Jesse Singer articles

You walk into a casino hoping for a lucky night. But while you might know that the IRS wants its share when you win, the bigger question for most of us is: can we write it all off when we lose? The answer is more complicated than most gamblers realize.

The lawyer told them they might not need a traditional will at all. All they need, he says, is something called a 'Lady Bird' document. That sounds simple enough—but is it really? And should they take that advice?

Retirement advice has a way of making people panic. One minute you’re minding your business, and the next you’re hearing about some “Rule of 173” that supposedly everyone else learned 20 years ago. So, are you too late?

You don't mind pulling your weight. But somewhere along the way, it started feeling like you're pulling everyone else's too. The laundry keeps piling up, the floors aren't cleaning themselves, and every conversation about hiring help seems to end before it begins. Is this just one of those annoying marriage problems everyone deals with—or is something bigger going on?

In 2026, scams don’t always come from sketchy emails or obvious strangers anymore. Sometimes they sound trustworthy. Sometimes they feel urgent. And sometimes they look so real that even careful people fall for them.

You finalized your divorce, split the finances, and thought that chapter of your life was finally over. Then your parents passed away and left you a large inheritance. Now your ex-wife is suddenly taking you back to court asking for more alimony. It sounds ridiculous at first…but family court does not always work the way people expect.

Losing parents is already emotional enough. But when there’s no will involved, families often discover they all have very different ideas about what inheritance law is “supposed” to look like. Is the oldest child really first in line?

You hit the jackpot. Life-changing money. But then reality kicks in—if you’re in the U.S., a big chunk disappears before you even see it. Meanwhile, Canadians keep everything. So what’s the deal with that?

It sounds completely backwards. You earn a solid middle-class income and see a big chunk go to taxes every year. Then you hear that one of the richest people in the world is paying a much lower percentage. Is it true? Is it fair?