Retirement Planning

From “I’m ready” to “is my plan crisis‑proof?” So, picture this: you’ve circled a retirement date, the spreadsheet says you’re fine, and markets aren’t melting down. Then unemployment jumps. Suddenly the plan that felt sturdy in calm waters starts to wobble a bit. Not because your portfolio cratered, but because the world around it shifted, job options thin out, healthcare gets pricier without employer help, and withdrawals you thought were optional become mandatory. Timing matters, and in 2025 the labor market isn’t the layup it was a couple years ago. Here’s the before-and-after most people underestimate: before a layoff cycle,…

What pros wish every retiree knew about hedging Look, options in retirement are not lottery tickets. They’re insurance. The point isn’t to “hit it big,” it’s to make sure a bad quarter doesn’t force you to sell stocks at the worst moment just to fund next month’s grocery run. Think of puts and collars as the umbrella you buy when the sky looks perfectly fine, because the best time to get protection is before everyone else realizes it’s raining. And yes, I’m saying now, while markets are still functioning, spreads are tight, and volatility isn’t screaming. Here’s the thing: hedges…

What most pros wish everyone knew about IRAs and “use” So, here’s the thing: IRAs are tax shelters first, everything else second. They were built to let gains compound without annual tax drag, not to let you borrow against your portfolio like a hedge fund. That single design choice explains almost all the confusion around “margin” and options in retirement accounts, especially in 2025 when broker marketing sounds aggressive but the fine print is still, well, fine. The legal anchor is dry but important. Internal Revenue Code §4975 treats borrowing in an IRA as a prohibited transaction. No loans to…

How pros think about options inside a Roth So, here’s the thing: smart investors don’t open a Roth IRA and start swinging for the fences with options. They use options to tilt the odds, measured risk, clear purpose, brutally simple rules. If you’ve googled “can-i-trade-options-in-a-roth-ira,” you’re already asking the right question. The answer is yes at many brokers, but the way pros approach it is boring-on-purpose. And boring is good when every dollar grows tax-free. What you’ll get from this section: how to use options to improve outcomes, not to gamble. We’ll set up a simple playbook that treats your…

Everyone’s Using Margin, But Not in Their IRA Look, margin is having its perennial moment again. Investors see stocks grinding near highs earlier this year, AI names running hot, and they want to, you know, press the gas. Quick reality check: FINRA-reported margin debt hit about $935 billion back in 2021, that was the record. It pulled back in 2022 and has bounced around since. The point is simple: borrowing against your portfolio is common in taxable brokerage accounts. But inside a retirement account? That’s where dreams of “juicing returns” usually hit the rulebook. In 2025, most big brokers still…

No, market returns aren’t the only thing, your job security matters, a lot Look, I love talking about market returns as much as the next Wall Street lifer, but the thing most FIRE plans gloss over is brutally simple: your timeline lives or dies on whether you keep getting a paycheck. Not just the S&P’s next 10% swing. When unemployment rises, it messes with your savings rate, your contribution schedule, and the sequence of cash flows you need before you retire, and sometimes after if you’re easing into part-time work. That’s not theory; that’s cash hitting (or not hitting) your…

What pros wish you knew: housing and taxes beat latte math Here’s the thing: the hard part about the “retire-in-high-cost-city-or-work-longer” question isn’t whether you can shave $80 a month by skipping cappuccinos. It’s whether your fixed costs and your withdrawal rate can take a punch when markets have a bad couple of years. Look, I get it, New York, San Francisco, Seattle, Boston, pick your pricey zip code, there’s family, friends, routines. But pros start with the bills that hit your account every month no matter what and then ask, “If the market stinks early on, do we still make…

What pros wish you knew about the “4% rule” in pricey cities Look, the classic 4% rule was built on a perfectly average America that, let’s be honest, doesn’t look like Manhattan, San Francisco, LA, Boston, or Seattle. The original research (Bengen, 1994; then the Trinity Study, 1998) used broad U.S. historical returns and nationwide inflation. It never assumed $4,000-plus rents, Bay Area property tax bills that make your eyes water, or Medicare premiums plus city-level surcharges nibbling at your cash flow. So, the 4% rule is a decent national benchmark. It’s just not a plan if your monthly “fixed”…

What the pros do when jobs get shaky Look, when unemployment starts creeping up and headlines get noisy, as they have in pockets of the market this year, seasoned folks don’t slam the retirement button. They widen the margin of safety first. It’s not flashy, but it works. Think: more cash on hand, slightly lower baseline spending, and tighter risk controls before making anything irreversible like filing for Social Security. If you’re Googling “should-i-delay-retirement-amid-rising-unemployment,” you’re asking the right question. Here’s the thing: pros assume bad news travels in packs. A layoff doesn’t always show up alone; it loves to bring…