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The 20 Something Playbook

The 20 Something Playbook

By: M.A.E. MacGregor
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The 20 Something Playbook is your guide through the good, the bad, and the ugly of this defining decade. Hosted by three sisters in their 20s. Volume 1 launching late spring 2025. Stay tuned!

Hosted on Acast. See acast.com/privacy for more information.

M.A.E. MacGregor
Social Sciences
Episodes
  • Chapter Five: From Overdose to 2+ Years Sober, Courtney Riddle's Journey to Sobriety at 26
    Jun 24 2025

    In this episode of The 20 Something Playbook we're joined by Courtney Riddle, a sobriety advocate and founder of Courtney Rose Style. Courtney shares her incredible journey of 2+ years of sobriety in her 20s, while battling OCD, anxiety, and depression. She opens up about her struggles, triumphs, and the lessons she's learned along the way.


    In her early 20s, she hit rock bottom and realized she needed to make a change. From the darkest moments of her addiction to her recovery, she’s holding nothing back in this raw and honest interview. Get ready for a real and unfiltered look at what it takes to overcome addiction and start living your best life in your 20s. If you or someone you know is struggling with alcohol addiction, this video is for you.


    We filmed in her beautiful rom-com style apartment in NYC. Decorated by Courtney, who you can tell works in fashion ;)


    In this episode:

    00:00 - 00:52 Intro

    00:52 - 02:49 Three words to describe your 20s

    02:49 - 07:38 Sobriety journey begins

    07:38 - 10:52 Drinking to cope with anxiety

    10:52 - 14:52 When drinking got bad

    14:52 - 17:12 Why my 20s are fabulous + talking about sobriety

    17:12 - 21:48 Social media, social anxiety, and why our generation drinks

    21:48 - 28:38 Fashion industry in your 20s

    28:38 - 33:25 Sobriety and mental health

    33:25 - 38:48 Sobriety advice

    38:48 - 42:18 Family and friend support

    42:18 - 46:08 How your definition of success changes in your 20s

    46:08 - 51:41 Dating sober and meeting “the one” in your 20s


    Follow Courtney on Instagram: @courtneyrosestyle

    More Interviews with Courtney (on @myteam.social on Instagram):

    Sobriety Chat 1: https://www.instagram.com/reel/C_MOi_2MejM/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==

    Sobriety Chat 2: https://www.instagram.com/reel/DAmWC_UMVhB/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==


    Follow Madison, Ava, and Elle:

    Instagram @20somethingplaybook

    TikTok @20somethingplaybook


    Listen to “The 20 Something Playbook”:

    Spotify

    https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

    Apple Podcasts

    https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

    Amazon Podcasts

    https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

    iHeart

    https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true


    Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ


    Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf


    Thank you West Gate New York Grand Central for hosting our stay in NYC.


    BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F


    To advertise on this podcast please email: macgregormadison@gmail.com


    Music from #Uppbeat (free for Creators!):

    https://uppbeat.io/t/doug-organ/theme-from-a-lift

    License code: BPZMSBJOKUAS89NB

    Hosted on Acast. See acast.com/privacy for more information.

    Show More Show Less
    52 mins
  • Chapter Four: Surviving NYC in Your 20s: Mastering LinkedIn For Success with Christine Göös
    Jun 17 2025

    Are you a young professional in your 20s trying to make it big in the city that never sleeps? Mastering LinkedIn is key to unlocking success in NYC! In this episode, award-winning marketing leader Christine Göös shares her top tips and strategies for optimizing your LinkedIn profile, growing your network, and landing your dream job in the competitive New York City job market. From building a strong personal brand to navigating online networking, we've got you covered. Whether you're a recent college grad or just looking to level up your career, this episode is for you. So, what are you waiting for? Press play and start mastering LinkedIn for success in NYC (and beyond)!


    In this episode:

    00:00 - Intro

    00:48 - 02:22 How we met + unhinged things she did in her 20s to make it in NYC

    03:37 - 04:08 How hard it is to move to NYC

    04:48 - Career pivots to get here

    05:27 - 06:31 Advice for moving to NYC

    06:41 - 07:46 Be your own publicist

    08:08 - 09:42 Building your brand and resume

    10:28 - 11:08 Posting content on LinkedIn + future-proofing your career

    11:08 - 13:13 Using LinkedIn for Gen Z + bad job market + getting laid off

    13:31 - 15:48 Job advice for 20-somethings

    15:48 - 16:03 Resume tips

    16:48 - 18:28 Unhinged story from her 20s

    18:28 - 20:04 Confidence advice

    20:08 - 20:42 Rock bottom in your 20s: miserable in NYC

    21:35 - 22:17 Before the Saturn return

    22:12 - 23:37 Panic attacks in Macy’s dressing room

    23:37 - 24:42 Fake it till you make it—confidence advice

    25:05 - 25:35 Three words to describe your 20s

    25:35 - 26:59 Writing tips + how to become a better writer

    26:59 - 29:09 Friendships in your 20s

    29:09 - 29:57 Long-distance friendships & family

    30:03 - 31:30 Fear/insecurity that held you back (stage fright)

    31:39 - 32:43 Work and relationships

    32:49 - 33:08 Met at a karaoke bar

    33:21 - 34:08 Titles don’t matter

    34:08 - 35:08 Redefining success from 20s to now


    Follow Christine Göös on LinkedIn: https://www.linkedin.com/in/christinegoos/

    Christine's podcast House of Content: https://podcasts.apple.com/us/podcast/house-of-content/id1681192360

    House of Content on Instagram: https://www.instagram.com/itshouseofcontent/

    Christine's website: https://www.christinegoos.com


    Follow Madison, Ava, and Elle:

    Instagram @20somethingplaybook

    TikTok @20somethingplaybook


    Listen to “The 20 Something Playbook”:

    Spotify

    https://open.spotify.com/show/1bAA0eOHthyeqJyIyWlcD3?si=Uiv2K4tmRKGHbD6Pns6KeQ

    Apple Podcasts

    https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

    Amazon Podcasts

    https://music.amazon.com/es-us/podcasts/5db7484e-4184-464c-b6d9-706adc37f7d5/the-20-something-playbook

    iHeart

    https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/?cmp=web_share&embed=true


    Watch Volume One of "The 20 Something Playbook" on YouTube: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=Krq-KY-PoR_uK9gJ


    Watch this episode on YouTube: https://youtu.be/jqRRqF9I6_Q


    Behind The Scenes | Filming the Podcast in NYC and California: https://www.youtube.com/watch?v=KNaj9QhEOls&list=PL1Rs9oUYUlEf6yeVawHLs6G3UUaj4EACf


    Thank you West Gate New York Grand Central for hosting our interview space (and stay in NYC).


    BOOK YOUR STAY HERE: https://westgate.prf.hn/click/camref:1100l5227F


    To advertise on this podcast please email: macgregormadison@gmail.com


    Music from #Uppbeat (free for Creators!):

    https://uppbeat.io/t/doug-organ/theme-from-a-lift

    License code: BPZMSBJOKUAS89NB

    Hosted on Acast. See acast.com/privacy for more information.

    Show More Show Less
    45 mins
  • Chapter Three: From Ice Cream Scooper to Self-Made Millionaire with Co-Founder of Dow Janes
    Jun 10 2025

    Ready to break free from the pressure of needing to have it all figured out? In this episode we chat with Britt Williams Baker, co-founder of Dow Janes - one of the fastest growing companies in the United States teaching financial literacy and strategies to build wealth. Britt went from scooping ice cream to becoming a self made millionaire in her 30s. She shares strategies, mindset shifts, and habits that enabled her to achieve financial freedom at a young age. From working in consulting, to attending Harvard to biking around New Zealand, Britt used her 20s for exploration. In this convo we dive into the benefits of living in the present and letting go of the need for perfection. So, if you're tired of feeling stuck and ready to start having the time of your life in your 20s, tune in!


    In this episode:

    00:00 - Intro

    01:00 - Down Janes origin

    02:00 - How we got Dow Janes

    01:55 - Three words to describe your 20s

    02:13 - 03:02 What were you doing in your 20s?

    03:06 - 04:06 Did you always know what you wanted to do?

    04:15 - 04:45 Biggest belief shift in your 20s

    04:45 - 05:54 Pivot moments + Harvard Business School

    06:05 - Relationships at 25

    06:33 - 07:17 Feeling lost in your 20s advice

    07:17 - 07:30 The 20s are for exploring

    08:05 - 09:20 Learning compound interest at 7 + first financial mistakes

    09:24 - 09:51 Not knowing how to use a credit card

    09:51 - 10:30 Finance advice for your 20s

    10:33 - 12:17 Career pivot: start-up to unemployed

    12:15 - Scooping ice cream a year before Dow Janes

    12:50 - 13:30 Why 20-somethings need financial help & COVID

    13:30 - 14:35 Book recs for your 20s

    14:40 - 15:45 Becoming a self-made millionaire in your 20s

    15:50 - 17:10 Rock bottom moments and navigating them

    17:10 - 18:20 Work-life conflict in your 20s

    18:23 - 19:10 How to know where you want to be

    19:45 - 21:05 Friendship in your 20s & biz with your best friend

    21:10 - 21:50 Feeling like you have no skills in your 20s

    21:50 - 22:30 Adventure and leaving your comfort zone

    22:40 - 23:35 Measuring success in your 20s

    23:35 - 25:55 Figuring yourself out with The Artist’s Way

    25:58 - 27:06 #1 financial tip: align spending with your values

    27:20 - 29:30 Navigating social media in your 20s

    29:40 - 31:15 Therapy and coaching in your 20s

    31:15 - 33:10 Transforming in your 20s

    33:10 - 34:05 Saturn return + “claiming what you want”

    34:05 - 36:15 Fertility in your 20s

    36:20 - 37:20 Advice for your 20s

    37:25 - 39:15 Dating in your 20s

    39:15 - 40:15 You have time


    For more on taking control of your finances, check out Dow Janes: https://www.dowjanes.com/

    Follow Dow Janes on Instagram: https://www.instagram.com/dow.janes/?hl=en


    Follow Madison, Ava, and Elle:

    Instagram and TikTok @20somethingplaybook


    Listen to “The 20 Something Playbook”:

    Apple Podcasts: https://podcasts.apple.com/ca/podcast/the-20-something-playbook/id1801522743

    Amazon Podcasts: https://a.co/d/0fYK00x

    iHeart: https://www.iheart.com/podcast/269-the-20-something-playbook-269958812/


    Watch "The 20 Something Playbook": https://www.youtube.com/@20SomethingPlaybook


    20 Something Playbook Episodes Volume 1: https://youtube.com/playlist?list=PL1Rs9oUYUlEcNigeakfAcHDyKl2mSlAJ6&si=az6nbfw7JV2UMTzr


    Behind The Scenes | Filming the Podcast in California: https://youtu.be/pq1GV7UpTyI?si=IIUrFAIvGA98j6qy


    To advertise on this podcast please email: macgregormadison@gmail.com


    Music from #Uppbeat (free for Creators!):

    https://uppbeat.io/track/doug-organ/theme-from-a-lift?rt=uc-referral

    License code: BPZMSBJOKUAS89NB

    Hosted on Acast. See acast.com/privacy for more information.

    Show More Show Less
    42 mins
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