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.

This one gets deep. Nicole kicks things off with a provocative question: throughout Jason’s career in journalism, has he seen anyone successfully get a story about themselves erased from the internet? The question turns into a vulnerable conversation about whether the internet is forever, how we can feel a sense of control over the uncontrollable, and what is the price of reputation.