Back Office Secrets
with Jenny Shih

Back Office Secrets: Your 5 Step Checklist for a Work-Free Vacation

hawaiiI don’t know about you, but during the grayest winter months, most people I know have one thing on their mind: sunshine, and how much they desperately need it.

Yet they’re all full of the typical excuses:

“I just can’t get away right now. There’s too much going on. My team is great, but they need me.”

“I don’t know if my clients could handle me being gone for that long.”

“Sure, I could head to Hawaii, but I’d be on my laptop the whole time. My travel companion would kill me.”

Have you caught yourself ever using one of those?

I realize you want to err on the side of caution. After all, your livelihood is on the line. But you started your own business to give yourself more freedom, right? So you should never have to sacrifice a chance to relax, refresh, and rejuvenate!

You, of all people, deserve to check into a gorgeous hotel, keep your laptop turned off, sprint to the beach, and leave work behind for a week at a time (or more!).

Here’s the good news: your work-free, stress-free vacation isn’t as farfetched as you may think. As a matter of fact, by putting a few simple ideas in motion, you can set your business up to run without you.

If you’re ready to finally take your work-free vacation, here’s my five-part checklist to help you make it happen.

Your 5 Step Checklist for a Work-Free Vacation

1. Establish solid systems

Systems are the motors that keep your business running smoothly. They make sure all your day-to-day details are taken care of while you’re out having fun.

Your business’s essential systems fall into two categories:

Technical systems: These tools automate logistical tasks so they run like clockwork. A few examples would be your shopping cart, your online scheduler, and the program you use to cue your tweets (like HootSuite).

Customer Satisfaction

Situational systems: These are procedural guidelines you set for your staff that prepare them for common events and challenges. New client acceptance processes and proper responses to customer complaints would be two examples.

You need to make absolutely sure your systems run flawlessly. Before you leave, take time to test them, then tweak your systems as needed. Not sure how to do that? Here’s a step-by-step guide to creating and implementing systems in your business.

Step 2. Have a fully-trained team

In order to leave your businesses behind for a week or two, you need a trusted co-captain to be your eyes and ears, respond to emails, address customer concerns, and keep your usual operations running.

Enter: your virtual assistant (VA).

If you don’t have a VA yet, make sure you hire one well in advance of your trip. Even the best assistants have a learning curve to battle, so take the time to teach her/him the ins and outs your business.

Already have a VA? Great! Make sure you take the time to train her in any additional “you-centric” tasks before you hit the road. It doesn’t have to take more than five minutes.

It might also be helpful to have a tech or web person on speed dial, in case something extra-tricky goes wrong. Be sure your assistant and this tech god or goddess have a good working relationship, so they can collaborate flawlessly on any emergency while you’re absent.

Step 3. Prep your blog, newsletter, and social media presence

Your writing and social media are crucial elements of your online presence. But you don’t have to waste time in your hotel room getting your latest blog post up and running.

Get your social media accounts ready to rock by having your assistant schedule your tweets and Facebook posts before you leave. While you might not be replying from the beach (which is fine!), this means you’re still feeding your people valuable content, even when you’re not around.


One of the biggest stress-free vacation wins is to have your blog and newsletters done and queued before you go. Start writing them a few weeks before, so you don’t feel rushed, and your readers can still get the great content you’re known for.

Step 4. Let your clients know

When you have a close personal relationship with your clients, you’ve got to keep them in the loop when you’re taking time off.

A few days before you leave, shoot them an email explaining you’re headed out for some much-needed R&R. Make sure they know that your assistant is on hand if they have any emergencies. Though most entrepreneurs worry their clients will panic about their departure, I’ve only had one client out of a hundred give me a hard time for taking a vacation. I didn’t let her whining bother me; I knew I needed that time to unplug in order to serve her and everyone else better in the long run.

Set up an email autoresponder to let people know you’re away from your computer for an extended period of time. State your return date as 3 or 4 days after you get back home. This way you have a chance to reacclimate and finish wading through your backed-up inbox.

Step 5. Let go of the reins

Alright. Your team is trained, your systems are chugging along, and your social media and blog posts are locked & loaded. Now, step away from the computer. It’s time to let your business run without you.

For many of us, this is the hardest part. The temptation to check your inbox every few hours, sneak peeks at Twitter, and step in personally on every customer service email (you know, just in case) can be almost painful.

Although I can’t guarantee new problems won’t occur, when you’ve taken all the steps above, your team (or VA) should be equipped to handle it with care.

Still worried everything’s going to go belly-up? Leave your assistant with a direct line to you in case – and only in case – something goes horribly wrong.

You’re Ready to Go!

Your team is prepped. Your words are ready. All systems are go. It’s time for vacation!

When you have all these steps in place, you’ve set yourself up to leave your laptop closed for as long as you like.

Now it’s your turn, vacationer-in-waiting. I’d love to know…

Have you taken a work-free vacation? What are your tricks for making that happen?

If you haven’t taken a work-free holiday, would you like to? What steps are you going to take to make it happen?

Share your experiences in the comments below so we can all help each other take that next vacation!

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About Jenny Shih

Jenny Shih of is a coach and consultant for small business owners. Her clients are “idea factories” with growing businesses who need help planning, strategizing, streamlining and systematizing. She helps new entrepreneurs define their niche, learn the basics of marketing, and start making money. And she helps experienced entrepreneurs set up systems so they can get out of the daily grind and spend more time doing what they love.

Jenny is the author of The System Flight Kit, everything you need to create effective systems in your business, and The Idea Flight Kit, a step-by-step guide for turning your ideas into something real. Download your copies right here. They’re FREE!


  1. Just perfect stuff for setting up a work-free vacation wrote in an organised way!

  2. Crystal Coleman says:

    Some great tips, but wanted to comment on the tip about Virtual Assistants. VAs are an integral part of an online business, however it does take more than 5 minutes to delegate to them, and depending on what your expectations are, a VA may not be the appropriate person to leave in charge of your business while you are out of the office. Online Business Managers work in a team and project management capacity inside your business long term, and are better suited to managing the business and ensuring the team has everything it needs to get stuff done. Whereas, a VA generally will work in the business on a task and execution oriented basis.

    I think the distinction is important, because anyone reading this may be seriously disappointed if they think they can hire a VA this week, spend 5 minutes training that person,and then leave next week.

    • Crystal, Yes, it does take more than 5 minutes. That’s a tongue and cheek reference to the post where I talk about how to delegate quickly and effectively to an assistant.

      VAs are definitely a crucial part of business, especially if we entrepreneurs want to take a vacation without working!

  3. Slowly developing systems and such in my own business, and it’s making a big difference. I can definitely see vacations in my future!

  4. I own a small business and getting away is not easy but if you can find someone who you trust and who can run the day to day of your business then getting away becomes a lot easier. The other thing i tend to do is tell this person that i will have limited contact and they need to be able to deal with any problems that arise by themselves. In the end run everything will be there when you get back at the very worst

    • From the sound of your comment, it seems like you may have some room for more front-end prep work with your backup person. Training does take time and attention, and the best backup support person for you is likely someone who is in your business with you for awhile, as opposed to just while you’re gone. Because you’re right, that would totally make things worse when you returned!