When the check comes at the end of a business dinner, who should pay? The bigger company? Does that even matter? These are the questions on our Executive Producer Morgan's mind after an awkward fumble at the end of a business dinner with a big tab. Jason gives a framework you can use to assess when you should throw your card down, and what to say if you can't.

Jason got a cold DM on LinkedIn that included a common ask that often creates friction. Today, Jason and Nicole call up the guy who made that ask to talk through his networking strategy and give him some tips on frictionless outreach.

You want to do something new... But you’re hesitating, because you’re not sure if it’s the right thing to do. Today, Jason will introduce you to a concept he calls the ticket. It’s a way to stop thinking about what you should do, so you can think about what you can do. And to see how it works, he’ll first tell you about a friend who’s in this situation right now — feeling stuck, at a crossroads, and searching for courage.

Today's caller is fighting with her fiancé; he didn't include her in a business deal, but she feels *strongly* that he should have. Today, the caller is joined by her fiancé to explain the situation so Nicole and Jason can determine which of them is right, and how couples should handle joint opportunities.

You’re trying to do something but don’t have… enough money. Enough time. Enough resources. Enough something. Today, Jason will reveal a resource you didn’t know you have: It’s the stuff all around you — but with a twist.

The Paris Olympics are over, but Jason says that three surprising business lessons from viral Olympics moments live on. Today, he shares those moments with Nicole (and yes, pommel horse guy sleeping is one of them).

If you want to earn people's trust and respect, ask yourself: how are you using their time? Today, Jason explains how he learned an important lesson about other people's time — and how he learned that lesson from an unexpected cautionary tale.

Listener Melissa calls the Help Line today because she's experiencing some analysis paralysis (haven't we all). Jason gives her a formula to help her determine which parts of her work she should change; plus, he shares how to failure-proof her pivot by making it into an experiment.

When we solve problems, we often start with the easiest part… But that’s often the wrong approach. Every big problem has one fundamental challenge — and if you don’t start there, then you’re just wasting your time. We’ll call this thing the monkey. You must know your monkey. Today, Jason introduces you to it.

Today’s caller is watching his company go through a big change... and as a result, his work is feeling less meaningful. Jason and Nicole help him realize that he's been looking for a solution in all the wrong places, and give their tips on how to make your voice heard at work.