Our First OW Offsite

Last week, my business partner and I did our first company offsite! We have been in business 5 years this November (crazy to say that!) and it was the second time we’ve been away together and the first time we’ve been away with the sole purpose of planning and strategizing the year ahead. At the end of last year, I knew that this time would be well spent since we had a great 2023 and I wanted to make sure 2024 was even better.

I had a lot of questions about what we actually did so thought I’d break it down for you here! As two moms with multiple businesses, we needed to make sure the 24 hours was packed to the brim with strategizing time, team bonding and thinking time with tangible takeaways for us to execute on when the retreat was over.

  • We arrived to the cabin Wednesday afternoon, got unpacked, did a little email work (since we were planning to be fully offline the following day).

  • Wednesday night we went out for dinner so we could spend time connecting, talking about our personal lives (we rarely get a chance to do this!)

  • We went to bed early so we could get started early the next morning.

  • We met in the kitchen around 7, had coffee and chatted about life and the day ahead.

  • At 8AM (aka when the sun finally rose) we ventured out for a walk without our phones. The best way to start a creative “deep work” day IMO!

  • At 9AM, our phones and email went on DND and OOO so we could really focus on each other and what we were trying to accomplish.

  • We wanted to create time for big sky thinking, asking and answering the questions that we rarely have time to, questions that are more than just a to do list item or email to respond to.

  • Our first prompt was the one I wrote about last week- we each answered the following question in our journal (both personally and professionally) and then shared it with eachother - it’s amazing how much overlap we had!

    • Imagine it’s one year from today, and when you’re looking back over the past year, you realize it was the best year of your life. What does that look like to you?

  • We added these journal entries to a google doc with a reminder to review them in Jan 2025 (so fun!) at our next annual offsite

  • Then, we talked about where we want OW to be in 5 years. While we don’t know exactly what’s going to happen, we have a general idea(s) of where we want to be from a lifestyle and business perspective. We wrote that down.

  • We then ordered in a healthy lunch and took a break (we took about 10 min breaks every hour and a longer one for lunch)

  • Our afternoon was more about strategy and execution.

    • What are the top 3 things we are going to focus on this year to help us achieve our goals?

    • What does our revenue need to be each month to achieve our overarching goals?

    • What tactics and strategies can we employ to get there?

  • We then put all of these ideas and plans onto our big calendar using color coded post-it notes so that we could look at things holistically. We included our personal travel plans as well as any potential collaborations or events on the horizon. It’s nice to have this on post-it’s as we all know - things change!

  • The calendar was our last activity of the day and as we finished up, we looked at our year from a birds eye view. We both felt invigorated, excited, and clear on our plan to achieve our goals.

  • To ensure we stick to our plan, I added everything into our Google cal and updated our “Projects in Progress” Google doc that we work off of daily. I also wrote out a big “2024 Strategy” doc and pinned it to the top of our “Projects in Progress” doc so we can remember what we are working towards.

My hot take: It’s been so long since we spoke in full sentences or fully formed ideas or thought about the future beyond the coming week. This time has inspired me to slow down to speed up so we can spend time expanding and creating our dream future for ourselves and our brand. You really do have to make the conscious effort to take this time but I couldn’t recommend it enough!

Happy to answer any questions if you have them!! x