I Took 5 Vacations This Year: Here’s How I Did It


I took five vacations this year. I cannot believe that my business is at a point where I have the luxury and privilege of being able to do something like that. To be able to take vacations with my family and know that my business will still run and even thrive when I’m out of the office. It has taken a great deal of hard work from my team and me to get us to this point, but I am excited to let you know it is possible. It’s possible to be the CEO and still take time off to enjoy a vacation, a stay vacation, or just get out of the daily grind and know that your business will survive without you there. 

As the CEO of a small business, it’s hard to get away. In fact, it seems almost like an impossibility. If you had told me five years ago, when I started my business, I would be taking five trips in seven months; I would’ve never believed you. I was in the day-to-day, fully embedded in my business, and it needed me to survive. If you’re anything like me, you probably started your own business with the hopes of having the freedom to travel, relax and rejuvenate instead of punching a clock day in and day out. But before we know it, we’re working 80 hours a week, not taking a break on the weekends, and inching closer and closer to that feeling of burnout. I know I was there when I was first growing my business, and I knew I didn’t want that forever for my life or my family. I hope to give you the tools I used to get me to where I am today and the encouragement you need to know that it is possible for the CEO to take time off. 

Hiring the right team 

We have a fantastic team at Succeeding Small, and I am so grateful for them. I have a leadership team that takes care of administrative work and client communication and a creative team that takes care of the actual work and delivery of my service. You do not need a gigantic staff to allow you to travel. Other ways to do it primarily rely on client communication and expectations. As a service-based business, having a team is incredibly beneficial, where we are able to continue to deliver work promptly that is not dependent on my time or my schedule. That’s how I wanted to build my business and in order for me to do that, a team was necessary.

Having the right systems 

Having thorough systems is what allows you to get everything that you do onto paper. Standard Operating Procedures(SOPs), Instruction manuals, and documentation about how to do things within the company are vital to allowing you time to step away. Problem-solving guides and resources are another helpful way to ensure team members can solve problems independently during your absence. If you are preparing to travel, think about these questions: 

  1. What will need to be done while I’m gone? Can I write instructions for those things so that someone can take care of them for me? 
  2. What problems can I foresee coming up? Can I document solutions ahead of time? 
  3. What do I do daily, and how can I document those steps so that someone else can replicate them? 


Whether you have an admin while you’re gone or a full team, your people can lean on these resources you have invested time in creating.

Setting the Right Client Communication and Expectations

Setting the right client communication and expectations is crucial for allowing you to step away from your business and take a vacation. If you are in a service-based business, customer service is very important, but it’s also important to establish boundaries for yourself to get the time off that you need and deserve. Don’t be afraid to tell your clients that you are going out of town. Here are some quick tips: 

  1. Tell them in advance, let them know that you will be traveling on these dates, and to reach out before or after that time if they need anything.
  2.  Have an automated email response. Whenever somebody sends you an email, they will get an autoresponder that says the dates you will be out of town and how client communication will be handled in your absence.

You can even have a website banner that announces when you will be out of town and when you will be returning. The goal is to communicate how people should handle their vacation time. You can set your own terms but know that your clients will be okay, and you deserve time away.

Establish the Right Team Expectations

It is essential to make sure your team knows when you will be gone. I inform my team of my vacation well before my planned trip and try to check in to make sure they have everything they need from me before I leave. If possible, you should also update your team calendar and any scheduling apps you use to avoid being accidentally invited to a meeting during your time off. We love using Honeybook for all our client communications and to help keep our team on track! I also make sure to let my team know if I am planning to work during my trip so they know whether or not they should avoid contacting me.  Sometimes I dedicate a day or two while I’m out to go and check my messages or attend a meeting. While I sometimes like to be available, especially if the trip is on short notice, other times, I try to step entirely away, and my team respects that. Whether or not you can step fully away or for how long truly depends on where your business, your team, and your systems are in terms of stability. I was not always able to completely step away from my business for long periods, but now, with the proper team and systems, I can do that multiple times a year. At the end of the day, you are responsible for your business, so make sure that your team and clients are adequately taken care of and prepared before taking a full off-grid vacation. One final note regarding team expectations, there is always at least one member of my team who I trust to contact me only in the event of an emergency. Having at least one person who can contact you is an excellent initial practice to ensure that nothing catastrophic happens while you are away on vacation. 


Invest In Digital Marketing

The final investment I made that allowed me to take time off for vacation and still grow my business is investing in digital marketing. Even while I’m away on vacation, I still want to grow my business and make money while I’m off relaxing. I want to generate new business that is not dependent on my time. I’ve invested in things like search engine optimization; that way, people can type in Google, “digital marketing company,” and be able to find my website and fill out my contact form. We’ve created social media posts in advance and scheduled them out, and we invest in content marketing and email marketing the same way. We are always still reaching people on an automated schedule, and digital marketing allows us to be able to make and generate sales in a way that is not determined or contingent on my schedule. Digital marketing has allowed me to take a break, knowing that I will still increase my revenue, grow my company and rest knowing we will thrive even when I’m not there. Not sure where to start with digital marketing? Contact our team today to schedule a free consultation!


To recap, I was able to take five vacations this year and still have a thriving company by: 

  1. Investing in the right team 
  2. Investing in the right systems
  3. Setting the right client communication and expectations 
  4. Setting the right team expectations 
  5. Investing in digital marketing. 


Disclaimer: You get to set your terms regarding taking time off work. If you want a working vacation, you can choose to do so. If you want to break away fully and be in the middle of the ocean for two weeks, you can do that instead. You have to set your own expectations for what you want out of a vacation and then come up with a strategy on what it will take for you to do that successfully. Taking time off freely takes time and infrastructure, but it is so rewarding whether you plan to step away sometime this month or are simply preparing your business for the future.

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