Your Business Needs More Than a CEO Day w/ Tracy Medeiros

Most entrepreneurs make time for their clients. Very few make time for their business.

It's easy to get caught up serving clients, answering emails, and checking off daily tasks without ever stopping to ask whether your business is actually moving in the direction you want. When every week feels the same, it's hard to find the time and space to think strategically, improve your systems, or make intentional decisions about what's next.

In this episode of the Business Chaser, Tracy Medeiros shares how her monthly CEO Day evolved into a full CEO Week and why creating dedicated time to work on your business instead of just in it can completely change the way you lead. She explains how regularly reviewing your metrics, updating your systems, revisiting neglected projects, and reflecting on where your time is best spent. can help you make better decisions, prevent burnout, and build a business that supports the life you want. So, if you're ready to stop operating on autopilot and start leading your business with greater intention, then this episode is for you.

Connect with Tracy:

Medeiros Consulting Substack - https://medeirosconsulting.substack.com/

LinkedIn - www.linkedin.com/in/medeirosconsulting

Instagram - https://www.instagram.com/medeirosconsulting/

Chapters:

00:25 Why a CEO Day wasn't enough anymore

01:50 How CEO Week creates space for real growth

03:25 Planning projects and reviewing what matters

04:45 Making CEO Week something you enjoy

05:50 Why intentional reflection matters 

06:50 Updating systems as your business evolves

08:00 Planning for growth without overplanning

09:25 Questions every business owner should ask

10:20 Building a business that supports your life

11:20 Creating your own version of CEO Week

This podcast is brought to you in partnership with Liz Chapman & CO

Upcoming Events:

Napa Retreat - October 5-8, 2026 - https://laurennajar.myflodesk.com/cetj223rsr

Growth & Connect Events - https://laurennajar.myflodesk.com/hb2a0mwbqw

Save 25% with Flodesk - https://flodesk.com/c/OR8VKL

Let’s Stay Connected:
→ Follow Lauren on Instagram: www.instagram.com/laurennajar
→ Learn more or work with me: www.laurennajar.com
→ Follow Business Over Cocktails on IG: www.instagram.com/businessovercocktails
→ Attend Growth & Connect retreats & events: www.instagram.com/growthandconnect

🎧 Subscribe & Review:
Love the episode? Don’t forget to subscribe, leave a review, and share with a friend who needs a business boost and a good chat over a cocktail.

Transcript

SPEAKER_00 0:01

Welcome to the Business Chaser, your quick pour of strategy, clarity, and momentum. We skip the small talk and get straight to the strategy here in these bite-sized episodes. We're here to help you grow smarter, market better, and chase what matters all in 15 minutes or less. I'm your host, Lauren Najar. Tune in and let's chat.

SPEAKER_01 0:24

Aloha, everyone. I'm Tracy. Thanks for having me back. I thought we'd talk a little bit about CEO week. And I know you've heard the concept. You've probably had mentors that have told you how or that how you should have a CEO week or a CEO day. And I have to admit, over the years, it has gone from I don't work Fridays. So it started as a Friday CEO day, which wasn't nearly enough. Then it emerged into a long CEO weekend, which I still like to do to treat myself because what I'll do is I'll go ahead and reserve a hotel room and just away from everything, no distractions, enjoy, you know, the luxury of the hotel room and their commodity, not commodities, accommodations. And then also get planning and everything that I needed to do, special projects or whatever. And now it has currently morphed into CEO week. So the last week of the month, I do not take any client calls, I do not take any client work. It is strictly for me to work on my business and not just in it. And I guess what sets it apart is it's a little different. I think you like this is not a new concept. So I think you've heard about it before. And you hear a lot of people say, oh, it's, you know, time to work on projects, it's time for planning, it's time to look at your metrics. Or it's just time for you to decompress and make sure that you fill your cup and you are ready to go that following week for, you know, the next three weeks. So I guess just how I do things in general is that you're the boss, you get to decide. So I just wanted to kind of show you verbally how I do mine so you can take bits and pieces of it and incorporate that into your business. Because I do think it's a very important piece of business because it allows for so many things. It allows for you to compress, it allows you time to think, what do you want next in your business? Or how is your business, you know, not performing the way that you want it to? And what tweaks? I think that's something that we don't necessarily all think about in a timely manner. Like if we're not taking time to look at our business and how it's performing, and is it, you know, pushing the needle forward the way we want it to be, do we give ourselves enough real time to locate what's wrong and make those changes instead of at the end of the year when we're looking at our metrics or we're looking at how things are going and reflecting on the previous year before we start the new year and seeing, oh, you know what, this doesn't actually bring in any return on investment. I should probably not put a lot of effort into that. I think if we have time every month to look at those things, it's a lot easier for us to recognize this is a problem. I need to find a solution, and let's make that tweak now instead of waiting until the end of the year or, you know, whatever that time frame is. So for me, it's really easy. I like to still have my same office hours that I have normal, which is nine to four, Monday through Thursday. And in that week, Monday is typically because Monday for me, no matter when in the month, is typically a planning day. It's it's making sure that I have everything set up for the week. I know what calls I'm having, I know what I need to prepare, I know what deadlines I have. So Monday is just an extended planning day, really. I like to kind of ease into it. I usually have breakfast with my husband, ease into it and also see what kind of projects have been neglected. There's so many times we have these projects that we've started the beginning of the year or whatever, and they just kind of get pushed to the side because we get busy or life happens or whatever. So bringing those back and saying, are they still relevant, or do we need to delete them and just get them off of our to-do list, or do we need to schedule some time this week to see if we can implement it? So there's a lot of things that go into a CEO week. That is important. I do feel that some sort of planning and looking at your metrics is super important to schedule into that CEO week. I also think that you need to have something to look forward to during CEO week, whether that is staying a day at a hotel or having lunch with like an extended lunch with a friend, or maybe it is, you know, you just taking the kids somewhere, but you do have something that you're excited to do that you don't often do, and you do that during that week as well. And then I also think that it's important to have, I'm lucky, I live on an island, so I get to go to the beach, but some downtime where you can go through some of those reflection questions about how things are going, not just for your business, but for yourself too. Cause as business owners, we can get wrapped up with what's going on and we get caught in the weeds. And sometimes we're just doing things on autopilot and that we need to kind of take a step back and say, you know, hey, this isn't what I want to be doing. I want to be doing some things with more intentions. So we need to take a step back, take a breath, and plan a little bit more of less of this and more of that. I know that's pretty, pretty vague there, but it's all going to be different with the different business owners and with different types of business as well. Then I also think, you know, it's also up to you and your body. Like if you are just kind of slugging into going into your office, I have an office that is very important just because I do not go into my office until I know what the plan is for the day. So my office door is usually closed if I'm not in it. And I don't go into it until I have that plan. So I don't waste a bunch of time trying to figure out like, okay, what are we doing today? So making sure that we have like those little systems in place as well that help us get to where we want, maybe that's taking just a refresh of your personal systems. Or maybe there's, you know, some sort of system in your business that's a little clunky. You've outgrown it. So time to kind of look at how your systems are. I always say there's certain things in your business that are living, breathing documents or living, breathing things in your business. And your systems are definitely living and breathing, and they need to evolve as you evolve. Your SOPs are some of those. Maybe you have a whole day where you are rewriting SOPs because changes came up and you want to make sure they're up to date. Or maybe, you know, if you have a team, maybe just thinking, okay, the holidays are coming up. We're going to want to do some team training. We're going to want to celebrate the end of the year. We're going to want to make sure we're prepped for 2026. Like some of that pre-thinking of what do we really need to do in the future to make sure that we are pushing our business forward in the direction we want it to go. So I think the biggest thing for CEO Week is you do need to recognize your projects that you want to work on. You want to do some planning. I'm always planning in 90-day increments, but then there's always kind of like a refresh. Every month we want to look at what worked, what didn't work, you know, even like how you feel with how things went. So, like maybe there was something that had some really good return on investment. Maybe it was something you absolutely hated doing. So then thinking, really thinking and giving yourself time space to think and really dig deep into this, not just like, oh, I have five minutes here, we'll think about and then we'll decide. And then you kind of put a band-aid on things. Really think about like, okay, is it worth my energy? Is it worth, you know, the way that I felt? Is it something I can delegate? If it's something I don't want to get rid of in my business, because it had such a return on investment, maybe we need to look at hiring someone to just do that because I don't want to do that again. It was horrible. Um, and I don't think we spend as much time as we should on those things, which I think really in the long run will move your business forward. It will help you scale, it will help you make money, it will help just how you feel and your stress levels, your nervous system, and even like, you know, that burnout. I think if we gave ourselves more time to think about how things are going. And there is such a thing as over planning. I would totally and, you know, totally recognize that that's a thing too. So we want to make sure that we're not hiding. That's another thing about looking at, you know, how your body feels is okay, are we hiding from something and we're just really planning? Maybe we have the next 10 years planned, which, as some as you know, there's a lot of things that happen in 10 years that are not in our control. So most likely we're gonna have to revamp that plan anyways. I think that's why when I plan, it's always objections or objectives, sorry. And for like the three to five years and and 10 years, I do go as as far as 10 years, but they're objectives. And then you kind of fill in the blanks when you have a closer, shorter time period that you have more control over. I think 90 days, six weeks, that kind of a time frame, you definitely it's long enough for you to accomplish stuff, and yet it's short enough where you have a lot of control in it. So I'm throwing a lot of stuff at you. This is like a fire barrage of just info for CEO week. But then I want you to end it to like really thinking not just your business and asking, like, where we stand right now, what does my business need from me? And what do I need from my business? So that's another reflection piece. But I think if you close the end of the week with that, it also helps just kind of that reignition of excitement in your business. Being held by your business. We have started a business for freedom, and sometimes we kind of go away from that, and it's just we're caught in the weeds of the day-to-day and we forget, like, okay, there were certain things that I wanted to accomplish, or I wanted to start this business so that I could have some sort of container and income to do something else. A lot of my clients are working with two businesses, or maybe it's a passion project and their business. And so their business is kind of a container for a bigger mission. And I think not that we need anything else to do in our life, but thinking about those things. Is this what my life is supposed to be? And I know we're getting a little hypothetical and deep over here. So I'm gonna probably end on that note. But again, I'm gonna just reiterate you're the boss, you get to decide, make this a time for you that you celebrate you, you celebrate your business, you put yourself on the right path for the next months. Maybe you're even into quarter planning, that you're setting yourself up for success. And so many things go into that. And it's gonna differ from people to people. So do the things that you enjoy doing that are gonna move your business forward.

SPEAKER_00 11:56

That's your quick hit of clarity and momentum for the week. If it sparks something, share it with a friend or tag us in your stories at Business Over Cocktails and or at Lauren Major. We love seeing what resonates. Don't forget, Mondays are for full-length episodes with rich conversations, and Fridays are the Business Chaser episodes. These are bite sized insights pulled from our guests to keep you inspired and aligned throughout the week. Do you have a question or takeaway? DM us at Business Over Cocktails. We just might feature it in a future episode. Cheers!