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We consider the case of a retired couple relying on summer rental income from a $1.1 million beach house. Local zoning changes are forcing a hard choice between lifestyle and portfolio stability.
Roger Whitney explores the idea that retirement always involves both excitement and uncertainty. While people spend years gathering information, running projections, and refining plans, there comes a ...
Living in San Francisco since 2001 is a surreal experience. I arrived a year after the dotcom bubble burst, and the city felt desolate, especially downtown where Credit Suisse was headquartered at 201...
Shifting your identity from working and saving to spending and living can be tough, but here's why you need to do it for yourself and your family.
Tuesday, May 19 - Monday, May 25, 2026 Most Commented score comments title & link 583 558 comments Whoopsies - learnings from regrettable decisions in retirement 94 181 comments Any retirees who plan ...
Could one outdated beneficiary form, missing trust provision, or overlooked document completely derail the legacy you intended to leave behind? Topics covered in this episode: The biggest misconceptio...
Joe Schmitz Jr. and Jeremy Keil explore the 2% Club of retirees and the unique challenges that come with significant retirement savings and a pension. https://youtu.be/G04JKpKyLJ0 Most retirement conv...
I took a job about 400 miles away from my family some 24 yrs ago. And last year i retired at 65. My parents have passed so its me, my sister and her 2 daughters. Ive never really been close with her 2...
I am 57 years old and still working full time, living on my own. My sister is 54, in poor health, and lives with my mom. Our mother is soon to turn 81, in reasonably good health, or at least has way l...
John Q. Taxpayer is in the home stretch of his career, looking for the best way to catch-up and build his tax-free bucket. Meanwhile, a pair of young financial nerds in Omaha are already strong savers...
Lucky Lou is 48, burned out and wants to punch at 50. How should he bridge the gap before pensions and Social Security? Joe Anderson, CFP®, and Big Al Clopine, CPA walk through the Rule of 55, 72(t)s,...
We recently asked ChatGPT two questions about using the Actuarial Approach and its Funded Status metric to evaluate a household’s retirement sustainability. ChatGPT had high praise for the Actuarial A...
A good friend of mine has a retired sister who met someone on a trip, fell madly in love, got engaged, put her house on the market, and moved out of state to join her fiance in Colorado. A couple week...
A higher cost-of-living adjustment isn't necessarily a good thing for retirees and other Social Security recipients.
Jesse Cramer and Jeremy Keil detail 7 real world lessons learned from working with hundreds of retirees. There’s a big difference between studying retirement… …and actually sitting across the table fr...
Financial Assessment (Meet with an experienced professional): https://bit.ly/PureFreeAssessment Today on Your Money, Your Wealth® podcast number 582, Joe Anderson, CFP® and Big Al Clopine, CPA address...
"Tom and Linda" are a married couple. They're both 55-years-old. Tom works as an operations manager for a regional manufacturer, and Linda works in corporate finance. They are both targeting retiremen...
I know this topic has been asked about relentlessly but I was hoping for some more specific guidance. I’m semi retired now, self employed and pulling the plug entirely by the end of the summer. Stress...
Retiring at 60 feels like a clean plan. Work ends, savings take over, and Social Security fills the gap later. What most people do not realize is that decision has already changed their benefit. In th...
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
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...
The problem with writing about FIRE since 2009 is that I've become completely sold on the lifestyle. I know how good freedom feels, so I have a natural tendency to want everyone to achieve it too. I'm...
Argentina offers Americans a lower-cost, safer lifestyle and a fast path to Argentine citizenship, with the right to dual nationality.
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...
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...
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 ...
I (71m) retired 8 years ago and having worked as a corporate sales coach, I told my staff often that “you are what you do everyday!” At the risk of offending you, I confess that my wife and I are a go...
A big single-stock win can feel like freedom one day and a tightrope the next. This plan walks through how a family holding ~$15M in NVIDIA shares can turn concentrated success into stable, low-stress...
Here is a question worth sitting with: which is actually harder to achieve, a top 1% income or a top 1% net worth? Most people assume income. The number sounds impossibly high, the competition sounds ...
I received a severence check from my company for the VSP. Boldin says I have enough to spare a 15k car to my daughter which will help her through Grad School. She will be living with me and we have be...
(No, not the go-go, slo-go, no-go adage) I just got my letter from Social Security saying, it’s time, bud, apply to claim your benefits. I’ll be 70 in a few months. For the last 2.5 years, my wife and...
Feeling happy? That could be because spring has finally sprung here in the Midwest. Or, more specifically, it could be because you're part of the Keen Wealth audience right here in Overland Park! A re...
Roger Whitney kicks off a new series on decluttering for retirement, explaining how the accumulation of “stuff”—from physical belongings to financial accounts to relationships—can unconsciously shape ...
We are hoping to retire in next 2-3 years. We met and married in San Francisco and loved that urban vibe when we were young. Kids came along and we relocated to Roswell GA just outside of Atlanta in t...
This is going to be a bit long. We are planning on getting LTC insurance, my wifes dad used his benefit and we have no kids. I am just not sure how to think about it. I conceptualize 3 different reaso...
My daughter has a significant disability but has been self-supporting and living independently for 15 years. She has suffered some setbacks in this economy. I also feel that she makes what I think are...
Most people think deciding when to take Social Security is a math problem. Run the numbers. Find the breakeven age. Pick 62, 67, or 70. Done. But that approach misses the point. This is not a math dec...
Tuesday, April 21 - Monday, April 27, 2026 Top Comments score comment 36 /u/Familiar_Kale_7357 said Multi generational living is back in America, and I don't really see a problem. 36 /u/davejdesign sa...
My husband and I are both 64 years old. My husband is disabled. We are currently living near my children and grandchildren, but we’ve realized it’s too expensive to live in our current state. I retire...
The decision to move to a different state should balance financial issues with the lifestyle you want, rather than simply choosing a low-income-tax state.
With Americans living ever longer lives, the age-old worry of outliving savings has become more pronounced.
Jeremy Keil explains how 5 smart moves could impact your ability to claim $180,000 or more as a couple in Social Security. If you’re about to file for Social Security, there’s a real possibility you c...
Dr. Wade Pfau explains four ways to beat sequence of return risk and turn your retirement savings into retirement income. For most of your working life, retirement planning feels relatively straightfo...
We were so close to moving to our dream neighborhood in our dream city. But it turns out that not living in the "cool city" isn't a bad idea. The post The Financial Benefits of Avoiding the ‘Cool Plac...
Lifestyle creep can quietly influence long‑term financial security. Here's how to check in on your spending and realign with your goals.
Men are living longer, so women are less likely to become widows.
Many doctors assume that once they move overseas, US taxes become simpler. In reality, living abroad can make your tax life way more complex. The post The Expat Doctor’s Common Pitfalls: Why Living Ab...
We are Gen Jones and are retired nearly 2 years now. Like many parents of our generation, we have an adult Millennial child still living at home. He has a skilled career and makes good money, but it w...
Roger Whitney breaks down how to create a diversified portfolio by explaining the core principles of diversification and asset allocation, then answers listener questions on topics like using allocati...
Bladder cancer survivors and a therapist share the realities of living with a stoma and how relatives can support loved ones as they rebuild their identity.