Solving the holiday work paradox

Turning a day off into a creative breakthrough (without burning out)

Hello friends,

When you work for yourself, there’s something about clocking in on a holiday that makes work feel less like work. I realize this is not a popularly held opinion. In fact, working on a holiday is often portrayed as sad and lonely, or as an unreasonable request from an out-of-touch boomer boss.

Holidays are a day to recuperate from the grind. To spend time with friends and family. But what if rest feels more like procrastination, and you're craving the kind of deep, uninterrupted creative work that seems impossible during regular business days? What if you need an excuse to get out of that family vacation where you’ll be expected to sleep on the floor because that’s what you did when you were 10 years old or surround yourself with thousands of strangers who also have that day off and thought going to the beach would be a good idea? There's a counterintuitive approach that transforms holidays from guilt-inducing "should be relaxing" time into the most productive and fulfilling days of my year.

The secret isn't working harder on holidays—it's working differently. When the world goes quiet and your phone stops buzzing, you have access to something rare: unguarded creative energy. No one expects responses. No meetings interrupt your flow state. The projects that keep getting pushed to "next week" finally have space to breathe. But this only works if you approach holiday work like a mini-retreat rather than business as usual.

Need clarity? Get outside.

My on-the-fly mini-retreat

I’m not a monster. I’m not suggesting we work every single day. Quite the contrary—I’m a big fan of taking time off to ski pow, ride bikes, road trip, and toast the end of times with dear friends. I no longer have the stamina I did when I began my entrepreneurial journey in my 20s (that hurts to admit). I need rest and recovery, time to turn it all off. I also crave creative time that competes with the never-ending to-do lists. So when Memorial Day rolled around, I decided I’d do something I needed, something that would reignite my creative spark. Because there’s one thing I am sure of—the next four or forever years are going to be full of chaos, and if I want to be able to rise to the occasion, I can’t have my nose down, buried in the minutia of running a business.

So rather than spending the day endlessly scrolling, ticking off house projects, shopping the sales, or fighting for a parking spot at crowded trailheads, I designed a mini-retreat:

• A proper sleep-in till 7 am, starfishing as the sun warmed the room

• Morning reading not of the news, but the newsletters of the creatives, thought leaders, and business owners I admire and that I’ve bookmarked

• Organizing the ah-ha moments that specifically relate to the projects I want to move forward in Notion so I can easily find them, unlike the black hole of Notes

• Cooking my favorite breakfast, chilaquiles

• A one-hour gravel ride that I can access out the front door, because being outside frees my mind

• Returning to my notes in Notion for an afternoon of scheming, digging deeper and researching more, and documenting the steps I need to take to move my projects forward

Take your time back

By 4 PM that Monday, I had more clarity on my creative projects than I'd gained in the previous month of "regular" workdays. I felt like I had reigned in my shiny object syndrome and shook the weight of the world for a moment. Not because I worked harder, but because I worked without the constant interruption of everyone else's urgency. The chilaquiles and bike ride didn't hurt either.

Your mini-retreat doesn't need to look like mine. Maybe yours involves sketching at a coffee shop, reorganizing your creative workspace, or finally tackling that idea that's been living in your head for months. The magic isn't in the specific activities—it's in protecting time for the work that matters to you, not just the work that pays the bills.

You don’t have to wait for the next proper holiday to create your own mini-retreat—it could be this weekend! You can spend it scrolling your phone and feeling vaguely guilty about all the things you're not doing, or you can design a few intentional hours that reconnect you with why you started your business or passion project. Your creative projects are waiting for you to show up. They don't need a perfect plan or unlimited time—they just need you to choose them over the hamster wheel, even if it's just for one quiet Monday morning.

xxoo,

Jen

UPCOMING WAYS TO CONNECT —>

📖 ☀️ SUMMER BOOK CLUB!

In previous newsletters, I’ve mentioned launching a summer book club. There are three books on my reading list, none of them fiction, and all of them provocative and chosen because I believe they will have a positive impact on my day-to-day and on the way I see the world. Exploring all of this with other humans would be more fun, with greater learning, and it will hold me accountable to actually read the books. No one has time for more Zoom calls in the summer, so we’re going to do it asynchronously through the Substack Chat so that you can chime in whenever and wherever.

The invite will go out to all paid subscribers, and it’s super easy to join:

• Procure the books

  • The Art of Making Memories, by Meik Wiking

  • Permission, by Elisa Altman

  • The Portable Feminist Reader, by Roxane Gay

• Read some or all of the books, no judgement (schedule below)

• Access the chat through the Substack app

  • You’ll receive an email to join the chat, and I’ll start one chat for each book

• Share whatever you want, when you want, from the comfort of your couch, pool floatie, or rock

  • It’s not a live chat and I’ll be popping in and out for about a week until I take a pause to move on to the next book

📅 Schedule:

• June 30th - July 7th: Discuss The Art of Making Memories

• August 3rd - August 11th: Discuss Permission

• September 1st - September 8th: Discuss The Portable Feminist Reader

I understand most people like to read fiction during the summer, so if that’s your jam, there are a million book clubs for that. The books I have chosen are written by authors whom I admire, and they are what I would want to read on my mini-retreats to fuel my creativity and keep me motivated and excited about what I’m working on and towards.

📚 The books:

The Art of Making Memories, by Meik Wiking. What’s the actual secret to happiness? Great memories! Meik Wiking—happiness researcher and New York Times bestselling author of The Little Book of Hygge and The Little Book of Lykke—shows us how to create memories that make life sweet in this charming book. I’m all about making the most of the summer, so we’ll start with this book because we all could use a little more happiness in our lives. The Art of Making Memories examines how mental images are made, stored, and recalled in our brains, as well as the “art of letting go”—why we tend to forget certain moments to make room for deeper, more meaningful ones.

Permission, by Elisa Altman: Who am I to tell my story? And how can we grant ourselves permission to write the stories we're compelled to tell when we've been told we shouldn't? This book speaks to what is at the heart of this newsletter and really what I do, and I know I’m not alone. Fun fact, Elisa and I shared the TEDx stage in Reno many, many years ago. She’s an award-winning author of the memoirs Motherland, Treyf, and Poor Man's Feast, and the highly acclaimed Substack of the same name.

The Portable Feminist Reader, by Roxane Gay: A dynamic and strikingly relevant look at a feminist canon as expansive rather than definitive. I was fortunate enough to see Roxane Gay speak in San Francisco a few years ago, and she is an absolute BOSS. She’s the author of multiple books and memoirs, including The New York Times best-selling essay collection Bad Feminist and the short story collection Difficult Women. She also publishes The Audacious Roundup, full of the most noteworth and dumbest shit that she comes across each week, all with her own witty critique. While feminist canon may seem like a heavy read over the summer, I think it’s perfect because you don’t have to read it start to finish. So if you’re like me and you open up a book right before going to bed, and three pages in you fall asleep, then this might be the book for you because you can actually get through a section and have a meaningful discussion with us in our chat without having to read the whole thing. A no-pressure way to end the summer book club!

TBH, I’m a bit nervous to start this book club because when you start something new in a format that people aren’t necessarily accustomed to, you run the risk of it flopping. So if it’s just me and you, please don’t be embarrassed for me. But I’m really excited to get into these books and have a summer reading list that feels manageable and uplifting.

❓Questions: Email me or send me a DM!

I WANT TO HEAR FROM YOU —>

How are you doing? What are you most concerned about? What brings you joy? What are you looking forward to? How are you managing?

Thanks for reading! All typos are intentional to make sure you’re paying attention.