How to have a guilt free holiday when you own the business


You know what it’s like, you’ve started your own business and there’s no way you can take a holiday.   Most people think that entrepreneurs can take a holiday whenever they want but the reality is often far different. I mean your business is your baby and there’s nobody who can do what you do, right?

Who will answer the phone? What if you miss out on that meeting with a new client? Who will manage the office? Who will do the work?

It’s not only this – for many business owners, the “time is money” mantra figures into their mental calculation of how much a holiday will really cost them.

So, even though I am writing this blog while on holiday in Canada, ironically on how to take guilt free holidays as a small business owner, I fully admit that I find it virtually impossible to unplug myself completely from business while I take a vacation for a week or more. That’s because I am one of those business owners who won’t leave for any kind of trip or holiday without my laptop and phone.

Even though I check in on things while I’m away, I’ve learned a few strategies to minimise the time I spend working (or thinking about business) and maximise my enjoyment of the holiday.

Here are some strategies I can recommend:

Overcoming feelings of guilt

As a business owner, it’s difficult to not experience feelings of guilt when you want to take a holiday.

We all know that working constantly, without a break and refusing to take a day off, is both an unhealthy practice and counterproductive for your business.

Slogging away at your business day after day can leave you mentally blocked and the best way to get unstuck is to step away from the business. Stepping out of the day to day activities of running a business allows your mental state some space to be creative and innovative once more. It clears your head, and provides the opportunity to reflect upon what’s happened during the last year and plan ahead for the next year.

I encourage you to reframe your thinking and start telling yourself that your business will benefit when you allow yourself some time to take a break. Tell yourself, taking a holiday is healthy, and when you return to work you will be rested and energised, which means you will be able to do a better job.

Preparation is the key

The key to maximising your enjoyment while on a holiday is in the preparation. I’m not talking about planning your trip, I’m talking about the preparation you should put into your business before you leave. Here are some things to consider:

  1. Be sure to let your clients know in person when you will be away and when you will be back. Let them know who to contact in your absence, or how to contact you should there be an emergency.
  2. Consider setting an out of office message on your emails advising recipients when you will be returning and who to contact in your absence.
  3. Be sure to prepare a file of important contact details to take away with you. Depending on where you are travelling to, it may be prudent to have a paper copy of these contacts just in case your electronic devices get stolen, break down or don’t work.
  4. Work out how you will manage your phone calls while you are away. All of the below options are appropriate and available to you.
    1. Change your message on the phone advising callers of your leave time and when you will call them back.
    2. Set up a temporary answering service.
    3. Have one of your staff answer calls.
  5. Discuss with your staff on how to handle various problems and emergencies. Set the boundaries on what you are happy for them to go ahead and deal with without your prior knowledge and what they need to tell you about before proceeding with action. For example:
    1. What to do if the internet/computers weren’t working?
    2. What to do if the company website appears down?
    3. Who to call for building maintenance?

Set some rules

I’m not talking about rules for your staff or clients, I’m talking about rules for yourself. What’s the point in spending all that time planning your trip only to be drawn into doing work every day while you are away? To avoid this from happening, set yourself a time of day and a time limit for checking in on business. Ideally, choose a time of day when you’re likely to be just hanging around the hotel room anyway or first thing in the morning (before the day get started) or an hour in the evening after dinner.

If you are a sole proprietor and part of your marketing is to post on social media as a daily routine, create and queue posts in advance by using a free tool like Hootsuite, or have a virtual assistant create content and posts for you. This will give you a “real’ break from your business.


When you get back                                                                                                                                                                                     

When returning from your holiday, try to keep your schedule as light as possible. Try not to schedule anything to go live – i.e. websites, meetings, ad campaigns, on the day you get back. Give yourself two or three day’s grace to adjust to your time zone if you travelled overseas. Allow some time to devise a plan for any new ideas that you thought of while you were away and to generally catch up before getting fully back into the routine.


The final word

Entrepreneurs often have to wear many different hats, but as the business starts to grow, you have to start outsourcing and delegating some of your responsibilities in order to stay on top of everything. As difficult as it may seem, taking a holiday (or a mini break) is a great way to see how the business can operate without you and answer the most fundamental question posed to business owners: Do the people on your team have what it takes to keep the business running in your absence? If not, identify the gaps and take steps in rectifying the issues. If so, be sure to show your appreciation to then upon your return.

Happy holidays.

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Lynda Schenk

An energetic and strategic marketing professional with over twenty years’ experience in industries ranging from wine, not for profit, transport, logistics and manufacturing. Lynda founded Purple Giraffe Marketing Consultancy in 2014 offering an end to end marketing service that draws on her proven ability to formulate brand strategies and marketing communications plans that build brand equity, growth and profitability.

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