best practices and fresh tactics to preserve and grow your wealth.
Delivered weekly
Kiplinger Tax Tips
Trim your federal and state tax bills with practical tax-planning and tax-cutting strategies.
Sent twice a week
Kiplinger Retirement Tips
Your twice-a-week guide to planning and enjoying a financially secure and richly rewarding retirement
Sent bimonthly.
Kiplinger Adviser Angle
Insights for advisers, wealth managers and other financial professionals.
Sent twice a week
Kiplinger Investing Weekly
Your twice-a-week roundup of promising stocks, funds, companies and industries you should consider, ones you should avoid, and why.
Sent weekly for six weeks
Kiplinger Invest for Retirement
Your step-by-step six-part series on how to invest for retirement, from devising a successful strategy to exactly which investments to choose.
Meet Steve. He is a partner with a big law firm in Washington, D.C. He is facing a mandatory retirement in just under a year, at age 65.
Unlike so many of his partners, he doesn’t plan to lobby to stay on as a partner or counsel. He is ready for what’s next.
Steve was divorced over a decade ago, and his two kids are grown and financially independent (for now).
From just $107.88 $24.99 for Kiplinger Personal Finance
Become a smarter, better informed investor. Subscribe from just $107.88 $24.99, plus get up to 4 Special Issues
Sign up for Kiplinger’s Free Newsletters
Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.
Profit and prosper with the best of expert advice - straight to your e-mail.
In this article, I detail what I think are six critical, and often overlooked, financial moves Steve should make before he retires.
Kiplinger's Adviser Intel, formerly known as Building Wealth, is a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.
1. Come up with a health care plan
Steve’s retirement lines up with his Medicare eligibility, thank goodness. One of the firms he previously worked for provides health care for life to its retired partners, and while that would be even better than Medicare, Steve wonders what his peers who call it quits before 65 will do.
He finds comfort in the fact that he will be on a government health plan, but he has no idea how much it will cost.
No matter which survey you look at, health care is always one of the top three expenses in retirement. Yet very few people do any planning around what it will cost.
Of course, it is impossible to know when it comes to long-term care, but you should be able to get a ballpark estimate of the monthly and annual costs of Medicare.
Because of Steve’s sizable income, his Medicare Part B and D costs will be quite high. However, he is eligible to file Form SSA-44 to reduce his premium due to retirement.
He will also want to work with a Medicare consultant to get advice on which Medigap plan makes the most sense for his needs.
2. Simplify your financial life
Steve, like most people we help, has a long list of financial accounts that tell a life story. A few old 401(k)s tell the story of his life as a young associate and counsel before finally making the jump to partner.
Two bank accounts that he never touches came about because he wanted to be able to easily transfer funds to his kids while they were away at school.
Others were opened in an attempt to obtain higher interest in an environment where decent rates were almost impossible to find.
He owns a whole mess of insurance policies, some of which he bought; others came from previous employers.
His financial life has become somewhat like my streaming subscriptions: hard to track, expensive and confusing.
While many people will delay this step until after retirement, when they have “more time,” I believe you should tackle this before then. This organization and simplification will paint a clear picture of your starting point, which really dictates how much you can spend in retirement. You can use this free tool to aggregate and track your accounts.
At this point, outside of one-off situations, you may be better off consolidating retirement accounts with a low-cost custodian.
We believe that a simple financial life beats an optimal one. This may sound crazy, but I’d rather have one consolidated bank account yielding 2.5% than have five where the average rate is 3%.
Obviously, when it comes to investments, we are seeking what is optimal, as small percentage changes can yield large results.
3. Figure out how much you spend
Steve feels fortunate that he hasn’t needed to create a budget since he paid for his kids’ college educations. So, it’s tough for him to say what he spends every month or every year. He just knows that it is less than what he makes.
There are several ratios to help you guess what you will spend in retirement. I think a good starting point for Steve is just to start with current expenses to figure out if he can maintain his lifestyle in retirement.
The easiest way to do this is to add up total debits across all bank accounts he uses and divide by 24. This should capture pretty much everything except for payroll deductions and will paint a pretty accurate picture of monthly expenses.
For our clients, we will further break out travel, health care, housing and anything else that will change significantly in retirement.
I’ve seen too many advisers get so granular with this that it keeps the client from taking any action at all. Start high level by just figuring out total expenditures.
4. Check your asset allocation
Steve has been handsomely rewarded for his ability to shut his eyes, save his money and do his job. Over time, his 90% allocation to stocks has really worked out.
However, the markets are scary sometimes, and he imagines that they would be even scarier if he were reliant on his investments.
As you approach your retirement, it is common to see investment swings positive and negative in multiples of your income.
Therefore, it is key to make sure your asset allocation is aligned with your goals. I generally advise keeping two years of one-time expenses in cash equivalents. That should keep you from losing sleep in your early years of retirement.
Beyond that, you should have an asset allocation based on your risk tolerance and return needs. The longer the time horizon for the money, the more aggressively it should be invested, generally speaking.
5. Maximize deferrals
Steve has seen his income consistently rise throughout the last decade. He is fairly certain that his last year of employment will also be his highest-earning year.
He plans to stick with the savings plan he has elected in previous years: some to 401(k), some to deferred compensation and some to defined benefit plans.
Looking for expert tips to grow and preserve your wealth? Sign up for Adviser Intel (formerly known as Building Wealth), our free, twice-weekly newsletter.
We project out tax rates for all of our clients. I believe it would be almost impossible to do the work well without having some sense of what taxes will be in the future.
One thing we see among almost all retirees who go cold turkey out of the workforce is a steep drop in the effective tax rate in the year after retirement. You usually go from a peak to a valley.
In this situation, it is generally best to maximize your tax deferrals, i.e., kick the tax can down the road. Typically, this is best to do through employer retirement and health plans or charitably, through a donor-advised fund.
6. Come up with an income plan
Steve knows that he needs a full financial plan, but he is most concerned at this point about figuring out where his income will come from once his paychecks stop. His situation is less than straightforward due to deferred comp, a pension and Social Security.
Should he elect for Social Security because he is retiring? Probably not. Steve is right that he needs a full financial plan to help ensure he is maximizing income, minimizing taxes and planning his estate.
An income plan is one component of this. It should dictate two things: how much money he can afford to spend every year and where that money will come from.
Generally, you want to take advantage of the low-income years that come after retirement by doing partial Roth conversions and living off of cash and taxable investment accounts.
You’ll get the highest amount of monthly income from Social Security by delaying until you’re 70, but this doesn’t make sense for everyone.
As Steve approaches this exciting new chapter, he should remember that planning for retirement doesn't have to be overwhelming. By taking these six critical steps, he can confidently navigate his transition and truly enjoy what comes next.
Related Content
- I'm a Financial Planner: These Three Things Are Missing From Almost Every Financial 'Plan' I See
- Three Pros (and Four Cons) of Hiring Multiple Financial Advisers: The View From a Financial Adviser
- What Is the Magic Number to Retire Comfortably?
- Timing Your Retirement: A Financial Professional's Guide on When to Say When
- Three Steps to Simplify Paying Your Taxes in Retirement
Profit and prosper with the best of Kiplinger's advice on investing, taxes, retirement, personal finance and much more. Delivered daily. Enter your email in the box and click Sign Me Up.

After graduating from the University of Delaware and Georgetown University, I pursued a career in financial planning. At age 26, I earned my CERTIFIED FINANCIAL PLANNER™ certification. I also hold the IRS Enrolled Agent license, which allows for a unique approach to planning that can be beneficial to retirees and those selling their businesses, who are eager to minimize lifetime taxes and maximize income.
-
Nasdaq Slides 1.4% on Big Tech Questions: Stock Market TodayPalantir Technologies proves at least one publicly traded company can spend a lot of money on AI and make a lot of money on AI.
-
Should You Do Your Own Taxes This Year or Hire a Pro?Taxes Doing your own taxes isn’t easy, and hiring a tax pro isn’t cheap. Here’s a guide to help you figure out whether to tackle the job on your own or hire a professional.
-
Trump $10B IRS Lawsuit Hits an Already Chaotic 2026 Tax SeasonTax Law A new Trump lawsuit and warnings from a tax-industry watchdog point to an IRS under strain, just as millions of taxpayers begin filing their 2025 returns.
-
Quiz: Are You Ready for the 2026 401(k) Catch-Up Shakeup?Quiz If you are 50 or older and a high earner, these new catch-up rules fundamentally change how your "extra" retirement savings are taxed and reported.
-
65 or Older? Cut Your Tax Bill Before the Clock Runs OutThanks to the OBBBA, you may be able to trim your tax bill by as much as $14,000. But you'll need to act soon, as not all of the provisions are permanent.
-
We Inherited $250K: I Want a Second Home, but My Wife Wants to Save for Our Kids' College.He wants a vacation home, but she wants a 529 plan for the kids. Who's right? The experts weigh in.
-
I'm a Financial Adviser: This Is the $300,000 Social Security Decision Many People Get WrongDeciding when to claim Social Security is a complex, high-stakes decision that shouldn't be based on fear or simple break-even math.
-
4 Ways Washington Could Put Your Retirement at Risk (and How to Prepare)Legislative changes, such as shifting tax brackets or altering retirement account rules, could affect your nest egg, so it'd be prudent to prepare. Here's how.
-
2026's Tax Trifecta: The Rural OZ Bonus and Your Month-by-Month Execution CalendarReal estate investors can triple their tax step-up with rural opportunity zones this year. This month-by-month action plan will ensure you meet the deadlines.
-
5 Best Splurge Cruises for Retirees in 2026Embrace smaller, luxury ships for exceptional service, dining and amenities. You'll be glad you left the teeming hordes behind.
-
Is Your Retirement Plan Built for 2026 — or Stuck in 2006?It's time to move away from the 4% rule and the 60/40 portfolio to an adaptable, tax-diversified strategy focused on reliable income and longevity.