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Episodes

Date Title & Description Contributors
2025-02-20

  It’s Time to Leave “Good Enough” Behind

You want to do something new. But there’s a problem: Your current thing is so comfortable. So how do you escape the trap of being too comfortable? How do you overcome the fear of leaving something behind, and move forward? Here’s how: Jason calls it tr...
  Money News Network author
2025-02-18

  How to Craft Cold Outreach That Actually Works

You have to reach out to someone— and they're a big deal. Maybe they run a huge company and would be a life-changing client for your business, or maybe it's the recruiter at a job you really want. Whoever they are, they're important, and you want to ge...
  Money News Network author
2025-02-13

  How to Prevent Miscommunications

You’re being misunderstood. You shared a great idea, or made something wonderful, or told someone something — and they are confused. Now you’re upset. Why don’t they just understand!? But here’s the problem: You started in the wrong place. Jason falls ...
  Money News Network author
2025-02-12

  "Am I the Problem? Why Do People Flake on My Plans? Help!"

Jason and his wife, Jen, keep trying to make plans with another couple— but this couple keeps flaking. Now Jason and Jen are wondering: Do they just not like us? To get some insight, they call up their friend Katie Sturino (body acceptance advocate and...
  Money News Network author
2025-02-06

  How to Make Each Day Count for More

Do you ever feel like time is moving by too fast? Well, Jason has good news: it is possible to create more time… in a way. Today, Jason will explain what that means, why it works — and how this year can be even richer, more memorable, and feel longer (...
  Money News Network author
2025-02-04

  "How Soon Can I Follow Up With a New Business Friend Without Being Weird? Help!"

Jason just had lunch with a professional contact he genuinely clicked with—someone he could see becoming a real friend. But now, he's wondering: Is it too soon to follow up and plan another lunch? If he reaches out now, will he seem too eager... or jus...
  Money News Network author
2025-01-30

  How to Fire Someone — or End Any Project — With Respect and Kindness

You want to end something. But you’re not sure how to tell people. You don’t want to disappoint anyone. You don't want to say the wrong thing… but you do have to say something. Today, Jason will teach you a four-part formula to effectively and compassi...
  Money News Network author
2025-01-28

  "Does Using AI Signal I'm Bad at My Job? Help!"

Today, Jason shares a question that's been stuck on his mind: if someone uses AI in their work, does that signal that they’re not good at it? In other words: does use of AI indicate a lack of natural competency or skill? To get some answers (and maybe ...
  Money News Network author
2025-01-23

  How to Make Space for Your Next Big Opportunity

We often don’t celebrate endings. We think of them as failures or mistakes — as if the end invalidated everything else. But endings can be many things: They’re how we preserve time and energy, how we reach a healthy conclusion, and how we prepare for s...
  Money News Network author
2025-01-21

  “How Do I Market and Position My Work So That People Actually Want It? Help!”

You do awesome work, you just need people to pay you to do it. So now, you need to figure out: how do you describe your work in a way that gets people to recognize that they want, or better yet, need it?  That’s the question that today’s caller, Lisa P...
  Money News Network author