How to Plan Your Christmas Break

Christmas means many things to many people. For some, it’s like crawling into your childhood bed and watching Agro’s Cartoon Connection; wave upon wave of euphoric deja-vu that revitalises your very being.


For many, it’s an opportunity to dabble in alcoholism whilst simulating a healthy relationship with your extended family. For others (see: Retail), it’s a wild, drawn out and somewhat painful journey akin to cross country skiing.

Without a bit of planning, don’t be surprised if you find yourself alone on Christmas morning watching Jingle All the Way 2 and yelling at the neighbours for enjoying themselves too much. Or worse, you could end up like this guy;


Here are a couple of tips to help pull off your own Christmas miracle.

How to ask your boss for leave

If you’re anything like me, school did little to prepare you for life in the workforce, especially having difficult conversations.

Difficult conversations are essential to your career and can include anything from asking for time off, a pay rise or telling Terry from HR that his body odour is attracting vultures.

When requesting -not demanding– leave, timing is everything. Be aware of the bigger picture as this is what your manager is (hopefully) thinking about when he makes decisions. If you approach your manager a week before you’re hoping to take three weeks off, or straight after the regional manager has doubled the sales budget, don’t be surprised if they maniacally laugh in your face;


Instead, win them over with your charm and logic:

“I really like how you handled that embarrassing problem with Terry, perhaps you could help me improve my communication skills? Also, I know 2016 is going to be a big year, therefore I’m hoping to take some time off in December. Can I send through some dates for your approval?”

If all else fails, be gracious in defeat. Circumstances can change quickly and Debbie-Downer is rarely top of the list for leave handouts.

How to plan activities

Christmas is lousy with expectations which makes planning things especially exciting. Avoid confusion by putting the feelers out early about any plans already in the works.

Next, establish any other limitations you may have such as money and patience; travelling even marginal distances over the Christmas break can be expensive and leave you emotionally inert at best.

For the actual planning, I’m going to draw from the Hoshin planning system which is what NASA turned to when, against the recommendations of literally everyone in the know, President Kennedy announced we would be going to the moon.

The method is especially helpful if you’re planning something ambitious like hosting Christmas lunch for your recently divorced parents, or the moon landing. The idea is simple and relies mainly on your powers of deduction.

Define perfect, then work backwards.

Step 1. Working within any constraints you may have, define your group’s idea of a perfect Christmas break. Once you finish arguing about this, grab a piece of paper and draw a horizontal line across the width of the page, noting the winning idea on the right hand side.

Now you have a timeline and a goal. For arguments sake, let’s run with your terrible idea to host Christmas lunch.

“Don’t touch me Michael. I don’t care what the lawyers said, that’s MY scarf!”

Step 2. Starting from your goal and working back across the page, jot down any key milestones that must have occurred for you to have achieved your goal e.g. you must have prepared lunch, which means you must have been shopping, which in turn means you must have somehow invited your divorced parents to lunch, which likely means you shouldn’t call people when you’ve been drinking.

Once you have the broader milestones in place, repeat step 2, however this time in finer detail – including shopping lists or items you need to pack etc.

This process should leave you with a comprehensive to-do list and a clear path on how to get from now to then. So if you ever feel overwhelmed by the task at hand, be it planning Christmas, moving house or anything in between, just ask yourself “what would NASA do?”