Over the past few years, I have come to the conclusion that the definition of the word “fun” can drastically change, depending on who you ask.

For me, I simply ask a few questions to qualify whether I will perceive the event as fun… or pure agony:

“Do I have to pay to park? Will I need to wait in a line or make a reservation to get in? Will I be surrounded by crowds of people who I can’t have meaningful conversations with?”

If the answer is yes to any of those questions, I will certainly be miserable.

I’m somewhat surprised I haven’t yet ordered the t-shirt from Amazon that says, “This is my ‘I don’t want to be here’ shirt”, for such occasions.

Clearly, I don’t belong on a cruise ship or in the downtown of big cities or at theme parks. It’s not that I am anti-social. In fact, I have recently come to the conclusion that I am actually the most extraverted person in the room, most of the time. (My Myers-Briggs is ENFJ. The “E” stands for extraverted.)

I need to be connecting with people in meaningful ways, in order to have fun. It has been my experience and observation over the years that paying to park, standing in lines, and being in the middle of loud crowds are all the antithesis to this.

This past week, I reached a milestone in my life: For the first time ever as a family, we went on a vacation that all four of us equally loved.

Why? Well, sure- it helps that the kids are older and more mature now.

But it is primarily because our trip to the Oregon coast fulfilled all of our needs as individuals-  and as a family.

Yes, I am going to make this about Enneagram. (As you know, I have a book coming out about it, so surely you will understand my fascination of seeing social dynamics through that lens.)

In our family of four, we have no one with an Enneagram 7; not even as a wing. It is actually the only number that goes completely unrepresented in our family’s lineup. Interestingly, 7s are the official “fun” number of Enneagram: the life of the party.

Enneagram 7 is also the epitome of FOMO: the fear of missing out.

I (jokingly?) imagine most Enneagram 7s would probably not be happy unless they were at a very “exciting” place where they do have to pay to park, wait in lines, and be surrounded by plenty of sights and sounds in a large crowd. Because to them, those things generate the concept of excitement: Nothing draws a crowd like a crowd…

As for me, I have JOMO: the joy of missing out.

I truly get a thrill out of avoiding all the things that most people seem to get all excited by. I instead seek the unique experiences that are off the beaten path; the ones that are much less marketable.

Based on our recent successful vacation to Oregon, I can see how my wife and kids are actually wired in a similar way, regarding what constitutes as a “fun” family vacation.

I am Enneagram 9 Wing 8: I am constantly seeking to manage the energy equilibrium of harmony (9), which I tend to find by overcoming challenges (8).

My wife is Enneagram 3 Wing 4: She is constantly seeking a sense of achievement (3), which she tends to find by planning unique and authentic experiences (4). (In her own words: “I like to be surrounded by beautiful things.”)

Our son is Enneagram 5 Wing 4: He is constantly seeking to gather knowledge (5), which he tends to find by immersing himself in unique and overlooked experiences (4).

Our daughter is Enneagram 2 Wing 3: She is constantly seeking ways to help and give to others (2), which she tends to find by chasing a sense of achievement (3).

Whereas there is no “fun” Enneagram 7 in our family, there are two numbers that show up twice:

My wife shares a 3 (The Achiever) with our daughter and a 4 with our son (The Individualist).

What that means is that a common theme in our family is to achieve and to be unique.

Funny thing is, when I graduated high school 25 years ago in 1999, I “achieved” (Enneagram 3) the Who’s Who award for “One and Only” (Enneagram 4); as voted by my classmates.

Yet I am the only member of my family without either an Enneagram 3 or 4 as my main number or wing.

However, “achieving” and “being unique” perfectly translate into my Enneagram 9 Wing 8 desire to manage the energy equilibrium of harmony (achieving), which I tend to find by overcoming challenges (finding ways to be unique).

During our weeklong family vacation in Oregon, we went on a giant dune buggy tour, we hiked to explore various natural wonders on the Pacific Coast, and we relaxed in the clean mountain air while detached from the distractions of the rest of the world.

So yeah, no Disney cruise ships for us.