Pause and celebrate

Hey Reader,

Five years ago, I did a 44-mile backpacking trip in the Sawtooth Mountains. The trail climbed steep ridges, crossed rivers, and wound through endless valleys.

It was incredible. In the middle of the trip, you could hike 20 miles in any direction and not get to a road. For three full days, we didn’t see a single other person.

I remember stopping high up on one ridge and turning around. Looking back, I could see the peak we'd summited days earlier, the river we'd forded, and the long stretch of forest we'd pushed through with heavy packs. We'd come so far.

I'm not naturally good at celebrating. My default is to hit a milestone and immediately start thinking about what's next. But over the years, my team has helped me learn to pause. This year, Kit hit $50M in annual recurring revenue. We stopped work and celebrated. We gave everyone gift cards and a day off. Without learning that habit, it would've just been another number tipping over.

Everything meaningful happens slowly. You do the same thing consistently over a long period of time, and then one day, you find yourself somewhere that used to seem, so far away. That's true for backpacking trips, and it's true for building a business. The wins can feel nonchalant when they finally arrive. You look at the number and think, "Oh, that tipped over. Look at that."

And in most cases, no one's going to throw you a party. Especially if you're a remote company or working solo, it's easy for milestones to not feel significant at all.

But taking even a little time to celebrate prevents burnout. It reminds you of the impact you're having and distills everything down to the essence of what you do. For me, that's building tools and sharing what I know to help creators reach financial freedom and achieve their dreams. It's so easy to get lost in the daily grind of solving problems and tackling the next thing on the list.

Life comes at you fast. There's always more to do, more problems to solve, more work ahead. But every so often, you need to stop and turn around. Look back at the valley you came through and recognize how far you've come.

Give yourself permission to pause and train yourself to notice the wins. If you're not good at celebrating on your own, let your team or accountability partners help you. Delegate and create systems. Even something as simple as a 30-minute call with your team to acknowledge what you've accomplished can make a difference.

Pause and celebrate. You've earned it.

VIDEO

Behind the scenes of recording 3 podcasts and hosting a creator meetup

Last week, I vlogged for the first time in years.

I spent 48 hours in Austin filming three podcast episodes with Noah Kagan, Chandler Bolt, and Ryan Holiday. We did a live recording of my show in front of an audience, and hosted a creator meet up with some of my favorite people.

Go behind the scenes of the trip—from studio setups and workshop time to gear hauling, creator dinners, and post-show meetup.

Leave a comment on YouTube with your thoughts and let me know what you'd like to see more of in future vlogs.

Watch video »

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How Ryan Holiday Built a Million Dollar Content Empire

Live on stage in Austin, Texas, Ryan Holiday pulls back the curtain on how Daily Stoic grew from an obscure philosophy into a global brand. We talk about building an audience one platform at a time and turning a single idea into a multi-platform content engine.

Ryan also shares why he stopped spending hundreds of thousands on ads and chose to build a content team instead. That shift changed how his work spread and how sustainable his career became.