Jeff Judge Jeff Judge
PLAIN-ENGLISH FINANCIAL PLANNING AND ADVICE FOR BUSY PROFESSIONALS
Topic Archive

Investing

9 viewpoints on this topic. All viewpoints

01
Investing May 10, 2026 6 min

Why your average return doesn't determine whether your retirement lasts

Everyone focuses on average returns. Nobody runs the scenario where the bad years arrive first. Here's why sequence of returns risk is the variable that actually determines whether your retirement holds.

02
Investing Apr 26, 2026 6 min

The 401(k) secret your plan administrator isn't going to volunteer

The funds in your 401(k) didn't get there by accident. Here's who chose them, why, and what that arrangement is costing your balance.

03
Planning Mar 29, 2026 6 min

Is the cash in your retirement account actually costing you money?

Cash in a retirement account feels safe. But every dollar of it carries a locked-in tax liability and a compounding opportunity cost. Here's what it's costing you.

04
Planning Mar 1, 2026 5 min

The "good enough" portfolio: why your second-best allocation usually beats your first.

Optimization is seductive, but the portfolio you'll actually stick with through three bad quarters beats the one that looks perfect on paper. A practical case for boring, durable allocation choices.

05
Investing Feb 1, 2026 6 min

Roth conversions in your sixties: the four-question filter I use before I touch one.

Half the Roth-conversion advice on the internet is built for the wrong client. Before you convert a single dollar, here are the four questions that decide whether the math actually works for you.

06
Investing Nov 23, 2025 4 min

Why age-based asset allocation is mostly wrong for high earners

The formula says your equity allocation should shrink every year you age. For many high earners, that's backwards.

07
Investing Sep 28, 2025 4 min

Stop optimizing your asset allocation. You're solving the wrong problem.

You're spending time optimizing your asset allocation when the real money is sitting in your fee structure. Stop optimizing the wrong thing.

08
Investing Sep 14, 2025 4 min

Diversification doesn't protect you from the risk that matters most

Diversification is the right tool. Applied as a religion, it stops protecting you and starts limiting you. Here's what it actually does and doesn't do.

09
Investing Aug 31, 2025 5 min

What target date funds don't tell you about your 401(k) allocation

Target date funds are designed for the median 401(k) participant. If you have a complex financial picture, you may not be the median participant.