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How to NOT Miss Next Summer’s Vacation

Whether you want to go skiing this winter or to the beach next summer, here are strategies you can implement NOW to make sure you don’t miss your next vacation.


Did you take a vacation this summer? I mean a real vacation, where the office survived without you, your laptop remained closed (or at home), and you only used your smartphone to find the nearest tiki bar. If not, when was the last time you did take a vacation like that?

If you’re like most entrepreneurs, when you started your business, it was with the idea that you would be the boss. As the boss, you would be fully in charge of your own schedule, and you would work fewer hours while reaping rich rewards. It’s a good dream, isn’t it?

The unfortunate reality is that most business owners never attain this kind of freedom. Why? Well, I can’t speak for everyone, but my experience working with entrepreneurs has turned up 2 common reasons business owners don’t take the vacations they deserve.

  1. Fear of delegating. I know… you do it better, faster, with more flair and fewer errors than anyone else. That’s why you’re the owner/ CEO/ president/ director. If everyone could do what you do, they wouldn’t be working for you, would they? Learn the 70% Rule and let it go.
  2. Poor planning. When you have events for your business do you wait until the last minute to schedule them? No. When something is a priority it gets put on the calendar, and whatever else comes up has to be worked around it.

If you’re running a successful business, then you (or someone on your team) must already be a good planner. So why doesn’t your personal life get comparable priority to networking events, conferences, and trainings?

Most business owners I’ve worked with give one of two answers to this question. It’s some variation of either (a) habit, or (b) fear.

When you started your business you had to work long hours, but at some point, you should have built a team you trusted to work for/with you. This is the time to pull back and stop working those 60-100 hour weeks, but most business owners either don’t realize that’s an option, or have built up so much momentum that they just keep on keepin’ on. Working that many hours becomes a hard habit to break …maybe even one you don’t believe you can break.


If your habits aren’t the problem, it’s time to look at what else may be stopping you from stepping back. Are you afraid your business will fall apart without you to guide it? If so, invest more time training your team before your vacation is imminent. Work with your staff to set up quality control procedures, step-by-step protocols, and give them time to work those while you’re still available for questions and guidance (ideally, well before you leave).

Are you afraid that your business won’t make any money without you to deliver services? If you are the sole service provider on your staff, make arrangements with your clients ahead of time. Set up procedures for how your team should manage client needs while you’re away. Give them solid examples of when it’s okay to call you and how to handle anything that isn’t critical or time-sensitive while you’re away. You can also look into ways to automate some of your income. If your business is entirely service-based, gather your knowledge into an ebook, white paper, or video training that can be offered at a low-cost, in a contest, or as a giveaway. You create the content, make a plan, and let your team implement it. (Again, preparation is key; if you can let them run a similar campaign while you’re there, all the better.) This way, new prospects are filling your pipeline while you’re on vacation, so you can actually enjoy yourself!

FACT: If you have the right team and systems in place, your business will survive a week or two without you.

Now that you understand what may have held you back from taking that realvacation, and have gotten some basic strategies to deal with those problems, I want to give you my favorite secret to make sure you get some fun in this upcoming year.

Plan your vacations in advance.

When you plan the upcoming year (or years, as I tend to do), make a calendar of all your important events, including vacations you want to take. You can use gCal, iCal, Outlook, or even a big printed year-in-view calendar if you prefer, but I like to have it both immediately accessible and easily put away, so I plan the entire year in an excel spreadsheet. (This isn’t for appointments; it’s simply for planning.) I use each column to represent 1 month, and each cell to represent 1 day, so when you read across you can see January through December and when you read down you see days 1-31 (or 30, 28, etc.) for each month. I also use colors to fill the cells so I can see (at a glance) what types of events are missing or clustered too close together (for example, holidays are gray, workshops/events are green, teleseminars/webinars are blue, etc.). Remember, you’re just planning here, so don’t go overboard: 1 event per day is enough.

Once you’ve created your planning structure, here’s what you do:

  1. Fill in all the holidays and vacations you already have scheduled.
  2. If you have marketing or business events planned, put them in.
  3. Insert any vacations you want to take, keeping in mind the pre- or post-event workload for anything already in your calendar.
  4. Plan the rest of your year (marketing campaigns, events, sales, programs, etc.).

If you have regularly recurring events (such as workshops, sales, or email marketing campaigns) you can space them out proactively instead of reacting to your cash flow. This helps you account for months that tend to be slow as well as your busy season(s). If you know business is frantic every June, obviously you won’t plan your vacation then, but maybe by planning next year in advance, you’ll get to enjoy that trip to the beach in July, as opposed to realizing at the end of August that you haven’t done anything fun yet this year.

This article was originally published on in August 2014.
Ariana Ayu is the author of the Business Mojo column on (a website and magazine geared toward entrepreneurs) which was published between 2014-2016. Ariana is the CEO and founder of several companies, including Ayutopia International, LLC, which develops profitable collaborative corporate cultures, personal celebrity brands, and custom branded websites. Her press and media appearances include USA Today, International Business Times, ABC, CBS, CBS Money Watch, the CW, Eyewitness News, FOX, NBC, Newsday,Virtual-Strategy Magazine, World’s Luxury Guide,, Miami Herald, BlogTalkRadio, and Hollywood Industry, among others.

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