Posted on 5 Comments

How To Take a Holiday

I don’t know about you, but I’m incredibly bad at taking time off and just switching off (from work). Which means I’m equally bad at taking a proper holiday.

This is mostly due to the fact that [my mind is always busy](I don’t know about you, but I’m incredibly bad at), which makes it difficult for me to just spend time in the moment, doing whatever I’m doing right then / there.

I’ve taken a couple of holidays (and trips) with my wife in the last couple of years though and I’ve come up with a couple of “rules” to help me be better at taking proper holidays (and actually switching off and getting some rest).

This is how to take holidays (as an entrepreneur):

  1. Book trips months in advance and pay for it up-front (as much as you can). This makes it difficult to delay your trips or even back out of it.
  2. Go to some place where you ideally don’t have broadband access. Alternatively go somewhere where the broadband is so excruciatingly slow that it’s really shitty to get work done.
  3. Fill your days with loads of activities. This serves as a distraction from work.
  4. When you are out on day trips, leave your smartphone at the hotel. This is hard, because it’s really convenient having things like Maps and Google to help you out, but not having it around forces you to stay disconnected.
  5. Leave your computer at home. This is the best way to avoid real work. Sure, you might take a tablet, but doing real work on a tablet is inefficient and shitty.
  6. Read actual books or get a Kindle. I absolutely love my iPad Mini and I always take it along on holidays to get some reading done. But I constantly find myself checking into e-mail or social media.
  7. When you are reading, avoid reading anything related to you work. Ideally you should be reading fiction, which mostly means anything except Harry Potter or 50 Shades of Grey qualifies as good reads.

I’ve by no means perfected my own blueprint, but doing these things have definitely helped me to switch off more on holidays and thus allowed me to come back refreshed. Which was the #1 goal of the holiday to start…

  • Gerasimos Tsiamalos

    Well if you find yourself trying to stay away from all these things then I guess you should stay home. At the moment I can only image what it’s like to run something like you do but “Word hard, Play hard” is a piece of advice that you should follow 🙂

  • Adam Bullock

    I too have/had the same problem as you. I find it difficult to switch off not knowing everything is running smoothly. I took a few days away in Spain 2 weeks ago and although I had my iPhone with me, I switched email off on it and only checked my email once a day on my MacBook for anything really important and ignored the rest. I told my colleagues that if they needed me in an emergency to either phone or SMS me.

  • Adam Bullock

    P.S. And I found it worked really well for me!

  • Charl Norman

    The key to this is not what to do while you’re on holiday. But what you do before you travel so you can go on holiday without your business unraveling or coming back to inbox hell. Put processes in place to remove yourself from key day-to-day operations of your company. Extract IP out of your head and document it so staff can follow. Stop keeping insight on certain tasks or procedures to yourself and share them with your second-in-command(s).

    In my business I was the only person that had context on every project, understood our infrastructure 100%, had a close relationship with every client, handled many routine tasks by myself – when I went on holiday it was hell. I had to work for a hour or two every morning (often hungover) just to keep things smooth back home.

    Take these tasks, procedures, knowledge, know how – document it and get your key staff to embrace it.

    Something that was hard for me to accept was the 80/20 rule. 80% doesn’t really matter – let your staff handle it. If there’s mistakes clients will get over it – and your staff will eventually evolve and learn. Just make sure the 20% is taken care of – properly.

  • Jason Adriaan

    damn solid advice.