When to Take a Holiday

I just got back from vacation on Monday. I took one week to do virtually nothing – working hardest to keep myself from thinking about work. Why take a holiday? Mental health is a one good reason. Another is your cannot get anything done (at least in Toronto) in July or August. Why? All the stakeholders for any significant decision are away. I have an old friend who has been at Well’s Fargo for the past six years. He worked in San Francisco and Chicago and he has recently returned to Toronto. He mentioned that there is no noticeable slowdown to the pace when working in the states during July and August. I found it hard to believe, especially in Chicago. In San Francisco however, the weather is nice (relative to the Canadian Winter) all year round, so it’s understandable that people would take time off throughout the year. In Toronto, July and August draw everyone out of their holes and the heat drives them out of the city.

So why bother with this post? Where is the strategy? Here it is: if you are running a start-up you have to choose your vacations strategically. 2ndSite being my second start-up, and the first one currently running more successfully than ever, I’ve always had to carefully consider when to take a break, sometimes IF I take a break. In a nutshell the strategy is this: take you time when the greatest number of decision makers are also taking their time.  So, here is when I take vacations and why.

March => By this point the weather has been so dismal for so long in Toronto that Torontonians are just dragging themselves around. Many decision makers go away with their kids because of March Break so I take advantage of the number of absentees to get a break if I feel like it.

July and August => Take two weeks in here if you can. NOTHING HAPPENS at this time in Toronto anyway, in the business world so you might as well.

September/October/November => Don’t even think about it.  In my books these are the fastest moving months of the year as Torontonians hunker down after summer slowness. And as the days get shorter, here is the rule as I see it: the less daylight you see, the harder you work. You have to keep yourself entertained!

December Holiday Season => I don’t believe in working Dec. 25 – Jan 1st. Anyone who goes into the office during this period just goes there to clean up their desk and talk about holiday parties with the other “slackers” who don’t want to use their vacation days up in this period.  That’s somewhat harsh, but it’s true.  My two cents is that all businesses should close during this period.

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