questions

I'm 60 with $250K saved and $1,800 in monthly expenses. Can I afford to retire at 65?

You’re 60, you’ve got about $250K saved, and your monthly expenses run around $1,800. Now you’re wondering: will that be enough to retire at 65? The truth is...it depends. Retirement isn’t just about your savings; it’s about how income, expenses, and lifestyle all fit together. So, let’s break it down carefully.
August 29, 2025 Jesse Singer

My boss made me share a hotel room with him on a business trip “to save money.” I felt uncomfortable and unsafe. What are my options?

Your boss says you have to share a hotel room on a work trip “to save money.” Now you’re imagining awkward silences, zero privacy, and possibly unsafe situations. No, you’re not overreacting—your comfort and safety matter. Here’s how to figure out your options, protect yourself, and set clear boundaries without torpedoing your career.
August 26, 2025 Jesse Singer

My boss insists on being called “Captain” and ends meetings with “Dismissed!” Is this a hostile workplace?

Look, sometimes bosses exhibit unusual behaviors—and if your boss insists on being addressed as "Captain" and ends meetings with commands like "Dismissed!", it makes sense that you might wonder if this crosses the line into a hostile work environment.
July 31, 2025 Jesse Singer

My boss told me he “feels my aura is off” and put me on unpaid leave until I “re-center.” Is that legal?

If your employer says your “aura is off” and puts you on unpaid leave until you “re-center,” you’re right to wonder if it is legal. So, let’s break it down so you understand your rights, what to ask, and how to respond.
July 30, 2025 Jesse Singer

My boss sends daily shirtless selfies titled “Motivation.” HR says it's “harmless.” What can I do?

Getting shirtless selfies from your boss every day—titled “Motivation”—isn’t very unprofessional, uncomfortable and possibly even unethical. And it’s even worse when HR brushes it off as “harmless”.
July 28, 2025 Jesse Singer

I maxed out 7 credit cards to fund my startup. Now I can't even afford ramen. Help?

You maxed out multiple credit cards chasing your startup dream—and now you're broke and living on fumes. Plenty of successful entrepreneurs have hit this exact same wall. What matters now is what you do next.
July 24, 2025 Jesse Singer