It’s easy when to make to-do lists.  I like cross stuff off too.

I large scale global events like the Olympics and World Cup.  We would organize dinners during this time for hundreds of people.  And I would also have an Operations person on my staff who wanted to figure this out, get it off their list, etc.  If they’re a great Ops person, they want to get it done early and click it off their list early.

The problem is this: solving these issues early costs a premium.  A restaurant in Vancouver for the Olympics would have grand dreams of wealth and daily buyouts a few years before the Games hit their city.  Because we were experienced, we had a more realistic view.  We understood supply and demand.  And we know that the longer we waited, the lower the prices would drop.

This would drive our Operations Department crazy.  Today, it drives my wife crazy.  Waiting to the last minute can make you a little nervous.  But are you willing to wait in order to save 30-50%?  Plan your flights.  Plan away on some details. But don’t let that side of your brain (the side that needs to know everything is all set) win.

Be flexible.  Have a mindset that allows you to take advantage of supply/demand.  When you’re looking for an Airbnb rental, resist the urge to lock that place up 6 months in advance.  I run a business that owns various vacation rentals.  I never give someone a discount if they’re booking 6 months in advance.  But if you catch me with an empty place the night before, I’m definitely willing to make a deal