After decades of trying to make it as an actor and comedian in Hollywood, Claudette Powell felt deeply unfulfilled. So she set her sights on a radically different life -- one that required her to pay off nearly $150,000 of debt. When she finally wrote that last check, she took a vow of poverty and entered a convent.

But leaving behind her material life wasn’t as simple as it sounded. This week: how paying off debt was only the beginning – and how money still finds a way to complicate life within convent walls.

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Hanna Sanborn was a single mom with newborn twins, struggling to find affordable childcare. Her best friend, Bryer Rossi, was burned out at work and looking for a way out. One day, Hanna floated an idea to him: “What if you quit your job and took care of my babies?”

What started as a running joke between friends turned into a lifeline that changed their lives and the way they saw each other.

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“This Is Uncomfortable” returns with four brand-new episodes about life and how money messes with it.

This season: Two best friends, struggling with work and unaffordable child care, come up with an unconventional solution that reshapes their relationship. A woman walks away from a Hollywood career to take a vow of poverty. Our “Money Fight” series is back, following a couple whose search for a dream home turns into a power struggle. And in our new advice series, "Work Drama," we tackle your uncomfortable work questions on toxic offices and pay discrepancies.

New episodes drop starting May 1.