How Dare You?

Anna Rogers
  • 5.0 (13)
  • ENTREPRENEURSHIP

You were taught to be nice. To be grateful. To not want too much, ask for too much, or take up too much space. And honestly? You got really good at it. This podcast is for the woman who's ready to break the Good Girl rules. Every week, host Anna Rogers, coach, author, ex-good girl, and woman with genuinely delusional dreams gets into the stuff no one talks about at the dinner table as she unlearns people-pleasing, breaks societal conditioning, and dares to take radical responsibility for the life she actually wants.

  1. 1D AGO

    Advice to My Younger Self (I'd Be Further Ahead If I Knew This)

    These are the lessons I wish someone had forced me to hear earlier. After building businesses, making money, losing money, navigating relationships, and figuring out who I actually am... if I could go back and have a conversation with my younger self, this is what I would tell her. From learning to trust yourself when nothing makes sense, to the moment I genuinely didn't think I was getting out alive — this is the raw, unfiltered truth about what I'd do differently. In this episode of How Dare You, I'm sitting down with my younger self and telling her everything I wish someone had forced me to hear earlier. From building businesses and losing money, to the moment I genuinely didn't think I was getting out alive — this is the raw, unfiltered version of what I'd say if I could go back. If this one hits, share it with someone who needs to hear it, leave a review, or message me on Instagram @heyannarogers — I'd love to know what landed for you. We'll dive into: The advice I wish someone had forced me to hear earlierWhy you don't lack clarity — you lack self-trustThe moment I didn't think I was getting out alive... and how it changed everythingWhat "outgrowing" actually looks like when it's happening to youWhy trusting yourself before you have proof is the hardest and most important thing you'll ever do

    45 min

  2. 3D AGO

    Why I Fell from the Face of the Earth...and Where I'm Going Next.

    I'm back… and I'm not the same person who left.... After moving to Bali, finally moving into the villa Tom and I spent a year building, and going down a rabbit hole of uncomfortable self-reflection, I realized something:  I'd been playing small. In my dreams, in my business, in the way I was showing up here. This episode is the unfiltered version of what happened...the mindset shift that changed my book from a quiet memoir to a full-blown manifesto, the moment a single offhand comment from a friend cracked something open, and why I'm now chasing a goal that makes my stomach drop just saying it out loud. If you've ever shrunk a dream to make it feel "reasonable"… this one's for you. Oh..and welcome to the How Dare You podcast.

    11 min

  3. 12/17/2025

    The Invisible Work That Separates the 1%

    What if the reason you’re not getting the results you want has nothing to do with talent, strategy, or timing and everything to do with what you’re willing to do when it’s uncomfortable? In this episode of Unrelatable, I unpack what the top 1% actually do differently. I break down what Taylor Swift, Tony Robbins, and Justin Bieber all have in common and how this has helped me explode in 2025. This started as a raw voice note but turned into one of the most important conversations I’ve had all year. If this lands, share it, leave a review, or message me on Instagram @heyannarogers I’d love to hear what this unlocked for you. We’ll dive into: Why the most influential people in the world still outwork everyoneWhat “putting in the reps” really looks like at the highest levelWhy volume, consistency, and refinement beat talent every timeThe shift that happens when your mission becomes bigger than youHow anchoring your work to impact not validation changes everything

    23 min

  4. 12/03/2025

    How I Created $250K Cash in 90 Days by Going All In

    What if the biggest leap you’re craving… is one brave yes away? In this episode, I’m breaking down the last 90 days. Tthe wild, batshit season that turned into a full-blown rocket ship. The stages, the travel, the quarter-million cash months, the identity shifts… and the real reason everything accelerated at lightning speed. We’ll unpack: How saying yes before you feel ready creates exponential momentumWhy living your life (not just working) becomes your most magnetic strategyThe identity shift that unlocked visibility, opportunities, and insane cash flowWhat actually fuels a “quantum leap” and why most women miss itIf this episode fires you up, share it and tag me @heyannarogers, I’d love to feature you.

    19 min

  5. 10/22/2025

    Behind the Scenes with Jay Shetty: What Most Entrepreneurs Miss About Success & Happiness

    I just got back from a three-week whirlwind trip through LA, Italy, and our first-ever Lifestyle Rich retreat in Greece. During a mastermind in LA, I had one of the coolest experiences as Jay Shetty walked into our villa and shared the behind-the-scenes of how he runs his multi–eight-figure brand. Something he NEVER talks about online. Instead to his topics around mindset, love, and relationships, he spoke about about systems, storytelling, and scaling without losing your joy. In this episode, I’m breaking down: The lesson that completely changed how I schedule my week (Creative vs. CEO days)How SOPs and structure actually create more freedomWhy storytelling is the future of selling onlineAnd Jay’s powerful reminder that there’s a strategy for success… and habits for happinessIf you’ve been craving more structure, flow, and meaning in your business, this episode will hit deep. If you enjoyed this episode, share it on Instagram or leave a review.

    26 min

  6. 09/23/2025

    Behind the Scenes of our Crazy Expansion in Business

    In this raw behind-the-scenes episode, Tom and I take you inside one of the most expansive, soul-stretching week. From speaking in front of 1,000 women… to closing multiple five-figure deals. In this episode, we share what really happened at Living Brave Live (including the standing ovation moment that changed everything) and how YOU can start taking bigger swings in business.

    20 min

  7. 08/04/2025

    How Conditional Enthusiasm is Stopping You from Exploding Your Business

    What if the reason your business isn’t growing… has nothing to do with your strategy and everything to do with your energy? In this episode, we’re talking about the silent killer of momentum: conditional enthusiasm. We’ll unpack: Why revenue is one of the worst metrics of "success"The unsexy truth about quantum growthThe invisible metrics high-level leaders obsess over (hint: it's not content volume) If you enjoyed this epsiode, feel free to share it and tag me @heyannarogers to get featured.

    16 min

  8. 07/22/2025

    The Future of the Coaching Industry: 3 Shifts You Can’t Afford to Ignore

    After 10 years in the coaching space—scaling four multi-6 and 7-figure brands, coaching thousands of clients, and running both a coaching company and a SaaS startup—I can see patterns and trends. The coaching industry is entering a new era. In this episode, I break down the 3 biggest trends shaping the next 5 years—and what it’s going to take to not just keep up, but lead. I'm breaking down: Why “money wins” marketing is dying How your STORY will become your most valuable asset The rise of brands, legends, and community-led movements (this is the future) 💸 Ready to future-proof your brand and actually stand out in this new era? Grab the SHE IS RICH™ Messaging & Storytelling Bundle — the exact storytelling strategies I use (and teach my clients) to sell high-ticket offers without sounding like everyone else. https://lifestylerich.co/she-is-rich

    22 min
See All (14)

5
out of 5
13 Ratings

About

You were taught to be nice. To be grateful. To not want too much, ask for too much, or take up too much space. And honestly? You got really good at it. This podcast is for the woman who's ready to break the Good Girl rules. Every week, host Anna Rogers, coach, author, ex-good girl, and woman with genuinely delusional dreams gets into the stuff no one talks about at the dinner table as she unlearns people-pleasing, breaks societal conditioning, and dares to take radical responsibility for the life she actually wants.

Information

  • Creator
    Anna Rogers
  • Years Active
    2025 - 2026
  • Episodes
    14
  • Rating
    Explicit
  • Copyright
    © 2026 How Dare You?
  • Show Website
    How Dare You?