When a business owner takes a holiday

Author Jarrod Carnegie
Read time 4 min
When a business owner takes a holiday

Recently I took 3 weeks off and travelled abroad—something that I have really missed thanks to the last few years and the global pandemic. But to take this time off, I had a lot more to organise than just my flights. What was I to do with all of the projects and the team, and how could I keep everything running as smoothly as possible while away? 

Here’s what I learned. Maybe you can take some nugget out of it for your own businesses. Or maybe it’s just a vent, while I wrote this on the flight home. ☺️

Since opening the doors at Thirtyfour Creative, I haven’t taken any time off. Except for the Christmas break each year, I’ve not even taken a sick day. Are sick days a thing when you’re the owner? This isn’t uncommon for business owners, but I was feeling the need for an unwind and an adventure.

I’m not complaining; everyone was affected by the pandemic, and travel wasn’t anything anyone could do. The pandemic was a negative for many companies and individuals globally; however, the marketing and design industry held it’s head high. Companies were forced to supercharge their online and digital presence to compete with lockdowns. Their teams became remote and their reliance on exceptional digital marketing a digital systems to manage their businesses became more required than ever before. The space of marketing and digital agencies was blessed during what was a terrible time for many. 

Since the pandemic, we’ve grown our team, expanded to help more industries and have gained customers all over the world.

Egypt, Italy and London. Very different places to travel in one trip. As a result of lockdowns, this was actually a delayed honeymoon. This added the pressure challenge to try and not work while away. So…how would we make this work?

Weeks prior to leaving, I had met with customers, and prepared tasks for myself and the team before and during the time I would be away. Planning everything out with the team was actually straightforward. I must say, one of the biggest pains, but one of the biggest rewards any business owner will have is finding employees that you can trust to take care of things. 

Staying up to date with tasks and questions from the team or customers proved manageable. All be it that I did in fact work while away, it was a relief to know that I was able to log in, do a couple of hours where needed but things were still moving along smoothly. 

The only strain I faced was the time difference. As I woke every day, everyone was logging off. On Top of that, on the days that we were in transit, I was completely uncontactable. Another fun hurdle is wifi. Even though the planes say they have wifi, it does bugger all. Every country, city, apartment, Airbnb or hotel has its ups and downs with wifi connection. Even if I was in a hotel and free to do a little work, there was no guarantee I could even open an email, let alone recreate a membership workflow to account for automatic renewals.

Working abroad really made me think of expanding the company overseas. Maybe Hawaii. Something tropical. Just joking…maybe. Timezones could be worked around I guess.

The trip was incredible though. Egypt was a personal bucket list item I checked off. We rode camels to see the Pyramids of Giza, visited the Temple of Karnak, took a Cruise down the Nile, drove a boat on Lake Como in Italy, saw the villa where Star Wars was filmed, waved to George Clooney at his house, consumed my body weight in pasta, pizza and vino and lastly made it to London to unexpectantly be there for the coronation of the King.

Egypt and Italy

So…what did I learn after taking a holiday as a business owner?

  • The words “I’m going to try not to work” mean different things to different people. It will be interpreted as “You’re going to try not to work”, “you’re going to do a little work” or “You’re going to work”. But it means what you want it to mean. Try to take the break.
  • You can’t control time. Dealing with time differences is a pain, but something no one has any control over.
  • Every customer is different. We all know this, so prepare for each of their needs where you can. We put extra hands at the ready for certain customers that we work to account for my leave.
  • Urgent is urgent. You can’t predict when it will happen, but if you put the right processes in place to handle these situations, it always works out. I would recommend putting “urgency” processes in place regardless of taking leave or just in general. They’re valuable even when you’re not taking leave. We’ve now adopted the term “Mission Critical” when something is raised as urgent. And “Abort Mission” when we find out it wasn’t.
  • Some will still expect you to be online no matter what you’re doing and you need to be there to solve their problems. In many cases, this comes down to customers just knowing “someone” is there to help. Manage expectations and people will understand the limit of when they can contact you.
  • Sometimes the only person that can answer a question, or action a task is you. And that’s ok! As the owner, it’s going to be often the case you know something the rest of the team doesn’t.

I love what I do and I was never going to “not work”. Replying to customers, emails, slack, design, it’s just part of why I started Thirtyfour Creative.

A huge thank you to my Thirtyfour team for keeping all projects on track while I was away. An even bigger thank you to all our customers that got my out of office and refused to email me back, even when I did reply to them haha. It means a lot knowing that we’ve built a company that has a relationship with our customers where they care about us as much as we care about them. Especially when I get messages like “Have the best time! No problem, we’ve got things sorted, we’ll do our best to not contact you until you’re back ha. Have a great trip and congratulations again! Can’t wait to hear all about it when you get back.”

A Final note to my fellow business owners.

Everything will not burn to the ground if you take a break. You need to rest and reset in order to provide the best possible survice for your customers and your team. If you want to connect and chat, I’m always open to speak with other business owners to learn and lean on for support. We’re all in the crazy game we call business together, might as well share cheat sheets where we can.

I’m back and ready to make some magic.

Game on!


Author Jarrod Carnegie