Essays

Design the Decision Before the Deadline Many financial decisions do not feel large until they are already urgent. A student loan repayment plan needs to be selected. A lease is ending. A job offer arrives. A house becomes available. A child is on the way. A car needs to be replaced. An insurance enrollment window … Read more

Your Portfolio Is Bigger Than Your Investments Ask someone to describe their portfolio, and they will usually start listing investments. They might mention a 401(k), 403(b), Roth IRA, brokerage account, or a few stocks they own. They may describe how much is invested in stocks, bonds, or cash. If they are especially engaged, they may … Read more

Every Account Needs a Job For high-earning professionals, it is surprisingly easy to accumulate financial accounts without building a financial system. A new employer offers a retirement plan, so an account is opened. A bank advertises a high-yield savings account, so money is moved there. Someone recommends a Roth IRA, so one is created. A … Read more

Cash Flow Comes Before Investing A lot of people want to talk about investing before they know what their money is actually doing each month. It’s understandable because investing feels productive. It feels grown-up. It feels like the part of personal finance where smart people are supposed to spend their attention. For pharmacists and other … Read more

Observation DRIP is usually presented as one of the simpler investing decisions. If an investment pays a dividend, the dividend can either sit as cash or be automatically reinvested back into the same investment. For many investors, the default advice is straightforward. Turn DRIP on. That advice makes sense. Automatic reinvestment helps avoid idle cash. … Read more

Observation A lot of personal finance advice sounds simple because it is repeated so often. Pay off debt before investing. Always take the employer match. Never hold too much cash. Use a target-date fund. Buy the S&P 500. Max the Roth IRA. Each rule has a reason behind it. That is why it gets repeated. … Read more

Observation Some financial rules get repeated so often they begin to sound almost unquestionable. “Always take the employer match” is one of them. And to be fair, the rule is usually correct. A workplace retirement match is one of the few financial benefits that feels obviously valuable. An employer offers additional money simply for contributing … Read more

Observation A common idea in personal finance is that small amounts don’t matter as much. Focus on the big decisions.Income. Housing. Debt. Everything else is secondary. It sounds reasonable. If something is small relative to your income, it shouldn’t have a meaningful impact. And in isolation, that’s usually true. An extra few hundred dollars in … Read more

Observation The Trojan Horse is usually described and remembered as a clever strategy. A hidden attack. A moment of deception. But the more you think about it, the less interesting the strategy becomes. The more interesting question is the decision. At some point, the people inside the city of Troy were looking at something that … Read more

Observation One of the most widely repeated rules in personal finance is simple. Pay off debt as quickly as possible. The advice sounds responsible. It sounds disciplined. It sounds safe. Being debt-free is often described as a milestone of financial success. Many people treat the elimination of debt as one of the primary goals of … Read more