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How to Take a Vacation as an Entrepreneur

Fall is here and we are reminiscing about that time we were enjoying the warmer weather. Anyone else thinking about taking a much-needed vacay before the end of the year? Contrary to popular belief, hard working entrepreneurs can take holidays…it just takes a little more planning than it does for the 9-5 salaried folks, who can be off on their (paid) vacations with a few clicks of their heels (or Expedia, anyway). Here are some creative solutions for how business owners can get away on vacation without returning to find the office upside down. Now let's set up that out of office alert, find someone to feed your fish, and get on the next plane to Rio!

Stay connected while you’re gone

The first school of thought around how to take a vacation as an entrepreneur is to stay on top of things even while you’re away. While this might seem restrictive, think about it: how hard is it to check how your site is performing with Google Analytics, peek at the bank account remotely, or add a task to your team’s Google Calendar or Trello board using your smartphone? You might feel more shackled by an inability to keep an eye on these things, if you’re the worrying type. Just be sure to:

  • Be clear with your team. Whether you decide to give them free rein or keep them on a tight leash, you need to set clear expectations. Do you want them to check in with you daily, only bother you with problems they absolutely can’t solve, or copy you on every single piece of correspondence? Be crystal clear and delegate functions specifically in order to manage your expectations – and everyone else’s.

  • Clear your desk. This doesn’t mean working around the clock for weeks to complete every single task before you go away; that kind of defeats the purpose of a vacation. What it does mean is prioritizing tasks and scheduling things to be done in advance, so your team (or automation) can execute them on your behalf for a seamless continuation of business while you’re away.

  • Clear your mind. If you’re stressed to the max, how much fun are you going to have? Now might be a good time to learn some unplugging strategies for business folk at, or practice those breathing exercises you vowed to do every day and haven’t gotten around to. It's completely okay to care about the outcome of you going away but keep in mind that everything needs to recharge, including you.

Turn off and tune out

By Referral Only, the real estate guru system for real estate gurus, advocates spending a whopping 1/3 of your time away from your business – and by away, they mean completely unplugged and cut off from your business, the better to be present to your family and your life, and to recharge so that when you do return, you are fully refreshed and ready to plunge back into the fray. Here’s how best to do this:

  • Trust your team. You hired them for a reason! If you aren’t sure you have built a team you can trust, here’s a good test: ask your best friend if he would leave his business in the hands of your team while he went away-away. If you’re a one-man show, you may need to trust your tech to do its job – or trust your clients not to bail on you just because you need free time just like everyone else.

  • Short and sweet. If the idea of completely cutting the cord for a week or two has you climbing the walls, start slow, with long weekends. If a four day weekend seems to cause no dire results to your business, you can gradually increase your time away till you’re sipping cocktails at Club Med just like everyone else.

  • Go with the flow. A lot of businesses have some kind of seasonality; take advantage of this to go away during the slowest possible times, knowing that even if you do lose some business, the effect of your absence is minimized while you relax.

Take a deep breath, start imagining what it would be like to unplug and take action. Aloha entrepreneurs!

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