Caveday’s Co-Founder Discusses Productivity And Work Habits During The COVID-19 Outbreak

Jake Kahana, along with co-founders Jeremy Redleaf and Molly Sonsteng, founded Caveday, a community that gathers around the idea of focus where they teach the principles of better work habits. Labs spoke with Jake to learn about his experiences by turning his program completely virtual.

WeWork Labs: Can you tell us what Caveday is?

Jake: Caveday is a community that gathers around the idea of focus, where we teach the principles of better work habits. From the time you were in kindergarten to where you’re at right now, no one really taught us how to focus, how to remove distractions, how to use our natural energy rhythms to improve the quality of our work. We help people create habits around organizing their tasks and to do lists, helping them schedule their days, and help them manage distractions and manage interruptions so they can get better quality of work done. Especially with remote work and also as entrepreneurs, the work can go on forever and there’s always more work to do. We believe that by improving our habits and improving the quality of work, we can improve the quality of our life.

WeWork Labs: What are some research that Caveday has based its principles on?

Jake: We are strongly influenced by Cal Newport who wrote about Deep Work, Mihalyi Chiksentmihaly who wrote about Flow, and Daniel Pink who wrote the book When, which is about taking breaks and energy. We also talk a lot about research that’s done at University of Chicago around use of cell phones. We also adapted to Sophie Leroy’s idea about Attention Residue, which is the opposite of multitasking, so we focus on mono tasking so you can get into that state of flow and keep your focus on that one thing without leaving any other energy of focus behind elsewhere.

WeWork Labs: Your team has managed to put schedule 13 Cavedays every week and have adapted to the whole world going virtual and the world working remotely. How has this experience been for you?

Jake: Our caves are normally three and a half hour deep focus sessions facilitated by our cave guides. We break down the day into deep focus work sprints of about 40-45 minutes with 3-5 minutes of energizing breaks in between. We started running remote sessions about two years ago to help some extra people who are in random time zones or couldn’t normally join a physical cave. That experience came in handy when we had to move everything remote in March because the world has gone remote. We are here to support anyone working from home in getting things done and learning how to focus.

WeWork Labs: What other learnings can you share with us regarding your experience with going fully virtual with your program?

Jake: We’re learning a lot about how each of us are managing working from home. There’s an increase in burnout habits because your work bleeds into your nights and your weekends and other areas of your house, not just your desk. Loneliness is also another challenge that we address at Caveday. We make sure that there are moments at every cave when you can share how you’re feeling and connect with somebody so you don’t feel like you have to be working 100% of the time. We help people structure their work day so that their comfy beds, phone notifications, and pets don’t become a constant distraction throughout the day.

WeWork Labs: Any last words for our Labs members who are hesitant to join or try out Caveday?

Jake: We’re giving away a free month and we’re not asking for credit cards. We just want to be super helpful and provide what people want in time of need. We’re here to be helpful and to offer something to the world that most people can benefit from right now.

More about Jake: Jake is a creative director, multimedia artist, and educator who spent the first decade of his career making ad campaigns you probably remember. He is a founding US Faculty member with The School of Life. Recent projects include: BettVR with Age, 45Villians, and You’re Better Than Brunch. He's proud to have his work in the permanent collection at both MoMA and his parents' fridge.

Any questions or you want to connect with Jake directly, please visit the Mentor Directory on the Member Portal or ask your Labs Manager for assistance.

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