I remember the moment vividly. It was so embarrassing. There was no hiding my mistake from my headteacher – someone who values my ability to respond well under pressure, plan effectively and make excellent decisions.

Last year, during the Easter holidays, my wife and I decided to take our three-year-old daughter to four major family attractions in five days (the other week was, of course, taken up with school work). It was knackering, but a big success and we all loved it.

I returned to school glowing, and when asked about the excursions by my headteacher happily rolled off what we’d managed to do. He answered with a statement that shook me to my core: “So you got one of those attraction passes, then?”.

The horror on my face had been clear to see. It didn’t take long for it to sink in – I’d wasted around £200 because I didn’t plan properly. You’d think my planning skills – not to mention the numerous school trips I’ve organised – as a teacher would have rendered this impossible.

It’s not the first time that I’ve struggled to properly plan – or even go on – a family holiday. Yes, as teachers, we have ample opportunity, but, like with most things, school always seems to get in the way…

First, there’s the work versus family time dilemma. It’s inevitable that some part of the break is spent working, especially during the Easter holidays. Pupils are in school for revision sessions that I try and support and as a leader, I am generally planning for the new changes to the curriculum. Trying to juggle the time spent working with the time I wish to spend with my family can be incredibly stressful.

Then there’s the cost versus quality problem. We’re all well aware of the rising costs of flights and accommodation in the school holidays. To get somewhere half decent, we have to think about the holiday ridiculously far in advance to ensure it’s a reasonable price. By the time the getaway comes round, sometimes I’ve forgotten it existed.

And so much of the holidays are taken up with the odd jobs you just never had time for in the term: DIY, dentist visits, visiting great-aunt Flo in Dorset, and the parents up in Scotland. By the time you’ve done all of that, there can be little time left for a holiday. Even in the summer, it can be impossible to predict availability.

I am incredibly lucky my wife also works in a school, but that doesn’t mean scheduling a break with family doesn’t keep me up at night. My brother is a doctor with limited time off. My sister-in-law works in air travel meaning she is often out of the country and likes to spend her school holiday time at home with my nephew. Planning an extended family holiday is a headache. It’s a jigsaw puzzle of aligning schedules, nearly as bad as writing a whole school timetable.

In my 13 years of teaching, I’ve managed two holidays abroad that have lasted longer than a week, the rest have been four or five nights maximum. While it might seem that it is easy to just get up and go on holiday, with a young family it’s incredibly hard to do. Whenever the topic of going on holiday is discussed at home, all of the variables above come into play. Trying to juggle them all is just too hard – and it’s put us off going abroad three times already this year.

Nimish Lad is a secondary teacher and senior leader in Northamptonshire. He tweets at @nlad84 and blogs here.