When Do Family Trips Stop Being Cool

In grade school, the Monday after spring break was always one of minor torment. My friends whose parents clearly loved them more than my parents did me, came back with peeling shoulders and their hair braided. Hair braids and hair wraps were the ultimate status symbol for a white suburban girl in the late 90s. The middle-of-the-pack girls who went to the Wisconsin Dells weren’t tan but at least had some stories to tell about the indoor waterparks. My family usually just went up to my grandparents and hung out with my cousins.

To be fair, we pale losers of the class were the majority, but that didn’t stop us from touching the girls’ braids and playing with them as we sat on the rug during reading time. While my friends couldn’t bring me a hairwrap to fit in with everyone else, some true friends did occasionally bring me back souvenirs– usually cute little trinkets like a hand-painted ceramic turtle that said “HUATULCO.” My friends had seen the world and I was convinced that Cabo, Sanibel Island, the Dominican Republic were all far-off lands I was convinced I would never know. I called my parents cheap and referred to us as poor on more than one occasion. I wanted Disney World. I wanted cruises. And I definitely wanted braids.

We were always more the roadtripping national park type, so when we eventually did start traveling to places like South Africa and Australia, someone asked my parents if they won the lottery. But in the span of 10 years, travel became our families signature thing, each trip more exotic than the next.

But my dad has always been a dreamer like that. While the rest of us became a bit jaded and took our weekend trips to Switzerland for granted, my dad has never lost his sense of wonder. In my family, my Dad is Joseph and the technicolor dreamcoat, and the rest of us (me) are the evil brothers who throw him in a pit, sell him as a slave and take the cash.  That’s how we felt he told us about his Big Idea™️: his desire for all of us to climb the highest peak in Africa. Don’t worry, I had to Google it too. It’s called Mount Kilimanjaro and it’s in Tanzania. East Africa.

School, work and life in general make it hard to coordinate anything with four mostly adult children.  I think Kevin and Tim would tell you they were in support of the idea of the trip, but like most men in their 20s, struggle with the planning and communication part. Because of that, when it comes to managing their involvement, I turn into the two-headed monster– one head, a girlfriend with trust issues and the other, an enabling mother (which is funny, because I am neither). I have booked flights for them more often than I care to admit. I offer to write emails to their bosses and professors asking for time off just to ensure they get the dates right.

Mom was going to be equally difficult to convince. Without explicitly saying it, Mom had little to no interest in climbing a mountain in Tanzania for seven days without bathrooms or showers. But if Kevin and Tim signed on, I knew she’d go (Morgan and I are not enough of draw). Mom’s mofo (I’ve given up telling her its fomo) is something to be taken advantage of.  She’d rather break her ankle doing something she doesn’t want to do than miss out on something loosely classified as fun.  Mom’s also healthily competitive, so on the off chance that the rest of us actually summited Kilimanjaro, she’d be as annoyed at herself as she was proud of the rest us.

Dad first mentioned his big dream after a hiking trip we took in 2012 to Nepal, a “vacation” that sent my Mom home with a broken ankle (she’s fine). But Dad, never one to be derailed, told us not to stow away our hiking boots for long, because after climbing Mount Everest hiking a small portion of the Himalayas for two days, we were obviously ready to conquer Kili. I was surprised to learn the lifelong dream of someone I’d lived under the same roof with for two decades.

For six years Dad penned us longing emails hoping to get my mom, brothers and sister on board. Here’s one: 

Tue, Oct 27, 2015, 4:40 PM

Re: Travel Crisis: Next Anderson Destination

Hey guys, I need your help.

I’m trying to figure out if we’re going on a trip this Christmas/New Years break.

Some of us have informally discussed climbing Mt. Kilimanjaro (19,341′) with the thought that if Mom and I ever want to climb this should be done now before we get any older. 

Problem is Mom doesn’t want to go, saying it’s too late to start training.  The Kilimanjaro training programs I find on the internet are eight-week programs (that’s like Nov. 1st).  So I don’t know if I should push it or what.  Mom doesn’t always say what she really means, like if she just doesn’t want to go, blame the training, or maybe too scared to break her ankle again, which I don’t blame her. Tell me what you guys think.

Some thoughts are: Try again next year, forget it, or go without Mom (I told her this, only half-joking).

Love, Dad

Dad’s email lacked his usual quips of anticipation and adventure, and his despondent “forget it” at the end moved me to call him to make sure everything was okay. On the phone he said something even more unusual: if no one wanted to go on a big trip and get the time off, he’d be open to spending a weekend together in New York. New York?  He doesn’t even like New York.

So after I hung up with him, I created a new family chain, added my mom to in, and added a clickbait subject: 

Fri, Oct 30, 2015, 1:14 AM

Re: Derrick Rose Being Traded To The Nuggets 

made ya look. 

In short, if possible: Dad would like to spend some family time with everyone whether its renting a hotel room in NY for or going somewhere. Everyone reply ranking their top 3. don’t pretend youre not on your phone all day. 

1. Kili climb (with or without safari) 

2. Mexico 

3. Morocco 

4. Other (reply all so ppl can support your write in candidate) 

5. Vancouver 

Kilimanjaro is on his life bucket list so hes trying to decide if he should go by himself at some point next year if interest isn’t there. 


We didn’t go. Dad’s emails got increasingly desperate each year. But when your family has to be clickbaited into caring about a free trip to anywhere in the world, perhaps it’s time for a course correction anyway. 

One thought on “When Do Family Trips Stop Being Cool”

  1. Amanda, you should write a book, actually you almost have written one. You are an author. I thoroughly enjoyed your thoughts, glad they are on paper………..


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