Jeremy Redleaf on CaveDay, Deep Work, and Disconnecting

Jeremy Redleaf on CaveDay, Deep Work, and Disconnecting

Jeremy Redleaf on CaveDay, Deep Work, and Disconnecting

At Freedom, we love our users – not just because they use our product, but because they’re cool – cool people working on cool stuff. Academy Award-nominated screenwriters, best-selling authors, editors, designers, star TV actors and writers, academic researchers, explorers, and entrepreneurs – the Freedom community is packed with curious, creative, and efficient go-getters. We love to share their stories and advice, because how better to learn about productivity than from the productive?

Meet Jeremy Redleaf.

Jeremy is a Daytime Emmy Award-winning performer, filmmaker, entrepreneur, and all round multi-hyphenate. He creates original content through all platforms via his shingle, Brackets Creative, the mad science lab for all his projects. One such project is his feature film 3rd Street Blackout that follows a technology-obsessed couple’s relationship through a blackout caused by Hurricane Sandy. Jeremy is also the co-founder of CAVEDAY, a company dedicated to improving our relationship with work through events, products, and services that focus on “deep work,” disconnecting from your devices, and co-working accountability. CAVEDAY currently holds monthly events in NY and LA, and soon many others!

With all of that under his belt, we figured we’d step out of the way and let him tell you how he manages to find the focus, motivation, and time to do the work that matters and add so many hyphens to his title.

As someone who has wears many hats – performer, filmmaker, and entrepreneur – how did you get to where you are today?

In high school, I worked at OfficeMax and I got offered a little bit part on Saturday Night LIve. I asked my boss if I could take off and he fired me for making up such a “Ridiculous lie.” When he saw the show, he tried to re-hire me, but I hung up my khaki pants and never looked back. Since then, it’s been my mission to never have a day job. I got to be a hyphen collector by being interested in a lot of things and having a strong desire to always control my time.


What started it all for you – at what point did you realize that tech/sites/apps were taking a toll on your productivity and time?

On some level, I knew I had an unhealthy relationship with my technology. I’m totally that guy who has had people be like “Dude, you’re always on your phone.” I’m also that guy who used to say “Uh, no I’m not.” I made a feature film called 3rd Street Blackout about a couple who has to face each other without their devices in the blackout of Hurricane Sandy. In making the movie, I read a lot of research and began to contemplate how I might be using my devices to hide and fulfill emotional needs. And then one day I woke up and looked at my calendar. It was all booked up with stimulating things, but it was so scattered. I didn’t have any time to sink into deep work. I started lamenting “How does anyone get anything done?”


In making the movie, I read a lot of research and began to contemplate how I might be using my devices to hide and fulfill emotional needs.


In January 2017, you helped found + run the first CAVEDAY in NYC – can you tell us a little more about what CAVEDAY is about and how you got involved?

Sure! So, after that, I was in my therapist’s office and he said “What would it take to get stuff done?” And I said “I feel like I need to take a cave day and go off the grid and only work on one thing.” And he was like “Great! So when are you doing that?”

I started taking solo cave days and not only did I get more done than ever before, I felt accomplished enough to take the next day off. But it was taxing and lonely. I collaborated with Molly Sonsteng (An event producer) and Jake Kahana (A creative director) to come up with a format for a facilitated day of group work.  People come, we take their phones, feed them, manage their energy and hold them accountable. It turns out there’s even more potential energy to tap into in a group setting. CAVEDAY currently happens monthly in NY & LA and in more cities and countries soon!


When you’re not participating in a CAVEDAY, how do you stay committed to practicing deep work every day?

Is this where I tell you how much I love Freedom? Seriously, I use it every day.

My lizard brain can’t be trusted. But I also try to get people to cave sprints together as much as possible. When I’m working with other people, all my resistance melts away.

Cave Day NYC
Photos by: Phillip Van Nostrand

As a multi-hyphenate, how do you prioritize what gets your time and attention?

It’s a daily struggle! Deadlines certainly play a big role in prioritization. Beyond that, I come up with an overarching goal for the year and try to anchor my bandwidth towards it. I see email as “playing defense,” so I try to start my day offensively before I open up that can of worms.


What resources or tools do you use daily and have found most beneficial to your productivity and working process?

Is this where I tell you how much I love Freedom again? I love RescueTime for tracking how much time I spend in each window, Inbox by Google for general inbox management, Mixmax for its power emailing tools, Fancy Hands for virtual tasks, Trello for task management, Dropbox for project files and Google Drive for universal collaboration. Whew!


What project are you currently most excited about? 

I’m shooting a digital anthology series that looks at people’s relationship to clothing as a way into their emotional life. That’ll be out in a few months.


What are your biggest distractors and what motivates you to combat them?

One of the things I talk about at CAVEDAY is how “distractors” are just the tip of the iceberg. Underneath them are emotional needs. The things that drive my distractions are: a desire for connection and stimulation, caring about status, and a fear of not being good enough. I spend a lot of energy building myself up. (We’ve turned some of the things we tell ourselves in the cave into posters.)

What motivates me to combat distractors is knowing that my most meaningful work REQUIRES that I do so. And when I do my best work, I live a healthier life and I’m so much better and connecting, taking in information, not caring about status and feeling inherently valuable.


How do you find a balance between being connected and overwhelmed?

Since starting CAVEDAY, I’ve gotten a lot firmer with my boundaries. I know that I need to be disconnected for periods of time and that it has to be a hard line. I can’t do “A little disconnected.” The body always knows and I try to listen. A lot of us cut off our connection to it when we work. Just keeping an open jaw and feeling your feet and belly can give you information about where you’re at.


What do you do outside of your work routine that helps you stay productive?

Let’s see… I warm up my whole body before doing work, I exercise at least three times a week, I try not to compromise getting enough sleep. I cap how much I can drink during the week. I ingest a ton of water (Studies show that even being 2% dehydrated can affect cognition). I’m in an accountability group. We meet once a month to set goals and positive consequences (Things that hurt but are ultimately valuable). I’m also in a men’s group that meets once a week. We challenge each other to be the best version of ourselves. I do a lot of things that take time away from work and the way I justify them is by valuing self-care and believing that they make my work (and life) better.


To learn more about Jeremey, or his work, visit his site at or follow him on Twitter @theleafisred

To learn more or get involved with CAVEDAY, visit the site