Not so long ago, we threw a little something out into the Instagram-verse as part of our October Challenge. One of the prompts? Take a CEO Day. Seemed straightforward enough, right? Well, apparently not. Almost immediately, the DMs and comments rolled in: “What even IS a CEO Day?” “Do I need one?” “Can I wear sweatpants?”
So here we are, answering all your CEO Day questions. And yes, you can absolutely wear sweatpants. They aren’t just for Fortune 500 executives in fancy Chanel designer suits; they’re for any leader who wants to stop drowning in the to-do list and start steering the ship.
Whether you’re deep in the trenches of a start-up or juggling a million things as a seasoned entrepreneur, this article isn’t just a casual FYI; it’s a loving nudge to all you fabulous fempreneurs to stop running on the hamster wheel and start running your biz like the sheEO you are. Ready? Let’s dive in.
The Art of Working ON Your Work (Not Just IN It)
Let’s talk about the art of working on your work, and not just in It. Now, don’t roll your eyes just yet. We’re not suggesting you start strutting your home office barking orders at your cat (unless that’s your thing – then, by all means, strut away). A CEO Day isn’t about flaunting a title; it’s about the vibe. It’s about zooming out from the daily grind and finally acting like the boss of your own business (or life) instead of the employee who’s constantly scrambling to make it through another day.
Let’s paint a hypothetical scenario so you can see what we’re getting at:
It’s Monday. Your alarm goes off, and before you’ve even had a sip of your morning coffee, your brain starts sprinting, juggling 47 tabs and counting. You check your phone – there’s already a string of emails demanding your attention, a Slack message from your VA asking for guidance, and a calendar notification reminding you about a client call in… oh, 10 minutes…DOH!
You mentally scan your day:
Finalize the social media schedule
Review the copy for the new sales page
Handle that weird invoicing issue from last week
Oh, and didn’t you promise yourself you’d finally map out a marketing strategy this week?
Cue the multitasking tornado. You’re toggling between your inbox and Instagram, juggling customer inquiries and “networking” (which is mostly you commenting “This!! 💯” on posts). Somewhere between your third cup of coffee and the fifth email titled “URGENT,” you have a brief moment where you think, “I really should be working on my big-picture goals.”
But then… ping! Another email. Another task. Another fire to put out. And just like that, the thought vanishes into the abyss. Spoiler alert: That’s not strategy – it’s survival.
What Is a CEO Day, Anyways?
Glad you asked. A CEO Day is reserved for high-level thinking and reflections. It’s about zooming out, seeing the big picture, and asking questions such as:
What are we building here?
Are we on track to hit our goals?
Why do I have 14 pens but no working printer ink?
It’s your chance to play the roles of visionary and strategist. CEO Days aren’t about “catching up on work”; they’re about creating the roadmap – dreaming, scheming, and goal-setting – for where your business is headed and ensuring the car still has gas in the tank.
But Isn’t a CEO Day the Same as Slow Management?
Not exactly!
While a CEO Day and slow management both emphasize thoughtful leadership, they serve different purposes. A CEO Day is a dedicated block of time reserved for stepping back from the daily grind and focusing on the bigger picture, while slow management is a mindset – a way of operating your business with intentionality every single day. It’s about resisting the hustle-at-all-costs mentality and choosing a pace that allows for sustainable growth, thoughtful decision-making, and, let’s be honest, fewer late-night “panic-working” sessions.
Why You Need a CEO Day (Like, Yesterday)
We know what you’re thinking: “Sounds nice, but who has time for that?”
Here’s the thing: You can’t scale a business if you’re stuck in the day-to-day rat race. No one ever said, “Oh wow, I really built a thriving company because I answered emails faster than anyone else.”
CEO Days are how you:
Avoid burnout: No one can sprint forever. CEO Days force you to slow down, breathe, and remember why you’re doing all this in the first place.
See the forest, not just the trees: When you’re knee-deep in tasks, it’s easy to lose sight of the bigger picture. CEO Days are like climbing a metaphorical mountain, looking down, and thinking, “Ohhhh, that’s where I’m headed – directly into Chaos Canyon if I don’t keep climbing up to Vision Peak!”
Strategize like a boss: Goals don’t set themselves. Systems don’t magically appear. CEO Days are where you do the boring-but-brilliant work that sets you up for long-term success.
To grow, not just maintain: You can’t scale your business if you’re always too busy just trying to stay afloat. CEO Days are how you level up.
Without big-picture thinking, you risk spending all your energy running in circles, checking things off to-do lists, and never actually moving the needle.
How Do I Plan a CEO Day?
That’s a great question.
Here’s a step-by-step blueprint for your next CEO Day:
1. Start with Reflection
Before you can look ahead, you need to glance in the rearview mirror.
What went well this quarter?
What fell flat on its face?
Are your metrics telling you a story of growth or stagnation?
This is your moment to throw a mini party for your wins (yes, even the small ones count – no need for confetti cannons) and hold a candid post-mortem for the flops.
2. Revisit (or Set) Your Big Goals
Remember that business plan you wrote forever ago? No? Exactly. Dust it off, or create one.
What are your top three goals for the next 6-12 months?
Are your current efforts aligned with those goals?
What needs to change for you to hit them?
Get specific. “Make more money” is not a goal; “Increase revenue by 20% through new client acquisition” is.
3. Map Out the Strategy
Now it’s time to connect the dots between your goals and your to-do list. Think of this as translating your big dreams into bite-sized action steps.
What projects will help you hit your goals?
Who needs to be involved?
What deadlines need to exist?
Bonus points if you break out the sticky notes and color-coded pens.
4. Review Systems and Processes
Here’s the unsexy part: Look at what’s broken.
Is your workflow efficient, or are you wasting hours reinventing the wheel?
Are there tools or automations that could save you time?
Are you delegating effectively, or are you still hoarding tasks like a squirrel with a stash of acorns for winter?
Small tweaks here and there can save you hours in the long run.
5. Dream Big
When was the last time you let yourself really dream? This is the part of your CEO Day where you ask yourself what if?
What if I launched that new product?
What if I expanded to a new market?
What if I finally hired that assistant I’ve been meaning to hire?
Dreaming isn’t indulgent; it’s where innovation begins.
How to Have the Most Glorious CEO Day of Your Life?
For starters, block off time in your calendar like it’s a sacred ritual – no, seriously, treat it like it’s a dentist appointment that you can’t cancel. Put your phone on “Do Not Disturb.” Bring snacks (snacks are non-negotiable). Wear something comfy (If you want). Heck, light a candle, build a pillow fort, or maybe even do a victory lap around your living room if it helps you channel your inner visionary genius. Who says strategizing has to be boring? CEO Days should feel like a retreat, not a hostage negotiation. Crank up your Spotify playlist and let those tunes fuel your creativity.
Remember: CEO Days are for dreaming big, so make the vibe as bold and as vibrant as you want.
Conclusion: Put Down the Fire Extinguisher and Pick Up a Vision Board
Let’s be real – running a business sometimes feels like you’re on 24/7 fire patrol, sprinting from one crisis to the next with a metaphorical extinguisher in hand. But here’s the thing: if you’re always putting out fires, who’s steering the ship? Well…..no one.
That’s why CEO Days are a must. They’re your golden ticket to stepping off the hamster wheel, taking a deep breath, and actually leading – not just reacting. It’s about plotting a course that doesn’t send you straight to Burnout Boulevard with a one-way ticket.
Moreover, it’s not about abandoning your daily tasks – it’s about zooming out, seeing the bigger picture, and deciding where you actually want to go. Because the goal isn’t to survive the chaos; it’s to build a business that thrives.
So, swap that fire extinguisher for a vision board and CEO the heck out of your life, one well-planned, visionary day at a time. Because the fires can wait. But your future? That can’t!
