Mark Twain once wrote that October is one of the most dangerous months to speculate in stocks — the others being July, January, September, April, November, May, March, June, December, August, and February. In other words: every month is dangerous for speculation.
It’s a joke, but Matt Dages, CFP® and Founder of Bright Wealth Management uses it to make a serious point. Most people think they’re investing. Many of them are speculating — and they don’t know the difference.
Listen to the full episode here: https://www.spreaker.com/episode/is-there-a-best-time-to-buy-stocks-10-11-26–75602878
Investing vs. Speculating: Two Very Different Mindsets
Investing means having a plan. It’s grounded in data, matched to a time horizon, diversified across assets, and built around a specific goal. Speculating is the opposite — it’s driven by emotion, price movement, and the fear of missing out.
Chasing a stock because a coworker mentioned it at the water cooler? Speculating. Holding 50% of your portfolio in one company because you believe in it? Also speculating — no matter how great the company is. A great business does not automatically make a great portfolio.
The difference isn’t just semantic. As you near retirement, the consequences of speculation compound. A 40% market drop two years before you stop working is a different kind of problem than it is at 35. The purpose of your money changes — and your strategy has to change with it.
Your Retirement Number Isn’t Your Retirement
Here’s something most people don’t account for until it’s too late: the balance on your 401(k) statement is not what you get to spend.
Every dollar in a pre-tax retirement account is subject to ordinary income tax when you withdraw it. If you want $4,000 per month in retirement income, you likely need to pull closer to $5,000 — just to cover the tax. A $15,000 expense could realistically cost $18,000+ from your pre-tax account.
Then there’s inflation. The dollar that fills your grocery cart today buys less every year. The number on your statement stays the same. The purchasing power doesn’t.
What a Living Retirement Plan Actually Does
The solution isn’t to panic — it’s to plan. Specifically, to build what Matt Dages calls a “living retirement plan”: not a one-time snapshot, but an evolving document that maps out year-by-year cash flow, accounts for taxes across different account types, builds in cost-of-living increases, and adapts when life does.
That means knowing your after-tax income before you retire, not after. It means planning across Roth, pre-tax, and brokerage accounts to control your tax bracket. And it means revisiting the plan regularly — not just setting it and forgetting it.
Bright Wealth Management meets with clients three to four times per year to update and adjust, because a plan that doesn’t adapt isn’t really a plan.
Start With What Your Savings Are Actually Worth
Before you can build a plan, you need an honest number. BrightTaxBill.com offers a free tax calculator that shows your real exposure — what Uncle Sam takes before a dollar hits your bank account.
If you’re within five years of retirement and you haven’t had that conversation yet, it’s worth having now. Reach Matt Dages and the Bright Wealth Management team at brightwm.com or by calling 833-777-4296.
Guessing is not a plan. Planning is.