How to enjoy your holidays as an entrepreneur

Planning a holiday can be stressful enough but, when you have your own company, it’s even more important to make sure you’re prepared for your time out of office

How to enjoy your holidays as an entrepreneur

When you run your own business getting time away isn’t always easy. No matter how much an entrepreneur might want to unwind with some mojitos or grab some meze beside the Mediterranean, worrying whether their startup can cope in their absence can make holidays a huge source of anxiety. But, in actuality,  getting away can be essential for entrepreneurs looking to stay happy and productive long-term.

This is something Mark Mason, founder & CEO of Mubaloo, the enterprise mobile app developer, knows first hand. Having spent almost five years growing the enterprise from the ground up, earlier this year he decided to have three months out, taking his wife and three-year-old daughter to visit family in New Zealand. “I decided to actually take a break and to recharge the batteries,” he says. “It’s rare in life that you get the opportunity to go and do something like that.”

But there are other good reasons to get away from it all. “If you’re completely focused on the business all the time, you can get caught up very heavily in it,” explains Paul Spiers, founder of Wave Native, the surf-wear brand. Taking time away can help refresh an entrepreneur’s perspective and stimulates the sort of expansive thinking that perhaps may be more difficult during the day-to-day running of an enterprise. “A natural entrepreneur will see a whole lot of opportunity on holiday,” he continues. “It opens your eyes to the world.”

However, whilst few of us would need much arm-twisting to flit off to Bali or spend some time kicking up our feet in Berlin, taking time away from your startup is always going to seem like a logistical headache.

Perhaps the first concern is ensuring there is a firm hand on the tiller in your absence. If there’s an appropriate second-in-command who can take over, then it’s important to trust in their ability to cope whilst you’re away and not attempt to micromanage from two continents away. “You have to give wholehearted responsibility to the people you’ve left in charge, otherwise you just keep meddling from a distance,” Mason says. “People only take responsibility when they’re completely given it.”

Sometimes, however, there might not be such a clear candidate and it can be tricky to know whether a member of a team is going to be able to rise to the challenge. In these circumstances, Spiers recommends providing these employees prior opportunities to prove themselves. “Give them smaller projects in advance so you can test their mettle,” he explains. “It is really about putting the trust out there.”

It’s not all about what happens inside a company though. Managing the expectations of clients and stakeholders, particularly those used to dealing with the big kahuna themselves, is essential to prevent any frantic poolside phone calls when a major customer demands to speak to the CEO. “They need to know in advance what the plans are and that the person who is managing the bulk of the day-to-day in your absence is competent and effective,” says Spiers. “There needs to be a continuity of confidence between you and your stand-in.”

One way an entrepreneur can help manage expectations is choosing to take their holiday during peak holiday seasons, such as August and December, when the majority of businesses have staff out on holiday. “During these months people expect that people are going to be away so there’s less of an urgency to resolve things,” says Emi Gal, the CEO and founder of Brainient, the ad-tech firm. “This means it’s less likely you’re going to get any fires to put out.”

But just because someone has no fires to fight doesn’t remove the temptation to regularly check in. Whilst there’s nothing wrong with checking your emails from Ecuador or tweeting whilst in Thailand, it’s important to keep some boundaries in place. Spiers recommends setting fixed times for picking up messages and handling emails. “Just allocate that time and try to be rigid and stick to it.”

This can be a major sticking point for any entrepreneur abroad. For business owners used to always being on, going from 60 to 0 and trading boardroom for beach isn’t the easiest transition to make. “It’s difficult, particularly if you’re a driven individual,” says Mason. But he feels that entrepreneurs owe it to their loved ones to pay them their full attention. “When you go away like that, you’ve got to respect their time and not constantly be on your mobile phone.”

However, for those still struggling to switch off, Spiers stresses that it doesn’t have to be all or nothing. “It doesn’t have to be an on-off switch; it can be halfway,” he says. If someone has a few ideas buzzing round their heads, getting them down on a pad can help them unwind. Alternatively, catching up on some reading, even if it happens to be Flotation for Dummies, can help a busy mind settle into a holiday. “Even if you are reading a business book, as long as it’s by the pool or on the beach then I think you’re halfway there,” he concludes.


A hundred hours off


Emi Gal, the CEO and founder of Brainient, tells us why long weekends can be the perfect option for time-poor entrepreneurs

Being an entrepreneur and running a startup is very stressful: it’s really good for entrepreneurs to take some time off to really reflect and think about things. But if you have to wait years before you can take two weeks off then you may burn out before you even get to that point. Instead it’s better to take smaller holidays more often.

I stopped taking long holidays because they very quickly just became emails with a view. I would be on holiday but actually my mind was at the office, just because there were things to solve, problems to address, fires to put out. 

So my favourite way to disconnect, reflect and take some time off is actually long weekends; you have enough time to disconnect and reflect but when you’re back the workload isn’t so big that you immediately go back into that space of stress and anxiousness. If you take less time, ironically enough, it’s easier to relax and actually disconnect because you know you’re going to be back very soon. 

Josh Russell
Josh Russell

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