Monthly CEO Days: How to Actually Make Time for Business Structure

Most business owners know what they should be doing to grow their business.

They know they need to work ON their business, not just IN it. They know they should be thinking strategically about where they're going, not just firefighting every day.

The problem isn't knowing. It's doing.

And here's what I've learned from working across retail and hospitality for over 20 years - from both the landlord side and the brand side, running my own businesses, and now supporting founders: The businesses that consistently grow aren't working harder. They're not more talented. They've just built a rhythm that makes strategic thinking as non-negotiable as paying the bills.

This is how you build that structure.

The Monthly CEO Day Practice

The businesses that consistently grow aren't the ones that think strategically once in a while when they happen to have time. They're the ones that build monthly time to work ON their business into their routine.

Monthly "CEO Days" - dedicated time where you step back from operations and focus on strategy - are what create momentum. It's not complicated, but it does require commitment.

Same day every month. First Tuesday. Last Friday. Third Wednesday. Whatever works for your business - but it's the same day blocked in your calendar for the next six months. Right now! Not next month when you've "got more time" - because you never will. You treat it like a client booking. Because it is - you're the client.

I run Founder Sessions - monthly work days for business owners doing exactly this. First Tuesday of every month. Same time, same structure. And here's what I've noticed: the founders who show up consistently, month after month? Their businesses look completely different six months later. Not because they're working more hours. Because they've created protected space to think properly about what matters.

The ones who keep meaning to do it but never quite get there? They're still having the same problems they had six months ago. Same cash flow issues. Same staffing dramas. Same vague sense they should be growing faster but don't know how.

And here's the thing that makes the difference: you actually protect it. If something urgent comes up, you reschedule it to the same week. You don't just skip it and tell yourself you'll do it next month. The businesses that grow treat this time as sacred. Because it is.

What You Actually Do on a CEO Day

Don't just block time and hope inspiration strikes. Have a structure you work through every time.

The framework I use with clients - and in my own business - comes down to three questions: (If you haven't worked through these yet, go back and do that first. Seriously. This whole thing falls apart if you're just vaguely thinking about strategy without a structure.)

1. What actually moved my business forward recently? What created real results in the last month - not what kept you busy, but what made an actual difference?

2. What would make the biggest difference in the next month? If you could only focus on ONE thing, what is it? Not ten things. One.

3. What's stopping me from doing that thing? The real answer. Not the polite one. Time? Money? Clarity? Confidence? Support?

Want the full breakdown of how to work through these? Read the framework here: 3 Questions To Help You Create Business Clarity

Why Creating a Business Structure Usually Falls Apart

Here's what I've seen happen with most business owners who try monthly CEO Days on their own. The first month, they show up. They do the work. They feel great about it. The second month, something comes up and they bump it. "Just this once" they tell themselves. The third month never happens. Not because they're uncommitted or lazy. It's because three things get in the way:

There's no external accountability. When it's just you deciding whether to show up, it's too easy to bump it when something feels more urgent. Without someone expecting you to be there, it never happens.

They're working in a vacuum. You can't see your own blind spots. You second-guess your answers. You spin on the same questions for three hours and end up more confused than when you started.

There's no follow-through. You do the exercise, you get clarity, you make a plan... and then nothing happens. Because there's no one checking in a month later to see if you actually did what you said you'd do.

I see this constantly. Business owners who start strong in January, maybe even make it to February, then it's April and they haven't done a CEO day in two months. They feel guilty about it. They know it matters. But without structure and accountability, it just... doesn't happen.

It's not a character flaw. You're not uncommitted or lazy. You're just trying to hold yourself accountable to something that has no external consequences when you skip it. That's nearly impossible.

How to Make Your New Business Structure Actually Stick

The difference between business owners who make monthly CEO Days happen and those who don't usually comes down to accountability.

You need someone - or multiple someones - expecting you to show up.

That might look like working alongside other business owners on the same day, even if you're each focused on your own business. Just knowing you're all showing up creates accountability.

Or it might look like having someone check in with you after your CEO Day to ask: "What came out of it? What's your priority? What's stopping you? What are you doing about it?"

This is exactly why we created Founder Sessions. Monthly work days where you show up alongside other business owners who are also building something properly. You're each working ON your own business, but you're doing it together. There's accountability built in because people expect you to be there. There's energy because you're not doing it alone. And there's structure because we work through the same framework every time.

But accountability isn't the only thing that makes this work. Sometimes you need more.

When You Need More Than Just Accountability

Sometimes the obstacle isn't just making the time happen - it's knowing what to do with it. You work through the questions but your answers feel vague. Or you're pretty sure you're not focusing on the right thing but you can't see what the right thing is. You're too close to your business to see what's actually stopping you. This is when you need someone to help you see what you can't see. Someone who can ask the questions that unlock clarity and help you spot the patterns you're missing.

Or you know what your obstacle is - you've identified it - but you can't seem to get past it. Every month it's the same thing blocking you and you don't know how to remove it. This is when you need strategic input, not just accountability. Sometimes that's a focused strategy session to work through options. Sometimes it's ongoing support to help you build the structure that solves it.

Or you're clear on what needs to happen, the problem is making it happen. You need someone who can help you break it down, build the systems, and work with you over time to actually implement what you've planned.

Different problems need different types of support. The trick is being honest about which one you actually need.

The businesses that have built this rhythm - monthly space to work ON their business that's actually non-negotiable - are the ones making real progress. Not because they're working harder. Because they're working smarter.

They've created space to think, clarity on what matters, and support to make it happen.

You can do the same.

Need Support to Make This Happen?

Look, here's the reality.

The businesses that have built this rhythm - monthly space to work ON their business that's properly non-negotiable - are the ones making real progress. Not because they're working harder. They're not. They're working smarter.

They've created three things:

• Space to think (protected time that doesn't get bumped)

• Clarity on what matters (so they're not just spinning on the same questions every month)

• Support to make it happen (accountability, strategic input, or both)

You can absolutely do this on your own. Block the time. Work through the framework. Hold yourself accountable. Some people manage it.

But if you're honest with yourself and you know you need proper support to make this stick - whether that's accountability, strategic guidance, or someone in your corner who gets retail and hospitality - that's what Market & Me does.

Founder Sessions - Monthly work days with other ambitious business owners. You show up, work ON your business using the framework, and leave with clarity on what matters. First Tuesday of every month.

Power Hour - Sixty minutes to untangle a specific challenge and/or chat through what you're stuck on. Pricing, positioning, priorities - whatever needs sorting.

Growth Partner - Ongoing strategic support for when you want someone who knows your business helping you make decisions and build the structure that gets you where you want to go.

Not sure what you need? Just get in touch. We're always happy to have a proper conversation about what would actually help: Book a discovery call.

This is part 3 of a series on working ON your business:

• Part 1: How to Work ON Your Business When You're Drowning in the Day-to-Day

• Part 2: 3 Questions To Help You Create Business Clarity

• Part 3: How to make it stick (you're here)