I Flew My Team First Class to a Retreat and Here’s What Happened

Jenna Kutcher 

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December 2, 2019



Writing the title for this episode kid of felt like writing a gossip column for a magazine. “I flew my team first class to a retreat and here’s what happened…” Before you think this is the setting of some new MTV reality show, let me explain why I decided to fly my team first class to Arizona for a trip that became part dreaming session, part spa retreat, and part girls trip that absolutely changed how we’ll all work together moving forward.

For this episode recapping our team retreat, it only seems right to have my team lead you through what it was like, what we did, how it was structured, and what they got out of it. So press play to hear from the voices who manage this show, answer your emails, write our content, and contribute to this business each day with their own superpowers.

By the end of it, I hope you take away a few ideas for connecting with your remote team and why a retreat just might be the thing you need to get to the next level.

Why I Planned the Retreat

Earlier this year, I affiliated for a launch and I set a big, seven-figure goal for that launch. That big goal was a direct reflection of what I knew my team could pull off, but I knew the work that each member would need to do to get us there. So, I promised that if we hit the goal, we’d take off on a three day trip somewhere warm where the drinks were fruity and the rooms had robes.

Here’s the thing… My entire team is remote which means some of these women had never met each other in person. Like we work together all year long with our emails pinging and our Slack messages knocking, but other than one quick Zoom call each week we never get to see each other’s faces. And we certainly don’t get to float around on giant inflatable Champagne bottles sipping pina coladas while dreaming up our next big thing.

So we hit the goal. Crushed it actually, and I stuck to my promise. A travel agent booked us all on first class flights to Scottsdale, Arizona and we all made our separate journeys to be together, all in one place, for the first time ever.

I wanted to thank my team for their work on that launch, and so many other projects, but I also wanted an opportunity for us all to really get to know each other and connect in a way that’s really only possible in-person.

What We Did

As my team explains in this episode, the retreat was loosely structured. And by that I mean we had schedule spa appointments, dinner reservations, and that’s about it for structure. The remainder of time was free-form relaxation and dreaming.

The first day was meant for getting settled in and for many of us, meeting for the first time in person. We ordered our first round of drinks by the pool and actually had to stop ourselves from diving straight into business talk.

I asked my team to consider a few questions before arriving in Arizona so that when we did get into a more focused dreaming session, everyone was ready with their ideas. These questions included: What is one process or system that we could refine or simplify? What is one thing you’ve always wanted to try? What is one way your area could move the needle more? What is something you are passionate about that could be applied to a new idea? What is one thing that just isn’t working that you wish we had a solution for?

We went from jumping in the pool to deep discussions about email lists, to ordering a round of pina coladas and chatting about upcoming guests for the podcast. These were the conversations we’d all been dying to have beyond the computer screen, accompanied by some delicious drinks and gorgeous weather.

Key Takeaways

My team summarized their key takeaways so beautifully in this episode, so I hope you’ll press play and hear it first hand from these women.

The themes that came up the most when discussing their key takeaways was a new sense of “team”, a deeper understanding of our shared vision, a closeness that will elevate our teamwork, and a renewed energy amongst all of us.

I love this quote from our email copywriter, Brooklyn: “Sometimes freelance or contract or remote work can be very isolating. But if I’m honest with myself, I’ve been in a place filled with people, like I’ve had a job where I’ve been surrounded by my coworkers and I still felt lonely. I think the key is that we have to be known. It’s not all work. We’re not all work, and we had a chance to come together and not be all work,” she continued, “I went from feeling like I’m not just on a team, but we are THE team… It’s important to realize that you are IT. You’re not just on a team.”

We’re Doing It Again

Before we’d even packed our suitcases, we had a plan in place to get back together in early 2020. Same place, but with a new plan for our time together. I can’t wait to see these women again and work together, like actually in the same place, on a new project. Press play on the episode above to hear my team’s reflections on this retreat.



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  1. Sara says:

    What an amazing time to connect in real life at a great hotel! Love this idea!


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A small town Minnesota photographer, podcaster, educator and puppy rescuer, my happiest days are spent behind my computer screen sharing my secrets with the world. I'm glad you're here.

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life). 

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