How to Have a Holiday - books

How to Have a Holiday

How should resilient startup leaders and founders plan their summer break in 2020?

Imagine, we’re back in January 2020, Christmas is done and you are sitting down to plan your summer trip! The flights, the boutique hotels perhaps, the campsites maybe? Whether drawn by ‘old stones’, giant mountains, blue waters or just a sun lounger, planning a holiday is one of the best ways to recover from New Year!

Fast forward to July 2020 – okay, there are flights; yes, hotels and bars are reopening – but re-closing (is that a new word?) too! And, suddenly, holiday looks like an unbearable risk and a waste of money.

So what are our options? Carry on working all summer or take a break – and if so, how?

For some of us, depending on the stage of your startup and the natural startup resilience you’ve built up, the answer is easy – no break, keep going! But if there is some basic infrastructure in place, then take a break!

A break needs to be two things – long enough for you to break the habit of always looking at your phone – and sufficient change that makes your mind switch to other things!

So here’s the advice I’m sharing with fellow founders this summer:

  1. Book your ‘holiday’ time as holiday and prepare as you would if you were going away and going to be uncontactable. That means, someone needs to check your urgent messages, key people – fellow founders, key clients and suppliers, investors – need to be told that you are going away and will not be available.
  2. Find something to do – something to distract you! Some people find relief in physical work – so fix something in the house / the garden you’ve always wanted to do. One of my friends is building a 40,000 litre water tank – don’t ask! Maybe spend some time cooking new meals – get a cookbook and order all the ingredients and have a fab food binge! The other option, is to travel in the mind – that is, get some new, different and unusual books – something to challenge you and occupy your thoughts – just so you’re not tempted to go back to check your phone or log into your shared cloud workspace!

You might have guessed, this summer, I’ve chosen books! Yes, the body will remain geographically challenged, but the mind can still roam free.

I’ve bought some obvious ones (for me) and some unusual ones from authors I don’t know and who I hope will take me on new journeys… Most are from recommended book lists – so, they promise to be stimulating company – do feel free to check them out with my brief synopses – there maybe a few books that you’d want to read too:

I’ll start with the book I am most excited about – it’s philosophy – yes, I *do* get excited about philosophy. On Humour by Simon Critchley promises to provide an answer to enduring questions of mine, like – can dogs laugh? Is humour uniquely human? And, did it evolve?


My next book, by Akala, I picked from Lewis Hamilton’s recommendations – and it promises to bring me new perspectives on race and history. Having learnt a little about the impact of neoliberalism and post colonialism this summer, this promises to be a fascinating read.


A couple of times someone has talked about Why Nations Fail (spoiler – institutions) so I felt this was a timely read as Cummings (unelected) deconstructs Britain’s democracy.

For a novel, I’m following Simon Sharma’s recommendation of a novel / biography/ travelogue in a corner of Europe that is still beyond most travellers – North Macedonia and Albania – To The Lake.

Sometimes on warm summer evenings, a little poetry is best. I’ve always held special the heart aching love that fills the war poets of the 1st WW, so Native Guard – Natasha Trethewey’s book of American Civil War poems, promises much for me too.

Another recommendation by author Diana Evans, led me to Anappara’s first novel, based in a sprawling Indian city, a novel of children detectives – the opening chapter tells me ‘…this story will save your life!’

For my next novel, I’ll be dropped into the racial injustice of the USA – An American Marriage – written by Tayari Jones. Recommended by Oprah and Obama, this story demands to be read.

Finally, history and decline – Why the West Rules For Now – but perhaps more, an overarching theory of history – which could have been known as the Philosophy of History, and brings me full circle back to my first book on philosophy – humour – and the uniqueness of our frail yet human condition.

Wherever you don’t travel this summer, remember always that writers and thinkers have written there before and are ready to open up our world afresh, if only we invite them into our minds.

Yes, not a business book in sight! Perhaps, startup and scaleup leaders need new perspectives.

…and happy holidays too – if I am a bit slow responding over late July and early August – it’s probably because I have my nose in a good book!