I have friends who HATED family vacations. They have a lot in common. They love their parents and siblings, but vacations were awful. They fall into two camps: 1/

Camp 1: vacation was the same thing every year. Sometimes it was a resort, or a time share, or a hotel room. That was it. Go to the same place, do the same thing. Secure, reliable, repeatable, predictable.
2/

Camp 2: vacation was exquisitely planned. They knew where they were going to be, for how long. Everything worked out to the 15minute interval. Parents pushing to keep the schedule so that the vacation isn’t “ruined.” 3/

We loved ours, and we have friend who love(d) family vacations. We have something in common: it was loose. There were goals (“see the nation’s capital”, “see the smoky mountains”) but the rest was improv and opportunity. “Where will we eat?” “What do you want to see?” 4/

We were part of an adventure, rather than minions executing someone else’s plan. We saw and did things together for the first time. We could stop and see anything interesting.
It always worked out.
And when it didn’t go great, we shared that adventure too.

I know people who can’t stand the idea of this. They say “I couldn’t relax if I don’t know exactly what to expect next.”

I’d say “they can’t relax” BECAUSE they’re obsessed with controlling what comes next.

And then I went into software. 7/

Software has been an enjoyable adventure whenever our “parents” tolerate inclusion and engagement and co-creating the experience. But here I met the under-involved and over-involved parents who abandon or over-plan their teams’ time.

People are people. 8/

I still prefer the way my parents did it: a goal or two, opportunism, co-creation, and the skills and resources to back it up so that a slip didn’t become a cascading failure. A shared adventure.

I’m not saying how you should be, but may I recommend a shared adventure approach?