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The secrets to a successful retirement? Planning, spending, and social connections.

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The secrets to a successful retirement? Planning, spending, and social connections.

Listen and subscribe to Decoding Retirement on Apple Podcasts, Spotify, or wherever you find your favorite podcasts.

How might you go about having a happy, successful, and wealthy retirement?

In her new book, “How to Retire,” Christine Benz, the director of personal finance and retirement at Morningstar, interviewed many of the nation’s top retirement experts and distilled their discussions into 20 lessons for doing just that.

In a recent Decoding Retirement podcast, Benz shared some of the top takeaways from those conversations. Lesson one, she said, is to visualize your retirement lifestyle and put habits in place to make it happen.

“The point is that we’re all wired a little bit differently in terms of what we want from our retirement cash flows,” Benz said. “A broader message of this book is there’s more than one way to do this. … You should give a little thought to what you specifically are looking for.”

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In one interview, Fritz Gilbert, the author of “The Keys to a Successful Retirement” and the Retirement Manifesto blog, emphasized the importance of taking thoughtful steps before retiring.

For her part, Benz said phasing into retirement, starting around age 50, is a best practice. And you don’t have to take concrete steps; you can just start thinking about which parts of your work you like and dislike.

“Starting early, I think, is such a valuable piece of advice from Fritz,” Benz said.

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Consider making decisions about your work life in the years leading up to retirement, either in “stealth mode” or through candid discussions with your employer. Then, take additional steps, such as saving contact information and personal files from your work computer.

You might also consider “dabbling” in retirement activities before fully retiring, Benz said, as this can help ensure you’re “in the driver’s seat” as you move into the next phase of retirement.

Michael Finke, a professor at the American College of Financial Services, pointed out in his interview with Benz that retirement is not all about relaxation, leisure activities, and free time. After all, you need something to relax from.

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“The best relaxation comes after you’ve actually accomplished something,” Benz said. “You need to figure out a way to have a sense that you are accomplishing something.”

His actionable advice: Find an “animating force” that provides a sense of purpose in retirement, such as volunteering, continued work in some capacity, or reengaging with family.

“The main point is that even when you step away from work, you need to look at where you will go for some of the balance and structure and purpose and identity that your work provided you with,” Benz said.

Read more: Retirement planning: A step-by-step guide

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In her interview with Laura Carstensen, the director of the Stanford Center on Longevity, Benz learned that work is good for us in that it helps us maintain social connections.

“Social connections mean a lot to our life satisfaction,” said Benz.

Given that, you should preemptively think about where you will find day-to-day interactions after leaving work. “Make sure that you are replacing work friendships with friendships outside of work because those work friendships may not stand the test of time,” Benz said.

Two elderly men playing a board game in Aveiro, Portugal. (Photo by: Nano Calvo/VWPics/Universal Images Group via Getty Images)
Two elderly men playing a board game in Aveiro, Portugal. (Nano Calvo/VWPics/Universal Images Group via Getty Images) · VW Pics via Getty Images

Understand that social networks may shrink with age, partly due to loss and partly due to self-selection toward a closer “inner circle.”

“As we age, we tend to want to spend more time with the inner circle, that very tight network of people who totally get us where, when we walk away from being with them, we’re like walking on air because we feel so completely understood,” Benz said.

Benz also noted that men, in particular, should be proactive in maintaining and building social circles outside of work.

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Carstensen’s point, Benz said, is that “it’s OK to have your network shrink a little bit as you age,” but “you don’t want that social network to get too small. You don’t want to be down to just, say, two or three people.”

In another interview, David Blanchett, the head of retirement research at PGIM DC Solutions, noted that retiree spending — even among high-income households — tends to trend down over time but then often flares up later due to uninsured long-term care costs.

This is often referred to as “the spending smile,” Benz said.

Given that dynamic, Blanchett “has always been a believer in people giving themselves a little bit of permission to spend more earlier on,” Benz added. But giving yourself permission to spend isn’t always easy.

“The problem is a real one,” Benz said, and it’s rarely addressed, since many retirees haven’t saved enough for retirement.

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Read more: Here’s what to do with your retirement savings in a market sell-off

Benz noted that she often meets people who bring up this issue. They’ve seen themselves as savers throughout their working lives, and that identity has become second nature. Now, however, with their portfolios at high levels, the idea of drawing down those savings feels uncomfortable.

And many genuinely struggle with spending — often for good reason. Part of the challenge, Benz speculated, lies in the word “spending” itself, which many associate with excess.

“There is this association of spending with profligacy,” Benz said, when that’s often not the case at all. For instance, some retirees provide meaningful support to adult children or other loved ones, particularly while they’re still young and may need it most.

How one should allocate assets when entering retirement?

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William Bernstein, co-founder of Efficient Frontier Advisors and author of “The Four Pillars of Investing,” endorsed a “safety-first” strategy in his interview with Benz. That approach focuses on securing reliable, inflation-protected cash flow to cover essential expenses.

The ideal way to achieve this is by building a laddered portfolio of Treasury Inflation-Protected Securities (TIPS), a structure that helps retirees manage inflation risk while ensuring their basic income needs are met.

For Bernstein, addressing portfolio cash flows and securing inflation protection are “jobs one and two” in a sound retirement plan.

J.L. Collins, the author of “The Simple Path to Wealth,” offered another approach. Benz described his advice about keeping retirement portfolios as simple as possible, especially considering the potential cognitive decline in older age.

Collins recommended using a simple index fund-based portfolio with a bit of cash, focusing on core stock and bond market indexes, rather than overly complicated investments.

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“[Collins] is very much on the side of trying to be as minimalist as you possibly can be when thinking about your retirement portfolio,” Benz said, “and there’s a lot to like about that idea.”

Each Tuesday, retirement expert and financial educator Robert Powell gives you the tools to plan for your future on Decoding Retirement. You can find more episodes on our video hub or watch on your preferred streaming service.

Finance

Holyoke City Council sends finance overhaul plan to committee for review

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Holyoke City Council sends finance overhaul plan to committee for review

HOLYOKE — The City Council has advanced plans to create a finance and administration department, voting to send proposed changes to a subcommittee for further review.

The move follows guidance from the state Division of Local Services aimed at strengthening the city’s internal cash controls, defining clear lines of accountability, and making sure staff have the appropriate education and skill level for their financial roles.

On Tuesday, Councilor Meg Magrath-Smith, who filed the order, said the council needed to change some wording about qualifications based on advice from the human resources department before sending it to the ordinance committee for review.

The committee will discuss and vote on the matter before it can head back to the full City Council for a vote. It meets next Tuesday. The next council meeting is scheduled for Jan. 20.

On Monday, Mayor Joshua Garcia said in his inaugural address that he plans to continue advancing his Municipal Finance Modernization Act.

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Last spring, Garcia introduced two budget plans: one showing the current $180 million cost of running the city, and another projecting savings if Holyoke adopted the finance act.

Key proposed changes include realigning departments to meet modern needs, renaming positions and reassigning duties, fixing problems found in decades of audits, and using technology to improve workflow and service.

Garcia said the plan aims to also make government more efficient and accountable by boosting oversight of the mayor and finance departments, requiring audits of all city functions, enforcing penalties for policy violations, and adding fraud protections with stronger reporting.

Other steps included changing the city treasurer from an elected to an appointed position, a measure approved in a special election last January.

Additionally, the city would adopt a financial management policies manual, create a consolidated Finance Department and hire a chief administrative and financial officer to handle forecasting, capital planning and informed decision-making.

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Garcia said that the state has suggested creating the CAFO position for almost 20 years and called on the City Council to pass the reform before the end of this fiscal year, so that it can be in place by July 1.

In a previous interview, City Council President Tessa Murphy-Romboletti said nine votes were needed to adopt the financial reform.

She also said past problems stemmed from a lack of proper systems and checks, an issue the city has dealt with since the 1970s.

The mayor would choose this officer, and the City Council will approve the appointment, she said.

In October, the City Council narrowly rejected the finance act in an 8-5 vote.

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Supporters ― Michael Sullivan, Israel Rivera, Jenny Rivera, Murphy-Romboletti, Anderson Burgos, former Councilor Kocayne Givner, Patti Devine and Magrath-Smith ― said the city needs modernization and greater transparency.

Opponents ― Howard Greaney Jr., Linda Vacon, former Councilors David Bartley, Kevin Jourdain and Carmen Ocasio — said a qualified treasurer should be appointed first.

Vacon said then the treasurer’s office was “a mess,” and that the city should “fix” one department before “mixing it with another.”

The City Council also clashed over fixes, as the state stopped sending millions in monthly aid because the city hadn’t finished basic financial paperwork for three years.

The main problem came from delays in financial reports from the treasurer’s office.

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Holyoke had a history of late filings. For six of the past eight years, the city delayed its required annual financial report, and five times in the past, the state withheld aid.

Council disputes over job descriptions, salaries and reforms also stalled progress.

In November, millions in state aid began flowing back to Holyoke after the city made some progress in closing out its books.

The state had withheld nearly $29 million for four months but even with aid restored, Holyoke still faces big financial problems, the Division of Local Services said.

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Finance

Military Troops and Retirees: Here’s the First Financial Step to Take in 2026

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Military Troops and Retirees: Here’s the First Financial Step to Take in 2026

Editor’s note: This is the fourth installment of New Year, New You, a weeklong look at your financial health headed into 2026. 

You get your W-2 in January and realize you either owe thousands in taxes or get a massive refund. Both mean your withholding was wrong all year.

Most service members set their tax withholding once during in-processing and never look at it again. Life changes. You get married, have kids, buy a house or pick up a second job. Your tax situation changes, but your withholding stays the same.

Adjusting your withholding takes five minutes and can save you from owing the IRS or giving the government an interest-free loan all year.

Use the IRS Tax Withholding Estimator First

Before changing anything, run your numbers through the IRS Tax Withholding Estimator at www.irs.gov/individuals/tax-withholding-estimator. The calculator asks about your filing status, income, current withholding, deductions and credits. It tells you whether you need to adjust.

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The calculator considers multiple jobs, spouse income and other factors that affect your tax bill. Running it takes about 10 minutes and prevents you from withholding too much or too little.

Read More: The Cost of Skipping Sick Call: How Active-Duty Service Members Can Protect Future VA Claims

Changing Withholding in myPay (Most Services)

Army, Navy, Air Force, Space Force and Marine Corps members use myPay at mypay.dfas.mil. Log in and click Federal Withholding. Click the yellow pencil icon to edit.

The page lets you enter information about multiple jobs, change dependents, add additional income, make deductions or withhold extra tax. You can see when the changes take effect on the blue bar at the top of the page.

Changes typically show up on your next pay statement. If you make changes early in the month, they might appear on your mid-month paycheck. If you make them later, expect them on the end-of-month check.

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State tax withholding works differently. DFAS can only withhold for states with signed agreements. Changes require submitting DD Form 2866 through myPay or by mail. Not all states allow DFAS to withhold state tax.

Changing Withholding in Direct Access (Coast Guard)

Coast Guard members use Direct Access at hcm.direct-access.uscg.mil. The system processes changes the same way as myPay. Log in, navigate to tax withholding and update your information.

Coast Guard members can also submit written requests using IRS Form W-4. Mail completed forms to the Pay and Personnel Center in Topeka, Kansas, or submit them through your Personnel and Administration office.

Read More: Here’s Why January Is the Best Time to File Your VA Disability Claim

When to Adjust Withholding

Check your withholding when major life events happen. Marriage or divorce changes your filing status. Having kids adds dependents. Buying a house affects deductions. A spouse starting or stopping work changes household income.

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Military-specific events matter, too. Deploying to a combat zone makes some pay tax-free. PCS moves change state tax situations. Separation from service means losing military income but potentially gaining civilian income.

Check at the start of each year, even if your circumstances seemingly stayed the same. Tax laws change. Brackets adjust for inflation. Your situation might be different even if it seems the same.

The Balance

Withholding too little means owing taxes in April plus potential penalties. Withholding too much means getting a refund but losing access to that money all year.

Some people like big refunds and treat it like forced savings. Others would rather have the money in each paycheck to pay bills, invest or set aside in normal savings.

Neither approach is wrong. What matters is that your withholding matches your tax situation and your preference for how you receive your money.

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Run the estimator. Adjust your withholding. Check it annually. This simple process prevents tax surprises.

Previously In This series:

Part 1: 2026 Guide to Pay and Allowances for Military Service Members, Veterans and Retirees

Part 2: Understanding All the Deductions on Your 2026 Military Leave and Earnings Statements

Part 3: Should You Let the Military Set Aside Allotments from Your Pay?

Part 4: This Is the Best Thing to Do With Your 2026 Military Pay Raise

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Stay on Top of Your Veteran Benefits

Military benefits are always changing. Keep up with everything from pay to health care by subscribing to Military.com, and get access to up-to-date pay charts and more with all latest benefits delivered straight to your inbox.

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Finance

The case against saving when building a business

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The case against saving when building a business
Listen and subscribe to The Big Idea with Elizabeth Gore on Apple Podcasts, Spotify, or wherever you find your favorite podcast.Would you rather play it safe, or grow your business? This expert breaks down why investing is everything.This week on The Big Idea with Elizabeth Gore, Howard Enterprise founder and the Wall Street Trapper Leon Howard joins the show to answer the question: How can I use a Wall Street mindset for my business? Howard offers expert insight on why it is absolutely critical that founders take risks and invest capital, versus just saving.To learn more, click here. Yahoo Finance’s The Big Idea with Elizabeth Gore takes you on a journey with America’s entrepreneurs as they navigate the world of small business. This post was written by Lauren Pokedoff
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