When Dalip Singh became taxi driver in New York City, he thought it’d be his ticket to the middle class. It would take years before he discovered that he’d instead bought into a massive lending scam, one that would go on for decades, pushing him and thousands of other drivers into extreme debt. Now, as Dalip and his family try to get ahead, they find themselves struggling against the exact systems they thought were meant to help them.

“This Is Uncomfortable” is Reema Khrais, Donna Tam, Megan Detrie, Peter Balonon-Rosen, Camila Kerwin, Phoebe Unterman, Marielle Segarra and Serena Chow

When you’re a kid, your parents make all the financial decisions for you. But what happens when you grow up … and don’t agree with their choices?

We’re off this week for the Thanksgiving holiday. This episode originally aired in July 2019.

This week, we’re running a story from our colleagues at the new Marketplace podcast “How We Survive.” It’s about the climate, but it’s not all doom and gloom. It explores solutions for avoiding some of the worst effects of the crisis.

If you liked this story, be sure to follow “How We Survive” wherever you get podcasts.

When Sonia Delgado divorced her husband after 30 years of a bad marriage, she thought she’d finally seized financial freedom. She’d no longer have to go along with her ex’s money decisions, which had landed them in chronic debt and insecurity. But when she learned she would have to pay him alimony for the rest of her life, it was as though the divorce had tethered her, once and for all, to everything she wanted to leave behind.

If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter. Each Friday you’ll get a note from Reema, Uncomfortable videos and some recs from the team. If you missed it, here’s the latest issue.

“This Is Uncomfortable” is Reema Khrais, Donna Tam, Megan Detrie, Peter Balonon-Rosen, Camila Kerwin, Phoebe Unterman, Marque Greene and Serena Chow.

Matthew Chow spent his adult life trying to build a close relationship with his estranged father. But just when he felt like he made real progress, his father passed away. In the will he found a secret his father had kept buried for decades — one that sent Matthew on a monthslong journey that  changed how he thought about not only his father, but the very idea of family.

If you liked this episode, share it with a friend. And to get even more Uncomfortable, subscribe to our newsletter. Each Friday you’ll get a note from Reema, Uncomfortable videos and some recs from the Uncomfortable team. You’ll also be the first to hear about our new season. It’s all exclusively for our email list, so don’t wait! If you missed it, here’s the latest issue.

“This Is Uncomfortable” is Reema Khrais, Donna Tam, Megan Detrie, Peter Balonon-Rosen, Camila Kerwin, Phoebe Unterman, Marque Greene and Serena Chow.

What happens when you stumble on something with the potential to change your life? Oscar (not their real name) was going through a rough patch in life when they found a bag of money in their dim basement apartment in Montreal. It was enough to propel their life in a different direction. First, they almost had a panic attack. Later, a gnawing regret consumed them.

“This Is Uncomfortable” is Reema Khrais, Donna Tam, Megan Detrie, Peter Balonon-Rosen, Camila Kerwin, Phoebe Unterman, Marque Greene and Serena Chow.

When Ibby Hanlon started experiencing mysterious and debilitating pain, she put her faith in the medical system to find a solution. After a series of unexpected events forever changed her body — and her finances — her trust in the system shattered. This week, we dissect trust between doctors and patients.

“This Is Uncomfortable” is Reema Khrais, Donna Tam, Megan Detrie, Peter Balonon-Rosen, Camila Kerwin, Phoebe Unterman, Marque Greene and Serena Chow.

The more Morgan Curtis learned about the source of her family’s multi-generation wealth — from gold mining, to fossil fuel investment, to slave ownership — the less she wanted anything to do with it. When she started to give away half a million dollars to social justice organizations in her late twenties, her dad told her he may write her out of her future inheritance. In this episode, we hear from them both.

For even more Uncomfortable, subscribe to our newsletter! Each Friday you’ll get a note from Reema, a story from a listener and some recs from the Uncomfortable team. It’s all exclusively for our email list, so don’t wait! In case you missed it, here’s the latest issue.

“This Is Uncomfortable” is a podcast about our money and our feelings. And a lot of the money stuff we have the most feelings about we also like to keep secret.

In season five, the secret’s out.

We’re revealing family secrets, learning about the true cost of divorce, investigating mysterious piles cash and so much more.

We’ll have new episodes every Thursday starting this week, on Oct. 14. Listen to the trailer above or wherever you get podcasts.

To get even more Uncomfortable, check out our newsletter! Each Friday morning we’ll bring you a note from Reema, new stories from listeners, tough money questions and all the TV, podcasts and TikToks our team is into. Here’s the latest issue.

How do you bounce back from getting scammed? Become a scammer yourself, obviously. The inside story of a young man’s transformation into an online scammer — and the lengths he goes to for money when no one is looking.

To keep up with us in the off-season, subscribe to our newsletter! Each Friday you’ll get a note from Reema, a story from a listener and some recs from the Uncomfortable team. You’ll also be the first to hear about our new season. It’s all exclusively for our email list, so don’t wait! In case you missed it, here’s the latest issue.