What I Did on My Summer Vacation
What I Did on My Summer Vacation
Spoiler Alert: I worked too much.
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We didn’t take a family vacation this summer. Originally, I had a grand idea that we’d go to Chicago, a favorite city of mine. I could see our 7-year-old enjoying Shedd Aquarium and the Field Museum, and maybe we’d take in a game at Wrigley Field. But this spring I made the choice to downshift freelancing in favor of spending more time on The Purse, and we decided flights and a hotel would probably be more than we could comfortably afford to spend.
As I’m always scheming, I came up with a Plan B: a road trip that included seeing friends in Western Massachusetts, a visit to the Eric Carle museum, and then a couple of days visiting the Baseball Hall of Fame. (Yes, we’re a baseball family now, if you haven’t caught on.) But that plan got nixed in part because our friends were out of town the week we were hoping to travel. My CFP class was on Wednesday evenings all summer, and even though it was remote, the idea of trying to sit through a three-hour session on insurance in a shared hotel room with Ken and our kid seemed downright awful. To make matters more complicated, Ken’s work schedule is such that it’s hard for him to be off on Fridays, and so Plan B fell apart as well.
Of course, I was an idiot, and I didn’t book camp that week because I thought we would be on vacation. But I also didn’t do a good job of protecting my schedule from freelance demands. And suddenly I had a bunch of work to do and no true backup care, which is why I ended up working from my in-laws’ study/guest room for the first half of the week and then giving up entirely and sticking our kid in two days of drop-off camp with a buddy so I could get through the rest of my to-dos and meetings. He had a wonderful week. I felt like an epic failure.
I love to travel, but I’ve always been really bad about making it a priority in my life. While Ken and I have had some amazing (and affordable) adventures over the years, we are also creatures of routine. Throw a kid into the mix, and it’s even more complicated. I’m in awe of people who decide to spend a year abroad traveling with their young kids. I definitely have strong “good for you not for me” feelings about it.
Yet at the same time, I feel terrible that I didn’t get my act together to plan a fun trip this year. As much as I try to ignore the treacly tropes that you only get so many summers when your kids are young and want to hang out with you, I definitely shed a few tears in July over my failed week off. I should have done better!
“We’re sold an image of summertime with kids as a joyful, carefree romp (bolstered by all of those picture-perfect Instagram posts), which doesn’t match the economic and social realities of how so many families operate today,”
wrote in her newsletter with the subject line, “This is Permission to NOT Take a Family ‘Vacation.’” In the newsletter, she shares the harrowing experience of taking a beach vacation with her toddler twins and older child, all three of whom were under the age of six. There was “not a single moment of relaxation for the multiple adults required to manage all three children,” she wrote. I can certainly relate, and I’ve only ever traveled with one small child in tow.
I think one of the reasons I have such a hard time pulling the trigger on travel is because it can be a big expense. And because we don’t travel frequently, it feels like more is on the line. As Kathryn Jezer-Morton wrote in The Cut, “Being a parent while on vacation means modeling competence and organization. There are stakes: Everyone’s supposed to have fun and relax. If the parents are stressed, the vacation is a bust. That’s science.”
Except I would replace “parent” with “mom,” because in our house, I do 99% of the travel planning, and I’m also usually the one who’s most likely to stress out and melt down when the trip doesn’t go exactly according to the plan. It’s embarrassing to admit, but it’s also true. And this summer, I just could not get my act together to make the magic happen.
Every summer when I was growing up, my parents would pack up the car and drive me and my brother from Cincinnati down to Destin, Fla., a 12+-hour trip that would inevitably involve traffic jams in Atlanta and a pit stop for barbecue in Alabama. The four of us would spend the week packed into a tiny beachfront condo with my grandparents, my aunt and uncle and cousins just a few doors down. We’d be at the beach all day, then dress up for dinner each night at some local fish restaurant, or my grandma would cook, and we’d sit around after dinner eating watermelon and watching movies we rented from the local video store. The trips were chaotic and fun, and they’re some of my fondest memories from childhood.
I haven’t been able to recreate such a tradition for my kid, and it makes me sad. We spend a lot of time in Cape Cod with my parents, but since the pandemic, when remote work became commonplace, it’s more likely than not that I work during our weeks here, and they don’t feel anything like a true vacation.
If I’m being honest with myself, our decision to not travel this summer wasn’t just about the money or the fact that it’s difficult to travel with a small child. My kid is not so small anymore, plus, he’s a total delight, and I like to travel with him.
No, this summer, our lack of a family vacation was about the time. And that makes me feel even worse. This is the ongoing struggle facing so many ambitious working moms (parents?): How do you do it all? And the unsatisfactory answer is you just can’t.
I feel a constant push/pull of working more to make more money versus taking time off to spend with my family. The math is even more complicated these days now that I’m freelancing and trying to build a business from scratch and also taking classes to become a certified financial planner. It was hard to take paid vacation days when I had a full-time job. Now I’m living in a reality where if I don’t work, I don’t get paid. Plus I do a lot of work (writing this newsletter, studying for my classes) that doesn’t pay much at the moment but will hopefully pay dividends in the future. Basically, all my time is spent either working for pay or working for theoretical future pay, and as a result I find it really hard to also budget in real time off. But then Instagram serves me up a photo of a happy family enjoying an idyllic beach day, and I feel like a giant jackass. The FOMO mixed with guilt hits hard.
In mid-August, when my work/study mania felt at its peak, I decided to make one last ditch effort to salvage summer vacation (at least in my mind). I planned to take the last week of August off so I could do some fun vacation-y things in Cape Cod with my kid and parents. I even told my major freelance client that I wouldn’t be around to work this week.
So it should come as no surprise that we got Covid the second to last week of August, and our Cape Cod plans got all screwed up. But of course we got sick! You can’t be firing on all cylinders all the time trying to squeeze the most out of your days (and nights and very early mornings) and not expect it to catch up with you. With everyone sick, I had to cancel camp and a lot of meetings, and the kiddo and I spent a lot of time hanging out on the couch watching movies. (I also spent a lot of time on my laptop while he watched a lot of YouTube.) This was not the picturesque, memory-making quality time I wanted this summer, but it seems like it is the quality time the universe served up.
But I haven’t handled it well. I’ve been mad and sad and not very pleasant to be around. Unfortunately, parents are also supposed to model organization and competence when everyone is home sick. But it’s hard when you’re the mother and you don’t feel good and there’s no one around to mother you. (Even though my mother wanted to mother me, but she couldn’t because we didn’t want her catching Covid, too.) As I said to Erika this week, I need to put “lying down in a dark room” on my to-do list, but there just isn’t time.
We did make it to the Cape this week, but we’re all still getting over Covid, and I’m working because I’m trying to make up for all the time I didn’t work last week. I’m tired and sort of sad and bracing myself for September and the start of the school year, which introduces a new level of mania. It’s exciting and scary at the same time, and I don’t feel ready for it.
I’m also trying hard not to obsess over how my son will look back on this summer. I hope he’ll remember all the fun he had playing with his baby cousin when they visited from the West Coast and all the amazing camps he got to go to with his best friends. I hope he’ll think back fondly on watching lots of baseball with his dad and learning the names of the starting lineup of the Boston Red Sox. I hope he remembers that when it was most important, I canceled everything and cuddled with him on the couch when he got sick.
I hope he only has vague (or even better no!) memories of his mother acting like a lunatic when the summer plans fell apart. I don’t want to think that my stupidly high expectations (and my stupidly busy schedule) ruined his summer. As with so many things about parenting (and working), kids (and managers/colleagues/readers) usually don’t see the imperfections until you start pointing them out. So as long as he’s safe and having fun, it probably doesn’t really matter if we didn’t make it through my ridiculous list of summer to-dos. Coney Island will probably be there next year. And hopefully I will get a do-over.
More than that, I’m trying my best to let go of the idea that I only get 18 summers with my kid, and I’ve already blown through seven of them. Because I’m writing this from my parents’ beach house, and we’ve had 40+ summers together, and I never get tired of hanging out with them.
How was your summer? Did you cross off everything on your bucket list? Take a fabulous vacation? Log too many hours in your cubicle at work? Fly across the country with a screaming toddler in tow? I want to hear the good, the bad, and the ugly.
Random Extras
I just finished listening to Kara Swisher’s Burn Book, and it was so good and funny and inspiring, and I highly recommend!
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There have been SO many good newsletters lately! To name a few: I loved
’s essay about being in her “try-hard era,” ’s recent newsletter about how much she shares online, and ’s new corporate office outfit diary, which is just so fun!
My kids are twenty-somethings now, and what I've learned is that trying too hard to create "memorable" moments is futile. What I remember from their childhoods and what they remember from their childhoods are completely different moments. Their memories are not under our control as parents. What your son will remember is how much he was loved. It us so clear from your writing that your family is the center of your world, and that is all that really matters.
I really, really appreciate the transparency you shared here. It is so easy to look at Instagram and think everyone's summer involves multiple weeks off to scenic destinations (mine definitely doesn't!) and I've always had a hard time reconciling the idea of "summer" with the reality that my full-time job still requires just as much of me. And my daughter is only 18 months so still in full-time childcare - I can't imagine how much more challenging it will be to juggle camps, summer care, etc. Just wanted to write in that it sounds like you're doing an amazing job (and your kid likely DID have a great summer) and thanks so much for sharing so transparently!