What fun plans do you have for the holidays?

Kathy Kay

SVP and Chief Information Officer at Principal Financial Group

For us, it’s all things family this year. We are seeing our first grandson, who was born earlier this year, and we’ll spend a few days doing fun winter activities, as well as eating way too much. Then we’ll spend time with our other children — one of whom married into a family of ranchers and farmers, so, we will spend a few days on their ranch completely disconnected. There, we plan to ride ATVs, hike and — of course — eat more great food! I couldn’t be more grateful for the time away to reconnect with family, and the ability to do so more safely this year.

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Prashanth Chandrasekar

CEO at Stack Overflow

I'm spending time at home with the family this year. Not to sound like a cliche — a tech enthusiast who loves sci-fi — but I'm incredibly excited to watch "The Matrix Resurrections" and catch up on episodes of "The Expanse." And when I inevitably have questions about "The Matrix," I'll go down a rabbit hole (pun intended) on the [Movies & TV] Stack Exchange.

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Zeb Evans

CEO at ClickUp

I have been journaling my entire life, and dedicate time twice daily to writing about my current goals and projects. At the end of each year, I do an annual journal review. I like to go someplace tropical and take a week or two to go back and reread my thoughts from the past. During this time, I don't take any meetings. I'm able to disconnect and do a lot of introspection.

The holidays are my favorite time to intentionally stop and breathe. It's important for me to prioritize reflection and gratitude for all that the year has brought! I spend time meditating and reading and celebrating all the progress and accomplishments achieved. This time away allows me to reset and come back to work refreshed and ready to take on what's next.

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Robin Schulman

Chief Legal Officer at GitLab

For the holidays, my family is enjoying time together at home and making/decorating/eating lots of festive cookies, as is our family tradition. Every year we add some new cookie-cutters to our collection — last year it was Lego-themed — and this year we added several dog shapes! I need to find a Tanuki-shaped cookie-cutter (GitLab's mascot).

On New Year's Eve, my family celebrates with a large pan of paella and mark midnight (usually EST because we cannot stay up much later!) by banging pots and pans as was my tradition as a child with my grandparents. January is usually spent cleaning up rogue sprinkles and edible glitter from our cookie escapades.

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Kurt Lin

CEO and Co-founder at Pinwheel

I have a few goals to check off during the holiday break. While swimming might seem like an activity best for summer vacation, I recently learned of the Total Immersion technique for swimming, and I’ve been keen to try it out. I’m excited to take the plunge and learn proper swim form. I also signed up for a speed-reading course, and to pair with that, I have a list of books to finish over the break: "Why We Sleep: Unlocking the Power of Sleep and Dreams," "Think Again: The Power of Knowing What You Don't Know" and "How the Word is Passed." The latter is actually recommended reading from Pinwheel’s “Pincil Me In” book club, and we can discuss it as a team when we return.

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Joel Flory

CEO at Co-founder at VSCO

This holiday break, I'm using the time to recharge. We normally do a soft close at VSCO for two weeks to give the whole team an opportunity to do so. For me personally, that will mean lots of pickup soccer, cooking, going on walks with my family and catching up on a ton of good TV we've been meaning to watch. I also use the time to rethink my calendar — sometimes I blow it all up so that I can start fresh for the new year and create some new routines. I've realized I do some of my best thinking in the morning, so am planning on blocking out that time and pushing most meetings to the early afternoon.

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Patrick Kann

CEO and Co-founder at Papaya

This year the holidays will be very special because we are going back to the country where I grew up, Brazil. Due to the pandemic, it's been two long years since I've been back. I will go to Sao Paulo and reconnect with my childhood friends, many of whom feel like family. Also, my wife and three kids will celebrate my sister’s wedding. Then, we will go to a beautiful beach town and enjoy quality time together where I'm looking forward to seeing my kids embrace Brazilian traditions, culture, language and food.

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Keith Smith

CEO and Co-founder at Payability

Like a lot of folks, my holidays are filled with people, food and a fair share of chaos. I'll be spending the holidays with a wonderful, healthy-sized group, full of characters, that retreats to a cabin in the mountains as part of my family's annual tradition. I'm one of two siblings, but my parents have always had a soft spot for people in need, so throughout my childhood I was blessed with a total of 19 different foster siblings. Some lived with us for just a few months until their own home life stabilized, while others became siblings in every way but blood and lived with my family for years, and are every bit as much a part of the family as my brother and me. This dynamic is never more on display than during the holidays where the "bonus kids" — as my father likes to call my foster siblings — come together, often with their own kids, to help us celebrate our big little family. I'm looking forward to a snowy Christmas day together filled with lots of laughs, catching up and time with family for a great start to the new year.

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Fara Howard

Chief Marketing Officer at GoDaddy

I’ll start my fun plans update with a daunting story. Last February, while chasing my three boys to their first double-black diamond run in Whitefish, I tore my ACL. I shook it off as a strain and skied for two more days (yes, I skipped that double black!) but soon learned I tore my ACL in three places and dislocated my knee. After an April ACL replacement, I worked hard to recover for the next eight months. So what are my fun plans for the holidays? I’m heading back to Whitefish to ski again! I’m so grateful that I get to do my favorite thing with my favorite people, my family.

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Blake Brannon

Chief Strategy Officer at OneTrust

My wife and I are escaping to Colorado with our three children to take them skiing for the first time. We plan to have lots of fun in the snow, drink plenty of hot chocolate and we're also taking a few board games to teach our kids. Then I've got a few books on the bucket list I hope to get through during the break to come back refreshed and motivated to tackle 2022.

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Alex Simon

CEO and Co-founder of Elude

I was able to sneak in one last vacation before hunkering down on the East Coast to spend the holidays with my family in my hometown. I got to see Rome, Lake Como and Switzerland, places I've always dreamed of spending time in during the holiday season. European holiday markets are really an incredibly festive experience, even when people are wearing masks. It was a much-needed escape and vacation, but the real treat is that I am heading home to relax with my family and hopefully catch some snow and winter wonder while at home. That's the part I miss most living out in LA, is that East Coast winter magic.

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