Celebrating 1 year of surprise weekend road trips and how to plan one of your own


One year ago this weekend we started a new family tradition to break the monotony of lockdown during a global pandemic — the surprise weekend road trip. And you know what? We’re going to keep the tradition going this summer to keep up some pace (and tolerance for the unexpected) leading up to a return to school and the office hopefully sometime soon.

The majority of the weekends in the last year I would secretly choose somewhere within an hour’s drive that was pandemic-safe, pile everyone into the car, give the kids vague clues full of dad jokes about where we were going, and eventually roll up on some kind of random thing that was more or less worth the effort for a BIG SURPRISE designed to mix up the weekend when every day feels the same.

  • We hit the superlatives – like the world’s largest ball of twine, the world’s largest strawberry, the world’s largest snowman, and the smallest dedicated park in the U.S.
  • We gawked at giant roadside attractions – like the Jolly Green Giant, the North St. Paul Snowman, and the last remaining covered bridge in the state of Minnesota.
  • We learned our history – like the site of the first women to vote, the history of Native Americans at Barn Bluff, and about the invisible 45th parallel that cuts across the Twin Cities.
  • And we attended just about any drive-true experience possible – including the zoo, the state fair, renaissance festival, holiday lights, dinosaur adventure, and baby bison at a state park. And LOTS MORE.

To be clear, my family has been extremely fortunate to be healthy, the means to stay home, and the worst thing we had to fight was boredom. And if there’s one thing I like to do, it’s fight boredom.

Of course, I shared these adventures online, and PR Week featured our little excursions: PR Week: A vacation during the pandemic?

Who needs a dreamy vacation to Hawaii this year when you can take a trip to see the world’s largest ball of twine or an enormous statue of the Jolly Green Giant?

Those are some of the magical sights Greg Swan has been seeing with his family during the COVID-19 pandemic. He has been organizing surprise road trips for his family each weekend, for 15 weeks now, hitting weird and wonderful destinations within a 60-mile radius of his Minneapolis home.

Then Kendra Pierre-Louis at Medium’s Elemental magazine interviewed me about it for a feature story: Boredom Is Spreading the Coronavirus: People who are rarely bored seem to have an easier time sticking to social distancing behaviors, new research suggests.

Swan’s behavior — creating a plan of activities to do to avoid breaking social distancing — can help even bored people stick with social distancing, according to Bieleke. That’s in part because boredom tends to overlap with a lack of self-control, “basically the ability to control your impulses or your behavior and to do things,” he says. It’s what allows us to do things — like socially distancing — even if we don’t enjoy them…

According to Bieleke, there are ways of encouraging motivation — and it looks a lot like what Swan is doing with his family. “He’s establishing some baseline motivation that you need,” says Bieleke. In other words: socially distance, but make it fun.

When a psychologist with a Ph.D. in boredom says your family’s surprise weekend road trip pandemic coping strategy is smart, you genuinely tear up a little.

It’s been a hard year, but we’ve had some fun, too. We just had to change our expectations and get creative.

Even with the world reopening a bit, it’s going to be another strange year of figuring out how to “do things” and “be around people.” We’re going to keep the surprise adventures coming as we help reacclimatize both the kids and ourselves to things like spontaneity, uncertainty, delight, disappointment, and all those feelings and experiences we took for granted before they were absent for a year.

If you’re interested in planning your own surprise road trips, here are a few tips from a year of planning these:

  1. Use Roadside AmericaAtlas Obscura, or the Off the Beaten Path books to find a nearby destination
  2. Do a little internet research in advance about the community, history, and area you’re visiting — and someplace you can get ice cream afterward.
  3. DO NOT TELL where you’re going. Hints are okay, but they must be vague. If you’re using a map app, start the trip before anyone can see the destination so they can’t cheat.
  4. When you get there, make a big deal out of the reveal. Really play it up. Get everyone out of the car immediately to revel in its amazingness.
  5. Take selfies. Post them on social. Brag about your adventure. Capture the memories!
  6. And then go get ice cream. All surprise road trips must end with ice cream. Those are the rules.

You can find more background and additional resources here: YOU NEED A SURPRISE ROAD TRIP THIS WEEKEND.

Shameless Plug

One of our recent campaigns for Arby’s at Fallon was named as a finalist for an ADDY Award, The One Show Awards, Clio Awards, Shorty Awards, and now two Webby Awards. I hate these voting things, but if you’re into this kind of thing would you mind registering an account and giving them a vote? THANKS!

Here’s what else I’m tracking this week…

RIP Calibri, the Font This Email Was Written In: While there are more than 700 font options in Word, Microsoft has commissioned five new custom fonts for Office, in a move away from the Calibri font that has been the default in Microsoft Office for nearly 15 years. The five new sans-serif fonts feature a variety of styles, including traditional, modern, and even one inspired by German road and railway signs. Microsoft is starting to gather feedback on these five new fonts today, and it plans to set one as the new Office default font in 2022. Here’s how the new Microsoft Office fonts look in Word when you’re reading documents. What’s your fave?

Zoom Together, Together: This week Zoom introduced a new participant feature called Zoom Immersive View, which allows meeting and webinar hosts to place up to 25 participants in one meeting space. Here’s a TikTok demo of Immersive View in action. The feature is similar to Microsoft Teams’ Together Mode, which also lets you see everyone in the video room sitting together. It only took a year, but we’re finally seeing some new ways to combat ‘Zoom fatigue’ in these tools!

Upgrade Your Phone to iOS 14.5: This week’s update of Apple’s operating system is a big one. You can now unlock your phone wearing a mask if you’re wearing an Apple Watch. You can set preferred streaming services other than Apple Music. You can choose from more diverse Siri voices. You can finally search in the Apple News app. There’s a new Shortcut action for taking a screenshot that can be incorporated into various shortcuts. You can send calls from unknown numbers will be sent directly to voicemail. And at some point you will get a pop-up messaging asking if you give Facebook permission to track you. Read about these updates and more here.


New Emoji Week!! One of the smartest things Apple has done to encourage users to install important security updates is to batch them with the introduction of new emoji, and that happened again this week. So let’s focus on the fun stuff! Namely, 441 new emojis in this release including heart on fire, face in clouds, gender options for people with beards, numerous skin tone combinations for couples, and a vaccine-friendly redesign of the syringe emoji. See a full thread of new emoji here. Or just update your iOS and check them out yourself!

Buzzword of the Week – Cheugy: There’s a new adjective to describe someone who is out of touch or trying to hard, and it’s taking over TikTok and therefore pushing its way into our broader lexicon. Here’s the TikTok video about cheugy that has sparked a new addition to Urban Dictionary, an Instagram account devoted to calling about things that are cheugy, and even the NYT wrote about it. Unlike “OK, Boomer,” cheugy isn’t directed to a specific age or generation and probably describes all of us in some way.

Key quote: “Certain types of words go through trends just like clothing and accessories do… They’re fashionable for a while and go out of fashion. The word for cool gets replaced every few years, cool sticks around as a background world. Groovy meant cool, now it’s dated. Coming up with a word like cheugy is a way to distance yourself from something that used to be really popular until very recently.

Business Reads of the Week: 1) The tensions in newsrooms over reporters’ social media presence are not just about politics. 2) There’s a surprising shift taking place in the way white entrepreneurs are approaching diversity. 3) The allure of small business internet. 4) Time’s 100 Most Influential Companies

Quick Hits:

See you on the internet!

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