How Dare You?
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.
How Dare You?
Why Big Dreams Feel So Scary (And Why That's the Point)
Use Left/Right to seek, Home/End to jump to start or end. Hold shift to jump forward or backward.
What no one tells you about having a dream so big it scares you...
In this episode of How Dare You, I'm breaking down why big dreams feel so scary and why it has almost nothing to do with failure.
From the identity gap that hits the moment you get serious, to the self-sabotage that disguises itself as being practical, this is the honest conversation about what going after something huge actually costs you before it gives you anything back.
If this one hits, share it with someone who's been keeping their dream at arm's length, leave a review, or message me on Instagram @heyannarogers, I'd love to know what landed for you.
We'll dive into:
• Why it's not failure you're afraid of
• The identity gap: who you are now vs. who the dream requires you to become
• Why wanting something this badly feels like a liability
• The self-sabotage that looks exactly like being practical
• What it actually takes to go all in before you feel ready
Um, we talk about what it's like to have a dream that's so big, so crazy, so audacious that it scares the living shit out of us. Welcome to this channel. My name is Anna Rogers, and I decided to start creating YouTube videos at least for the next 30 days, where I document what it's like to be a 38-year-old woman who wants to create a big, extraordinary life for herself. Now, I've been thinking about what really separates people who succeed and people who don't, what drives certain people to have these big crazy dreams and what pushes them to keep working. I was speaking to a friend a couple of weeks ago, and she was just like, You and Tom have built multiple companies. And she goes, Why do you do it? She was just like, You're already successful, you've built the company. So she's like, Why do you keep doing it? And my simple answer to her was just like, we love the game. Entrepreneurship is hard. I say this all the time. I refuse to sugarcoat this when there are a few coaches online who be like, yeah, and it's easy, and you just post content and you just sell. I'm like, no, entrepreneurship is hard. I saw a meme the other day and it said, if you cannot afford therapy, she's like, become an entrepreneur because it is like free therapy. She was just like, you will meet your shadows, you will be confronted with every single thing, like abandonment issues, like um being rejected, like all of these things will come up as an entrepreneur. Why do we keep doing it? It's because we love the game. We are obsessed with the game. We are not building towards an endpoint, but rather we are building for who we become. And that is the difference between entrepreneurs who make it. If you think about it, if you just stop at, I have this milestone, then you're constantly just going to just do a little bit until you reach out. And then you reach out, and maybe you'll self-sabotage and you'll go back a little bit. But if you are actually in the long-term game, if you have this big, crazy, audacious dream and you are optimizing for that. You're like, I do not know how I'm going to achieve this dream, but I'm gonna keep going for it. And that's what I feel like. I have set out this big, crazy, audacious dream, and every single day I am scared. Every single day I say to Tom, I'm like, what am I doing? I shared this with someone and I said, I don't know, this is my big goal. I shared my big goal and I go, it sounds freaking crazy. I don't know how I'm going to do it, but all I know is I have to keep focusing on the who. So rather than focusing on how, how do I do that? What strategy do I need to do? Um, you know, what type of XYZ? There are a million hows, but if I keep just focusing on the who, who do I have to become to actually achieve this dream? Now, for me, my dream is to sell a million copies of my book. Did my stomach just drop as soon as I said that? Yes, 100%. As soon as I said that, as soon as I vocalized this big crazy dream, all the fear and all the doubt started pouring in. Who do you think you are? English isn't even your first language. I know that I have to keep focusing on the who. Who do I have to be in order to make this happen? I am the type of person who is committed to growing her brand. I am the type of person who will create videos on YouTube every single day, even though only 20 people view it. The other day I spent 30 minutes and I filmed this awesome video and I recorded it and I put it up and then I checked back the next day and it had like seven views. And there's always a decision when that happens. The decision is either you go and you look at it and you get disheartened because you're not seeing the results that you want and then you stop, or you go, you see it and go, all right, game on. And that's what I did. I took a screenshot of that video, and I go, two years from now, a year from now, I'm gonna look back and I'm gonna post be posting videos, and there'll be 500,000 people watching, a million people watching. And that is simply because I decided to start. That is simply because I am focusing on who I have to become in order to achieve this goal. So I want you to think of whatever goal that you have in your mind. And I want you to vocalize this, start saying this out loud. Start talking about this goal, start normalizing it, start saying it until the time comes where you say it and it doesn't feel like your heart is about to drop. And when we normalize big goals and big dreams, our nervous system starts to feel like, oh yeah, I've heard that before. Yeah, we're gonna make that happen. Yeah, that's what we're working towards. Versus if you're keeping your dreams just in your head or in your journal and you're just writing it, but you're not actually taking action, you're not actually doing the steps to make that dream happen, your nervous system will always be scared, will always be afraid. It will not calibrate to the level that you are trying to go to. And it is humbling, it is humbling to put in and put in the effort and not see the results that you want, but you have to know that just like anything, it is putting in the reps. And so, do I know how I'm gonna sell a million copies of my book? No idea. I know that it hasn't been done as a Filipina. I know that there is no Filipino author, Filipino author who has even made it to a best-selling list. I know that usually self-published books don't even make it to any best-selling list, but I'm not worried about that. I am choosing not to get stuck in the how. I am choosing not to get stuck in the logistical aspect of it, but I am pouring my heart out into writing the best book, into getting my message across there, into showing up on social media and creating content every single day, because I know that I am just growing the brand. And I know if I grow a brand, all it takes is one video that goes viral, and then people will hear about my book, and then people will be like, I want to join, I want to jump in. This is the exact message that I've been waiting to hear. And so, for you, what is that big, crazy, audacious dream that makes you feel so scared? The question is, who do you need to become to achieve that dream? And once you connect back to that, once you truly answer that, then you know that you do not have to be worried about the how and you just need to start taking actions. I started this journaling practice a few years back where I would write down in my journal, and I'd be like, this is, you know, this is my plan, this is what I'm thinking. And then with a different colored pen, I would write on the top part, and I would write as if I was the Anna who has already achieved that goal. So I source inspiration from the future me, and I go, what does future me have to do in order to make this happen? How does she think? How does she operate? Because I know that Anna, who has already sold a million copies of her book, will not hesitate to start a YouTube channel, will not hesitate to start creating content even though no one is viewing it. And it's humbling. Oh my gosh. Like people pay me thousands of dollars for me to coach them, and all of a sudden I'm creating free content on YouTube. And I realize that Anna, the one who has already sold a million copies, the one who has impacted a ton of women with her message on how not to people please and how not to play small in the one life that they have here on earth. I know that she would not stop whenever things get hard. I know that she would be willing to put in the reps because she knows that that is how you get to the endpoint. I am obsessed with the game of entrepreneurship and the game of business and the game of improving myself on a daily basis. That is what turns me on. It is how do I become the best version of myself and how do I keep working on myself? And that is like a lifelong journey. You know, I say this all the time. When I wrote my book, I did not write it from the other side of clarity. I did not write it from I have everything figured out, follow me. I wrote it from the depths of how am I still playing small and how do I break myself, break my patterns, break my loops. I write myself when I catch myself mid-chapter, I'm like, oh my God, I'm still doing this. But I'm so excited because I know that me working on myself is just one step closer to getting to where I want to go. And so, my message for you: if you are watching this and you have a big crazy dream and it scares you, keep going. Keep going and outsource your decisions to your future self. Ask that future version of yourself, how would you think, how would you act, how would you operate, how would you respond to adversity and challenges and roadblocks. And that is the fastest way to actually making sure that your dreams are going to come true, to actually making sure that you can get what you want, even though it feels crazy, even though it feels so far fetched and impossible. So I hope you enjoyed this video. Like, comment, subscribe. I want to know, drop a comment in the comment section like what is a big crazy dream that you have, and what is stopping you from actually getting there?