For many, retirement is an imagined finish line. A date circled on the calendar. A number on a statement. A moment when the alarm clock turns off for good and life finally begins to slow down. Every day becomes a Saturday!
And then it arrives.
https://prosperion.us/wp-content/uploads/2026/05/first-monday-of-retirement.jpg7351200Steve Boorenhttps://prosperion.us/wp-content/uploads/2017/02/whitelogosized.pngSteve Booren2026-05-05 15:12:212026-05-05 15:15:22The First Monday of Retirement
What does a typical meal cost today? Maybe $12 for a quick stop — or $15 if including a drink. Sit down somewhere nice, and you’ll owe closer to $20. Now fast forward 30 years. The $12 lunch — once only $5 — is headed toward $30.
Investors often learn about this critical principle in finance: the time value of money. But recently, I began thinking about this from the other direction. If there’s a time value of money, there’s also something I call the money value of time. In the long run, that may matter even more.
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Where do those tax problems actually show up, and why do so many thoughtful investors ultimately pay more than necessary? In most cases, it’s not a lack of knowledge that drives this problem, but timing. The biggest tax mistake investors make isn’t misunderstanding the rules; it’s waiting too long to act.
https://prosperion.us/wp-content/uploads/2026/04/tax-2.jpg8331250Steve Boorenhttps://prosperion.us/wp-content/uploads/2017/02/whitelogosized.pngSteve Booren2026-04-07 12:42:182026-04-07 13:08:32Where Tax Mistakes Actually Happen and Why Timing Matters Most: Part 2
Most investors think about taxes once per year. April arrives, documents are gathered, numbers are calculated and a return is filed. Then, for a while at least, taxes fade into the background. But even before you file that return, several factors have likely influenced your tax outcome, potentially in significant ways.
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A great irony of investing is that people crave certainty when the world offers very little of it. Yet beneath all that motion, something remains surprisingly steady: Dividends.
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Most investors instinctively define risk as market volatility — the uncomfortable reality of stock prices rising and falling over time. When markets drop sharply, the losses feel immediate and visible. Investors see account balances decline, and the headlines only amplify their fear — creating an emotional impact that is powerful and persuasive.
But volatility is only one kind of risk.
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There is a curious trait built into human nature: When something is painful, frightening or deeply disorienting, we don’t just want it to end — we want to forget it ever happened.
COVID fits that description perfectly.
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Somewhere around age 62 — about the time many people begin thinking seriously about retirement — the focus shifts. The conversation moves from accumulation to preservation, from maximizing growth to ensuring durability. The question is no longer, “How much can I build?” but rather, “Will this last?”
They aren’t flashy. They don’t dominate headlines. They rarely fuel cocktail-party conversations or social-media bravado. In a market obsessed with price momentum, dividends can feel like the broccoli of investing — nutritious, dependable and routinely ignored in favor of something more exciting.
https://prosperion.us/wp-content/uploads/2026/02/stair-steps-2.jpg5501200Steve Boorenhttps://prosperion.us/wp-content/uploads/2017/02/whitelogosized.pngSteve Booren2026-02-24 11:25:102026-02-24 11:25:10The Quiet Power of Dividends
Recently, I met with a prospective client who leaned forward, lowered his voice and said, “I have one question — and I want your honest answer. The United States is bankrupt.”
https://prosperion.us/wp-content/uploads/2026/02/empty-wallet.jpg8001200Steve Boorenhttps://prosperion.us/wp-content/uploads/2017/02/whitelogosized.pngSteve Booren2026-02-18 10:37:232026-02-18 10:37:23Debt Is Real; Panic Is Optional
Most people reading this column — whether early in their careers or well into retirement — have had their entire financial lives shaped by the events between 1975 and 2025. And yet almost none of us were taught to study that period carefully. Instead, we’ve been conditioned by markets, media and our own wiring to obsess over what’s happening today and what might come next.
Such a short-term obsession is the enemy of good investor behavior.
https://prosperion.us/wp-content/uploads/2026/02/vietnam-protest.jpg7831200Steve Boorenhttps://prosperion.us/wp-content/uploads/2017/02/whitelogosized.pngSteve Booren2026-02-09 11:01:572026-02-09 11:01:57Looking Forward with the Perspective of the Past 50 Years
The biggest success determinant has nothing to do with cleverness or timing. Instead, it has everything to do with having a plan and sticking to it.
Amid all the noise in today’s world, it’s easy to get distracted from the foundation of your financial plan. By returning to those core principles, you can recalibrate to your highest priorities, both for now and the future.
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Among the greatest long-term threats to retirees and investors is inflation. The world was reminded in recent years — and almost overnight — just how quickly inflation can roar back to life.
The First Monday of Retirement
The $12 Footlong
The Money Value of Time
Where Tax Mistakes Actually Happen and Why Timing Matters Most: Part 2
The Hidden Tax on Your Wealth: Part 1
Predictability in an Unpredictable World
Where Does Your Risk Live?
When Markets Panic, Memory is the First Casualty
The 62-Year Scorecard
The Quiet Power of Dividends
Debt Is Real; Panic Is Optional
Looking Forward with the Perspective of the Past 50 Years
Your Plan (and Behavior) Matter More Than the Headlines
Overcoming Inflation Using a Familiar Friend (Part 2)
Understanding Inflation, the Silent Killer (Part 1)