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How To Take A Vacation Without Worrying About Your Business

Ah, summer – a time for watermelon, sunscreen, and warm-weather travels.

Except if you’re an entrepreneur, of course. Small business-owners and solopreneurs can’t take summer vacations. Can they?

Check all that apply:

▢  Stepping away from your office for more than a day is inconceivable.

▢  You haven’t taken a proper vacation in years. (Turning off the computer for 12 straight hours does not count as vacation.)

▢  If you do go away (usually under duress from your family), you only choose destinations with high-speed Internet (and 4G backup), and an extra room to set up your home office.

▢  When you establish a vacation office and have an Internet connection, you find it hard to step away and actually enjoy your vacation. There’s always work to be done, regardless of where you are.

Unfortunately, this is a reality for many entrepreneurs – hard-working business owners who assume many or all of their companies’ primary responsibilities.

But here’s another reality: carefree travel is possible, even for the busiest workaholic. All you need is the right assistant.

Step #1: Hire a Business-Grade Virtual Assistant

We’ve all heard horror stories about inept admin assistants who let a business fall apart while the entrepreneur was away.

This is NOT that story.

To prepare your small (or even one-man) business for head-honcho away time, what you need is a business-grade virtual assistant. Unlike general admin assistants, business-grade VAs are skilled in the areas you require: customer service, website administration, social media, logistics – you name it, there’s a business-grade virtual assistant who can fill those roles.

Business-grade virtual assistance is not defined by skillset alone: expert VAs also have the experience and maturity to cope with the unexpected, problem-solve, and hold things together while you’re away. What’s more, they know when your help is truly required and will get in touch if – and only if – an urgent situation arises. In other words, hiring the right VA means you can cut loose and enjoy your time away, knowing that your business and clients are in capable hands.

Step #2: Train Your VA

Even the most skilled virtual assistant cannot step into your company, 100% prepared on her first day. Arguably, the most important part of the VA process is training your assistant to understand your company, your procedures, and your expectations.

The key is to bring your assistant onboard at least a few months before you plan to be away. This gives you both plenty of time to iron out the details: put in place any ongoing processes and agreements; delegate everyday and occasional tasks; and make sure your VA meets your expectations. The leisure of enough time – no pressing deadlines or travel looming on the immediate horizon – means you’ll have time to work out the kinks and get comfortable with your virtual assistant before you ever step out of the office.

When vacation finally does roll around, your VA continues with business as usual – and you enjoy yourself, knowing that your VA is capable and trustworthy. Of course, some tasks – those responsibilities that no matter how much training you do, only you can fulfill – will need to be put on the backburner during your time away, but your VA will keep your core business functions running effectively and smoothly, and make sure that you don’t lose any valuable opportunities.

Step #3: Prepare for Vacation

Here are some tips to help you prepare for travel:

  • Does this have to be put on hold? When you work with a business-grade VA, you can often delegate more than you think. Run through all the roles you fill and double-check your assumptions – does this really need to be put on hold while you are away? Now that you’ve been working with your assistant for a few months and have come to trust her abilities, is there anything else you can hand over?
  • If this, then that. To put your mind at ease, schedule a Skype powwow with your VA to anticipate any unexpected occurrences that could come up while you’re away. Establish an if-this-then-that list: a set of guidelines that will help your VA handle almost any situation.
  • Create a contact plan. One (or several) of your if-this-then-that scenarios will involve true work emergencies that should include contacting you. Agree on what constitutes a “call-worthy” situation. This way, you can rest easy knowing that your VA will never take on more than you want her to handle. And if she does call it’s either because the roof blew off your office, or you just won a million dollar contract!
  • Ensure a backup VA. Serious VA companies, like Boldly, offer you a trained VA backup – not just a fill-in, but rather a virtual assistant who understands your company and can step in if your VA is sick.
  • Get technical assistance: If your VA needs additional help with technical issues, like website maintenance and server troubleshooting, contact your VA company to set up temporary tech help.


Remember, trust is like a muscle – you have to build it. Your business VA has the skills and maturity to take care of your business while you’re away, but the most important component to a relaxing vacation is trust. Give yourself – and your assistant – the time and preparation necessary to build confidence and establish a good working relationship. You can always build up to a two-week vacation by taking 2-3 days off and testing the waters.

When you finally do step out of the office, your vacation will thank you.

About the author Sandra Lewis is the Founder and CEO of Boldly. She's passionate about helping Businesses, Organizations and Executives increase productivity and move their work forward with the right skills and resources. Setting an example of the efficiencies gained working remotely, she’s been leading her entire team on a virtual basis for the past decade.

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