Book it and Enjoy the Anticipation!

I’m writing this the day after getting back from my holiday to Ireland. It’s a national holiday and the whole country is off today but I’m at my desk – it feels like a bonus day to get some work done. And I can’t complain, after 3 and a half weeks off this summer. So on the subject, let’s talk about planning your calendar, because the way I do it is not normal. I am in the minority when it comes to time planning. Which is good news. Mark Twain said “whenever you find yourself on the side of the majority, it is time to pause and reflect.” I’ll always be steering you to be on the side of the minority – it’s the only way to achieve significantly better than average results. 

 When I was in Ireland my mum couldn’t believe that I was mapping out 2024. I was trying to co-ordinate a couple of holidays with other family members, and I had a fold-up wall calendar with me. So my mum couldn’t believe it was still summer of 2023 and I was messing around with a 2024 calendar.   

 There is a paradox: Structure = Freedom. If you want real freedom, you need structure and discipline to get it. I used to love the freedom of taking a holiday or day off whenever I wanted – on a whim, and usually decided and arranged at the last minute.  

 I was annoyed when my eldest son George started school and Catherine told me we could only go on holiday at specific dates set by the school i.e. not during term time. But I quickly learned the effect of structure = freedom. The fact we were forced to plan ahead for school holiday dates ended up meaning we took far more holidays in the year than we did when everything was last  

 My 2024 calendar is already as full as I want it to be with OSA events and holidays aligned with school holidays. Way more structure than most, but the result is more freedom. I end up taking about 3X as many holiday days as I did when I left my calendar wide open and unplanned. The lesson is plan 12 to 18 months ahead for your holidays and events you want to attend and you will be able to do so much more without any stress or disorganisation. It’s just easier. 

 Lesson two – never finish anything without booking the next one. Use this as your fail-safe. Refuse to fly home unless your next holiday is already booked. You’re chilled, you have plenty of downtime while you’re away to do a bit of research and get your next trip in the calendar. At a minimum, decide where you’re going and when you’re going and get it scheduled.  

 This lesson applies to anything by the way. I refuse to end a meeting with my team without the next one in the calendar. An OSA event never finishes without the next one being confirmed. I won’t hang up the phone with my accountant or coaches or anyone I speak to monthly without the next call date booked. Even a dinner or a weekend with friends I try my best to get the next one scheduled before we finish this one. Try it out. You won’t look back. 

 If you don’t do the things above, all you have are intentions (not bookings) and the problem with intentions is you blink and six months have gone by and nothing has happened. And then when you try at the last minute you hit hurdles because there are lots of clashes. When you schedule it, things become real. And it’s so much easier to schedule way in advance. 

 If you do the things above you get the added bonus of anticipation. You get to look forward to things for months and months. You can get excited. You can talk about it. It’s like being a kid looking forward to Christmas and counting down the days. Anticipation gives you more bang for your buck. A lot of the value you get from a holiday is the looking forward to it. Studies have even shown that peak happiness happens in the moments before you actually receive the thing you are anticipating. The research says anticipating is a powerful, positive emotion that will help you live a happier life.