Maybe it isn't difficult for you, but I have a very hard time pulling the trigger on a vacation. That is, I find it difficult to settle on specific dates and then make them firm by booking flights. I am always afraid that perhaps I selected dates that would turn out to be inconvenient for those I am hoping to visit, or I will pick dates that coincide with air traffic control or flight crew strike, or hurricanes and goodness knows what other events that might delay or cancel my trip. Of course I do know that it is possible to change plans including flights, but not without a cost.
Most of my travel is international and therefore it is necessary for me to book well in advance in order to get the best price and choice of flights, but I agonize for days before I make my booking final, and I don't do that until I have checked with family and friends where ever I plan to visit to make sure they will be available.
This year my plan is to visit Ireland first, then from there fly to Paris and take a train to the west of France, returning to Texas from France with my two grandsons who will spend three weeks with us before they returned back to France.
I was delayed in making my reservations although I knew what dates I would be traveling and had double checked with family and friends and all was well there, but my delay was in waiting for my grandson's passports to be renewed. Finally that issue was resolved and what do you know! We discover that my daughter in law will be expecting her second child the week before I am due to arrive in Dublin!
Now, that could be perfect if she has the baby on time, except that I have always hesitated to turn up at the same time as a new born child, I mean, who wants their mother in law under foot when they are trying to adjust to childbirth and a new baby? And what if she is late and I just barely miss the event altogether?! These days I only travel to Ireland once a year as the cost and the effort are becoming too much for me - plus I will have used up almost all my vacation time for the year and so will have to wait almost a full year before I meet my new grandchild! However, that trip is in the can and it is just a matter of trusting the universe. (See this post for my thoughts on that).
So, with the major trip organized I started to think about my minor trip, minor only because it is a domestic flight (to visit my son and his wife and their son in Seattle, WA.) And so I checked the possible dates with them, they were sure that the date range I suggested would work, and then I worried over how many days, which days to travel, luckily I didn't have to worry about which flights as there is only one direct flight per day from Austin to Seattle, and only one coming back again. Direct flights are the least stressful, no matter what time they are. With only one flight the possibility of lost luggage is minimized and there is no connection to miss, and just one flight to be on time for. (See post here for more on the things I stress about when I get over the hump of actually booking my flights).
Why is it so difficult for me to commit I wonder. How big a mistake can one day sooner or later be? In fact, so far, in the almost 20 years since I moved to the US, my trips have been extremely successful... ah, but perhaps that is because I take so much care in selecting the dates?