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September 11, 2019

Taking a Work-Free Vacation as a Small Business Owner


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Tired of paperwork?

Running a small business and taking a vacation are two activities that don't get along together. However, it is important to understand that even you need time to relax and enjoy life outside of your business. 

Whether it's going on vacation or taking a weeklong hiking trip, time off isn’t just an essential perk for employees - business owners get exhausted too! The sole purpose of a vacation, break or any leisure activity is to help any individual improve physical health and productivity. According to a new survey by Glassdoor, “of the U.S. workers who get vacation time or paid time off, those employees, on average, only take about half of their allotted time”.


For a small business owner, leaving the business unchecked can be scary. However, technological advancements provide the tools necessary for you, or any other business owner, to unplug from reality for a short period But, but….? No Buts, let's figure out ways that we can help you plan your time off.

Assign Accountable Staff Prior to Leaving

Recognize how we are continuously referring to small business owners, rather than owners of well-established organizations. The reason why we are limiting our research is that small businesses lack the structure that would naturally hold the business together; hence, why small business owners are reluctant when it comes to vacations. Regardless, if managed properly, the business owner can delegate essential tasks to a few trusted managers or employees. In return, they would be responsible for your tasks while you're on your “work-free” vacation.

Get Ready in Advance


Different from employees, who can easily take some time-off, business owners have to through a delicate planning process that starts a month prior to the event.

Prepare Mentally

Can I entrust my work to my team? What about capacity, will my team manage the workload without me? What if clients call, who has the necessary expertise to answer? 

These are a few questions that will cross your mind when getting yourself mentally prepared for your vacation. But do not worry, there is an answer to every question that you may have. Furthermore, if you plan the vacation in advance then you will have the time necessary to prepare your employees for your absence. Entering a work-free vacation with a clear mindset is essential. 

Get Your Business Ready

After deciding that you are ready for a vacation, you will have to start preparing work for your absence. There are multiple ways that you can start organizing your work. First, you may want to alert clients of your plans at least one week before leaving and make sure you redirect them to another responsible individual within your business.

Second, you may want to finish up any of your tasks that are due prior, during or a few days after your vacation. This way, you won't have to worry if anything during your vacation, plus you are giving yourself a few days after your break to catch up with everything that has happened. Bear in mind that tasks come on a random basis, and you have to think of someone who is going to substitute for you while you are away.

Lastly, a set of guidelines have to be set regarding communication. When can you be communicated, how can you be communicated, and who is going to contact you? The backup person, be that the manager or your partner should be the one reaching out to you at times of need. Please read this part carefully, “at times of need”, don't ask for daily updates, don't check up on the work, just don't do it unless it's necessary. I know this can be difficult but work stimulates stress. In fact, a study from the American Psychological Association claims that work is one of the most common sources of stress. Hence, why we are advocating for a work-free vacation.


Get Your Team Ready

You are almost ready for your vacation. You finished preparing yourself mentally, you created a short-term sustaining structure for your business, and now you need to start talking, preparing and training your employees and crew members. Although we're in the last phase of preparation, this should happen at least two weeks prior to your leave.

Trust is an essential component of this phase. If you have trust in the ability of your staff to deliver in times of need than there should be nothing to worry about. Simply, make sure you hold one or two presentations highlighting the main tasks that have to be done during your leave. If you end up assigning anyone as the head of the business than give them a trial run. Let them run a business while you there, encourage them to participate in your presentations and have them with you in client meetings. This should set a basic understanding of what needs to be done from their end.

“We’re seeing a continuing trend of executives unplugging completely while on vacation, It may indicate that managers have a stronger level of confidence in their teams and processes and, as a result, feel more comfortable leaving others in charge.”- says Paul McDonald, a Robert Half senior executive director. 

However, not always do we have a team that we fully trust and that is completely OK for a small business. If you have the slightest doubt in your team's ability to deliver than there are a few alternative routes you could take.

Define Alternatives

In today's digital economy, it's easy to connect with staff while you're away. So, here are a few backup plans for you to think about prior to leaving. Bear in mind, these options may vary depending on the industry, business size, number of employees and more. 

Working Remotely


As discussed, technology has made working remotely highly feasible. Although not advised, you can continue to advise your team from a remote area using various digital tools. A typical combination would include:

  • A project management tool: Asana or Hubspot

  • A time and location tracking tool: Atto 

  • A communications platform: Slack

If your small business does not use any of these tools than do not worry that's why we are planning everything ahead of time. Nonetheless, even remote working can be intrusive to your vacation. As such, you will need to find a way to schedule work so that it doesn't affect you or your off time.

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