In this episode of the One of a Kind Financial Show Daily (September 23, 2026), host Mike Milligan links current market movements to long‑term retirement planning. He begins with a concise market recap—Dow down 0.36%, S&P flat, Nasdaq up 0.45% to a record, Russell 2000 up 0.51%, VIX at 14.21—and notes a five‑day decline in crude prices tied to Saudi pipeline restarts and limited Hormuz shipping. He cautions listeners to watch oil supply dynamics rather than headlines. Milligan then examines an unusual S&P signal where the index neared its 52‑week high while many constituents hit new lows, drawing historical parallels to 1999 and 1929 but warning against over‑interpretation. He urges investors to test the robustness of their plans against concentration risk. The core of the episode is a rapid‑fire history of U.S. retirement tax policy: 1974 ERISA‑created IRAs, 1978 Revenue Act Section 401(k) (effective 1980‑81), 1986 Tax Reform Act limits, 1997 Roth IRA creation, 2006 Roth 401(k) availability, 2019 SECURE Act (RMD age 72, 10‑year stretch rule), and 2023 SECURE Act 2.0 (RMD age 73‑75). Milligan frames the government as a “silent partner” that repeatedly rewrites the retirement agreement. He stresses the need for flexible, model‑driven withdrawal strategies, comprehensive tax‑rate scenario planning, and thoughtful Roth conversions that consider current tax impact, Medicare, Social Security, state taxes, heirs, and cash flow. The episode closes with a call to action: contact the show via text, share the episode, and obtain his new book, The Retirement Handshake, which expands on these themes. Legal disclaimer and affiliation disclosures conclude the broadcast.
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Stock market records, oil prices, retirement taxes. Today we're connecting what happens on Wall Street with what actually ends up in your pocket. Here's the question: what good is winning the investment game if you never learn the withdrawal rules? I'm Mike Milligan. This is the One of a Kind Financial Show Daily for Wednesday, September 23rd. You're here to learn and grow, so let's get to it.
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Tuesday gave us a split screen. The Dow Jones Industrial Average fell 0.36% while the S&P 500 finished essentially flat. The NASDAQ gained 0.45%, closing at 27,244. That was another record close, but the Russell 2000 led those 4 benchmarks on Tuesday, gaining 0.51% to 2,889. The VIX reading after the stock market closed, 14.21. Not a lot of volatility or risk in the market right now. Oil offered some relief. Reuters reported a 5th consecutive daily decline for both major crude benchmarks. Improving Saudi crude flows after the east-west pipeline restart and signs of shipping movement through the Strait of Hormuz helped the supply outlook. But don't confuse an improving supply outlook with a signed peace agreement, folks. Reports about reopening Hormuz remained conditional, not a declaration that the conflict was over. Here's my takeaway. Watch the barrels moving, not just the headlines flying. One encouraging day is a development to evaluate, not a reason to declare the problem solved. That's it from the market yesterday.
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Now back to Monday's unusual market signal. The S&P 500 gained 1.49%, finishing within 1% of its 52-week high, even as 30 members of the S&P 500 touched new 52-week lows, And only 7 touched new highs. According to historical analysis, that combination of a strong rally near high with new lows outnumbering new highs pointed back to December 21st, 1999 and July 23rd, 1929. Those dates get your attention, I bet. They do not give you a calendar for the next crash, but Those were periods of time that we know the rest of the story. 2 historical comparisons are not reliable forecasting models, and new lows outnumbering new highs does not mean most stocks fail that day. Here's the fresh follow-up. Tuesday, 5 S&P sectors rose and 6 fell, even as the Nasdaq set its record. That's another example of mixed participation, not proof that Monday's exact signal repeated. My question is, is not, is this 1929 all over again? It's, would your plan still work if the investments leading today stopped leading tomorrow? Review concentration. Review the money you'll need soon. Protect the money you don't want to, you don't want to lose. Don't turn an interesting historical comparison into an emotional trading instruction where you lose sight of the long run.
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That brings us to my new book, just released, The Retirement Handshake, and the chapter called The Rules Keep Changing. Picture a worker making that first retirement contribu— contribution. The retirement sees a savings account. I want that worker to also see an agreement about when taxes get paid. See, you supply the work, the discipline, and the patience. The tax benefit can be valuable, but deferring a tax doesn't erase it. Traditional IRA withdrawals are generally taxed except for amounts representing after-tax basis, which is not really common these days because we have Roth contributions and traditional contributions. Well, in The Retirement Handshake, I called the government the silent partner. That's a metaphor. They don't literally have ownership of your account, but they do get to set the rules. Now, look at these milestones. 1974, ERISA created IRAs, initially serving workers without employer plan coverage and providing a home for retirement plan rollovers. The retirement savings framework expanded. In 1978, the Revenue Act added Section 401. Its provision took effect in 1980 with implementing regulations following in 1981. In 1986, the Tax Reform Act restricted deductible IRA contributions for certain taxpayers covered by workplace retirement plans based on income. All right, that's where the rules went backwards and brought new restrictions. In 1997, Congress created the Roth IRA, available beginning in 1998. That offered a different handshake No contribution deduction, but qualified withdrawals could be tax-free. 2006, Roth 401 contributions became available under legislation passed in 2001. Workers in participating plans gained another way to choose their tax treatment. 2019, the SECURE Act raised the required distribution starting age to 72, for affected savers and replaced lifetime stretch withdrawals with a 10-year deadline for many non-spouse beneficiaries, with a few important exceptions. And then in 2023, SECURE Act 2.0, signed late in 2022, moved the starting age to 73 for some workers. Under current law, it moves to 75 for those born in 1960 or later. Some changes expanded choices. Others changed deductions or withdrawal requirements. The story isn't that every change hurt savers. It's that the agreement kept changing. Now, think about the next 20 or 30 years of your life. How many revisions will there be to when, if, and how you take money out of your retirement accounts? And what tax rate will apply when you need the money? The truth is, neither of us know. That uncertainty deserves a place in your plan, your tax strategy. With taxes being the biggest expense of your life, we need to build flexibility and not rely on a prediction. Start with a written inventory. Money that would generally be taxable when withdrawn, money with qualified tax-free treatment, and money held outside of retirement accounts. Then ask your planning and tax team to model different withdrawal sequences and tax rate scenarios. A Roth conversion deserves some analysis, not automatic applause. Converting pre-tax money generally creates taxable income now, so the decision is about what you pay today versus what you may avoid later. And then ask the team to include Medicare premiums, Social Security taxation, state taxes, your heirs, and the cash available to pay the conversion bill. Compare smaller conversions over time with doing nothing and with a larger conversion. Don't ask only, how do I pay the least tax this year? Ask, how do I support my life with the most useful after-tax income over time. Here's the line I want you to remember: a plan on paper is not a plan frozen in time. Write it clearly, review it regularly, give yourself choices when markets, laws, or life changes.
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That's it for the One of a Kind Financial Show Daily today. And that's the connection between today's market story and the retirement handshake. You don't control the next market leader and you don't control the next rewrite of the rules. You can control how thoughtfully you prepare. If you want to connect with us, text the word ideas to the number 600-700 to start a conversation about your one-of-a-kind financial plan. And share this episode with someone who knows their retirement balance sheet, but hasn't thought through how they'll spend it. I'm Mike Milligan. My mission is to educate, coach, plan, and most of all, I never want to miss a moment. The One of a Kind Financial Show is for educational purposes only. We're not here to give individual investment, tax, or legal advice. Review decisions with your qualified financial professional. Mike is an investment advisory representative with Advisory Alpha LLC, Ideas by Mike doing business as One Oak Financial, and Mike Milligan LLC doing business as One Oak Collective are unaffiliated entities of Advisory Alpha LLC. To get a copy of the book, The Retirement Handshake, go to amazon.com, search, and, and order it the way you consume books. We'll see you tomorrow.
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