535 | The Top 10 Ten Investing Mistakes We All Make

Most investors — even sophisticated ones tracking every basis point — leave real money on the table through simple oversight. Cody Garrett, CFP® at Measure Twice Money, recently outlined ten mistakes that trip up DIY investors and financial advisors alike. Brad and Cody walk through each one, from asset location missteps to overlooked HSA opportunities, with a focus on making optimization practical rather than theoretical. Timestamps & Key Points [00:01:50] Asset Location Where you hold investments matters as much as what you hold. Stocks generate capital gains and qualified dividends taxed at lower rates, making them better suited for taxable accounts. Bonds produce ordinary income taxed at your marginal rate, so they belong in tax-advantaged accounts like IRAs. Getting this backwards can cost thousands annually in unnecessary taxes. [00:15:46] Investing Contributions Log into your accounts and confirm contributions are actually invested. Cash sitting uninvested earns nothing. Enable auto reinvestment for dividends and capital gains distributions so you're not manually managing every transaction. [00:20:29] Return on Hassle Chasing an extra 0.5% APY by constantly switching high-yield savings accounts rarely justifies the time spent. Compare the hours invested against the actual dollar savings. Often, fixing asset location or maxing an HSA delivers far greater returns for less effort. [00:24:14] Charitable Giving Donating appreciated securities directly to charity eliminates capital gains tax while you still receive the full fair market value deduction. Donor advised funds allow you to bunch multiple years of donations into one tax year for additional tax benefits. [00:33:01] Family Giving Distinguish between "oops money" (emergency support) and "ooh money" (wealth transfer). Consider whether financial help is better given now when children need it most, or later through inheritance when they may be financially stable. [00:39:23] Maximizing HSA Contributions HSA contribution limits change annually. Verify both your contributions and employer contributions don't exceed the current limit. An HSA is the most tax-advantaged account available — triple tax benefit — so maximize it if eligible. [00:41:38] Understanding IRMAA Income-Related Monthly Adjustment Amounts increase Medicare Part B and D premiums based on income from two years prior. Planning Roth conversions or other income events requires awareness of IRMAA thresholds to avoid unintended premium increases. [00:43:02] Early Retirement Concerns Don't let health insurance costs delay retirement. With strategic income management, many early retirees qualify for subsidized ACA marketplace plans with low or zero premiums. Model your expected income and explore options before assuming coverage will be prohibitively expensive. [00:47:25] Retirement Order of Operations Develop a tax-optimized withdrawal strategy. Generally: spend taxable accounts first while doing Roth conversions, then tax-deferred accounts, then Roth accounts last. Your specific situation may vary based on pension income, Social Security timing, and legacy goals. [00:52:25] Holistic Wellness Financial optimization means nothing without mental health, strong relationships, and physical wellness. Don't sacrifice life experiences or relationships chasing marginal financial gains. Maintain perspective on what truly matters. Action Items Review asset location to ensure stocks are in taxable accounts and bonds in tax-advantaged accounts (00:01:50) Enable auto reinvestment for dividends in your brokerage account (00:17:57) Evaluate the actual dollar savings versus time spent when considering account switches (00:20:29) Maximize HSA contributions according to current limits (00:39:20) Consider donating appreciated securities instead of cash for charitable giving (00:25:27) Related Resources Measure Twice Money Advice Only Network Nectarine Quotes to Remember "Optimize your taxes, don't sacrifice growth." (00:15:27) "Is t…