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Generating a reliable source of income is one of the most important, and often challenging, parts of a successful retirement. Those of us fortunate enough to have a decent defined benefit pension have a leg up on this. Combine this with an inflation protected social security benefit, and some savings, and a retiree has a chance at a modest, yet comfortable retirement. I’ve seen this firsthand. My in-laws were a truck driver and a part-time registered nurse.
After nearly a four decade career, I sometimes wonder how I survived many early retirement offers and frequent company downsizing initiatives. One reason may be that I picked up a lot of career advice from colleagues and bosses along the way. I listened to some, but not all. Here are some:
– My first boss on the first day told me, “Be nice to people on the way up. You need their help on the way down.”
-Always ask “why”?
I thank everyone in advance for any assistance and advice you can provide regarding my Roth conversion scenario. I am currently 56 with a potential retirement age of 58 (approx. 2 yrs). My wife is younger and will continue working for another 8 years following my retirement. I plan on deferring Social Security as long as possible, age 70. I have $850,000 in a regular IRA and an additional $600,000 in a company sponsored 401K. My wife and I file jointly and are currently in the 24% tax bracket ($206,700- $394,600).
The recently enacted One Big Beautiful Bill Act included a number of tax provisions of interest to HumbleDollar readers. Given the emphasis on retirement planning on HumbleDollar, the new bonus Deduction for Seniors has potential to provide a significant tax savings for seniors.
This has been discussed in previous posts over the last few weeks, but the details are worth a quick review. Taxpayers who reach 65 by the last day of the tax year, starting in 2025,
OVER THE JULY FOURTH weekend, a friend asked me what I thought about the new financial instrument known as a “stock token.” Developed by the online broker Robinhood, a stock token is designed for investors to buy stakes in private companies such as OpenAI, creator of ChatGPT. It’s a novel concept because private company investments are typically inaccessible to individual investors.
Despite the appeal, I urged caution. Why? These tokens may not perform as expected because they aren’t the same as actual equity in a company.
On July 4th, the president signed a significant new tax and spending bill into law. The text of the bill runs to almost 900 pages and affects nearly every corner of the tax code, including personal, business and estate tax rules.
Below I summarize the provisions I see as most relevant to financial planning. It’s important to note that many of the provisions are retroactive to the beginning of 2025.
The formal name of the law is the “One Big Beautiful Bill Act,” and it is,
Key Medicare benefits are being stripped away, and patient care is being handed over to profit-driven corporations.
On June 25, 2025, in an unprecedented move, Dr. Mehmet Oz and Robert F. Kennedy Jr., through the Centers for Medicare & Medicaid Services (CMS), announced that Original Medicare will now require prior authorization for a list of 17 services.
This marks a major shift—and a serious rollback of a key protection retirees have relied on for decades.
What’s Changing?
I’ve been working to educate myself on the US pension system, particularly the retirement decumulation landscape. It’s a challenging endeavor, but through diligent research, I’m slowly grasping the essentials. From an outsider’s viewpoint, the complexity that various US administrations have introduced into this system is striking. As a UK citizen, I find several aspects particularly perplexing:
The Sheer Number and Variety of Retirement Accounts: In the UK, it’s largely about defined contribution and defined benefit pensions,
I met a few months back with the vice-president of Fisher Investments. One of the benefits of our meeting was a hardcopy brochure titled “99 Retirement Tips.” You can get an electronic version via this link, without having to attend an actual meeting, though it may still come with some very persistent phone calls from Ken and Company.
It makes for a brisk though useful read as every retiree could benefit from going over the basics every now and then.
This is a decision I had to make several years ago when I turned 65. I started out with a no premium five star local Advantage plan to take “advantage” of the free perks for the first year, then switched to traditional Medicare with a plan G supplement, the most expensive plan. To most this would seem quite contradictory, but let me explain my reasoning. Medicare allows first time enrollees to trial an Advantage plan for up to a year,
STATISTICIAN GEORGE E.P. Box once made this observation: “All models are wrong,” he said, “but some are useful.” This certainly applies to finance, where many of the concepts are imperfect but can nonetheless still be useful. Below are four such examples.
Market valuation. Are stocks overpriced? It’s a question without an easy answer. Even academics who have studied the topic can never be entirely sure. Consider the cyclically adjusted price-earnings (CAPE) ratio.
Here is an interesting article I just read on my weekly Boldin (previously New Retirement) newsletter.
Someone on HD asked if my inflation adjusted retirement income today still equaled my base salary when I retired.
The answer is a resounding no. For every dollar of base pay in 2009 I would need $1.50 today. Since my pension does not have a COLA, any automatic adjustment is up to Social Security, but that is less than a quarter of our income.
So, now I am 50% behind – no panic yet, but I am glad I didn’t start out say,
What triggered this post was a Facebook meme claiming the wealthiest 0.1% have gained $4.4 trillion in the past two years, that they have grown their wealth at the expense of average Americans and that “without them your wealth would have doubled”
When I read that, my reaction is “that’s just wrong and so what, they earned it.” I wish I was that smart. But that is not the typical reaction. Many people readily believe such a meme and are willing to bash the wealthy.
My 2014 Honda Accord recently hit 99,000 miles. It’s nothing fancy to look at, but it drives well. Recently I’ve been having an issue with the starter. The push start works intermittently. Sometimes it starts on the first push, sometimes it takes multiple tries. I think the most it has taken is 6 tries. I’ve kept up with the maintenance, but I drive it infrequently, so the time between service has spread out. It was due for an oil change,
