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Dealing with Disappointment: 5 Things I Learned from a Rough Family Vacation Last Week

Dealing with Disappointment: 5 Things I Learned from a Rough Family Vacation Last Week

I know, I know. Simply being on vacation should be reason enough to not complain, right? Having money to pay for gas, a cabin, and fun activities should override any thoughts of disappointment if it didn’t go as you planned.

Aaaaand there’s the issue: it didn’t go as I planned. 

Before you roll your eyes and label me “entitled,” hear me out. I realize none of us actually deserve to go on vacations. The majority of the world has probably never come close to even having such thoughts. 

But since I live in middle-class America and my husband and I both work hard to be able to play, here we are. If you’re already annoyed, feel free to shut me down and go back to scrolling social media from your couch.  

If you’re somewhat in my boat though, I have a question for you: 

How do you deal with disappointment on vacation? Not disappointment in a normal week when friends cancel your movie plans. Not on a regular day when you thought someone else was making dinner.

I mean on the trip you worked hard to afford. On the trip you spent time planning for. The trip you got sick on or had to go home early from.

Definitions of Vacation:

Webster’s: An extended period of leisure and recreation, especially one spent away from home or in traveling.

Mine: A time away from home with no chores, work, or problems, relaxing with friends or family in a beautiful setting and an awesome rental we got for a smokin’ deal. Daily housekeeping and complimentary cookies not necessary, but colds, flus, or fractured body parts are not allowed. 


Is assuming everything will go smoothly and we’ll have the time of our lives too much to ask? Apparently.

Our youngest has dealt with Long Covid since January 31. You know… back when we wore coats and still had Christmas lights up.

The medical community thought it would last approximately two-to-eight months. Now we’re hearing about people who have dealt with it for over two years with no end in sight.

*s i g h*

We naturally assumed his immune system was weaker, but never dreamed he’d get the obnoxious virus again (for the third time) while on vacation.

After looking forward to high school camp since 2019, disappointment hit hard when he woke up sick the day he was leaving. He went back to bed, his good buddy went to camp solo, and I had a few questions for God.

What the heck? Hasn’t he dealt with enough this year? Aren’t daily headaches, brain fog, fatigue, and body aches enough? Isn’t missing four months of school and a whole lacrosse season enough? Wouldn’t you want him to go to camp and learn more about You? When are You gonna give him a break?

To say our son has dealt with some disappointment this year is an understatement. He made the most of our wonky vacation and still pushed himself to have fun.

Four days after we all celebrated his recovery, one of the friends we were on vacation with got sick and their whole family had to leave early.

Insert disbelief and disappointment on top of an already weird living situation and other sadness. This not-great combo took my attitude from bummed to depressed.

Lessons Learned

Here are 5 things I learned about disappointing vacations:

1. I can’t control the weather.

No doy, Sherlock. So why do I assume other people might have to deal with no snow on their ski trip, but expect to have fantabulous weather on our vacation? I’m sorry you had rain in Hawaii, but there better not be high temps in the forest!

2. We take our issues with us. 

Because, you know—people. If you’ve ever moved to another town, state or country, you know your issues get packed too. So unless you’re going to vacation alone, buckle up. ‘Cause that argument you had in the car with your super fun sugar pie honey bunch on the way to the super fun cabin in the mountains? It just might resurface while you’re eating watermelon and swinging in a hammock by the super fun lake. 

And your first day on vacation will not. Feel. Fun. 

3. You can only plan so much.

For heaven’s sake, I made a spreadsheet for meals, a list for grocery shopping and another one for things not to forget. You’d think with a fair amount of planning you could avoid issues, inconveniences and pitfalls.

Even with the best of intentions there needs to be some element of flexibility. Especially for times when you lose your list.

4. Inconveniences aren’t the same as suffering.

  • Did our only car get stolen? No
  • Was anyone dying in the hospital? Nope
  • Did anyone get bit by a hippo? No siree

5. You can probably have a do-over.

Just because the last vacation felt like a train wreck doesn’t mean our next one will. So I talk to myself and ruminate on next summer:

You still had some great moments. You still made memories. You still smiled a bunch. Focus on the positive. Work hard, save money, plan another trip.

My son, Doogan, counseling in Day Camp, where I counseled 6 summers.
My niece, Stingray, counseling in Child Care, where I counseled 4 summers.

Friends for life. No, we weren’t drinking.
Mom friends, counselor sons, crazy photo-bomber.

Amazing how a few days in a different environment and routine can make some of the annoying, inconvenient details fade. I can still get sad about all the changed plans and things we didn’t get to do, but I’m moving on.

don’t ask

Have you ever experienced a disappointing vacation? Tell me in the comments how you dealt with it. Your experience could inspire another reader!

Kicked Out of the Bank: When Rejection Suddenly Strikes You and Your Family

Kicked Out of the Bank: When Rejection Suddenly Strikes You and Your Family

A few years into Baja living, my husband learned to roll with the inconvenient punches, knew exactly how to pay all the bills in person, and understood the cultural norms.  But of all the places we visited in the city, going to a Mexican bank never felt fun.  Funky restaurants? Yes.  The Italian gelato shop?… Continue Reading