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Most people don’t retire poor because of the market. They retire poor because of a few small habits that never felt like mistakes at the time.

In this episode, I go through five of them: the raise that disappears, the 401(k) cash-out when you change jobs, the permanent car payment, debt that follows you into retirement, and the open checkbook for grown children. I also share one simple rule that keeps all five from happening to you.

Nobody offers a retirement loan, so it pays to get this right early.

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The safest investment in America has a government guarantee, a pen on a chain, and an interest rate of one percent. I explain what that guarantee actually promises (your dollars, not what they can buy), why an account can go up while you get poorer, and why the fear of losing money in stocks is real but aimed at the wrong target.

You don't have to get over your fear. You just have to match the money to the time. Money you need soon gets a boring, safe home. Money you won't touch for years gets a job.

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You saved for forty years. You avoided the stinkers. You bought the index fund and left it alone. Then you retired, and the fear showed up anyway: "When will I run out of money?"

In this episode, I explain why that fear hits hardest after the paychecks stop, even for people who did everything right. Nobody can tell you the date, but you can build a system that keeps you from being forced to sell in a bad market. I walk through how to give yourself a paycheck again, why a cash cushion matters, and why you should decide your bad-year rules before the bad year arrives.

You may not get certainty, but you can get shorter phone calls.

If you'd like to comment on this episode, or request a subject for a future podcast, leave me a message in Fan Mail. I read every one.

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Retirement planning doesn't need a spreadsheet with forty variables. It comes down to about five numbers, and you can work them out on the back of an envelope.

In this episode, I walk through what you spend, what's already guaranteed, and how to find your gap. I also show what waiting ten years to start saving really costs, and the one place where waiting actually pays you.

Your assignment is one envelope and about ten minutes.

If you'd like to comment on this episode, or request a subject for a future podcast, leave me a message in Fan Mail. I read every one.

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What are you actually buying? If your answer is a ticker symbol, a tip from your brother-in-law, or a stock that "used to be forty dollars," this episode is for you.

Ben Graham's idea was simple: a stock is a piece of a real business, and price is not the same thing as value. In this episode, I explain why that difference matters, how cheap stocks turn into value traps, and why the market's bad days are usually mood, not business.

I'll also tell you about a retired schoolteacher who came to my office with a highlighted newsletter and a very strong stock tip, and I'll give you the one-sentence test to use before you buy anything.

You don't have to pick stocks to think like a value investor. You just have to know what you're paying for.

Have a comment or a topic request? Leave me a message in Fan Mail. I read every one.

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Ben Graham never met a modern index fund, but I think he would have liked it. In this episode, I look at what Graham asked of the defensive investor and see how the S&P 500 measures up. I also tell you about a client who just couldn't leave a good thing alone, and I explain why Graham would still ask the question that matters most: what are you paying? If you'd like to comment on this episode or request a subject for a future podcast, leave me a message in Fan Mail. I read every one.

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Margin of safety sounds like a complicated investing term, but the basic idea is something we use every day. We leave early for an appointment, keep extra money available for an unexpected expense, or allow some room for a mistake when making an important decision.

Investing is no different.

In this episode, I explain margin of safety in plain English and show why investors should not build their financial future on the assumption that everything will go exactly as planned. Stock prices can fall, companies can disappoint, and our estimates can be wrong.

The goal isn't to predict the future perfectly. It's to leave yourself enough room to be wrong without letting one mistake become a financial disaster.

A simple idea that can make a big difference in how you think about investing.

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The market drops, the headlines turn red, and every instinct in your body says get out. In this episode I break down why selling at the bottom feels like survival — it isn't — and share Ben Graham's take on why the market's mood swings have nothing to do with what your investments are actually worth. More importantly, I'll walk through exactly what to decide today, while you're calm, so you're never making that call on the day you're not.