Why High Earners Still Feel Broke (And How to Fix It Without Cutting Everything)

Your tax deadline is April 15, right? Not exactly. Matt and I walk through three different “doors” that close at three different times, and the first one may be hiding in your Q4 paychecks. We get into what to check now if you want to max out your 401(k), why late-year withholding can be surprisingly useful if a bonus, RSUs, or capital gains knocked your tax payments off course, and which moves really do need to be finished before December 31. Then there’s the good-news door: a few 2026 contributions can still happen in 2027. The goal here is not to give you more year-end stress. It's to keep you from discovering a deadline after it’s already passed. Find out more about Mike at https://www.mortonfinancialadvice.com and connect at https://www.linkedin.com/in/mwsmorton/

AI feels private, but how much of your financial life should you actually put into a chatbot? Matt and I look at the line between useful context and oversharing, including the information I would keep out of an AI prompt, how privacy settings differ across consumer and business tools, and why anonymizing your question can still get you a strong answer. We also get into the bigger financial risk: AI can sound completely confident even when you forgot to give it the one fact that changes the recommendation. I’ll show you how I use AI as a research assistant, when I stop trusting the chatbot to make the call, and the simple question to ask before a real financial decision leaves the screen and hits your account. Find out more about Mike at https://www.mortonfinancialadvice.com and connect at https://www.linkedin.com/in/mwsmorton/

Free $1,000 for your child sounds like an easy yes. But should you put another $5,000 into a Trump Account, or would that money work harder somewhere else? Matt and I break down who gets the free money, what these new accounts can and can’t do, and where they belong alongside your retirement savings, 529s and Roth IRAs. Plus, I share a tax strategy that could turn a decent benefit today into a much bigger opportunity for your child later. Find out more about Mike at https://www.mortonfinancialadvice.com and connect at https://www.linkedin.com/in/mwsmorton/

An LLC and an S corp are not the same thing, and confusing the two can leave you paying for complexity you don't need. Join me and Matt this week as we break down what an LLC actually protects, why it doesn't automatically save you money on taxes, how an S corp election works, and the surprisingly complicated math behind those promised tax savings. We also walk through the roughly $100,000 profit threshold where an S corp becomes worth investigating, the QBI and Solo 401(k) gotchas that can change the calculation, and a simple way to figure out whether your business has actually reached the point where any of this is worth your time. Find out more about Mike at https://www.mortonfinancialadvice.com and connect at https://www.linkedin.com/in/mwsmorton/

Everyone told you to keep three to six months of expenses in cash. That number hasn't aged well. This week Matt and I break down why the old rule is broken, the two-pile system that stops you from lying to yourself about what's actually an emergency, and the floor times runway formula I use instead of a flat multiplier.