10 Vacation tips for online business owners

It’s THAT time of the year when everyone starts taking a vacation, and you may need some vacation tips! Taking time off may arouse images of tropical beaches or exotic cities; those who own your own business may have slightly different visions: customers to take care of, extra work piling up, and a mountain of urgent emails awaiting your return. 

The dream of owning your own business and having the freedom to choose what you do with your time can easily lead to being a slave to your business and vacations a thing of the past. Taking time away from your business to refresh and decompress is SO important, but too many entrepreneurs understandably find it difficult to do so. 

How can you take a vacation when you ARE the business?

Vacation tips blog promotion graphic with swimming pool.


Tip 1: Understand the importance of taking time off

For the sake of your mental and physical health, periodic breaks from thinking about your business are good for you! Not only is it good for you, but it also helps to refresh your creativity, energy, and enthusiasm for your work. So, unapologetically take a vacation knowing that it is better for your business long term that you remain healthy, sane, and NOT burnt out.

Tip 2: Consider the time of year you take your break

If you’ve been in business longer than 12 months, you may see a pattern of repeating months when business slows down. This is a great moment to take a vacation. If your business booms during the summer months, such as wedding industry professionals or real estate agents, consider taking your vacation during the winter months. This alleviates the workload pressure when you are on a break.

Tip 3: Prepare a delegation plan

If you are lucky enough to have a team or a virtual assistant, decide ahead of time what tasks you can either skip or delegate to someone else on your team. If you do this well, you will give your team members time to process how to do the extra tasks. It also gives some room for them to ask you any follow up questions well before you head out on your vacation. You can also reassign and reschedule any undone tasks for yourself when you return, instead of walking away feeling like you’re behind on work.

Tip 4: Put in work ahead of time

If you know 6-8 weeks ahead of time that you will be taking time off, start bulk piling tasks in preparation for your vacation. Try as much as possible to complete extra tasks to put your mind at ease while away AND to make it easier when you return.

Tip 5: Set your email auto responder

 Remember to set a warm and friendly out-of-office email message so that clients understand your lack of response. It removes any chances of clients feeling like you “ghosted” them by not responding to their email.

Tip 6: Decide how connected you’ll be

Set your boundaries! Decide how much you want to connect to your business while you’re on vacation. Do you want to keep your phone on “just in case”? Will you check your email once a week? Or, will you totally disconnect? Any of these scenarios is perfectly fine as long as you stick to it and keep your boundaries. It may be tempting to take your laptop to the pool with you, but if you decided to totally disconnect, then respect that boundary. It is also important to communicate these boundaries with your team!

Extra vacation tips for disconnecting include:

  • Remove your “work”  apps from your phone home screen while you’re on vacation.
  • Or take it the next level and delete your work apps such as email, Asana, Slack, or Voxer while you’re on leave
  • If you’re a photographer, leave your phone behind and play around with old-school photography and buy film!
  • Leave your laptop at home, don’t even take it on vacation with you!

Tip 7: Let your customer know you will be on vacation

Don’t be shy about talking about your upcoming vacation on Instagram or through your monthly newsletters. Give your customer a few weeks’ notice to ask any urgent questions before you go on leave.

Tip 8: Disconnect from the online business world

You may be tempted to catch up on business podcasts or business books while you’re on vacation. Take this opportunity to read a fiction novel instead! Or listen to a comedy podcast! Fill your time with activities that help you disconnect from your business brain and get lost in the refreshing world of your vacation. In the words of our Image Curator Katie “I read fantastic, totally for pleasure books on vacation. And wine—a happy hour in some sunshine takes me far far away from work/life stress every time”

Tip 9:  Let go

Just BE on vacation. Everything will be waiting for you when you return and you can sort it out then! Time is short, make happy memories with the ones you love now. Trust your team to take care of the business OR if you have no team, you will have the rest of the year to “catch up” when you get back. Give yourself permission to let go!

Bonus tip:

To prepare for when you return from your vacation, make a list for the first day back in the office. Outline in the list what are your priorities to focus on. This will help you be mentally ready to leave on vacation knowing that you will have a clear “to do” list when you return to keep you focused.

If you found these vacation tips helpful, you may also like our free guide: 5 Things Every Solopreneur Should Automate – it is perfect for entrepreneurs about to take a vacation.


At Social Squares we are pleased to offer small business owners the following benefits through membership with Social Squares: 

  • Gain access to our meticulously curated catalog of over 6,000 elevated visuals, including lifestyle, mockup, and flat-lay images 
  • Receive 30 customizable Instagram caption templates each month
  • Collect over 100 fresh images added to our catalog each month
  • Find the right image faster with your brand color palette and keywords with Custom Curation 
  • Join our exclusive Facebook community 
  • BONUS: When you become a Social Squares member, you’ll get instant access to our Digital Marketing Essentials guides, videos and live group coaching calls


Mood board of Social Squares images and perfect for setting a vacation mood.

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