The 20 Something Playbook

M.A.E. MacGregor

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Society & Culture

Welcome divas 💌 Podcast about the good, bad & ugly of your 20s. Hosted by 3 sisters creating the TV series they’ve dreamed of since their teens ✨ New episode bi-weekly on Tuesdays at 1am EST. Hosted on Acast. See acast.com/privacy for more information.

2d ago

Getting Laid Off Changed Maddie's Life (And Her Sisters Have Thoughts)

Maddie got laid off… and four weeks later, she's the happiest she's ever been. Is it possible that losing your corporate job could give you your life back? This week on The 20 Something Playbook, we're unpacking Maddie's unexpected layoff, the freedom of stepping away from corporate life, and what we're learning about navigating your 20s when nothing goes according to plan. We're talking about: ✨ Getting laid off and finding unexpected freedom 💌 How your network can help you find your next opportunity 💸 Why saving money matters more than you think 🫶 The importance of reconnecting with former colleagues and asking for referrals 🥂 Making the most of an unexpected life change 💃 Our chaotic night out, spontaneous adventures, and why our best friend has to be there for the whimsy powers to work Plus, Maddie shares the advice from a former manager that completely changed how she's approaching unemployment: don't spend all your time trying to find your next job. Make time for the life you've always wanted to live, too. Whether you've been laid off, are navigating a career change, or are simply figuring out your 20s, we hope this conversation reminds you that an unexpected ending can open the door to something better. 💌 WELCOME TO THE 20 SOMETHING PLAYBOOK We're three sisters talking about the good, bad, and ugly of your 20s, from careers and relationships to big dreams, unexpected detours, and figuring it all out together. Subscribe for more sister chats, life lessons, and a little whimsy along the way. 📍 Instagram & TikTok: @20SomethingPlaybook ✨ More from us: https://www.20somethingplaybook.com/ #GettingLaidOff #LifeInYour20s #CareerAdvice Hosted on Acast. See acast.com/privacy for more information.
Sep 29

Maddie Got Laid Off + Our Craziest Jobs

Maddie got fired... well, technically laid off. So naturally, we had to talk about it. Fresh off a mass layoff from her first corporate job, Maddie breaks down exactly what happened, from the mysterious “room hold” invite to getting locked out of Slack minutes later. Then we get into some of the craziest jobs and work environments we’ve experienced, from serving to competitive dance, and why somehow getting laid off still wasn’t the wildest one. We also talk about navigating career uncertainty in your 20s, toxic work environments, empathetic leadership, rejection, and how difficult experiences can give you a whole lot of perspective. If you’ve ever been fired, laid off, worked a nightmare job, or simply had a very 20-something career crisis... this one’s for you. Welcome to The 20 Something Playbook, where three sisters talk about transforming through the good, bad and ugly of your 20s. ✨ Follow us on TT/IG @20somethingplaybook https://www.20somethingplaybook.com/ #20Something #Layoff #CareerAdvice #Podcast #WorkStories #Twenties Hosted on Acast. See acast.com/privacy for more information.
Sep 15

We went FERAL for Finding Emily iykyk

Well folks the time finally came... Elle got to see Finding Emily and... well you'll have to listen to this episode to find out! ;) TT/IG/YouTube @20somethingplaybook https://www.20somethingplaybook.com/ Hosted on Acast. See acast.com/privacy for more information.
Sep 1

3 Things We Had to Unlearn in Our 20s

What did you believe about life before your 20s that you don't believe anymore? In this episode, we put each other through a chaotic round of questions — from the beliefs we've outgrown and the compliments that mean the most to us, to embarrassing stories, friendship, curly hair, getting older, and the things we're still figuring out in our 20s. This game turned into a lot of oversharing, sibling debates, and learning things about each other that we probably should've known already. Because growing up means realizing that some of the things you thought were true… really weren't. 💌 Welcome to The 20 Something Playbook — the good, bad & ugly of your 20s, hosted by three sisters figuring it out together. IG/TT/YT @20somethingplaybook New episodes every other Tuesday! Hosted on Acast. See acast.com/privacy for more information.
Aug 18

M.A.E. Chats: I'd Jean Grey For You

In this episode, we’re talking all things Spider-Man: Brand New Day — major spoilers ahead! 🕷️ We dive into Jean Grey’s villain arc, her mission to save her sister, and why we walked out of the theatre saying, “I’d Jean Grey for you.” We also get into Peter Parker’s loneliness, depression, nonexistent work-life balance, and why this movie felt so relatable now that we’re in our 20s. We talk about growing up alongside Tom Holland’s Spider-Man, the nostalgic 2000s feeling of the movie, the music and filmmaking choices we loved, and all the little details that made it feel like so much care went into it. Then we somehow spiral into Finding Emily, our obsession with cozy nostalgic movies, Zendaya and Law Roach, London, writing our own rom-com, and why we desperately want to live inside the movies we love. And, of course, we end with an extremely important public service announcement about theatre soda machines. 🥤 Basically: Spider-Man spoilers, Jean Grey, 20s nostalgia, movie-nerding out, rom-coms, and questionable beverages. Follow us on IG/TT/YT ⁨@20SomethingPlaybook⁩ Hosted on Acast. See acast.com/privacy for more information.
Aug 4

We Tried "Birthday Maxxing" 🎂✨ | Toronto Flower Market, Whimsy Haul & Turning 24

We accidentally discovered the ultimate way to celebrate your birthday: Birthday Maxxing. 🎂✨ For our 24th birthday, we spent the weekend exploring the Toronto Flower Market, sipping matcha, hunting for whimsical treasures, and fully embracing our post-London obsession with all things Notting Hill. From cozy birthday traditions to a mini mid-twenties identity crisis, this might have been our most wholesome birthday yet. In this episode of M.A.E. Chats, we're talking about: ✨ Birthday Maxxing 🌸 Toronto Flower Market ☕ Cozy cafés & matcha 🎀 Whimsy Maxxing 🇬🇧 London trip stories 🫖 Notting Hill 🎂 Turning 24 & your mid-20s 💐 Birthday ideas in Toronto If you love cozy vlogs, London-inspired aesthetics, wholesome sister podcasts, and figuring out your twenties, you're in the right place. Subscribe for new episodes every other week! Follow us on IG/TT @20SomethingPlaybook Website: https://www.20somethingplaybook.com/ #BirthdayMaxxing #TorontoFlowerMarket #WhimsyMaxxing #Turning24 #TorontoPodcast #Toronto #GenZ #CozyVibes #NottingHill #TwentiesPodcast Hosted on Acast. See acast.com/privacy for more information.
Jul 21

The Most Whimsical London Itinerary ☕📚 | Notting Hill, Hidden Gems & Cozy Cafés

We spent one unforgettable week in London, England trying what TikTok calls "whimsy maxxing"—embracing spontaneity, saying yes to unexpected adventures, and making the most of every moment. Instead of following a packed tourist itinerary, we mixed iconic London attractions with hidden gems, local neighborhoods, bookstores, markets, live music, and some unbelievable luck. In this episode, we share: * Our favourite hidden gems in London * Budget-friendly ways to experience the city * Borough Market * Wimbledon on a budget * Harry Styles at Wembley Stadium * Harry Potter Studio Tour * Soho shopping * Marylebone Bookshop * Portobello Road Market * St. Paul's Cathedral *Thirsty Thursdays * Why we think London is one of the best cities in the world If you're planning a trip to London, looking for a unique London itinerary, or just love travel stories, this episode is for you. Subscribe for new episodes every other week. Follow us on IG/TT/YT@20SomethingPlaybook Website: https://www.20somethingplaybook.com/ Hosted on Acast. See acast.com/privacy for more information.
Jul 7

M.A.E. Chats: The Lore on Why We Don’t Drink

We get asked this question all the time: "Why don't you drink?" People always assume something dramatic happened to make us sober... that we had strict parents, a bad experience, or a religious reason. The truth? None of those are true. We simply... never started drinking. Somehow, that's become one of the most confusing things about us. In this episode, we're sharing why the three of us have stayed sober throughout our 20s, how we navigate weddings, parties, work events, and friendships, and why we've never felt like alcohol was something we needed. We talk about: ✨ Why we never started drinking 🍸 Navigating bars and weddings sober 💬 The questions people always ask us 👯 Making friends in your 20s without alcohol This isn't about convincing anyone not to drink. Our friends drink. Our family drinks. We simply chose a different path, and we're sharing what that has looked like for us. We'd love to hear your experience. Are you sober? Sober curious? Or did you simply never get into drinking? Let us know in the comments. 🎙️ New episodes every other week on Tuesdays. Follow us on IG/TT @20somethingplaybook Hosted on Acast. See acast.com/privacy for more information.

Welcome divas 💌 Podcast about the good, bad & ugly of your 20s. Hosted by 3 sisters creating the TV series they’ve dreamed of since their teens ✨ New episode bi-weekly on Tuesdays at 1am EST. Hosted on Acast. See acast.com/privacy for more information.

Creator

M.A.E. MacGregor
Years Active

2025 - 2026
Episodes

55
Rating

Explicit
Copyright

© M.A.E. MacGregor
Show Website

The 20 Something Playbook