How to Take a Vacation From Your Online Business Like a Boss

How to Take a Vacation From Your Online Business Like a Boss

Although plenty of online entrepreneurs build amazing virtual teams to support our businesses, most of us are sole proprietors.

Meaning we’re the one-and-only bosses of our endeavors, and although we trust our virtual assistants to handle a huge variety of tasks, we aren’t 100% comfortable handing them the reins while we take time off.

We’re not worried that if we step away momentarily everything will collapse in a heap … but we ARE worried that mistakes will be made, details overlooked, and clients left hanging.

And yet, most of us are tired, creatively tapped-out, and in desperate need of a vacation!

So how can we make that possible?

Do we just put everything on hold?

Hire more help?

Check emails while sipping cocktails?

If you’re eyeing your calendar and hoping to take a break in the near future, you’re in luck. I’ve got a 5-step plan that’s guaranteed to set your team up for success while you rest, refresh, and rejuvenate!

Step 1: Plan Ahead

Sounds obvious, but bears mentioning since many of us don’t realize how far ahead we need to be planning. If you’re working with relatively new team members or a mixed group of seasoned vets and newbies, I’d start preparing the whole crew for your departure at least 2 months in advance.

Meaning, let them know when you’re leaving, when you’re coming back, and what needs to get done in order to keep your business running while you’re busy relaxing.

This gives you plenty of time to do any necessary training, dry runs, and reassignment of duties before you actually head out. (You might even be able to hire new freelancers and get them up to speed before you go, if it turns out you’ll need more hands-on deck.)

Planning 2 months out also gives you the chance to manage your calendar proactively; with that much lead time, you can turn down or reschedule opportunities when you know you’ll be out of the office.

About 1-2 weeks before your departure date, consider slowly handing off duties to your team members.

This is like getting everyone ready to take the training wheels off … but doing it while you’re still there to catch them if they lose balance!

Step 2: Communicate

In the months leading up to your vacation, keep your absence top-of-mind for everyone. It doesn’t need to be the leading item on every agenda, obviously, but you don’t want it to slip anyone’s mind either.

When your whole team remains aware that you’ll be stepping away from the business, questions, and issues that might’ve been overlooked during the planning stages have plenty of time to surface.

Talking about the upcoming break in routine will help you work out the kinks together.

Be sure to set expectations for when you are out of the office, too. Don’t just communicate which tasks need handling, discuss, and clarify how they should be handled.

Step 3: Get Your Team Onboard

Before you go, you’ll need to have plans in place for all areas of your business. Who will be handling your inbox and fielding social media messages? Will they let people know you’re away, or respond “as you”?

What about blog and social media posts? Will those continue in your absence? You can’t launch any new offerings during vacation time, but your team should definitely keep everyday tasks rolling along.

List out everything that gets done in a week, and create checklists and guidelines, including FAQs, so your contractors feel fully supported. (Another great reason to start prepping early; plenty of time to codify everything.)

Then think about who should be the team leader and primary point of contact while you are away. Your VA? A longtime team member who knows the ins and outs of your business?

Even if you’ve got a great team member in charge, also make a decision tree that guides your contractors when they have questions or encounter problems.

  • Who should they call first?
  • Who’s next?
  • What constitutes an actual emergency that requires them to reach out to YOU?

Step 4: Automate

Remember that some aspects of your business don’t actually need humans to manage them. Think about functions within your business that can be automated while you are away.

Are you comfortable using an email auto-responder? Willing to set up your Google calendar to refuse appointments while you are out?

Allowing tech to bear some of the burden will simplify your prep, and ease the minds of your team members!

And, of course, automation extends beyond communication and scheduling. Are your sales funnels automated so that you can continue to make income while you’re relaxing on a beach somewhere?

Will your affiliate programs keep humming in the background? If not, why not??!?

Step 5: Log Off and Enjoy!

Final step: trust that you’ve done everything you can to prepare your team; trust that a few things will go wrong and that the world will NOT end; and trust that you deserve to enjoy your time off!

It can be difficult to completely check out when you’ve spent years building a business from scratch, but it’s not a vacation if you’re attached to your phone and keeping tabs on emails.

Let go and allow yourself to rest and recharge.

Promise me you will!



PS. Need more time off without losing your income? Click here to Download the Work Less Summer Business Planner.

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