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How to Plan Fun. Maybe.

October 2, 2020

There are two types of people in the world: those who have organized groups of friends and those who haven’t.

If you are planning something, perhaps a vacation, or a weekend trip or perhaps you are already going on a trip but need to agree on things like accommodation, budget, or buying certain tickets in advance, I’m about to share with you my number one piece of advice to keep you from pulling your hair out.

This might be an obvious post for many people, but it’s something I struggle with because I want to get everybody involved and not leave anyone out. I usually drive myself crazy doing it.

It’s inevitable that some of the people will have to go look at their finances, schedules, commitments, assess their interest, talk to their partners, etc. There might need to be discussions about all these things as a group. Great. That is how you can make a trip that everyone enjoys.

But here’s the one word that can ruin everything for everyone. The word that has the potential to tear the group apart as you pull out every last strand of your hair.

The word? “Maybe”.

While the group waits, shows fill up, vacation rentals get rented, people who did have open dates get another opportunity and need to know if we’re going or not. “Time kills the deal”, as they say in sales.

This is why group trips and reunions and other multi-household outings often remain daydreams and exist only in the words “Someday we should…”

When you propose something and someone says “maybe”, respond with: “Great! I’m excited that you’re interested. When will you know for sure?”

Now there’s three types of reponses to this:

  1. They give you a specific date on when they will know.
  2. They realize you are actually going to make this happen and they actually aren’t interested and they back out.
  3. They say “I don’t know when I’ll know”.

#1: Assuming they give you a date that doesn’t have too much associated opportunity cost, tell them great and that you will need to know on that date.

#2: I tell them something like, “Bummer! But thanks for letting me know.”

#3: I have a more challenging situation. There seems to be interest. Or this is actually procrastinating giving the offer serious thought? Or perhaps they are waiting for something better to come along? Or they just really don’t know when they will know because they are waiting on someone else’s decision?

In any case, I find it best to make it clear that this maybe means no.

Depending on the situation you might ask questions to help them such as, “what needs to happen so you could make a decision?” or “How can we make this happen?”. But make it clear that until they are committed to going they are a no.

Posted Under: Everything Else Tags: #Pondering

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