If you've ever started a new habit with the best intentions — only to watch it fall apart two weeks later — this episode is going to hit different. I sat down with Ana Cordera, the NYC-based creator and speaker behind Ana Builds Habits, and honestly? I felt like I was getting free therapy the entire time.

Ana breaks down why most habits don't stick (spoiler: it has nothing to do with discipline or willpower) and what you actually need to do first, before you build a single routine. We get into identity, perfectionism, the messy middle of building a creator brand while working a 9-to-5, and what Coco Gauff writing "I will win the French Open" the night before she actually won has to do with your creative journey.

— Introducing: Ana Cordera!

— Why habits really fail (it's an identity problem, not a discipline problem)

— The running story: how Ana learned to commit to a new identity

— Growing up across multiple countries & how structure became both a superpower and a trap

— Taking $10K worth of coaching — and the real shift that finally clicked

— The tactical moves that helped Ana claim the identity of a creator

— The mindset coach question that moves you out of overthinking and into action

— Coco Gauff, the French Open, and reverse-engineering your success through identity

— What Ana's week actually looks like: balancing a 9-to-5, wedding planning & a creator brand

— How to build a household that actually works when two people have different work styles

— The habit that surprised Ana the most: Alyssa Liu and the joy of the process

— What people romanticize about being a content creator (and the real difference between influencers vs. creators)

— Unfavorable habits Ana has had to break — including one that's still a work in progress

— Why rest is Ana's hardest habit to build (especially living in NYC)

— How to schedule a doom-scrolling session (yes, really — and it works)

— What to do when confidence and doubt show up at the same time

— Using a physical challenge to build confidence in a totally different area of your life

— How Ana recharges creativity when she hits a wall

— Rapid fire: the messiest thing about Ana

— What Ana is still figuring out: learning to let go of the outcome

— What Ana is most excited about right now (personally & professionally)

✨Connect with Ana✨

@anabuildshabits | Keep up with Ana on LinkedIn

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

That little voice in your head telling you you're not smart enough, interesting enough, or capable enough of building the life you want? There's a name for it - and it's been running your life longer than you know.

In this episode, I dive into the psychology of core beliefs: deeply ingrained, usually subconscious convictions we hold about ourselves that quietly shape every decision we make. I get really real about the core belief I uncovered that had been silently keeping me small, and I break down exactly how to find yours, challenge it, and replace it with something that actually serves you.

TIMESTAMPS

[00:00] — What is a core belief and why it matters

[01:15] — CBT (Cognitive Behavioral Therapy)

[04:00] — I uncover my own core beliefs (and get uncomfortable)

[07:00] — Why I always collaborated instead of going solo creatively

[09:00] — The New Year's Eve conversation that changed everything

[13:00] — How strengths can mask and protect negative core beliefs

[16:00] — Step 1: Take stock of your thoughts

[18:00] — Step 2: Challenge the belief — demand the evidence

[19:00] — Step 3: Replace it with a belief that actually serves you

[20:30] — Backing up your new belief with your real strengths

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

Have you taken the Enneagram test, had your entire personality confirmed in three paragraphs, and then... kept scrolling? Same. But according to my guest this week, that's exactly where most people go wrong.

I'm sitting down with Ashton (aka Enneagram Ashton) — public speaker, author, and Enneagram coach who built a thriving business helping people go from "cool, I'm a 4" to actually using that information to grow.

In this episode, I pick her brain on what it actually means to use the Enneagram (hint: it's not about finding your perfect match), the myths I know we've all believed about entrepreneurship, the sting of getting ghosted on a business deal, the rollercoaster of money and consistency, and how she recharges her creativity.

Whether you're Enneagram-obsessed like me or totally Enneagram-curious, I think this one's going to stick with you.

✨Connect with Ashton✨

Follow @enneagramashton on Instagram

Check out her website: enneagramashton.com for The Support Squad membership & The Enneagram Advantage program

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

Are you holding back in your career, your creative work, or your relationships — not because you don't want to win, but because you're secretly terrified of losing? Yeah. Same. In this quick but mighty mindset episode, I'm breaking down one of the most powerful moments from Andre Agassi's memoir Open — and how a single question he asked himself mid-match completely changed how I approach my voiceover auditions (and honestly, my whole life).

If you've ever found yourself playing it safe, second-guessing your instincts, or trying to be what everyone else wants you to be — this one's for you, babe.

Timestamps:

• [00:00] Welcome + what we're diving into today
• [00:30] Why Andre Agassi's memoir Open is an unexpected must-read for creatives
• [01:00] The match that changed everything — playing to WIN vs. playing not to LOSE
• [02:00] How this hit home: losing a 2.5-year voiceover client and the spiral that followed
• [03:30] The trap of trying to "do all the right things" — and why it makes your work go flat
• [05:00] What "getting messy again" actually looks like in practice
• [06:00] The mindset shift that got Maddie a callback AND an avail within ONE week
• [07:00] The question to ask yourself in every arena of your life

Resources Mentioned:

• Open by Andre Agassi

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

Emma Palmer is a lot of things — actor, producer, sustainable fashion co-founder, podcast host, mom — and she's living proof that there is no single right way to build a creative life.In this episode, we get real about the messy, nonlinear path of being a multi-hyphenate creative. From founding Lady Farmer (a sustainable lifestyle brand) with her mom, to stumbling into Bright Holler Productions after a conversation with her therapist, Emma's story is full of unexpected pivots, hard-won money lessons, and the kind of gut-trust that most of us are still learning.We also get into: nanny share childcare hacks for working moms, why tax codes actually favor entrepreneurs, the puzzle-piece theory of building a career, and why 'if you can do anything else, do that' is the most useless advice in entertainment.

Timestamps

• [00:00] — Intro — Meet Emma Palmer: actor, producer, sustainable lifestyle brand co-founder
• [01:00] — Balancing a toddler, multiple businesses, and actually getting stuff done
• [02:30] — The nanny share genius — childcare hack for working creative moms
• [07:30] — How Lady Farmer was born out of a gap in sustainable fashion
• [09:30] — Launching via Kickstarter and the pivot they didn't see coming
• [13:00] — Hitting pause on the Good Dirt Podcast — and coming back stronger
• [14:00] — Bright Holler Productions: how a therapist, a church, and a Scout bag launched a company
• [19:00] — Redefining Rich — the book that changed how Emma thinks about self-employment
• [26:00] — Corporate vs. creative: owning your time vs. being owned by your time
• [31:00] — Why you're usually your own biggest obstacle (and how to get out of your way)
• [35:00] — Financial lessons for creatives: entrepreneur tax advantages no one tells you about
• [38:00] — Ebbs, flows & the puzzle-piece philosophy for navigating the messy middle
• [43:00] — From wanting to be a teacher to running two businesses: the evolution of a dream
• [51:00] — Mindset work, CBT, and learning to take that big swing
• [55:00] — Retiring the 'do anything else' advice — why creatives need to create their own work
• [57:00] — What's messy, what's exciting, and what Emma's still figuring out

Resources Mentioned

• Redefining Rich by Shannon Hayes
• Write One Song by Jeff Tweedy

✨Connect with Emma✨

Podcast: The Good Dirt Podcast

Follow @weareladyfarmer on Instagram

Follow Emma on Instagram: @maryemmakingsley

Bright Holler Productions Website

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

Okay, real talk — have you ever gotten SO obsessed with an idea that you've basically already accepted your Grammy/Oscar/Olympic gold medal in your head... before you've done a single thing to actually make it happen? Yeah. Same. In this solo episode, I'm taking you back to a crystal-clear memory from the 2006 Winter Olympics and a lesson my mom dropped on me at 12 years old that still hits just as hard today: you're speed skating in your head. We're getting into shiny object syndrome, romanticizing the reward, and the one question you need to ask yourself before you blow up your whole life for a new dream: Am I willing to make the sacrifice — even when the reward isn't guaranteed?

KEY TAKEAWAYS

• You're watching someone's highlight reel — not the years of work behind it. Get honest about what's actually behind the curtain before you dive in.
• The sacrifice always comes before the reward, and the reward is never guaranteed. Are you willing to pay the price first?
• Shiny object syndrome isn't about being lazy — it's about falling in love with the idea of the thing instead of the reality of it.
• Giving yourself permission to put a goal down for this season is not failure. It's self-awareness.
• The question to ask yourself: Do I want the glory, or am I actually willing to do the work?

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

What happens when everything falls apart and you finally commit to the thing you've been running from? In this episode, I sit down with David Millstone—actor, producer, and co-host of the Every Day Courage podcast—to talk about coming to acting at 42 after major life shifts, building a career on your own terms, and why the creative journey is never, ever done.

If you've ever felt like you started too late, pivoted too many times, or worried that exploring multiple creative identities means you're not "serious" enough—this conversation is for you. We're talking about the long game, learning from every version of yourself, and why your job as an artist is to keep naming new mysteries.

TIMESTAMPS:

[00:00] - Intro: Meet David Millstone—actor, producer, creative explorer

[01:00] - From theater kid to newspaper editor: The early pivot away from acting

[03:00] - The life change that catapulted him back to acting at 42

[04:00] - "What doesn't kill you makes you stranger"—rebuilding confidence

[06:00] - Acting as exploration of self-states vs. catharsis

[07:00] - The Body Keeps the Score and relational cycle analysis

[08:00] - Why acting should be a conversation, not a monologue

[15:00] - The pivot to producing: When acting alone wasn't enough

[25:00] - What David learns from younger actors about the business

[40:00] - Breaking free from the "actor as victim" mentality

[45:00] - Building your career with agency and intention

[57:00] - The "no plan B" myth and why it's bulls**t

[1:00:00] - Where to find David + Season 2 of Every Day Courage

✨RESOURCES✨

· Get Messy: Authenticity and Transformation: Sasha Feldman’s Journey from Actor to Therapist

· Get Messy: Building Confidence through Creativity with Michelle Simone Miller

· Get Messy: Walking the Bridge of Life: Presence, Change, and Identity

·The Body Keeps the Score by Bessel van der Kolk M.D.

✨Connect with David✨

Podcast: Every Day Courage with David Millstone and Stephan Dweck

Website: davidmillstone.com

Instagram: @davidmillstone

✨Connect with Maddie✨

Explore Maddie’s Website | @messywithmaddie

What happens when you stop waiting for validation and start creating your own opportunities? In this episode, I sit down with my friend Taylor Meskimen—actress, audiobook narrator, musician, and all-around creative powerhouse—to talk about the messy, beautiful reality of being a multi-hyphenate artist.

Taylor opens up about finally booking her first major TV role on 9-1-1 (after YEARS of auditioning), why she almost quit the traditional acting path, and how creating her own work has changed everything. We get real about the scarcity mindset that plagues creative industries, the golden nugget advice she learned from her dad (actor Jim Meskimen) about self-promotion, and why audiobook narration might be the best-kept secret in voice-over.

If you've ever felt like you're doing everything right but still waiting for someone to give you permission to succeed—this conversation is for you. We're talking about playing to WIN instead of playing not to lose, getting out of your own way, and remembering why you fell in love with your craft in the first place.

TIMESTAMPS:

[00:00] - Intro: Meet Taylor Meskimen, multi-hyphenate artist

[01:00] - Balancing multiple art forms: acting, voice-over, narration, music

[03:00] - How voice-over became Taylor's financial foundation

[06:00] - The curse and blessing of creating your own schedule

[08:00] - Writing her first feature film with best friend Alexandra Du Parc

[11:00] - Why writing made Taylor a better actor

[14:00] - Advice from three generations of artists (including her grandmother from Happy Days!)

[17:00] - The golden nugget: Why self-promotion isn't selfish

[20:00] - Being your own biggest obstacle

[22:00] - Booking 9-1-1

[25:00] - The old DPN days: When auditions were collaborative and in-person

[29:00] - Breaking into audiobooks: Taylor's insider tips

[32:00] - Why the audiobook industry is uniquely welcoming

[34:00] - Combating scarcity mindset in creative careers

[37:00] - How COVID changed the audition landscape

[42:00] - What it felt like filming 9-1-1 and proving herself on a major TV set

[45:00] - Creating momentum through making your own projects

[49:00] - Animation, video games, and different voice-over styles

[51:00] - Making bold choices that stand out

[58:00] - The role of luck (and naiveness) in booking jobs

[1:00:00] - Playing to win vs. playing not to lose (Andre Agassi wisdom)

[1:02:00] - Rapid fire: What's the messiest thing about Taylor?

[1:04:00] - What Taylor's excited about: Music, guitar, and upcoming projects

[1:06:00] - Where to find Taylor and her work

✨Connect with Taylor✨

Email: [email protected] (for audiobook tips!)

Instagram: @tmex

Website: taylormeskimen.com

YouTube: Taylor Meskimen

The Role - Short Film

✨Connect with Maddie✨

Explore Maddie’s Website | @maddiemcguirecoaching | @maddiemcguire4

Hey there! Welcome back to Get Messy - This episode is a heart-to-heart with my best friend Flannery, a Hollywood writer and creative producer who's learned that the path to success doesn't look anything like what we were told.

We're getting vulnerable about our early years in LA—when we were told to sacrifice everything or leave, to show up perfect, to never have a plan B. Spoiler alert: that advice nearly broke us.

From meeting a French sculptor on our girls’ trip in Paris who never discusses work with friends, to navigating vocal damage from years of pushing too hard, this conversation explores what it really takes to build a sustainable creative life. We dive deep into the writing process, learning to take feedback without losing your voice, and why calling red flags "pink" cost us years of our twenties.

Timestamps:

[00:00 - 06:45] Identity Beyond Your Job Title

[06:46 - 13:00] The Paris Lesson: How Americans Lost Themselves

[13:00 - 22:00] The "All-In" Myth That Nearly Destroyed Us

[22:00 - 31:00] Writing Real: Structure, Soul & Starting Scared

[31:00 - 42:00] What Success Actually Looks Like

[42:00 - 50:56] Selah: The Power of Pausing

[50:56 - 56:18] Red Flags Aren't Pink: Boundary Setting 101

[56:18 - End] Everything Is Messy (And That's the Point)

5 Key Takeaways

1. Your art gets better when you live a full life. The industry has shifted from wanting "types" to craving authentic, multifaceted humans. If you're not living, experiencing, and connecting with the wider world, your work suffers. Permission granted to have interests outside your career.
2. Red flags stay red—stop calling them pink. When someone shows you who they are through their words and actions, believe them the first time. Protecting your time and energy isn't rude; it's survival. This is especially crucial for empathetic, caretaking personalities.
3. Just write the damn thing. You'll learn more from writing a messy first draft than from endless prep. Structure matters, but not more than getting started. You're going to rewrite anyway—even working writers do "a zillion million rewrites."
4. Success without presence is empty. If you're living for someday (retirement, that big break, when things are perfect), you're missing your actual life. The pursuit of success IS your life—make sure you're spending it in alignment with your values.
5. Radical honesty unlocks authentic connection. Flannery's marriage and closest friendships only happened when she stopped performing and started being brutally honest about what she wanted. The people who can't handle your truth aren't your people.

✨RESOURCES✨

· Forged in Fire, Held in Love by Nomad The Poet

✨Connect with Flannery Maney✨

Explore Flannery’s Website | @flannerymaney

✨Connect with Maddie✨

Explore Maddie’s Website | @maddiemcguirecoaching | @maddiemcguire4

I recently did this gratitude practice that had me talking to my 22-year-old self—the girl in the thrift store crop top heading to auditions with way too much eyeliner and so much hope. And when I looked at everything I've accomplished since then, I realized something powerful: I'm still in the game. I'm still choosing myself every single day. In this episode, I'm getting vulnerable about what it means to build a legacy instead of just padding your resume, why "you always got you" has become my life philosophy, and how the most important relationship you'll ever work on is the one with yourself. I share my journey of expanding into grad school for therapy, investing more in my voiceover career, and navigating that weird space of feeling bold and directionless at the same time. I talk about impact over achievements, staying in the game even when you're unsure of the next play, and why feeling a little lost might actually mean you're honoring yourself and creating your own blueprint. If you're navigating the messy middle of building your dream life, questioning your next move, or wondering if you're "doing enough"—this one's for you. Consider this a love letter from me to you.

Timestamps

00:00 Gratitude Practice with My Younger Self

01:00 The Thrift Store Shirt and LA Auditions

02:00 Still in the Game: Reflecting on a Decade

03:00 Expanding the Game: Grad School and Growth

04:00 You Always Got You

05:00 Living a Life of Impact

06:00 Don't Wait for Coach—Storm the Field

07:00 Building Your Legacy, Not Your Resume

08:00 What My Grandpa's Eulogy Taught Me

09:00 A Love Letter to You

Key Takeaways

1. The relationship with yourself is the only one you can never escape—make it beautiful by always having your own back.
2. Building a legacy is more important than building a resume; focus on the virtues of your eulogy, not just your achievements.
3. Feeling directionless while being bold might mean you're honoring yourself and following your own blueprint instead of someone else's.
4. Impact matters more than accolades—whether through storytelling, counseling, or your unique gifts, lead with how you want to affect others.
5. Stay in the game, whatever game you choose—show up, be present, and throw yourself full body into what matters to you.

✨RESOURCES✨

· Activations App - Meditations and activations for personal growth

· "The Mountain Is You" by Brianna Wiest - On self-sabotage and building the life you want

✨Connect with Maddie✨

Explore Maddie’s Website | @maddiemcguirecoaching | @maddiemcguire4