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How to Take a Working Vacation That Feels Like a Vacation

Sailun Tires

Being self-employed has many benefits. You can follow your passion, have more control over your work/life balance and enjoy more creative freedom. However, entrepreneurs often lead a way of life that is dictated by their business or businesses and granting oneself the time to enjoy a vacation is often forfeited for the desire to maintain or grow the company.

There is a potential answer however, in the growing trend amongst the self-employed to take a ‘working vacation’. It is more affordable than ever to outsource your receptionist-duties to a telephone answering service and an overseas virtual assistant can answer emails and complete admin duties for a relatively low fee. 

With internet access available across virtually all major cities in the developed world, a vacation with a set amount of daily work, is a good option if you cannot completely escape the demands of being your own boss.

Why You Should Take a Vacation

There are several reasons that taking a working vacation is a great idea. If you are self-employed, I’m sure that you’re more than aware of the destructive impact stress can have on your personal life – according to the Polyvagal Theory of psychology – we all need time to get into the ‘rest and digest’ mode to heal our immune systems, body & mind. This means being around friends & family and adopting a more relaxed state of mind. According to the Polyvagal Theory, this is vital for your physical & mental health, with digestion, immunity and blood pressure all benefitting from this timeout.

There are also some great work-related reasons to take a vacation. For example, being relaxed is actually the best state of mind for idea generation. Ever had a great idea in the shower or mowing the lawn? If so, you are certainly not alone – inspiration hits you when you’re not actively trying to summon it. 

Inform Your Clients

Once you have set a date for your vacation, it is a good idea to inform your clients. Set expectations in terms of response times to emails & phone calls. Politely inform your clients if you have internet access or not on vacation. If relevant, give your clients another point of contact for your business whilst you are away. 

Your clients should expect you to take time off, it’s normal to take a vacation – so don’t be worried about informing them!

Set up Automated Responses on Email

If you use Outlook Express to access your emails, go to “File” then “Info” then “Automatic Replies” – remember to set an automatic reply for people inside your company and those outside it. Give an alternate contact email if applicable.

You can also schedule your social media post, email marketing campaigns and access Google Ads via the smartphone app. 

Delegate Tasks

As mentioned, if you are a solopreneur (someone who works alone), you can always look to outsource specific tasks to virtual assistants and have all of your telephone calls dealt with by a 24/7 answering service. The service you get from a telephone answering company will vary substantially. Some companies will give you a dedicated virtual receptionist who will be briefed on the specifics of your business – enabling him or her to provide a service similar to someone working from your office. Any messages are then transcribed and emailed and/or texted to the business owner or relevant stakeholder(s). 

If you are delegating tasks to people who work for you, make sure you provide detailed (but as simple as possible) written and even video step by step guides so that if an employee forgets how to do a task, they can refer to the guide rather than bother you whilst you are on vacation. Set aside time to do this and remember that you may have to show people several times if the tasks or jobs aren’t particularly straightforward.

Prepare Yourself Mentally

If it has been a while since you took a vacation from work, then it’s quite likely that you will feel some level of anxiety. Trying to force yourself not to think about work – can make you feel more stressed and make it harder to do. 

If you tell someone not to think of a black bear – chances are the first thing that comes into their mind will be a black bear! Not the most relevant of comparisons, but the point is – you cannot force yourself to stop thinking about something, so just try and accept the feelings and have a set way of dealing with them.

One way is to keep busy when you are away. Plan things to do each day and you could even schedule in some meditation and/or yoga to start each day. Have set times each day to check your emails and your phone – but try not to do this too often. Aim for 2 or 3 times per day maximum.

Taking a book – ideally one that isn’t related to work – can help you to escape mentally from work. Adult coloring books are also increasingly popular, thanks to the relaxing & calming effects they tend to have on people.

If you are going to work whilst you are away, then have set hours for each day and try and stick to them – even if you just have the evenings off and treat yourself to an hour extra in bed – it can provide a refreshing break to the old ‘groundhog day’ routine.

Have Realistic Expectations 

Chances are you will have some interruptions whilst you are enjoying your vacation and it may be quite difficult to switch off, especially within the first few days. If you accept this and try not to get frustrated, it should help you to enjoy your vacation a little bit more! 

Bon Voyage! 


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