Discover the Best Insights for Every Stage of Retirement

The 'Take That Uncle Sam' Quiz: Are You Overpaying in Retirement?

Test your retirement tax knowledge with our short quiz.

Chasing the Sun: How Savvy Retirees Are Affording the Two-Home Lifestyle Now

Living in two cities as a snowbird has its financial challenges, but when you do it the right way, it's fun and affordable. Here's How to Protect Your Wealth As a Seasonal Snowbird

Is a Roth Conversion Just Not That Into You? Here's When It's a Perfect Match (and When It Isn't)

Sometimes a Roth conversion isn't right for you — or at least not right now. A financial adviser explains what you should consider before getting involved.

How can I live half of the year in another place?

Should I just rent furnished places in both location for six months each? I don’t want to buy, leaving a property for six months at a time. I want to be in climate that allows me to be outside enjoyin...

Summer contract work could improve my finances substantially

I don't really want to go back to work yet. But there is a contractual position - if I take it and succeed for 3 to 6 months, we can boost our retirement finances substantially. However, I have anxiet...

Financial reviews in retirement

Switching from saving to withdrawing has been harder than we expected. We finally hit our number and retired, but now I’m unsure what kind of monthly or yearly reviews I should be doing. We’re already...

Your weekly /r/Retirement roundup for the week of May 05 - May 11, 2026

Tuesday, May 05 - Monday, May 11, 2026 Most Commented score comments title & link 28 126 comments Question about paying off mortgage. Advice appreciated. 86 47 comments Soon to enter Retirement Phase ...

What was the best gift you received from a coworker?

Our Executive Director is set to retire next week, and I’m eager to find a thoughtful yet practical gift to convey my appreciation for her leadership and support. I’m particularly interested in sugges...

3 Questions To Ask Before Unretiring So Your Dream Job Doesn’t Become a Nightmare

Thinking of unretiring? Before you decide to return to work, make sure you know the answers to these critical questions.

Ask the Tax Editor, May 15: Deductions for Self-Employed Retirees

In this week's Ask the Editor Q&A, Joy Taylor answers questions on available tax breaks for retirees with a side hustle.

The $9 Trillion Shift: Why Your Retirement is Less Safe in an IRA and How to Protect It

IRAs now hold a $9 trillion surplus over 401(k)s, largely due to rollovers. Learn how to secure your retirement savings against legal risks and hidden fees.

I'm a Divorce Lawyer: A Rushed Gray Divorce Can Quietly Destroy Your Retirement — Slow Down and Focus on These Details

When you're navigating a gray divorce, don't rush to split assets. A settlement that looks good on paper may contain losses you won't have time to recover from.

The Best Time for Roth Conversions May Be Now

Most physicians spend their peak earning years maxing out pre-tax retirement accounts, reducing taxable income, and deferring the tax bill ... Read more

2027 Social Security COLA Forecast Surges Amid Spike in Inflation

Driven by a recent spike in fuel and food prices, the 2027 Social Security COLA forecast has jumped to 3.9% — a significant increase over the 2026 raise of 2.8%.

These Social Security Hacks Could Put More Money In Your Pocket

Social Security isn't simple. Learn the key claiming strategies—spousal, survivor, disability, and more—to maximize your benefits and avoid costly mistakes.

Some Companies Are Pausing 401(k) Matches in 2026: What It Means for Your Taxes and Retirement Savings

Some employers are suspending or scaling back retirement contributions, leaving workers with new questions about savings, taxes, and long-term planning.

Wife joining me in retirement in a month

I've been retired for 2 years as of June 1. My wife has decided to pull the trigger as of the end of June, with her last day (using vacation for the rest) on June 12. We've been talking about the 'nex...

I’m 62 With $4 Million Saved. I've Been Offered a Buyout, but I Love My Job and My 'Work Family.' Should I Take It?

We asked financial advisers whether this 62-year-old should take the six-month buyout and retire, or work a few more years.

How To Make This Popular Retirement Strategy Work

It can take creativity, patience, and hard work to make the “working-longer” retirement strategy work for you.

The Best FIRE Software Just Got Even Better

The best financial planning software for FIRE just got even better! Check out the incredible new features that have changed how I invest! Read more → The post The Best FIRE Software Just Got Even Bett...

Time Fixes Most Financial Mistakes Because You Grow Richer

One of the issues we frugal people despise is going through buyer’s remorse. We don't want to feel stupid or ripped off, so we tend to buy fewer things and experiences. Minimalism and early retirement...

Balanced Funds: Are They a Good Choice in Retirement?

Balanced funds simplify investing while you’re saving. But proportional withdrawals can limit flexibility in retirement when it matters most. The post Balanced Funds: Are They a Good Choice in Retirem...

‘You Can Still Do It’: How One Woman Figured Out Retirement on Her Own

She was self-employed, single, and unsure she’d saved enough. Then the Boldin Planner showed the full picture, and the answer surprised her. The post ‘You Can Still Do It’: How One Woman Figured Out R...

Why Argentina Could Become Americans’ New Plan B

Argentina offers Americans a lower-cost, safer lifestyle and a fast path to Argentine citizenship, with the right to dual nationality.

Sending out a goodbye email when it’s time to go…

What are your thoughts on these? I’ve seen farewell emails from people I’ve worked with, some send them to one or two people, and bcc everyone else. Some send out an email, but everybody is in either ...

Why advisors should see life settlements as a planning option

Allowing clients to surrender or lapse life insurance policies before gauging value on the secondary market amounts to a fiduciary fail, argues Cole Hallman of Citizens Life Group.

How am I doing on my way to retirement

In spite of two divorces, two bankruptcies, and one short sale, I have been able to somehow amass about $500,000. I am going to retire at the end of this year at 66. I already started taking SS, and h...

Using up PTO days vs getting them paid out.

The place I work allows you to accumulate your vacation time up to what you earn for two years. In other words, if you get 24 days a year, you can accumulate 50. Many soon-to-be retirees here will use...

What You Need To Know About The GLP-1 Medicare Bridge, $50 Drugs

Learn who qualifies for Medicare’s GLP-1 Bridge, when $50 Wegovy and Zepbound access begins, and key rules beneficiaries need to know before July 2026.

Our New Health Plan Offers an HSA. Is the Triple Tax Benefit Worth the Hassle of Saving Decades of Receipts?

Should we sign up for a Health Savings Account (HSA) and embrace even more healthcare paperwork? We'd rather plan vacations than track receipts.

5 Ways the OBBBA Rewards the Midwestern Millionaire: You Won't Want to Ignore These Tax Planning Opportunities

Diligent savers who take steps to capitalize on these tax-saving opportunities can keep more of their wealth and even help build a tax-efficient legacy.

Will Your Retirement Plan Collapse Under These 5 Stresses?

Retirement plans that are properly engineered have less chance of collapsing under the weight of increased longevity and other stresses. Will yours stand up?

Retirement Location, Location, Location: Can Florida Be Beaten?

Many retirees have made Florida their home, but is it right for you? Where you choose to set up your retirement life means considering more than the weather.

Turning 65 This Year? Take Our 2-Minute Quiz And See If You're Ready For the Big Transition

Take our 10-question quiz to test your understanding of the critical milestones and decisions you'll encounter as you turn 65.

Living Off Your Acorns – A Book Review

There’s a new retirement book that’s worthy of your attention, and it’s being released TODAY. I received an advance copy of Dana Anspach’s new book, “Living Off Your Acorns – […] The post Living Off Y...

5 Do's and Don'ts for a Successful First Meeting With Your Financial Adviser

The first meeting with a new adviser can be intimidating, but you can reduce your worry and ensure you're hiring the right person by following a few rules.

The Coming Social Security Crisis And The Fight To Save It

Over 20% of Americans are receiving Social Security. SS benefits will be reduced in 2033. What changes are being considered? How will it affect you? Read to learn more.

Why Your Social Network May Be Your Most Valuable Asset

Most people spend decades planning for the financial risks of retirement. Almost no one plans for the social ones.

I pulled the trigger, July 3rd will be my last day.

I just informed my manager that I'll be retiring July 3rd. Pretty exciting. The plan has been afoot for a while now, but I needed to let them know. I've tested the numbers, I've created my fund for th...

Retiring in the Next 12 Months? Answer These 3 Questions First

Jeremy Keil walks through three critical questions future retirees can answer before their paycheck stops Most people spend decades preparing for retirement by focusing on one number: How much have I ...

Why You Need to Start Your Social Security Claim 4 Months Early: 7 Steps to Prevent a Delay at the Worst Possible Moment

Even a perfect Social Security plan can fail if you hit a login wall, an ID check snag or a direct-deposit problem. Here's how to make sure that doesn't happen.