How to Take a Working Vacation

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How to Take a Working Vacation

For many small business owners, the idea of taking a vacation can feel like a pipe dream. With so much on your plate, it feels like the work is never done, and you’ll never be able to fully disconnect. I can relate—growing my own business has become more than a full-time job, it’s a lifestyle. It is one that I would not trade for anything, but I’ll be the first to admit that getting away from it all is a challenge, and to some extent, always will be.  

Though some entrepreneurs are able to completely shut-off their phone and computer and walk away, I don’t think that this makes sense. This creates more stress because you’re always left to wonder if something is going sideways. Instead, it is better to maintain a healthy level of connectivity while still enjoying the sun and getting a chance to relax.  

Luckily, technology has made it so that we can be out of the office, or even the city, while remaining connected to our businesses when necessary. If you’re considering taking a working vacation, try these tips, tricks and tools to get away from it all while still having your business at your fingertips.

Tip 1: Use Cloud-Based Programs

The first step to a working vacation is to be sure you can easily access your work from your laptop, tablet or phone. Cloud-based software programs such as QuickBooks Online or Xero don't tie you down to a desktop computer, making it safe and easy to work from home, a cabin or the beach. All you’ll need is reliable wifi or 3G connection.

When I’m out of the office, I manage e-mail and document sharing with Google Suite, engage in work discussions using Slack and check in on my company’s financials using Xero’s accounting software. Find a cloud-based task or project management software that fits your business (we like using Flow), and you’ll be able to easily track project progress and completion. These tools allow me to collaborate with my team from anywhere.

Tip 2: Outsource What You Can

Bolster your full-time team (whether that’s just you or a growing staff of 10) with outsourced services. Many growing businesses fall into the trap of not requiring a full-time administrative assistant or bookkeeper, but are no longer able to realistically stay on top of the workload themselves. This is the sweet-spot for outsourcing your workload!

Outsourced services not only help you remove actual work from your plate, but also free up precious mental space. Knowing your bookkeeping and payroll are up to date means a vacation without worrying about missed payments, cash flow or unpaid employees.

Adding a virtual assistant to your team can help you streamline your personal workflow, especially when you’re away. They’ll be able to handle e-mail management, flagging what needs your attention urgently while you’re away and filing the rest for your return.

Tip 3: Automate Tasks

This time-saving tip isn’t exclusive to your working vacation, because it will save you time both on and off the beach. However, knowing that your smaller tasks are automated makes it easier to just handle the big-picture thinking while you’re away from your desk. We automate recurring expenses within Xero for hassle-free bookkeeping.

Tip 4: Set Check-In Times

The best way to stay connected while vacationing is to set predetermined check-in times with your team. This ensures your team gets your attention as needed, but gives you the freedom to relax by the pool and spend quality time with your co-vacationers.

If your team knows that you’re only available from 9am-11am, they’ll prepare their queries in advance, take advantage of your working hours and respect your time off. If you're still worried, you can designate one employee to send an alert in case of an emergency. That way, you can rest assured knowing anything else can wait for your next designated check-in.

Tip 5: Trust Your Team

One of the biggest reasons small business owners are wary of taking time off is because they feel they have to be fully involved in all aspects of their business. While having a hands-on approach is good, hiring employees that you can truly place your trust in is far better. Trust your own good judgment—you hired them for a reason!  

Being a business owner means being a manager and communicator. Learning to delegate tasks and place trust in your people. More often than not, they’ll rise to the occasion when given the opportunity to take the lead for a while. Carefully select your outsourced partnerships and allow yourself to build a trust-based relationship with them. To truly grow your business, you need to know where to focus your energy, and where to trust others.

Ready to take your first working vacation?  Consider outsourcing your bookkeeping or back office services—Enkel can help. We’re experienced in supporting small businesses and entrepreneurs in creating financial solutions that allow them to grow their business—and take a day or two off!

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Omar Visram
About Omar Visram
Omar Visram is the Co-founder and CEO of Enkel Backoffice Solutions Inc. Headquartered in Vancouver, Enkel provides bookkeeping, payroll, accounts payable and accounts receivable services to over 300 organizations Canada-wide.