113 | Stop The 2 AM Decision Spiral. How Female Founders Pressure-Test Their Biggest Decision in 15 Minutes

Still wide awake at 2AM, spinning through every possible scenario?

If you're stuck between the "safe" job that's slowly draining your soul and the scary leap into building something of your own—you’re not alone. But there is a way through, and it starts with asking a better question.

In this velvet-boot episode, Dawn shares a powerful client story that mirrors the decision spiral so many high-achieving women face: leave the suffocating but successful corporate job or risk the unknown building a business on your terms. You’ll learn how to pressure-test your biggest decisions—emotionally and practically—in just 15 minutes.

Because your life isn’t lived in spreadsheets. It lives on Tuesday afternoons.

If you’ve been stuck between safe and scared, this one’s your flashlight in the fog.

Download the free guide: 10 Ways AI Will Make You a Better Leader. Inside, you’ll learn how to pressure-test tough decisions using both data and emotion—plus 9 other ways to lighten your leadership load with AI.

 Key Takeaways

• Stop outsourcing clarity to spreadsheets. Strategy matters, but so does how your life feels at 3PM on a Tuesday.
• There’s no “easy” path—just the one you can live with. Every option has a flavor of hard. You get to choose yours.
• Success on paper doesn’t mean success in your soul. If you're winning by someone else's rules, it's time to rewrite your own.
• Use emotional modeling to guide decisions. Don’t just look at numbers—imagine waking up in each scenario.
• Leadership isn’t just a title—it’s what you do even when you're terrified. Especially when you're thinking about the path forward for someone else.

Resources & Links

• 10 Ways AI Will Make You a Better Leader – Free Download
• Join the Conversation: AI for Founders Free Community

Related Episode

• Episode 093 – The Dirty Secret About AI No Female Executive Wants to Admit — And Why It’s Hurting You
• Episode 091 – The 4‑Day AI System That Ends Friday Afternoon Panic Forever

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Transcript

She's That Founder
113 | Stop The 2 AM Decision Spiral. How Female Founders Pressure-Test Their Biggest Decision in 15 Minutes

That decision keeping you up at 2:00 AM. I watched someone find their way through it last week, and I think it might help you too.

Hey, hey, Hey. Welcome to She's That founder Thursday edition. These are the quick rants kick in the pants, velvet boot moments that represent me standing in the future, pulling you towards an even stronger, better, more powerful version of yourself with AI as your copilot and a little bit of mindset work.

I'm Dawn Andrews, and today I'm sharing about what it actually takes to see clearly when the stakes are high. So I'm on a call with a client I've been working with for months. She's got a big corporate job. The kind people dream about senior leader seven figure salary. Her name opens doors and she's sitting there telling me about this lunch she had with a potential client for a business.

She hasn't even started yet. She says, I let it. Dangle out there, just casually mentioned. I'm thinking about starting my own thing and Dawn and her voice gets really quiet. I have no worries about the substance. My worries are about the process, getting the clients, getting them to pay me, getting them to actually hire me, and I can hear it in her voice.

That thing that happens when you're standing at the edge of something and you can't see the bottom. Like I remember standing on SSON Hawaii with exactly those kinds of nerves in my stomach. She tells me she spent the night before at her friend's house just talking processing. And this friend is the one person at work that she's told about this because she trusts her, but also because, and this is the part that got me.

 She says I needed to bring her in. I was worried she might wanna leave when I do, and I want her to feel like there's a path forward. So even in the middle of her own terror about leaving, she was thinking about someone else's future. And you know what that is? That is leadership. The real kind. But here's what's keeping her up at night.

She's got this corporate job that is killing her slowly. The kind of slow death where you can't quite name what's wrong because everything on paper is right. Good salary, good title, good benefits, except Tuesday afternoons feel like drowning. And Thursday mornings she opens her calendar and feels that weight before she even gets outta bed.

And she has the inkling, like in the little edges of her vision of something else, her own business, her own clients, her own terms. But she doesn't know if she can make it work, if people will actually pay her if she's just fooling herself. So here's what happens. She makes lists.

 She talks to her friend. She has lunches with potential clients where she lets it dangle out there and then goes home and questions every word she said. She lies awake at night running scenarios. What if I can't get clients? What if I fail and look like an idiot for giving up everything I have? What if I'm not actually as valuable as I think I am?

Oh man, I know. Can I tell you what I think is really happening? I think she's trying to make a decision about her life by only looking at a spreadsheet. And the spreadsheet is terrifying because it's all downside risk and unknown variables. But here's what we started talking about. What does Tuesday at three o'clock in the afternoon actually feel like in each of those scenarios?

So if you stay where you are, what you're telling me is that you're in another meeting where you don't have decision making power. You're managing up. You're in a power struggle with HR that doesn't matter, but is still somehow taking all your energy and you come home exhausted from battles that aren't even yours.

 Do I have that right? And then on the other hand, if you leave and it doesn't work. Yes, there's financial risk. Yes, there's ego risk. Yes, people might think you failed, but what does Tuesday at 3:00 PM actually feel like in that scenario? Maybe you're having coffee out with a potential client, or maybe you're solving a real problem for someone who actually wants your help.

You come home tired, but it's the good kind of tired. And here's the question that changed everything for her. What does it feel like to wake up Monday morning in each scenario? If you stay, you open your calendar and know that every decision has to go through three layers of approval, that you're building someone else's empire, that you're making someone else wealthy while you trade your hours for dollars.

Even if they're very, very good dollars, you feel that weight before your feet even hit the floor. And if you leave, you open your calendar, and yes, maybe it's emptier than you want. Maybe you're scared. Maybe you don't know how you can fill it. Maybe you're just straight up stressed out, but you own it every hour, every decision, every client.

How does that feel? On Monday morning, she got really quiet on our call. And then she said something that I will never forget. I think I've been so afraid of failing at my own thing that I forgot to ask if I'm actually succeeding at this thing, because what nobody tells you about the safe choice is that sometimes safety is just slow suffocation with good benefits and the scary choice.

The one where you jump off the cliff not knowing what the bottom looks like. The one where you don't know if clients will pay you. The one where you have to figure out. So, so, so much as you go, that might be the only choice where you actually get to lead instead of just manage. Here's what I want you to know.

The decision that's keeping you up at night isn't about spreadsheets and pro con lists. It's not even about money. And believe me, I know money matters and we're not gonna pretend that it doesn't, but it's about choosing your hard. Because girl, everything is hard. It's hard to stay in the corporate job where you're suffocating and it's hard to leave and build something from scratch.

It's hard to have more clients than you can handle and struggle with success, and it's hard to fight to fill your pipeline. It's hard to be married. It's hard to be single. Nothing in life comes without consequences or trade-offs without its own particular flavor of difficult. So the question isn't, how do I avoid the hard?

 The question is, which hard do I want? Do you want the hard of waking up every day building someone else's dream, or the heart of waking up every day building your own? Do you want the hard of knowing exactly what your Tuesday looks like for the next five years or the hard of not knowing what next month or even next week looks like, but knowing that it's yours?

 Because your life isn't a business plan or a spreadsheet. It is made up of moments, and one of those paths, maybe the scary one, maybe the safe one gives you the hard, you can actually live with the gift of where we are right now with tools that let us model the mechanics and the emotional reality of our choices is that you don't have to just guess.

You can actually look at what Tuesday feels like, what your calendar looks like, what weight you're carrying or not carrying when you wake up. And when you can see that, when you can feel that, when you can honestly ask yourself which hard you're willing to carry, the decision will become obvious. Not easy.

' cause girl, it is never easy but obvious. So if you're lying awake, running scenarios, know this, everything is hard. Staying is hard. The leaving is hard. You get to choose which consequences you're willing to live with. So ask yourself, what does Tuesday at 3:00 PM feel like?

And what does Monday morning feel like and which hard do you actually wanna carry? Because those moments, that's your actual life. Listen, if this is home for you, if you've been stuck between safe and scared and you need to see it more clearly, go grab 10 ways AI will make you a better leader.

At hello, Dawn. Live slash 10 Ways, it's free. One of those 10 ways is how you pressure test your [00:08:00] biggest decisions so you can see both the numbers and what it would actually feel like to live that choice. Download it, use it. This week, you deserve sleep. That decision you're wrestling with.

 You've got this. You just need to ask the right question, not can I make this work or am I good enough? Or do people value this or want me in this capacity? But. Which hard do I want? And the path that scares you. The one where you'd actually be building something that's yours. Pay attention to that one.

 Take care of yourself, lovey. See you next time.