Investing
9 viewpoints on this topic. ← All viewpoints
Investing essays here focus on the small set of decisions that actually move long-term outcomes: asset allocation, fee structure, fund selection inside a 401(k), and the trade-offs between simplicity and optimization. There is intentionally no commentary on the market this week and no predictions about the next twelve months. The viewpoints below assume you already know that's not the game worth playing.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Most investing edge for individual investors comes from removing self-inflicted damage, not from picking winners. These essays cover the structural choices — fees, allocation, taxable-vs-tax-advantaged location — that compound over decades and almost never come up in a market headline.