Work sucks, I know. (All work except writing these articles, I mean.) Whether you need tips to clear specific work hurdles (not getting a raise; confronting your coworker about stealing your lunch from the office fridge every day) or just need a little motivation about how to have a healthy work-life balance or start pursuing your creative dreams, these podcasts will make your case of the Mondays a little less blah and a little more funny and inspiring. Everybody may be working for the weekend, but that doesn’t mean your Monday through Friday has to be an insufferable slog.
Work Sucks, I Know!
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If you recognize the title of this show from the lyrics of Blink 182’s “All the Small Things,” you’ll immediately appreciate the vibes of this funny, conversational show about people and their jobs. Comedian (and butcher) Michael Timlin’s Work Sucks, I Know! is a play on Studs Terkel’s 1974 bestseller, Working: People Talk About What They Do All Day and How They Feel About What They Do, and he talks to comedians and writers about the ins and outs of their jobs, what keeps them sane, what they do for money now and what they hope to do for money in the future. I don’t often recommend specific episodes but go immediately to Ashley Ray (of “TV I Say, with Ashley Ray”) to hear about how Ashley does the bare minimum at her Google job so she can get a paycheck and health insurance while pursuing her artistic dreams. It’ll inspire you to create a boundary in your own job, give yourself a break if you’re not at your dream job just yet, and save space for the work you have in your biggest dreams.
Ask a Manager
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When Alison Green started her blog Ask a Manager, she was the chief of staff for a successful nonprofit, where she was responsible for hiring, firing, promoting, managing, all of that. She admits she’s not the perfect manager, but on every episode of her podcast Ask a Manager, she took calls and talked directly with listeners about how to deal with clueless coworkers, toxic bosses, impossible employees, and navigate all kinds of workplace weirdnesses. Her ethos is rooted in getting things done, being straightforward, taking criticism gracefully, and brutal honesty. Her episodes are specific (seeing an email you weren’t supposed to see; working for a micromanager; your employee lying about a reference) and helpful. Listening will feel like you have a smart expert you can call on the phone. The podcast is over, but the blog is still going strong.
Scope Creep
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If you’re a freelancer, you’ll find friendship in Jamie Cox and Liz Talago, hosts of Scope Creep, the show for anyone who took the step to ditch the corporate hellscape and build a business that’s good for your mind, body, and bank account. Jamie and Liz are two brand strategists navigating solopreneurship on their own terms, and they’re sharing everything they’ve learned—and are in the process of learning—with their listeners. Some advice is specific, like how to phrase an email. Sometimes they’ll provide more general encouragement you need when boundaries seem impossible, clients seem to be pounding at your door, and your inbox seems to be exploding. It’s no-nonsense advice about how to be a girlboss (whether you identify as a girl or not) minus all the nonsense that comes with girlboss culture. No mood boards, no manifesting. Promise.
Help Wanted
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On Help Wanted, Entrepreneur editor-in-chief Jason Feifer and money expert Nicole Lapin join forces to give personal, helpful answers to your most baffling questions about work and money, whether you’re the boss or have (an even slightly annoying) one. Jason and Nicole bring themselves into this show—a favorite episode of mine featured a caller who had sent Jason a terrible pitch over LinkedIn DM. Jason walked him through his bad pitch on the call. This is real advice about specific issues that you can take home (or to work) with you.
Entrepreneur Struggle
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On Entrepreneur Struggle, DCP Entertainment CEO Chris Colbert talks with fellow business owners and freelancers about the challenges and lessons learned as they start and grow their companies. Regardless of what you do for a living, each week you’ll learn ways to help improve your life and your business. Chris is positive even about work’s messiest stuff, and guides his interviews with kindness and understanding. His guests are people at the top of their game (Bridget Todd, Danielle Moody, Steven Satterfield) who share advice on all sorts of relatable situations (becoming your own brand, creating a mission-driven business, building a family business, fighting imposter syndrome, and more).
The Best Advice Show
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The Best Advice Show dishes out great advice from writers, musicians, entrepreneurs, and more—and often their advice is stuff that will help you have a happier Monday. (Don’t use the words “love” and “passion” in your cover letter; do the stuff nobody is asking you to do.) Host Zak Rosen sits down to hear one piece of his guests’ best advice, and has a brief conversation about what that advice means to them, and how he can connect that advice with his listeners. Episodes are short and frequent, so you can add listening to your morning routine. And even the silly, non-work episodes (act like you’re on vacation all the time!) will help your work week more bearable.
Roy’s Job Fair
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Work can suck—and it can also be very funny. On Roy’s Job Fair, comedian Roy Wood Jr. (former correspondent on Comedy Central’s “The Daily Show with Trevor Noah”) explores the human condition every week through the prism of employment. He sits down with real people from all lines of work about their most memorable jobs; employment vacancies they’re looking to fill; scams they’ve run at the office; and of course, cringe-worthy office romances. You’ll relate to the stories and also pick up some advice.
Make Your Damn Bed
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You’ve heard that making your bed is a great way to start the day. On Make Your Damn Bed, host Julie Merica offers bite-sized, daily motivation to play while you flatten out the covers or try to fold a fitted sheet. So while you’re starting your day with this important habit, you’ll be fed real talk about prioritizing people over profit, the curb cut effect, being perceived as annoying, and more. Each episode lasts approximately one bed-making long, and each season is 66 days—long to encourage long term healthy habit integration into your daily life. You’ll skip out your front door with your bed made and your mindset in a better place.
Nudge
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Nudge is a business podcast rooted in psychology—packed with simple, evidence-backed tips and real-life examples about kicking bad habits, getting a raise, and growing a business. Host Phil Agnew and his guests—admired entrepreneurs and behavioral scientists—spend 20 minutes tackling puzzles we encounter day to day, and help us figure out how we can conquer them. This is my favorite business podcast because it doesn’t feel like one: It’s a human podcast that just so happens to offer tons of science that will make you better in your 9-5.
WorkLife with Adam Grant
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From TED and hosted by organizational psychologist Adam Grant, WorkLife with Adam Grant interviews luminaries in fields all across the spectrum (Pixar’s co-founder and longtime president Ed Catmull, Hidden Figures author Margot Lee Shetterly, Chobani CEO Hamdi Ulukaya, Yo-Yo Ma, Abby Wambach) to find out how we can have more balanced and fulfilling work lives. Topics go one layer beneath what you get from most work-advice shows and offer insightful tips in creative ways. The production level is top-notch. Episodes are full of tips and actionable takeaways, but they also give you a bird’s-eye view of what a healthy work life looks like, and will help you look at your job in a new light. Topics range from pulling inspiration from video games to finding the perfect mentor, fighting the sins of work culture, making good arguments, and more.
Work Appropriate
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The workplace is littered with landmines of potential misunderstandings and screwups, and it turns out, we’re all stumbling our way through it. Anne Helen Petersen has created a space we can learn from each other in Work Appropriate, which covers the work wars you’re waging every time you clock in. She’s diving in to ways to feel confident if you have ADHD or are neurodivergent, thrive in an industry that seems to be sinking, set up boundaries to separate work from life, or even just gracefully make it through a day of potentially awkward conversations. Petersen, the author of Can’t Even: How Millennials Became the Burnout Generation, is the smart friend you’d want to call after a tough day at the job. If you’re not suffering from tricky power dynamics or a question of email etiquette, your actions might be causing strife for those around you. Which means this podcast is for anyone who communicates with anyone at work, and that’s basically everyone.
How’s Work?
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Fans of Esther Perel and her chart-topping podcast Where Should We Begin? know that Esther is a master in counseling people through prickly relationship issues. On How’s Work? she’s tackling the office, focusing on the hard conversations we’re afraid to have in our jobs. Colleagues navigating the new etiquette of a work from home workforce. Newsrooms whose journalists feel that covering breaking news has broken them. A doctor who wants to walk away from his profession, during a pandemic. And lobbyists whose fight for racial equality ends up dividing them. Listen in as coworkers, cofounders, and colleagues discuss their dilemmas and Esther weighs in on her sage advice that applies to more than just the people in the room.
