Are you tired of feeling stuck in your 20s? Do you feel like you're not living up to your potential? In this episode, Madison, Ava and Elle sit down with founders, authors, and co-hosts of the popular “Almost 30” podcast Krista Williams and Lindsey Simcik about how to heal and overcome the struggles of your 20s before turning 30. From letting go of past traumas to building healthy habits and relationships, we'll dive into the most important lessons you need to learn to set yourself up for success in the next decade of your life (and beyond). Whether you're struggling with anxiety, depression, or just feeling lost, this video is for you.
In This Episode:
0:00 – Setting the tone for navigating the decade of uncertainty, growth, and self-discovery.
3:40 – The Lie About Purpose & Your Career: Krista and Lindsey break down the myth that your career must be your purpose — and what it means to choose your own path instead.
8:56 – Whose Voice Are You Listening To? Is it your dad? Society? Yourself? A conversation about questioning the motivations behind your decisions.
13:48 – Figuring Out Your Gifts: How human design, astrology, and even your friends can help you understand what you actually bring to the table.
18:49 – The Portfolio Career Reality: Why your twenties may look more like a patchwork of skills than a linear trajectory — and that’s okay.
23:00 – From bartending to burning out — the jobs that humble you and the wisdom that comes after.
25:00 – Lindsey opens up about cheating, shame, and how rock bottom became her greatest teacher.
29:37 – Madison shares her fears around being single — and the rollercoaster of being deeply true to yourself while longing for connection.
31:45 – Are Your Standards Too High? (Spoiler: No): The girls unpack what “lowering your standards” really means and why soul-level connection over surface-level checklists.
34:15 – Krista keeps it real on the maturity gap, dating while fulfilled, and what the masculine can (and can’t) give you.
38:00 – How strong female friendships become the training ground for honest communication.
41:30 – Madison gets vulnerable about mental health, sickness, and the messy beauty of speaking the truth through it all.
44:10 – Krista opens up about depression, anxiety, and why sobriety helped her meet herself for the first time.
49:00 – Tiny lifestyle tweaks that made a huge difference — and what they wish they knew sooner.
50:44 – Almost 30’s new book is a companion for your twenties — with tools, stories, and love on every page.
52:10 – The most important reminder: you’re exactly where you’re supposed to be.
Order Krista and Lindsey’s book Almost 30: A Definitive Guide to a Life You Love for the Next Decade and Beyond NOW: https://static.macmillan.com/static/smp/almost-30-9781250327208/
Follow Almost 30 on Instagram/YouTube/TikTok: @almost30podcast
Follow Madison, Ava, and Elle:
Instagram & TikTok @20somethingplaybook
YouTube https://www.youtube.com/@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
Thank you West Gate New York Grand Central for hosting us. BOOK YOUR STAY HERE: https://be.synxis.com/?adult=1&arrive=2025-06-07&chain=19007&child=0&clickref=1011lBkz4fuk&depart=2025-06-08&level=chain&locale=en-US&promo=PRTZ&rooms=1&utm_campaign=partnerize_wgr&utm_medium=referral&utm_source=partnerize
Music from #Uppbeat (free for Creators!): https://uppbeat.io/t/doug-organ/theme-from-a-lift
License code: BPZMSBJOKUAS89NB
© 2025 iHeartMedia, Inc.
