Our past retreats were located in Mexico, Canada, and Indianapolis. Now, we can finally check Portland Oregon off our list. As a native Oregonian myself, Portland has always had a special place in my heart, and I was excited to show it off. The team started planning around 4 months in advance, starting with hotels and flights and after those details were set, we began researching and diving into the details. We wanted to find a good balance of food, fun, and outdoor time. I thought I had a pretty good sense of everything that Portland had to offer, but I learned a TON along the way.

We wanted to pick a time of the year that most people could make it. Juggling schedules can be a demanding process, but we were happy that the majority of the team were able to make it. We planned the trip to coincide with the World Domination Summit, a 4-day conference geared towards goal-setting, inspiration, and creativity. The dates were set, June 26th-July 5th. It was an added bonus that the team would be together for the 4th of July. For a few of the team members, it was their first time in the US, so you can imagine the fun we had showing them the ropes on our country's big day!

We wanted to start the week off strong, so we planned most of our work-related meetings right up front. The idea was to front-load "the important stuff" so if last minute changes happened, we would have time to adjust and shift the schedule around. The team arrived on Wednesday and our biggest meeting days were the following two days. We set up shop in the downtown location of WeWork, which was the perfect accommodation for our team—complete with cold brew on tap and a ton of other amenities.

We scheduled the first few workdays from 10am to 6pm, with meetings sprinkled throughout. We even sent out an agenda beforehand to make it easier to plan ahead, squeeze in leisure time, and run errands if needed. During the week, we kept most evenings open aside from our company dinners and team building events.

After a day of meetings on Thursday, our first dinner together was at Andina, a Peruvian restaurant in The Pearl. Not only was this the first meal we shared together as a team, but for some this was the first time meeting face-to-face. We booked a private room in the bottom floor in a cozy little wine cellar style room. It had the perfect feel to it, big enough to accommodate our group, but the room was cozy and we were able to talk to everyone and enjoy catching up. I'm pretty sure we ended up ordering one of everything—we let our server pick the restaurant's "can't miss" items. It was such a delicious meal and I highly recommend if you're looking for accommodations for a small group.

We wanted to do something less formal and intimate, so after a long workday on Friday, the team ventured across the river to my house where we enjoyed a BBQ dinner together in the backyard. It was the perfect way to end the work week and helped pave the way for a weekend of fun activities and some much needed downtime.

On Sunday we had the pleasure of visiting one of our favorite 1SE users! Heather Champ has been using the app for years. She posts her compilations each month, and they almost exclusively star her gaggle of farm animals. Heather lives just outside of Portland, so we piled in a few cars and made the trip to go visit and see her now infamous baby goats. After learning about each of the goat families, feeding the babies their lunch, and meeting some chickens, we wrapped up our visit with a final group photo. Thanks again, Heather!

We're lucky enough to have users from all over the world and we've been thinking about ways we can include users into our retreats. We loved this opportunity to meet one of our longtime users, so we're hoping to incorporate this again for our next retreat. A 1SE meet-up perhaps?

After our last day of meetings, we had a special farm-to-table dinner out at Kruger's Farm on Sauvie Island. The evening kicked off with a tractor ride out to the marionberry fields. We picked berries and walked through the fields, mesmerized by the rolling hills and farmland. The weather couldn't have been more perfect. It was a cool 70 degrees, almost golden hour, and you could smell the berries ripening in the evening sun.

After we had our fill of berries, we hopped on the tractor and were taken a little way down the road. As we approached, we could see a huge Oak tree and underneath a table set up for us. Along with the chef, bartender, and our server, we were the only ones in sight. It was a nice change of pace from our week of activities. Having that much space all to ourselves felt extra special after spending 5 days working together, planning our company's next steps, and bustling around downtown Portland. The opportunity to get out into the fresh air and wide open spaces made this evening one of my favorite experiences of the trip. At one point, the conversation quieted, and I looked around to see everyone just listening to the sound of the wind in the oak tree. We didn't have to say much, it was a silent agreement that this was exactly what we needed. After a few toasts and even a few happy tears on my part, we settled in for dinner.

After dinner, we played a few rounds of cornhole and took advantage of the golden hour lighting. We were even able to squeeze in some team headshots. All in all, this event was my favorite part of the retreat, a magical evening with fantastic company.

Our next adventure was a wine tasting trip in the heart of the Willamette Valley. We used Back Country Wine Tours and visited 3 wineries total. We didn't have to worry about a thing, and our lovely tour guide Katie drove us across the rolling countryside and even provided a delicious lunch at one of our stops. We spent the day touring around and learning about what makes the Willamette Valley such an abundant and bountiful area for wine.

Our last meeting in Portland was all about brainstorming the next retreat. Each team member got to throw out their own ideas, and it was a fun way to get people excited for the next retreat. In the month that has passed, planning has already begun. We're looking at a few dates in February or March, and right now we've narrowed it down to 4 locations: Japan, Costa Rica, Mexico, and Peru.

These retreats, while valuable for our team morale, are getting bigger and bigger and with that, more complicated to plan. We have 4 people on the planning committee, and after we narrow down our options, we'll have a team vote. Based on those results, our CEO and COO will make the final call on location. Once the location is picked we plan on sending a couple of us on a "recruiting mission" to get a good feel for the area and start ironing out the details.

The New Year always brings a fresh set of challenges. Who knows how big our team will be by then? We'll be taking a few key learnings from this trip and using it to plan our next.

We are so excited for the future of our retreats. Each one is different and poses its own set of challenges. We're excited to see how these voyages develop over the next few years and can't wait to document more of this process along the way.

Huge shoutout to Stephanie Lee and the team at Buffer. They have been a huge inspiration for our planning team—especially their in depth articles on their own retreat planning process. They have quite the undertaking when planning for a team of over 80, so we'll continue to look to them for guidance as we grow.

If you are on a distributed team and have experience with planning company retreats, we'd love to hear from you!

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