How To!

How To!

You've got questions. We find answers. We all need advice, but it's not always clear who to ask. Each week, we invite a listener on the show to tackle a real problem, like protecting our elderly loved ones from scammers, emigrating as a throuple, and speaking without saying "um" - all with help from world-class experts: attorneys, doctors, entrepreneurs, authors, researchers - who actually know what they're talking about. Think of it as eavesdropping on someone else's therapy session, without the co-pay or awkward silence.

Episodes

August 4, 2026 26 mins

Last week, our expert Arthur Brooks gave us some surefire advice for resetting the parent-child relationship so your kids don't treat you like an emotional ATM. On this episode of How To!, he's going to teach our listener, Karen, how to balance the books, so to speak, by taking some withdrawals of her own. He has some surprising tips for how to restrain yourself from swooping in to save the day when it would be better to let them f...

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Today on How To!, Freddy, a physician, scientist, and father, struggles with how to mentor his 12-year-old daughter, who prefers her safe comfort zone and strongly resists new experiences, travel, or unfamiliar foods. Host Mike Pesca brings on stand-up comedian and Parenting is a Joke podcast host Ophira Eisenberg to discuss strategies for nudging risk-averse kids to embrace uncertainty without overwhelming them. They explore why t...

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July 21, 2026 34 mins

Today on How To!, Michael, a retired FDNY captain who used to rely on a uniform every day, finds himself staring blankly into his closet and canceling dates because he does not know how to dress. Host Mike Pesca brings on Tavia Sharp, an executive image and personal brand strategist and founder of Styled Sharp, to help Michael navigate post-retirement style, move past 1990s baggy clothing trends, and overcome the challenge of findi...

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Comedian and Wait Wait... Don't Tell Me! panelist Paula Poundstone splits her time among a grueling tour schedule and a chaotic home life, but she wants to find the focus necessary to manage her household staff and stop letting her deep aversion to conflict ruin her business. Enter Nedra Glover Tawwab, relationship expert and author of Set Boundaries, Find Peace, who advocates for establishing extreme clarity and asserting direct w...

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July 7, 2026 30 mins

Originally Aired on Oct 12, 2021 On this episode of How To!, the second in a two part-series, Dan Christensen, a bus driver in Portland, Oregon, and Matt Smith, a crisis intervention trainer and the co-founder of Aegis Training Solutions, are back to teach you what to do when a fight is already underway. Dan talks about his experience with the 2017 Portland train attack that left two people dead. How do you stay safe? What is your ...

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June 30, 2026 33 mins

Ofra splits her time among a number of hobbies in her retirement, but she wants to stop feeling rudderless and find the focus necessary to write a book of observational humor based on her twenty-year career as a psychotherapist. Enter David Epstein, workplace researcher and author of Inside the Box, who advocates for creating artificial structure and imposing concrete deadlines rather than falling into the trap of endless optionali...

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India splits her time between contract production and agency work, but she wants to stop prioritizing other people's projects to scale her personal brand. Enter Simone Stolzoff, workplace researcher and author of The Good Enough Job, who advocates for building a multi-pronged freelance career rather than recklessly burning your ships. He introduces India to an evaluation rubric for vetting new business, advising her to decline any ...

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June 16, 2026 32 mins

Steven racks up acquaintances on group mountain bike rides, but he cannot turn a casual trailhead hello into a real friendship. For decades he coasted on the built-in connections of being in a band, working in a lab, and having a wife who did the social legwork. But now he needs to make some new friends. Enter Dr. Marisa G. Franco, University of Maryland professor and New York Times bestselling author, who studies adult connection ...

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This week we're sharing a special episode from our friends at Mentally Stronger with Therapist Amy Morin — the Webby Award–winning podcast hosted by psychotherapist and mental strength trainer Amy Morin, whose TEDx talk has been viewed more than 25 million times and whose books have sold over a million copies in more than fifty languages.

Every week, Amy shares a practical, research-backed mental strength strategy you c...

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There's one thing that all of Helena's personal projects have in common: they remain unfinished. The family photo album is empty, as is her mom's recipe book. And the lavender garden is still unplanted. Helena is not lazy. In fact, she's a busy lawyer who has no problem finishing tasks at the office. But she's also a busy mother raising a family, and free time is hard to come by. So how can Helena banish her distractions? On this e...

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June 2, 2026 33 mins

Today on How To!, Ross, a TV director who enjoys a drink but feels intimidated by the pretension of the wine world, levels up his wine knowledge. Mike brings on journalist and The Corrupt Wine Writer Substack author Joel Stein to cut through the snobbery, explain why you shouldn't be afraid to ask for help at a wine shop, and offer practical tips on how to order confidently at restaurants without overspending. They discuss why "dri...

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May 26, 2026 32 mins

Guitarist and orchestrator Dillon Kondor knows his way around a stage. It's everything in between the songs that trips him up. Speaking to a crowd, filling the silence, not coming off stiff or defensive, that's where his confidence disappears. After too many gigs derailed by awkward pauses and self-protective sarcasm, Dylan reaches out to Mike for help. On this episode of How To!, Mike brings in the perfect guide: singer-songwriter...

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May 19, 2026 35 mins

Brian stepped up to coach his 7-year-old daughter's soccer team to save their season, but there's one major catch: he's never actually played the sport. Now battling imposter syndrome and the pressure of intense parental expectations, he feels completely overwhelmed. On this episode of How To!, we bring on former Major League Soccer goalkeeper Jeff Attinella to demystify the art of youth coaching. They discuss the growing problem o...

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Al has over a million American Express points and dreams of booking another once-in-a-lifetime luxury vacation for his family. But the opaque, frustrating system of transferring and redeeming rewards has him completely paralyzed. On this episode of How To!, Mike brings on Elliot Rosenberg, founder of the luxury points concierge Stratys, to demystify the credit card game. They discuss how airlines secretly devalue their miles and wh...

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May 5, 2026 30 mins

When Betsy joined her last workplace, she thought it was a perfect fit. It was on a list of Best Places to Work and she got to be creative while helping people. But as the startup rapidly grew, the company culture changed and Betsy started to lose herself amid the stress. Then she got laid off. Honestly, Betsy was relieved, but now she's gotta figure out what's next. On this episode of How To!, we bring on James Altucher, author, p...

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April 28, 2026 28 mins

Tyler holds himself to high expectations, placing a deep value on self-sufficiency and the social contract. But as a science teacher and dad to a blended family, he gets incredibly frustrated when others do not hold themselves to those same standards. On this episode of How To!, Mike brings on psychologist Dr. Ryan Martin, known as the Anger Professor, to talk through the realities of male anger and why our closest relationships tr...

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To move or not to move? That is the question for Tiffani. She is desperate to get out of her hometown in rural Oregon and find a place with affordable housing, better dating prospects, and a ballroom dance studio nearby… or at least a P.F. Chang's closer than a four hour drive away. The problem? Her preferred destination would mean moving clear across the country. On this episode of How To!, decision coach Nell McShane Wulfh...

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April 14, 2026 39 mins

Brett has spent her career in foreign policy — shaping strategy, advising governments, moving pieces on a board whose outcomes she may never live to fully see. It's meaningful work. It just never feels finished. So she's started thinking about a different kind of problem: the kind with a beginning, a middle, and an answer. Oh, also, and these mysteries keep presenting themselves in her workplace, and Brett loves mysteries! On...

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April 7, 2026 37 mins

Living with a cat often feels like a game of high-stakes interpretation, especially when an 18-pound Maine Coon is performing a 4:30 AM tap dance on your head. Today on How To!, Mike Pesca is joined by cat owner Steve, who shares the reality of navigating the vocal demands of his feline companions, Mr. Bad and Vincent Then, cat behavior consultant Dr. Mikel Delgado steps in to debunk the "alpha" dominance myth and the false promise...

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March 31, 2026 44 mins

Relying on filler words like "um," "like," and "you know" is a universal habit that clutters our speech and betrays our nerves, but simply willing yourself to stop only makes the problem worse. Today on How To!, Mike Pesca is joined by renowned data journalist and author Nate Silver, who bravely steps up as the guinea pig to have his own fast-talking, filler-heavy conversational style diagnosed in real-time. Then, communications co...

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