Ask Tim: I Won $2M But My Ex-Wife Wants a Cut
If Chicago fails to convince you spring is right around the corner, I can assure you: Chicago is miserable until like May. March shows up acting optimistic, then the wind cuts through your coat like Edward Scissorhands. April flirts with 60 degrees for eight minutes, then disappears. So you stay inside, which turns you into […]
12 Ways High Earners Avoid Tax Surprises
April turns plenty of smart people into sprinters. The calendar gets loud. The inbox gets louder. A tax return becomes a race instead of a review. High earners pay for speed. Multiple income streams create multiple places for tiny errors to hide. A missing form. A cost basis hiccup. A withholding gap that looks harmless […]
Market Flash: Iran War Fears Has Investors Pressing Sell Button
U.S. equities sold off hard this morning as the Iran conflict escalated and shipping risk in the Strait of Hormuz jumped from “headline noise” to “macro variable.” The S&P 500 slid ~2% on March 3, volatility popped, and the market’s reflex was classic: sell cyclicals/growth, buy energy exposure. Ask airlines how that’s going.
Is Disability Insurance Necessary if You Have Significant Savings?
Probate is the legal process of validating a will and distributing property after death. Courts supervise the procedure to ensure debts are settled, heirs are identified, and instructions in the will are carried out. If no will exists, state law decides how assets are divided. While probate provides order and oversight, it often creates delays […]
How Much Can You Withdraw in Retirement Without Running Out of Money?
Retirement today lasts longer than ever. For many Americans, it spans thirty years or more, stretching across multiple market cycles, tax regimes, and phases of life. What once felt like a simple question — “How much can I withdraw each year?” — now invites a complex answer.
Ask Tim: Paying Off the Mortgage Before Retirement?
If you live in the Northeast, you already understand this truth: winter has a way of turning regular life into a budgeting exercise. One week you are cruising through your routine, and the next you are staring at a driveway that looks like a small ski resort. Big snow has a funny side effect. It […]
Market Flash: Tariff Whiplash, AI Anxiety, And Oil’s Comeback Tour
U.S. equities started the week getting slapped around by a twin headline: tariff uncertainty and a fresh wave of “AI disruption” nerves. Monday’s selloff bled into broad risk sentiment, then Tuesday saw a rebound led by software and mega-cap tech as investors rotated back into “AI winners.”
Quick Answers: How Much Life Insurance Do You Actually Need?
Life insurance is about protecting the people who would feel the impact of your absence. And while every family’s needs are different, there are a few reliable frameworks that help you land on a clear, defensible coverage amount.
Ask Tim: My Kid Might Get Paid to Play College Football… and I’m Afraid We’re About to Screw This Up
Every so often, a “money question” shows up wearing a disguise. It looks like a sports decision. Or a prideful decision. Or a family decision. And then — quietly — it becomes a tax decision, a contract decision, and a long-term planning decision.
Market Flash: Cooler CPI and a Consumer That’s… Just Fine
U.S. equities returned from the long weekend. Futures were down — the S&P 500 fell ~0.8% and the Nasdaq fell ~1.2% with the day’s narrative driven less by a macro shock and more by renewed concern about AI-driven disruption and crowded positioning in the same names that have carried performance.