She's That Founder: Business Strategy, Time Management and AI Magic for Impactful Female Leaders

078 | How I used AI To Run My Business Retreat (While Actually Resting)

• Dawn Andrews • Episode 78

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Ever wish you could step away from your business and have it keep moving without you? 

Last week in San Francisco, I did exactly that because my AI assistant ran the whole thing.

In this episode, you’ll discover how to stop carrying the entire mental load of your business, from thinking and planning to solving everything, by handing it over without handing it off to a human.

You’ll see how AI can plan your projects, handle the details, break creative blocks, and give you space to rest without losing momentum, so you can reclaim your time, protect your energy, and focus on the high-value work only you can do.

In this episode, you’ll learn…

  • How to use AI as your strategic planner to design work sessions that leave you energized, not exhausted
  • Ways AI can act as your personal concierge to kill decision fatigue and free your brain for real CEO work
  • The “choose your own adventure” method AI gave me to break through creative blocks
  • Why letting AI take the load gives you the mental space to wander — and why that’s part of the work

This episode at a glance:

[03:14] – Your AI assistant never sleeps, never judges your questions, and costs less than a nice dinner out.

[07:56] – Wandering is part of the work. And AI can give you the space to do it.

[14:22] – Ask AI to create your restore/rebuild/reignite plan, and watch how it balances your goals and your human needs.

[21:08] – The goal isn’t to replace your creativity — it’s to remove the cognitive overhead so you can focus on what only you can do.

[28:41] – You’re not meant to carry it all. You’re meant to lead. Let AI handle the rest.

Resources and links mentioned in this episode:

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Dawn Andrews:

I'm actually recording this sitting in a hotel room in San Francisco where I have just spent a week running a business retreat. But here's the thing, I wasn't the one running it. My AI assistant was while AI handled the logistics, the strategy, the meal planning and even my creative blocks, I got to wander through Macy's, sit by the bay and have a lovely lunch and still move my business forward in ways that actually mattered. I came home rested with three major projects advanced and a completely new relationship with what it means to work with intelligence instead of just working hard. If you've ever felt like you're carrying the entire mental load of your business, if you're the one who has to think of everything, plan everything, and solve everything, this episode is going to change how you think about delegation, because what if the person you're delegating to isn't a person at all you're listening to. She's that founder the show that helps ambitious women stop drowning in decisions and start owning their CEO seat. I'm Dawn Andrews, and today we're talking about something that might sound impossible, how to actually rest while advancing your business using AI as your ultimate force multiplier. So let me paint the picture for you. I was headed to San Francisco for a week, which is where I'm sitting now. My son's at culinary camp. I've got a hotel room to myself, and theoretically this is my chance to work on the big stuff, the projects that always get pushed aside when I'm in reactive mode. The old me would have approached this like a productivity boot camp, packed schedules, 12 hour work days, up at 5am maybe a gym session. If I was lucky, I would have come home exhausted but feeling like I'd maximized the time.

Dawn Andrews:

But here's what I've learned after 23 years in business, grinding harder is not the answer, even if I'm pulled to do it over and over again, the answer is working smarter, and working smarter means having the right support systems.

Dawn Andrews:

The problem is, as founders, we think support means hiring people, but before you're ready to hire that executive assistant or operations manager, especially if it's a reach for your budget, there is another option, an AI assistant that never sleeps, never judges your questions, and costs less than a nice dinner out. So I decided to run an experiment. What if I let AI handle everything, the planning, the problem solving, even the creative blocks, so I could focus on what only I can do, the vision, the strategy, the actual CEO work.

Dawn Andrews:

Here's exactly how it worked part one, using AI as your strategic planner. So this was the first challenge. The first challenge was designing the retreat itself. When I'm sitting in my office at home, my to do list is ridiculously long, and it goes in so many different directions, but I knew that if I was taking this time away, I wanted to move my business forward, and I also knew I was coming from a place of a little bit of burnout.

Dawn Andrews:

I'll just tell you guys, it's been an epic year over here at home, but I needed something that would leave me energized and not depleted the old way I would have spent hours researching retreat models or how other experts that I admire had done their own retreats. I would have listened back to podcasts and taken notes poop, trying to balance productivity with self care and probably overthinking every detail. In fact I know I would have done that, and instead, I opened chatgpt, and I said, help me design a retreat. I arrive Sunday afternoon and check out Saturday morning. I have dinners with friends on Wednesday and Friday. Create something that leaves me and my business in a much better state. After I spend time there, I want to feel rested, joyful and accomplished without pushing too hard.

Dawn Andrews:

And here's what blew my mind. Ai didn't just give me a schedule. It gave me a framework, restore, rebuild and reignite. It's structured each day with morning movement, strategic building blocks, creative play and evening resets. It even included journal prompts for each day, like, what would my business look like if it felt easier to run and more fun to grow? And that was a great prompt to answer the force multiplier here, AI handled all of the strategic thinking about how to balance productivity with restoration with revenue, and I didn't have to figure out the optimal flow or worry about over committing, which is my tendency, it gave me a structure that honored both my ambitious goals and my human needs.

Dawn Andrews:

So here's what happened next. I used AI as my personal concierge. This is where it got really practical. I'm in a city that I used to live in that I loved, but it's been a while since I've been here, and I'm a dawn. From person than when I used to live here. So I have specific health goals. I'm avoiding seed oils. I'm focusing on hormone friendly foods. I'm trying to support my energy rather than crash it.

Dawn Andrews:

So again, this might mean hours of research, reading reviews, checking menus, mapping locations to my schedule, decision fatigue would set in before I even started working, and instead, I told AI exactly what I needed. I said, I'm in San Francisco. I love good, healthy food. Treat me like a local and suggest the best places for me to eat that align with my retreat schedule and my food goals, right? It's just bananas, and it gave me a curated list of actual restaurants with reasons why each place fit my criteria. It suggested Blue Barn gourmet for their organic farm to table salads. And I hope you take these away so that you can enjoy San Francisco like I did. It suggested Green's restaurant for plant forward dishes set by the water, even specific dishes to try, even specific ordering instructions if I needed them. It also suggested true food kitchen. And I said, Girl, my AI. Girl, this isn't actually in San Francisco. And without missing a beat, it pivoted to local alternatives, alternatives with whole 30 friendly options, and other restaurants that had a commitment to ditching seed oils entirely. Force multiplier, right? Ai became my personal nutritionist, my local guide and my logistics coordinator rolled into one. I spent zero mental energy on meal planning, and got to eat incredibly well all week.

Dawn Andrews:

So here's what happened next. AI as my creative partner and block breaker. So this is where the magic really happened. Wednesday rolled around, and I hit that retreat panic that maybe you all have felt at various times. I know you've felt it on vacation. You know that feeling where you're like, oh my god, I only have X number of days left. And for me, it was, I only have three days left, I'll never get everything done. What should I do? I had four major things on my mind coming into this retreat as strategized with AI as my partner. The four things were moving the AI for founders playbook forward, banking, podcast content right here, doing it now, getting my money in order again, and dealing with a huge stack of papers that I brought from my office, old me would have spun out and tried to do everything at once and ended up scattered or honestly, wanting to take a nap, like that's probably what would have happened. And it kind of did happen on Wednesday, actually.

Dawn Andrews:

And instead, I asked AI, I'm feeling that panic, help me approach this day strategically. And here's what it gave me, it kicked out a priority map based on energy and return on investment money first, because it gets your nervous system settled based on energy and ROI. And the irony of this is, this is what I coach my clients to do, but it's very difficult, as you might know, as an expert in your field, to turn that expert advice back on yourself.

Dawn Andrews:

So I've trained my AI assistant to understand who I am and how I work, and it coached me back to me. So it suggested money first, because it's fast and it gets your nervous system settled. Then the AI for founders playbook, because it's a strategic asset. Then content creation while I'm energized, which I'm doing this afternoon, after lunch and paperwork last with a 25 minute time box, just to reduce the weight of the papers, which I don't know if I told you, but I brought basically all the piles of papers that have been sitting around my office for the last year. I packed them and brought them with me.

Dawn Andrews:

But that's another story, but the real breakthrough came when I got stuck on working on the AI for founders playbook, it was just a moment of, like, lack of motivation, not really clear which thing I wanted to start on next. I just felt blocked and I was procrastinating. So I asked AI to help me break through the procrastination, and it gave me a choose your own adventure approach. Pick one module, use a five part template and do a 15 minute brain dump. When I said that none of the modules it suggested were actually inside the playbook, it immediately pivoted and asked me, please share your playbook. I'll help you pick the best one to finish today. Again, force multiplier.

Dawn Andrews:

AI provided objectivity when my emotions were running high. It gave me structure when my brain was scattered. It became my brainstorming partner, my strategic advisor and my creative unblock tool all at once. If this is blowing your mind and you're thinking, I need this kind of AI support in my business, then you're going to need that AI for founders playbook. It's 12 custom agents and workbooks that handle everything from weekly planning to content creation to Team feedback. These aren't generic chatgpt prompts. These are founder specific tools, things that I actually am using, like I am building in the playbook, the things that I am using in my business. So these are founder specific tools that understand.

Dawn Andrews:

Your unique challenges, you can grab them at free range thinking.com forward slash, AI dash playbook and start building your AI support team now. And I'm still building the playbook, so you can get on the wait list right now, check the link in the show notes and start building your AI support team now. So with all that said, let me tell you about my favorite moment of the whole week, Tuesday afternoon. I was just so antsy when you're dealing with adrenaline recovery, sometimes you feel like your skin is literally being peeled off, and so I needed a break, and instead of pushing through, I decided to walk over to Macy's. I'm not a big shopper. I'm not even really a Macy's shopper, but it just felt like a calm place to go wander. So with no agenda, no productivity goal, I just went and wandered. I touched fabrics I didn't need, I looked at shoes I'd never buy, and I felt my whole nervous system exhale, and in that moment between handbags and watches and sprayed colognes, something hit me that this is part of the work. Wandering is part of the work.

Dawn Andrews:

So when I got back to my hotel, I shared this insight with AI and said, turn this into a podcast intro. Within minutes, it had crafted a polished opening that captured the essence of that moment I walked into Macy's today, not for anything important, not for strategy or clarity or sales, I just needed a break. And you know what hit me between the handbags and earrings, this is part of the work again. Force multiplier AI helped me turn a random moment of self care and insight into content that would resonate with founders who need permission to pause, and maybe that's you, if you want to know your AI readiness level, I've created a quick assessment that shows exactly where to start with AI in your business. You can take that quiz at free range, thinking.com forward slash AI dash quiz and get your personalized roadmap to working with artificial intelligence instead of just working harder.

Dawn Andrews:

Here's the shift I'm inviting you to make, from I have to figure it all out to AI can handle the cognitive overhead of running a business. You don't need to carry the entire mental load. You don't need to be the one who thinks of everything, plans everything, researches everything, and solves everything. AI can be your strategic planner, your personal concierge, your creative partner and your objective advisor. It can handle logistics so you can focus on the vision. It can provide structure when you're scattered and perspective when you're stuck.

Dawn Andrews:

So here are three things you can try this week. First, ask AI to plan your next strategic work session. Use my retreat framework. What do you want to restore, rebuild or reignite, and let AI create that structure for you. Second, allow AI to be your personal research assistant, whether it's finding restaurants that fit your dietary needs, sourcing a specific software solution or even planning your kid's birthday party and putting together a shopping list. Stop doing the mental labor that AI can handle. And third, use AI to break through creative blocks.

Dawn Andrews:

Next time you're stuck on a project, use the five part template. Purpose, prep, steps, pro tips. Next moves. There you go. Let AI help structure your thinking. The goal isn't to replace your creativity or judgment. It's to remove the cognitive overhead so you can focus on what only you can do, the vision, the relationships, the strategic decisions that grow your business. I know now, and it's not even the end of the week yet that when I come home from San Francisco, I will have advanced three major projects with a month of content outlined. In fact, three months of content completed. My finances organized, amen, and that paper stack finally tackled.

Dawn Andrews:

But more importantly, I'm coming home rested, energized and clear on my next moves, which is gold. That is the power of working with AI as your force multiplier. So if you're ready to build your own AI support system, the AI for founders playbook walks you through exactly how to use our custom agents and workbooks to handle everything from weekly planning to content creation to team management and feedback, you'll get the exact prompts and tools I use, plus templates for customizing them to your business. Get on the wait list for it. Now the link is in the show notes and start delegating to your AI team today. I just want you to remember you're not meant to carry it all. You're meant to lead. So let AI handle the rest.

Dawn Andrews:

All right, that's a wrap on today's episode of she's that bounder. If this resonated with you, take a screenshot and share it on LinkedIn tag. Me at dawn Andrews, so I can see your biggest takeaway. And if you're ready to stop drowning in decisions and start owning your CEO. Seat with AI as your partner. I'll see you inside the AI for founders community on LinkedIn. Until next time, keep building something beautiful and