There are pros and cons to planning ahead. One big pro is that you can often save money if you make reservations ahead. You may also be able to secure tickets to popular venues too since if you wait those venues may be sold out. And, there's lots to be said for the happy anticipation and good preparations you can engage in when looking forward to a terrific event. That said, there are definite cons to planning ahead too.
First, the weather. If you plan ahead for a great beach vacation and it rains the whole week, that's truly disappointing. That happened to my family several years ago. We rented a great cottage closet to lots of beautiful beaches and it rained the entire week. We managed to make the best of it, but it wasn't the vacation we dreamed of. Another drawback of planning ahead is that unexpected, wonderful events may arise in the meantime. For example, if you plan a great vacation ahead then a close relative decides to get married that week, then you've got a dilemma on your hands. Other unexpected work or personal events may get in the way. There's been times when I planned ahead, and I had to forgo the reservations since the unexpected event could not be missed.
If you plan ahead with good cancellation policies in place, that can be a win-win. You save money and secure a good place or event, but are able to cancel if need be. That's not always possible, however, and you'll sometimes make the gamble because it's worth it. When I make a decision like that, I know that I may have to give away the reservations or tickets, but I'm okay with that because it seldom happens, and in the long run, planning ahead seems to work out well. Onward.