How I Took a Full Month Off in Italy (While My Business Runs Without Me)

Rachel Cook: As you're listening to this, I am in Italy. In fact, I am in Tuscany, in a little town called Poggibanzi, in a beautiful villa with my entire family. This is our month long trip and we've already been in Italy for a few weeks. We've already seen Florence, we did a day trip through Venice, and now we are getting ready for a big family wedding here in Tuscany. Right now, I am probably, uh, lounging at the pool, watching my kids and their cousins play, enjoying the beautiful scenery. Y'. All, I plan to have my under the Tuscan sun moment. What I'm not doing is refreshing my inbox in a panic or, or wondering if everything's falling apart while I'm away, because I know it's not going to. The business is going to keep running. Clients will continue being taken care of, content will go out, all of it, without me at the wheel this month. And I want to be really clear about something. A trip like this, a month away, is not about me, uh, crossing my fingers and, and hoping that everything hangs in there without me. A month away is not about luck. It's about planning and systems and those you can build. This is the episode where the entire Summer Success series comes together. I'm gonna walk you through exactly how I planned a month away where my business can actually run without me. That's what this episode is all about. If you've ever wanted to take an extended vacation, if you've ever wanted to take a sabbatical, if you just want to know that it's absolutely possible, keep on listening.

Narrator: Are you ready to grow from solopreneur to CEO? You're in the right place. I'm your host, Rachel Cook, and I've spent the last decade helping women entrepreneurs

Rachel Cook: start and scale service based businesses.

Narrator: If you're serious about building a sustainable business, it's time to put the strategy, systems and support in place to make it happen. Join me each week for candid conversations about stepping into your role as CEO. Hard lessons learned along the way and practical, profitable strategies to grow a sustainable business without the hustle and burnout.

Rachel Cook: Hey there, CEOs. Rachel Cook here, founder of the CEO Collective and host of the Promote Yourself to CEO podcast. And this is the episode that's bringing everything together from the Summer Success series Over the last six episodes. This will be episode six in this series. We really talked about how to set yourself up for success so that you can both enjoy the summer and use this strategically in your business. And one of the things I hear all the time from My clients is, is they wish they could have more real time off. Not just a long weekend, not just a single week. They want to have a real vacation. And I get it. I mean, when we typically go on vacation every single summer, it's usually about two weeks that we'll go on vacation and usually it's to the beach with our family. But it honestly takes just the first couple of days for me to even relax. Like it takes a few days for my nervous system to just let everything drop and actually be in the moment and be present and enjoy. So we need a little bit of a longer stretch to really rest and recover. For a lot of us, a week isn't even enough because by the time you get to that point where your nervous system is calmed down and you actually feel like you're enjoying yourself, suddenly it's time to come back home. So I've had a lot of clients who want this kind of extended break. And I truly believe that having a longer break, not just once a year, but a couple times a year is just so good for you. There's so much research about why we need to step away and have just white space, have thinking time. I think it's Bill Gates in who's the one who's famous for going off to a cabin for two weeks every year just to read and journal and think and allow his brain to like, come up with new ideas and just be present. This is something that I've always had as a practice in my business is at least a two week vacation in the summer and a two week vacation in the winter, plus a couple others throughout, throughout the year. But this month's a little bit different because we're taking a full month in Italy. And I wanted to share with you what went into planning for a full month away from the business. Because whether it is going to Italy or some other, you know, dream location, maybe you want a sabbatical where you can just have that thinking time. Maybe you just want to enjoy the home you live in and you have a staycation. I have had clients who took the entire month of December off. I've had clients who took the entire month of August off. I have a couple right now who are planning their sabbaticals during the summer. I've had clients who spent a month for their 50th birthday going scuba diving and getting scuba certified in Guam. You know, I've had people do amazing things and this gets me so excited because this is one of the perks of being a small business owner, right? Is that you, you're the one making the rules, you're the one calling the shots. And if you want to take time to live your life, to try something new, to go somewhere new, you should absolutely be able to do that. A month in Italy is kind of a dream come true for us, but I'm not going to lie, it took a lot of planning. A month away isn't something you just wing and hope that your business will figure itself out. This is something you design. And in fact, I would say I designed this with just as much intentionality as I designed every maternity leave I ever had. Um, even though my kids are now 16, 16 and 13. Um, I really, really was intentional about how we, we planned so that I could take this time and not feel like I've got to be plugged into the business all the time. So whether you are planning a full month or your first just real week off, you have a team or you're entirely solo, the way you build that is going to be the same. And so I'm going to walk you through the process. First is this started a long time ago. It started over a year and a half ago and grew into a bigger trip for us. We knew about Italy over 18 months ago. My brother in law got engaged. He and his fiance love travel and they wanted to have a destination wedding in Tuscany and they wanted the whole family there. So it started as a 10 day trip around the wedding. In fact, the day this episode goes out, we will be celebrating their. What would you call it, rehearsal dinner. Um, and the wedding will be tomorrow. I'm crossing my fingers that the weather is just perfect and beautiful. But what started as a 10 day trip, we decided to turn into a longer trip. And here's why we stretched the timeline on this and the reason this trip matters so much to me. First, my kids are older now. My twins are about to be juniors in high school. They're 16. They are learning how to drive. Um, I'm so aware of how few summers we have left before they graduate high school and eventually leave the nest. And my husband and I have really talked about the intentionality we want to have as parents during this season. As someone who had, uh, a complicated childhood, I really, really, really want to have a strong, steady relationship with each of my kids. And so I've got to prioritize that now. Right. Because the relationship I'll have with them the rest of their lives is really based on the relationship that we have and that we've built while we are all living in the same House. So we, uh, decided to make this a longer family trip. My kids are the perfect age. The twins being 16, rising juniors, my youngest being 13, rising 8th grader. They're the perfect age to explore Italy. And what makes it really fun is that my kids are interested in this. You know, I couldn't imagine taking a trip like this, um, and not having an interest in ancient history or an interest in art or whatever. And my kids are all excited. Like, they've all been looking forward to this. They all have their little lists of the things that they want to see and that they want to do. So I feel like this is such a solid age to do a big trip like this because they're really going to remember it, they're going to enjoy it. We've built in a lot of time to do the sightseeing. We're definitely going to Rome after this stretch in Tuscany so that the kids can see all the ancient things. And we also get to show them things that my husband and I saw over 20 years ago, which is wild. We had a month in Europe after we graduated, uh, college. It was something that we planned and oh my God, we did it. That broke, you know, 23 year old way. Um, but we spent time in London, Paris and Rome, and that's when we got engaged. So I'm excited to see what's different from that trip. I'm sure it'll be a lot, but I'm really excited to share some of these things with my kids. And the other thing is, we've had a rough few years as a family. You know, the last few years, really more than that, of caregiving for my mom, of managing things for both of my parents, of losing mom. I was not able to get away for very long. I remember last summer, I had just moved mom into assisted living and memory care, and I literally moved her in. And then we were going on vacation and I was a train wreck so much of the time because I was worried about her. I was worried about how she was a jack adjusting. Even though I had other people, like family checking in on her almost every day. I had a. I had lined up so many people to take care of her. I just couldn't really enjoy myself. I was just so stressed out. And my kids know this, right? Um, my kids went through this too. And so this is kind of a reclamation for us. This has been something on the calendar to really look forward to, to really focus on my family. We're doing things with my husband's entire family around the wedding. But then we have so much time, just the five of us together. And this is the season where I really get to put myself and my kids and my husband first instead of feeling like I'm constantly triaging. So we knew this for over 18 months, that this was going to be the date, this is when we were going to be there. They had already booked the beautiful villas that we were going to be at, which is amazing. And then we decided to add the time on. Right, we decided to add more time on to extend it from just the initial 10 days around the wedding to just about a month. So it was this time last year when I really started planning out what 2026 would look like, that I made sure I started alerting my team to the calendar. This is really important because I plan really the summer is when I plan the next year. I start laying it out kind of in broad strokes first, but I get more detailed as we get closer to the end of the year. And then I get more and more detailed as we get to the 90 day plans. But this let me kind of shape what 2026 was gonna look like. I had to make some decisions about what 2026 was gonna look like if I was taking this extended period of time. And I also brought my team into it so that it could be part of the conversation for our annual and quarterly planning. This matters because when you're taking this much time off, you wanna make sure the business can keep running. You don't wanna have to just shut everything down, like close the doors, um, and then restart from scratch when you get home. You want to keep that engine moving, you want to keep your marketing going, you want to keep sales going, you want to make sure clients are taken care of. Right. Like you still need things to happen if you're really going to be gone for this extended timeline. So we knew the dates that we were going to be gone. Once we added the time, um, into the calendar, we made sure that this became part of our planning conversation. And then I mapped out exactly what needed to happen using my client growth engine as a framework. And that's what I'm going to share with you today, how you can take this idea and actually make sure every part of your business is going to be okay. I didn't just make a brain dump list. I actually strategically thought through every part of how my business operates. And that's why I use the client growth engine. It really becomes an ecosystem. It's part of our operating system. And it's a great way to make sure that everything can run without me for a month. That's why it is so, so powerful. So I started at delight. I started with Delight. How am I gonna make sure my clients are taken care of? And that is the most important, right? Because that's where my absence could be felt the most. My existing clients, clients who have already joined me inside of the CEO collective, who are attending CEO retreats, anybody who is an active client right now. So the first step was to map out the calendar for all of our clients and look at what was going to be impacted by my absence. The first thing I had to adjust was the dates of the CEO retreat for June. If you saw on the calendar. I normally host CEO retreats on the second and third Friday of June, but because we are leaving June 15th, I needed to go ahead and move those retreat dates up so that we could host both the in person and the virtual retreat before I travel. That was a simple shift. That was a really simple shift. I was able to plug that into the calendar more than six months in advance. So no one was surprised. Um, no one had to change their calendar because they had plenty of, uh, heads up that this is what was happening. The harder part of the calendar to adjust was my weekly strategy and support call. So inside of the CEO collective, our signature program where I work with all of those clients, we have multiple calls going on every single week, every single month. My team already hosts several of those calls. So my team hosts our Monday CEO date calls to set your week up for success. They host their Wednesday co working calls. So those are already handled and covered. But I didn't want to cancel multiple weeks of strategy and support calls because this is something my clients really look forward to. They love knowing that at least once a week they can get support and make a decision or get questions answered or get feedback from us. So I didn't just want to cancel those and have, you know, three or four weeks of no live support on the calendar. Instead what I did was I invited some guest stars. The guest stars are a small hand selected group of people who have been in the CEO collective. Honestly, some of them have been in for three or four years and they know everything I teach inside and out. They know the 90 day CEO operating system inside and out. And they also have now the opportunity to bring their own expertise to the table. So we have Chris Caruso, who is a financial planner who works with LGBTQIA and Gen X women. She's a, uh, financial planner and just so incredibly smart, has built such an incredible business over the last few years. With us inside of the CEO collective and also, of course, has a ton of insight into all things money and wealth building questions for small business owners. We have Elise Arsenault, who owns the global actor, and she has been with us for multiple years now. I just recorded an episode with her and her right hand, Priscilla, all about how she has built her business and built her team over the last few years. So she has so much experience to share about building her team and letting go of control and delegation and leveling up her own leadership. And then Gabby Day, who is another longtime client who owns Bright Body, and she is also one of our 90 day CEO operating system certified professionals, and she runs my ads. So she's going to be hosting a strategy and support call and bringing her expertise all around ads conversion, the client growth engine, and marketing. And what I love about this is these are all people who are multiple years into this operating system with me. So the newer members who are maybe still in year one, they are going to get the opportunity to talk to someone who is a couple years ahead of them, and they're going to be able to ask questions about what it was like to implement these things into their business and the challenges they bumped up against and how they had to adapt things. And they also get to ask questions about things I'm not a specialist in. So this was a way I could cover those calls, make sure that my clients were well supported and they have kind of a perk. Here is the opportunity to just hear someone else's perspective. So that ensures that even though I'm gone, my clients are getting well taken care of. They are getting so much amazing opportunity to get feedback, to get insight, to get clarity from people who truly I trust, absolutely trust. So that was looking at the delight side of things that clearly the CEO collective is my biggest concern there. Um, everything else that we have that would have been part of the delight side is already set up. Right. So the rest of our offers are all automated on demand. And my team can handle any incoming questions or issues that any clients have. None of those other ones have live access to me the way that the CEO collective does. So next I go from delight to invite. Okay, so sales calendar. And how does a sales calendar impact delight? The sales side is important to think about because you can't just think about when you're gonna sell something. You also have to think about what the delivery timeline is gonna look like. If you don't think about those two things, then you risk ruining the experience for your clients. So I normally do an Enrollment for the CEO collective in May. And that means I'm mostly onboarding people in June. This year I moved it up to April and I did that very intentionally. Inside of the CEO collective, we do more personalized one on one onboarding with every, uh, single client. I have shifted to this over the last couple of years mainly because I have found this is the way, uh, for me to get people off to the fastest start. I do market research, I do voice of customer research, I do a deep dive on every single business and their online presence. Then we have a one on one conversation so that I can figure out what their CEO ceiling is. And out of that I deliver to them a strategy playbook, an actual written PDF. It's usually over 50 pages long that maps out their entire business strategy, their marketing strategy, the positioning, the differentiation, the voice of customer research, their client growth engine, additional goals that they're focused on, and then breaks down a timeline of like, here's what to focus on next. It's intensive. It takes a lot for me to deliver. I am front loading my work. Um, in the year that people spend with me, I'm going to spend the most time with them that month. But it gets them off to the fastest start. It ensures that I know pretty much as much as I can know about their business. So every time for the remainder of the year that they're talking with me, I have a real grounded frame of reference. I actually know what's going on in their business and it helps kind of give them a track to run on. I'm giving them their game plan instead of saying, well, go check out this training. Like I've already cut through and hand selected what my recommendations will be instead of them having to go through hours and hours and hours of recordings. So moving the enrollment earlier to April meant I could onboard everyone. In May, I could go through that entire process, have their one on ones, deliver their CEO strategy playbooks, and make sure that they were prepped before the first CEO retreats and make sure that they are comfortable before I leave for the month. Now one thing I did decide to do while I am in Italy is I am going to be checking in a couple times a week. And this is a decision I made to do some asynchronous check ins, not live calls, nothing on the calendar. But I just want to stay lightly reachable and this is one you don't

Narrator: ever have to do.

Rachel Cook: All or nothing. Okay. This is not going to interrupt my whole trip, um, but I'm easing back in this year. It's been a slow, steady six months of me easing back in and ramping back up to my normal, um, amount of work after losing mom and after the year that I had. So I didn't want anyone to feel abandoned right after joining the CEO collective. And I also just want to make sure that I have peace of mind that I'm not letting anything hang over me. So I'll be checking in. Erica, um, will be handing things to me that I need to respond to, but she honestly can handle most of it. This is just my own little peace of mind thing. So the rest of the calendar while I'm gone doesn't require me to deliver those programs. It's already set up. So if you purchase the CEO retreat on demand, it's ready for you as soon as you sign up for it, you get access to everything. You're going to automatically hear from us. All of that is pre built and automated. But the CEO collective, I have to be really strategic about it. Okay, then there are parts of the engine that are already running pretty well without me. And then don't require, require me to sit here and like push send. And this is where things start to break down for a lot of people. A lot of times when people take time off, they do one of two things. They either scramble to pre create everything at the last minute, or they just shrug and say it'll be fine for a month. And they come home to an audience that hasn't heard from them for weeks at a time. So I don't do that. I have on occasion, gone a few weeks without sending a newsletter or sending a podcast episode. But honestly, this is one of the things that I commit to in my business. I want to make sure that every week something is going out from me, something useful for my community. So in my nurture marketing of my client growth engine, I have my podcast as the central pillar. Everything is built out of the podcast and from that we have a newsletter, we have show notes, we have social media, all of it. Well, I batch create this all well in advance. In fact, right now as I'm sitting here, I have batch created all the way through the end of August. So it's not even that I batch created just for this time I'm away in Italy. It's that I like to batch create well in advance. And that allows me to schedule it well in advance. I'm never scrambling for it. I just like having things already in place so that I can put my focus on other projects behind the scenes. So I like to have that buffer it just gives me a lot of peace of mind. That buffer is also something that if anything were to happen in my life or my business, that then I don't break that commitment to having this podcast go out right. So if I get sick or my kids need me or maybe I just had a really crappy week, like I don't have to sit down and force myself to do it. I've already done the work. So that's part of the system is I work well in advance. My engaged systems run on their own. People sign up all the time for our email list and they are signing up all the time for the CEO date checklist or the mid year review. There are so many free resources on my website, so we always have people joining our uh, email list which is the primary way that I communicate to you all. And then the final part of my client growth engine Attract right now is ads. Now ads are something that do take a heavier lift to get going. They take a heavier lift to set up and make sure they're working for you. But I have amazing people on my team who are keeping the ads running. Gabby Day and her team are absolutely phenomenal and she has everything completely under control and I trust her implicitly. So literally she can make creative direction decisions. She can tweak and change all she needs to. She has everything locked and loaded. When I return, I will add back in attract marketing that requires my time, energy and attention. So attract marketing like speaking or being interviewed or getting in front of other people's audiences, all of that requires more of my time, energy and attention. So I'm literally just pressing pause on that. And if I'm going to be honest, like I haven't done that attract ah, marketing in quite a while. That is why I brought the uh, ads team in last year was because during my caregiving year I just knew that I would likely not have the time, energy or attention to do much, you know, attract marketing. I wouldn't have the time and energy to create a lot of discovery content for TikTok or for Reels. I wouldn't have a lot of time or energy to be public, uh, speaking or getting interviewed. I just didn't have the time last year. So that is something I will bring back in those strategies. Getting in front of other people's audiences have always been some of my strongest strategies. But for now I just gave myself permission to lean heavy on ads because it can run without me. Okay, so let me pause for a second because this is a lot that I just described to you right this is the client growth engine doing its job. This is what I mean when I'm saying this is an operating system. Everything I just described, making sure the attract marketing is happening. My ads are going, making sure there's a way for people to engage with my business. They sign up for the CEO date checklist or they sign up for the mid year review or any other free resource we have. They uh, are going to get the podcast episodes that I've already pre recorded and they're going to get the newsletters that I've pre scheduled. They're going to see things that I have batched well in advance and the invitations are going to continue to go out while I am gone. There will be sales of the On Demand CEO Retreat. There will be sales of the client growth engine. There will be sales of CEO Planner, and my clients are all going to be well taken care of. Anybody who's buying something from me, all of that is set. It's going to be delivered to them automatically. My team will be there to answer any questions or troubleshoot any things that come up. My team has got our, uh, live calls and support covered. We've got our guest stars in place. This is what a real operating system looks like, right? And this is the difference between a business that requires you to be in the chair every single day so that you can push send versus one where you are working in advance. You are giving yourself plenty of buffer. You are planning around things that are really important to you in your life. So this is what we do here at the CEO Collective. This is what we mean when we want you to have the lifeproof business. Yes, we want you to be able to handle anything that life is going to throw your way. But we also want you to have an amazing life first business. We want you to be able to enjoy it and not always have to be reactive. We want you to be able to plan the things that are important to you. So if you want to understand more about this process, go check out the On Demand CEO Retreat. It is currently bundled with the client growth engine and this is the last time we're offering it at this price point. The price is going back up after June 30th. So if you're ready to take that next step and be more proactive in your planning and in your systems. The link is in the show notes. Okay, there's one more thing I did to prepare for this and I think this is probably the most important part of the puzzle, right? It's talking to your clients early and on repeat. This is the part a lot of people skip. They tend to leave for vacation and they've barely told anybody. And that does not protect your relationship. In fact, it might damage your relationship. This is something that is so critically important to me. I've said often, business grows at the speed of relationships. And I know how it feels to be blindsided with somebody who I had signed on to work with, and then they just disappeared, and I can't get ahold of them, and I'm confused, and it feels like they just ghosted me. Right. And I have heard so many stories about this where somebody signs up for something and then they're looking, and the person they just spent a lot of money with is off on vacation, spending the money that they just paid them. Right. It feels gross when that happens. So I think it's really, really important that you communicate very clearly and very early what is happening so they understand what to expect. If you don't set expectations, then you're setting yourself up for disappointing people. And we don't want to blindside people, leaving them feeling confused or distrustful because they thought they were going to have access to you. So I will say all of my clients are reasonable, wonderful people. So many of them have been excited, as I have shared that we are going to Italy. They have been so excited for me, especially those who have been with me a long time, because they know what a tough season I'm coming out of. And I truly believe that when you take the approach that your clients are all reasonable, wonderful people, they understand that just because they sign up for a product, a program or service does not mean you are on call. It does not mean that you are available 24 7. Um, it does mean that you have to clearly articulate how and when you are available. Okay? So I don't leave it to chance. I start telling people early. I start bringing it up in calls and conversations. It's been on the calendar, right? It's been on the calendar. I made sure every Monday in the CEO Collective, I send out an email newsletter. I made sure more than a month in advance, we had announced who the guest stars are going to be. I lined up those guest stars earlier this year, probably in February. So I made sure that we have been communicating this at first. Just, hey, this is coming up. We're so excited. And we sent an email, we changed the calendar. We're repeating it more than once. We've told every member of the CEO collective exactly what this means for them. Okay? They're not getting live access to me first of all the time zones, just make that impossible. Because, you know, if I'm doing a call at noon, um, Eastern standard time, I'm sure that's like six or seven in the evening. In Italy, that's just not going to work. That's when we're hanging out with family, having aperitivo and having little, I don't know, olives and bread or something. We're having a good time in Italy then. So I'm not going to be sacrificing that to jump on a call, but I will check in so they can get some asynchronous access. And I'm not just saying it's just async access. Right. I don't want to be spending my whole time responding via email or DMs. I want them to know that I have lined up a rockstar group of guest hosts to cover my calls. I have been really sharing with them what I think they should talk to these guest stars about. And the how to reach me is really just like in case of emergency. So it's early, it's clear, it's repeated, it's conversation that's been happening for a while. And I've also shared with them like a part of my role as a coach is to model what's possible. Last year, I modeled what was possible through a year of caregiving. The last six months, I've modeled what was possible through navigating grief and losing mom. Now I'm navigating what's possible with having a short period a month where I'm doing something that I've dreamed of with my family. And this is also a way that I'm able to help my clients give themselves permission to build their business this way too. Okay, one last detail. Because it matters just as much as the planning and the leaving. I built a buffer when I come home. We land really late at night after a very long travel day. Have to go from Florence to London, from London to Baltimore, from Baltimore, drive back down to Richmond. And as, uh, someone with chronic illness, that's a whole nother episode I could record. I've had to be very careful about how I plan out this trip because travel really does wear me down. And traveling with a bunch of kids who I guarantee are going to be a little cranky after a super long travel day. Coming home, it means I don't want to be, uh, getting in the door at one in the morning from returning from Italy just to feel obligated to jump on a, you know, on my computer first thing the Next morning, leaving well and returning well are really important to me. So I'm giving myself some buffer time. There is a note to future me in the calendar that says, take your time easing back in. The only thing I've committed to is jumping back into my Thursday Q and A call. It is happening the day after we return. So I have a little bit of an adjustment time. I will be excited to see everybody and to share, you know, insights that came out of everything. But I'm giving myself time to decompress, to settle, to reset the house, to get back fully present and then start once. I am, um, a little more well rested after that travel. So here's what I want you to take from all of this. A month in Italy, where I am, um, fully present with my family while my business keeps taking care of people. It is not luck, okay? It's not because I'm special. It is because I have spent years building systems. And instead of being the system, because if you are the system, you are the ceiling. This engine, this operating system, is what lets you step away. The business doesn't run on my stamina. It doesn't run on my motivation. It doesn't run on hustle. It runs on the systems that we built. This is the whole series. This month we calibrated, uh, our mid year review, right? We recalibrated, we protected the time by writing notes to future me by setting summer hours and a summer schedule. We built some infrastructure over the summer months or we're planning out what infrastructure we're going to focus on during the summer months. A strategy. We're going to focus on working on our business. And we pre sold the fall and the system holds. The business keeps running even with me across the ocean. That is a lifeproof business and it is available to you too. So if you want to build your version of this, your version of being able to go to Italy for a month, then I encourage you to get started with the on Demand CEO retreat and the client growth engine. They're bundled together now through June 30th and after that, the price will go up. This is your last chance to get those two at this price point of, uh, $4.97. The link is in the show notes. You can find it@theceocollective.com thank you so much for spending this summer success series with me. I'm going to go and enjoy the rest of my time in Italy and I will see you here next week with a start of another new series that guess what? I pre recorded before I left for Italy and I can't wait to share more insights with you when I am fully back, fully rested. I'm sure there will be a lot that comes out of this trip that will be unexpected, that will be inspiring and lessons that I can't wait to share with you.