Help Wanted

Jason reaches into the mailbag and selects two questions. One from someone about just starting out, one from someone figuring out what comes next.

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.

When we want someone to trust us, the instinct is to present ourselves as the perfect fit. But what if that's actually the thing that's making people skeptical? Jason shares the time-tested but counterintuitive tactic he uses in his own business.

The boom of online courses, coaching and consulting has opened up a new revenue stream for anyone with a teachable skill. This is all fun and games, until you get to the little detail of pricing. How do you set a price on… yourself? That’s the question that made listener Kelsey call the Help Line. To give her the cheat code on pricing strategy, Nicole and Jason phone a friend who knows the course landscape inside and out: Matt Gartland, CEO at Smart Passive Income Media. For more Matt, check out all things SPI: https://www.smartpassiveincome.com/ Originally aired in 2024

You’re ready to move on from something— but you’re struggling to leave. You keep asking yourself, “Is this worth staying for?” Today, Jason will help you answer that question. And he starts with his own version of this problem. Are you ready to meet Drunk Party Jason?

Do you have a sneaking suspicion your coworker is mad at you? At best, this feeling can darken your day. At worst, this feeling can turn your workplace into a toxic environment. Jason and Nicole tell you how to handle this hunch, using a very personal example: a time Nicole thought Jason hated her! Originally aired in 2024

Someone upset you and you wanna respond immediately. But Jason's learned that your short-term impulses rarely serve your long-term needs. Today he shares a framework that's helped him navigate moments of stress more effectively and shows you why the most satisfying response is rarely the smartest one.

What happens when you hire someone, and they charge way more than you expected? That happened to our caller, Kassi Underwood, whose babysitter handed her a steep bill. (So steep, a screenshot of it went viral on LinkedIn!) Jason and Nicole give advice on how to course-correct, and how to prevent making this big mistake in the first place. Originally aired in 2024

We’ve all held back from asking for what we wanted and ended up feeling hurt. But what you might not realize is that it's also hurting your potential partnerships. To ask Jason and Nicole for help on the show, just fill out this form!

Nicole recently almost did a deal with one of her friends... until that friend pulled out of the deal. Now, Nicole has an emotional email sitting in her drafts: should she send it? Today, Jason shares the thought exercise he applies before sending any email he's not sure about.

Got a question for Jason and Nicole? Fill out this form, and they might answer it on air. If you’re the kind of person who says yes to everything and is now exhausted because of it, this episode is for you. Jason breaks down a simple, practical way to decide what’s actually worth your time, and what you need to let go of so you can make room for growth elsewhere.

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.

We all want things we think we can’t have. But until we try, how do we know what’s possible? Like asking Nicole and Jason your work questions directly! Just fill out this google form to have your question answered on the podcast.

When a friend asks for help—but hasn't exactly returned the favor in the past—what do you do? Today, Jason and Nicole unpack the emotional and professional layers of helping people who haven’t helped you back—and how to make peace with whatever you decide.

When someone asks, “So… what do you do?” do you have an answer that actually opens doors or one that trails off into confusion? In this episode, Jason shares a simple framework that helps you explain your value clearly and confidently.

You’ve heard Jason coach Nicole on LinkedIn — now it’s Nicole’s turn. In this episode, she pulls back the curtain on the strategy, content experiments, and psychological triggers that helped her nearly double her Instagram audience in 2025.

Each year, Jason looks back at what people were predicting about the future 100 years ago. In this episode, he picks three of his favorite predictions from 1926 and breaks down what they can teach us about our own vision of the future.

Nicole had two podcast guests cancel on her recently: one gave her TMI, the other essentially ghosted her. Today, Nicole and Jason give you the script to cancel respectfully.

Welcome to 2026! In this episode, Jason celebrates a milestone in his parenting and uses it to explore a bigger idea. The most important changes in our lives and careers rarely announce themselves. They happen quietly, without clear finish lines or moments of celebration. To kick off the New Year, this is an invitation to pause, look back, and recognize the progress you have already made. Even if it felt like just another day at the time.

Today, Jason and Nicole dig into two stories that seem very similar. Both stories center on couples who are fighting because one spouse makes more than the other— but the premise of the individual fights are very different. Jason and Nicole play Judge Judy and give their verdict on which spouse is right— and share their advice for couples navigating the emotional side of a pay disparity.

Jason skips resolutions and picks a theme instead. In this episode, he shares the simple year-end ritual he uses to set direction without boxing himself into narrow goals. He explains how it works and how you can choose a theme that actually sticks.

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.

Most of us avoid asking for help because we don’t want to be a burden. But what if that instinct is actually wrong? Today Jason explains the secret psychology behind why asking for help could just be the best thing for our relationships.

If your boss is a nightmare... do you stay or do you go? Nicole and Jason can help you answer this by going through one simple thought experiment. But first, they each share the most ridiculous thing a boss has ever asked them to do. And in Nicole's case, it involves being sawed in half…

Today, Jason shares a strategy that will help you do the thing you’re afraid of. To start, he’ll show you how this helped a friend who’s been afraid of starting a new project.

Today's caller has a problem: ever since she was promoted, her coworkers— who now report to her— have been giving her the cold shoulder and stalling on their deadlines. Today, Jason and Nicole help her plan a conversation that will repair the relationship, which hinges on an often overlooked superpower in leadership.

You have the right stuff: You’re talented, smart, and good at what you do. But the right people aren’t noticing. So here’s a difficult truth you must take seriously: you are a high-quality person, but you can’t compete on quality alone. Today, Jason shows you how to get noticed another way.

Nicole knows LinkedIn is a good tool for advancing her work, but when it comes to using that tool effectively? She's stumped. For anyone who can relate, Jason (a LinkedIn Top Voice!) gives his proven formula for writing an engaging LinkedIn post that will grow your network.

Kaitlyn Allen, a reader of Jason’s newsletter, writes in because her start-up is closing. Instead, she shared something far more surprising and far more useful. In this episode, the conversation instead highlights an empowering way to turn fear of failure into something else. Something that can power your next big innovation.

When someone says something nice, do you have a hard time just saying thank you? Yeah, so does Nicole. In this episode Jason and Nicole dig into why it can be so hard to just say “thank you” and actually enjoy praise. They break down awkward deflections and why your first instinct may be to downplay your own wins. If you’ve found yourself saying “Oh no, stop!” This episode is for you!

Who actually wants the work you put into the world and how do you know whose work is worth listening to? This week, Jason opens the mailbag to take on both sides of that puzzle. From standing out in the noisy world of creators, to reentering the workforce with confidence, to figuring out whose advice is actually worth trusting, Jason breaks down the real questions behind the questions - what work matters and why?

One in three people admit that they've felt like their partner was holding them back. If you've found yourself in that situation, what should you do? Today, Jason and Nicole talk about times they've felt like they've downplayed their achievements to loved ones, and what that has meant for the future of the relationship.

What do The New York Times and Notion have in common? A lot more than you’d think. They’re both proof of a pattern that quietly runs the world. Once you see it, you can’t unsee it. Suddenly, change makes more sense, opportunities reveal themselves, and that next move you need to make might just become obvious.

In case you missed it, New York Times Opinion released a video originally titled, "Did Women Ruin the Workplace?" that featured a debate on the different qualities men and women bring to the workplace. Today, Jason and Nicole are NOT debating that, because they are in agreement: women did not ruin the workplace. Instead, they explore how deeply leaders should engage with their team’s personal lives, and Nicole reflects on her own experiences navigating gendered expectations in leadership.

We all have something we’re bad at. But maybe that’s not the problem. In this episode, we explore how your weaknesses might actually highlight your greatest strengths. Discover why focusing on fixing your flaws may not be the best use of your energy and where you should be spending your time instead.

Today's caller is a personal trainer who wants help growing her social media audience so that she can find new clients. Jason and Nicole tell her she's looking for the solution to her problem in all the wrong places. Instead, they give her the client acquisition cheat code that anyone can use at home.

Someone once told you to reach out, and you meant to. You thought about it, replayed the conversation in your head, and then never did it. In this episode, Jason explains why we hold ourselves back and what happens when we finally follow through. The correct follow-up can open doors.

Is the "work wife" and "work husband" culture inappropriate? Today, Jason and Nicole untangle a viral Reddit "work wife" story gone wrong and weigh-in on whether they think the "work spouse" nickname should get fired.

Jason asked his readers one question: What do you regret most? And the answers poured in. This week, Jason shares some of those stories not to dwell on the past, but to help us all feel a little lighter about it. From missed opportunities to money mistakes to “what if” moments, this episode breaks down five powerful strategies for handling regret and turning it into forward motion.

There are some bizarre headlines making the rounds in business news... but, beyond the headlines, there are some important lessons on the line between building buzz and eroding trust, how to find meaning in your work, and brand integrity. Today, Jason and Nicole mine those lessons from the weirdo headlines.

Do past mistakes keep you up at night? They used to haunt Jason, too. That is, until he discovered a surprising way to shrink regret down to size. In this episode, he shares how to stop replaying the “what ifs” and start feeling lighter about the choices that got you here.

So you want to (or have to) bootstrap your business. Nicole is self-funding the business that makes this very podcast, and she will tell you: it is not easy. To share best-practices around protecting your bottom line and mental health, Nicole and Jason are joined by Christina Stembel, who has self-funded her business Farmgirl Flowers. Learn more about Christina and her biz here: https://farmgirlflowers.com/about Originally aired on 06.19.2024

Want to live a life you’re proud of at 90? Start saying yes. In this episode, Jason shares the essay that changed his perspective forever. (Click here and scroll down to see the very awkward photo of him at 22 that proves he actually practices what he preaches.) Because yes may feel risky or even cringe, but it’s also the only way to build memories, create opportunities, and discover what you’re truly capable of.

Today's caller is ambitious, but every time she wants to level up, she questions whether she deserves it. Jason and Nicole share the mental exercise that stops imposter syndrome in its tracks.

Jason sat down with Shark Tank’s Robert Herjavec and learned a sales technique so simple and so unexpected that it can change the way you pitch, present, and connect with anyone. He unpacks how it works, why it’s unforgettable, and how you can use it everywhere in your life. You may even find the results shocking.

Today, Jason and Nicole dissect a real cold email their Producer Morgan received— and it's not pretty. They talk about what went wrong, and how to write an email that people actually respond to.

Big decisions can feel paralyzing because we treat every choice like a lifelong commitment. But what if you stopped thinking in terms of permanence, and instead saw each new step as an experiment? Suddenly, risk becomes data, failure becomes progress, and every move teaches you something useful.

Today, Nicole and Jason are tackling a question that parents are increasingly struggling with: is it bad to post photo of my kids online? Nicole has decided not to post photos of her daughter, but Jason has a framework that helps him determine what's appropriate to post. Would you follow this framework? Listen to find out! Listen to the Money Rehab episode on the risks of posting photos of your kids online.

When failure happens, what happens next? In this episode, Jason shares a simple way to reframe setbacks so they feel energizing instead of defeating. Through stories from the business world and his own career, he shows how to turn every failure into progress and keep moving forward.