MY COWORKER RECENTLY retired. He is 50 years old and has been with the company for over 25 years.
The company offers a decent 401(k) match (100% match on 6% of your salary) along with other great benefits.
In his case, how can he generate income? How can you retire early if most of your assets are in retirement plans?
Most tax-advantaged accounts have restrictions on withdrawals, but there are a few strategies that many people don’t know of:
 

While life is good, there are a few things I have to work on. 
Let’s begin with the number 36. No, Chrissy isn’t trading me in for a couple 36 year old studs, 36 is the waist size I reached early in 2025. I was not happy with that. Now, sadly, some of my 36 inch pants are whispering into my ear; 38,38,38. It’s like an evil form of tinnitus that speaks instead of rings. It’s not that I don’t exercise,

Have you ever heard of a film called “Cash on the Barrel Head” or Chester A Riley or William Bendix?
William Bendix played Riley in a sitcom, “ The Life of Riley” the story of a middle class factory worker for whom life, including financial life, was an ongoing challenge.  Nothing seemed to go right for the good-hearted, but inept Riley. 
I remember the film from my early days in employee benefits around 1961. It was an educational/training film trying to make a point to workers. 

I’m an index investor, which obviously means I don’t pick stocks. It’s a comfortable position. When you own the entire market, you’re not making choices, you’re just participating in the market as a neutral observer.
My strategy has always been simple: buy broad index funds, reinvest the dividends, ignore the noise. No stock picking, no market timing, no cleverness required. The kind of investing you can explain at a dinner party without boring your guests too much.

Unusual events happen from time to time.  Since 2022 the S&P 500 has had some remarkable years.  Recently foreign stocks have also done very well.  This is a boon to retirement portfolios, and particularly welcome for those entering retirement.
The opposite situation is the “lost decade” which I recently posted about.  Some say these are rare and if we are lucky the timing will be such as to have slight impact on retirees.  But fingers crossed is not a strategy.  

I received this letter from Fidelity this morning. Interesting that they are now saying that some major index funds may not be diversified investments. What can you do about it? Invest your portfolio in other funds such as fixed income, international, value, or small cap?
 
Index Fund Policy Changes
Dear Shareholder,
Effective November 10, 2025, the “Principal Investment Strategies” and “Principal
Investment Risks” sections of the prospectus of each index fund shown in the table
below was modified to indicate that the fund may operate as a non-diversified fund,

For 2026 our Plan G Medigap premiums increased about 14% to $311.03 and $324.86. Our Part D premiums increased from $18.00 to $72.30 per month. And, the standard Part B premiums increased to $202.90.
These premiums total $1,186.29 per month for both of us,  $14,235 a year. IRMAA adds several hundred dollars more per person, per month. 
Even ignoring IRMAA, the basic premiums – unrelated to income – can be a hefty hit to income for retirees, 

When I sold my business and retired last year, I decided to keep two years of expenses in cash to avoid thinking about portfolio withdrawals immediately. I’ve worked through most of the first year’s buffer, and with recent strong equity returns, I’ve moved some gains into a money market fund to replenish my cash reserves.
Since this cash is earmarked for spending 24 months from now, I was initially planning to just leave it sitting in the money market fund—rates are still around 4% at the moment.

In a recent post, “lost decade” investment periods were mentioned. Looking at safe withdrawal rates, there is an assumption of portfolio continuity.   Uniform returns over a long period of time coupled with consistent withdrawals.    In such an environment, a portfolio which yields 6% annually can sustain a withdrawal rate that begins at 4% and the portfolio will increase in value.  But over 30 years it may decrease in purchasing power.  [1]
But what if a “Lost Decade” occurs? 

The  recent discussion about withdrawal rates – 4% and all  that – got me thinking about the importance and confusion surrounding that decision.  I don’t  personally have to deal with it and gladly so because I’m sure I would not handle it well. My withdrawals are those required by RMDs. 
The current RMD table is based on the 2012 Individual Annuity Mortality (IAM). The table is more generous than a “single life” actuarial table. It is calculated using the Joint Life and Last Survivor expectancy for an individual and a hypothetical beneficiary who is exactly 10 years younger.

“The riskiness of an investment is not measured by beta but rather by the probability—the reasoned probability—of that investment causing its owner a loss of purchasing-power over his contemplated holding period. Assets can fluctuate greatly in price and not be risky as long as they are reasonably certain to deliver increased purchasing power over their holding period. And a non-fluctuating asset can be laden with risk.” — Warren Buffett, in his 2011 Berkshire Hathaway shareholder letter.

I just responded to a post by norm60189. He mentioned that Jack Bogle popularized index funds. My post got me thinking about my favorite Bogle quotes. Here are three, with my interpretation of the saying.
“Don’t look for the needle in the haystack. Just buy the haystack!”
Research has shown that annually the majority of active managers do not eat the market. As a result investors are better off not trying to pick individual stocks but buying broad market indexes.

Jack Bogle is frequently quoted. Jack was the founder and chief executive of The Vanguard Group and is credited with popularizing the index fund.
Here’s one of my favorite Bogle quotes:
“The stock market is a giant distraction from the business of investing”.
Warren Buffett is also often quoted.  Because Mr. Buffett purchased individual stocks, it was possible to observe how he approached investing as a business.  For example, Buffett eschewed tech stocks, yet had a large stake in Apple.

I consider myself a pretty ordinary guy living a normal, down-to-earth life. If you ever had the misfortune to meet me, you’d quickly realize there are no airs and graces about me. With that mental image in mind, you might understand my surprise when a fellow retiree I play sport with came out with: “how the other half live” after I mentioned booking a short break at a nice coastal hotel for me and my wife Suzie later in January.

Would love some insight/suggestions/experience from this well versed and knowledgeable group.
My husband has two tax deferred accounts that have a substantial balance and that he needs to rollover into an IRA now that he is fully retired. We currently have brokerage accounts at Schwab and Vanguard and I am torn between rolling over these 2 accounts fully into one of these two brokerage houses. I like having both accounts so I don’t see closing one but want to make one our primary account.