This Is Uncomfortable

What happens to your retirement savings when you leave a job? And if you’ve forgotten about an old 401(k) account, how do you track that money down? That’s the mystery Reema is trying to solve this week, as she confronts her own financial anxiety and goes searching for retirement accounts left behind at previous jobs. Along the way, she talks with retirement expert Geoffrey Sanzenbacher about just how common this is -- only about 15% of people roll their retirement savings over to a new employer's plan! And she asks behavioral economist Katy Milkman why this kind of chore feels so hard. Plus, brain hacks that will help you get through that daunting financial to-do list. If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU.And follow us on Instagram and Tiktok!

Betting used to mean going to a brick-and-mortar casino or placing a wager with a bookie. Now, with the rise of prediction markets, people can bet online on real-world events — from elections and the weather to cultural moments and global news — but at what cost? In this episode, Reema talks with clinical psychiatrist Dr. Timothy Fong and financial psychology expert Hanna Horvath about how gambling is becoming more normalized and woven into everyday life. What does that shift do to how we think about money, how we understand risk, and how we relate to the world around us?Even if you don’t gamble, we’re curious to hear more about the connection between loneliness and spending. What does that look like in your life? Give us a call at 347-RING-TIU or send us an email at [email protected] don’t forget to follow us on Instagram and Tiktok!If you or someone you know is struggling with gambling, professional help is available in every state. You can call The National Problem Gambling Help Line at 1-800-GAMBLER.

It’s bound to happen in any friendship: an unfulfilled Venmo request, a trip that’s way out of your budget, or a dispute over splitting the bill at a restaurant. This week, we’re answering your questions about navigating tricky money situations with friends. Reema is joined by comedians and real-life friends Josh Gondelman and Alison Leiby to talk through everything from expensive bachelorettes to Venmo nickel-and-diming. If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU.Follow us on Instagram and Tiktok!

For a lot of us, money is a source of anxiety and guilt. Reema recently joined the podcast “Happier with Gretchen Rubin” for a roundtable conversation with Gretchen and Haley Sacks (a.k.a. Mrs. Dow Jones) about why money feels so emotionally loaded – and the small, realistic changes that can make managing it feel easier.

Maybe you’ve heard that little voice: What if I could make a little money from this? The urge to monetize your hobby can feel tempting, but is it worth it? Reema talks with people who’ve tried to turn their pastimes into side hustles and finds out what they’ve gained, lost and learned along the way. Then, she speaks with a leading expert on creativity about how money can quietly reshape our motivation – and how to keep our hobbies from turning into just another job.If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU.Follow us on Instagram and Tiktok!

Steve Burns didn’t set out to become a children’s TV icon. He moved to New York with only a duffle bag full of clothes, $300 in his pocket, and a dream to become an actor. When Steve got hired to host “Blue’s Clues” from 1996 to 2002, he found himself disoriented by fame and uncertain of his career trajectory. Reema talks with Steve about finding meaning outside of work, feeling like an imposter in a role he never expected, and how he redefined his money values … when he escaped to the forest. Have you ever struggled with imposter syndrome in a new job? We want to hear about it, so give us a call at 347-RING-TIU or send us an email at [email protected] you can check out Reema’s interview on Steve’s podcast, “Alive with Steve Burns” here. Follow us on Instagram and Tiktok!

With more layoffs in the news, a lot of workers are feeling spooked. It can be hard not to spiral into what ifs: What if the next paycheck is my last? What if I can’t find another job? We look at how to cope with that uncertainty and what you can do to help protect yourself. Reema talks with psychologist Ellen Hendriksen, career coach Melody Wilding, and financial educator Jannese Torres, who share practical ways to stay grounded and prepared – from reframing your anxiety to strengthening your safety net. Have you ever struggled with layoff anxiety? We want to hear about it, so give us a call at 347-RING-TIU or send us an email at [email protected] us on Instagram and Tiktok!

Think that a prenup isn’t for you? Think again! Prenups are not just for rich people: they can protect you against debt and mitigate future issues like spousal support and custody. You’ve got to talk honestly about money if you want to build a shared financial life together, while still protecting yourself. This week, Reema Khrais talks with family lawyer Sahar Taylor and financial therapist Aja Evans to understand how prenups work and the deeper emotions underneath.If you liked this episode, share it with a friend. If you have thoughts, strong opinions about prenups - if you’ve signed one or are trying to decide if you should - we’d love to hear about it! You can email us at [email protected] or call 347-RING-TIU to leave a message.Follow us on Instagram and Tiktok!Correction (Feb. 20, 2026): Previous versions of this story misstated the percentage of prenups among married Americans.”

Reema is joined by Sam Sanders (host of KCRW’s “The Sam Sanders Show”) to answer your questions about money and dating. We’ve got questions about scammers, secret investments, and secondary partners. If you liked this episode, share it with a friend. And if you have a sticky money situation you need advice on, call and leave us a message at 347-RING-TIU or email [email protected] us on Instagram and Tiktok!

How much do you share with your partner about your finances? Sometimes, a little privacy starts to look a lot like a secret. And secrets (especially the money kind) have a way of becoming problems.On this week’s episode, Reema talks to people on the streets of Portland about their real-life money secrets, and chats with divorce lawyer Randy Kessler and couples counselor Jeff Guenther, who’ve seen how financial secrecy can fracture relationships — and sometimes bring people closer.If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU. Have you ever kept a big money secret from your partner? We want to know! And follow us on Instagram and Tiktok!

Author and journalist Aymann Ismail wants his kids to grow up with a real connection to their Egyptian roots, including speaking Arabic. For his family, that means committing to a private Islamic school -- and figuring out how to afford tuition.Reema sits down with Aymann as he walks through his family budget and the financial trade-offs that decision requires. They talk about what’s at stake for him, financially and culturally, and why holding onto Arabic feels especially urgent right now.If you liked this episode, share it with a friend. And if you want to tell us what you thought about the episode or about a tricky financial decision you’ve made, email us at [email protected] or call 347-RING-TIU. And follow our new social accounts on Instagram and Tiktok @ThisIsUncomfortablePod

Ever wrestled with an unusual work problem and didn’t know where to turn? In our recurring advice column, “Work Drama,” we try to find answers to your sticky work situations. This week, Reema is joined by culture writer and podcaster, Sarah Hagi (host of “Scamfluencers”) to unpack some uncomfortable workplace problems – from scammy bosses and boundary-pushing coworkers to negotiating for a raise and navigating workplace friendships.If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU.

Job hunting has a way of testing your limits. It can be hard not to question yourself (or spiral) when the process stretches on far longer than you imagined. Reema is joined by career coach Phoebe Gavin and writer Rachel Meade Smith to talk about the emotional side of the job hunt -- practical ways to navigate it, and how to get through it without losing yourself. Do you have a job hunting horror story you want to share with us? Or general work drama that you’d want advice on? Give us a call at 347-RING-TIU or send us an email at [email protected].

What does it mean to have “enough” money? Reema Khrais explores the feeling behind this question — the fear, comparison and the way “not enough” can follow us around even when things technically look okay on paper.She talks with experts and people who’ve landed on very different answers, including someone whose definition of “enough” meant closing her bank account and giving up money altogether.If you liked this episode, share it with a friend. And let us know what you think by emailing [email protected] or calling 347-RING-TIU.