Caveday Wants to Help You Stop Procrastinating

Caveday Wants to Help You Stop Procrastinating

We’re all guilty of it. Letting projects sit till the very last minute. Ignoring your inbox till it hits triple digits. Dragging your feet on those engagement/wedding/baby shower/sweet 16 invites. Sometimes the toughest thing to do is to just do the thing you’ve been putting off.

Enter Caveday, a day-long event that starts with turning in your cellphone and ends with a feeling of satisfaction of having actually done that thing you’ve been meaning to do.

We asked Caveday co-founders and facilitators, Molly Sonsteng, Jake Kahana and Jeremy Redleaf, to tell us about why they started the company, tips they use to stop procrastinating and how we can all learn to work better.


Where did the idea for Caveday come from?

Jeremy Redleaf: The three of us have been friends for a little over a year and bonded over productivity, entrepreneurship, and time consciousness. At one gathering, Jeremy mentioned that in order to finish his latest screenplay, he went off the grid for a day and “Into the cave.” We were curious if there was a way to create a space for a group of people to have that cave-like productivity that never seems to happen at home or in the office. As an experiment, we hosted the inaugural Caveday in January and were floored by the response.

How has it evolved since the first event?

Jake Kahana: We’re constantly testing and learning. We’ve played with lots of different hypotheses and variables including adding group interactions and reflections, ways to keep energy up, changing the timing of each sprint and break. Everyone works differently and we’re constantly asking ourselves how we can serve the full spectrum of experiences. I think we’ve got a pretty good grasp on what makes a great event, but we continue to tweak and learn as we grow.


What’s been some of the most surprising things you’ve seen people work on at a Caveday event?

Molly Sonsteng: Besides the expected writers, coders, entrepreneurs, and designers? We’ve seen people clear their inbox and write wedding thank you notes. Magicians working on their routines and stand up comedians writing out jokes to perfect their set. Anyone who’s passionate about their work needs a space to dive deep into it. We’re happy to provide that, whether they’re using Google Docs or pulling a rabbit out of a hat. (You know, as long as the rabbit is quiet.)

As the organizers and founders, what do you do to prepare for the event?

JK: Beyond the normal spreadsheet ninja-ry and customer service that any event requires, we’ve got some private rituals and exercises we run to make sure we’re in the right place energetically to facilitate deep work.


Do you create Caveday’s for yourselves?

JR: Absolutely! We try and run weekly mini-caves for ourselves and the community here in NYC. They’re small gatherings of 2-12 people and they’re a fun way to keep the spirit of Caveday alive and practice getting to a flow state in our work. We’re putting together a toolkit to help people host mini-caves around the world. (If you’re interested, get in touch!) From time to time, the three of us will get together and run a caveday to work on Caveday. It’s excruciatingly meta.

What’s been the biggest learning from running these events?

MS: Ultimately, that no one has taught us how to work. In school we’re assigned homework and are just expected to know how to finish the work or how to study. When we get a job we’re expected to sit at a desk for 8+ hours and be productive. But with meetings, social media, email, and a lifetime of developing bad habits, we need someone to teach us how to work. We need accountability and permission to not check our phone and email. We need guidelines and coaching to relearn how to work. We’ve discovered that you can accomplish more in a day than some people do in a week or a month. And if that’s the case, then people shouldn’t have to bring work home with them and let work bleed into their nights and weekends. If we improve the quality of our work, we improve the quality of our lives. (Which just happens to be our mission statement.)


What’s the single most popular blocker you’ve heard from participants?

MS: You might think it’s phone or social media. But we’ve observed that it’s mostly email. We’ve learned the average email goes unread for only 6 SECONDS! Having alerts and keeping email open all day ends up pulling people from their real work into reading and responding to email. It’s important but it’s such a time suck. No one has become successful just on their email writing abilities. It’s finding flow and depth in your work where success happens. Emails have to get read and responded, but people can’t seem to help to check their inbox all the time.

What’s the one thing we can all do to feel a bit more productive in our day-to-day?

JK: In a word, monotask. Focus on just doing one thing at a time. Do it until it’s done. If or when you get stuck, just sit with the problem. Write about the problem. Draw out the problem. But don’t move on to something else. One thing at a time. Don’t check email while you’re on the phone. Don’t load up your email while you’re bored or stuck. Don’t eat lunch at your desk. Which, by the way, is probably the second thing we’d recommend. Taking smart breaks is an incredibly important part of energy management. And if you can take 20-30 minutes to eat lunch in a new location, let your mind rest and re-energize, you’ll get back to your work more productively.

What’s next?

We’re launching CAVEDAY in DC and LA in September. If we should come to your city next, let us know! And we’re still making time for our own projects. Jake runs a community called You’re Better Than Brunch, Jeremy makes films and Molly runs secret games in public and sells very tiny smores.

Ready to finish that unfinished project? Get tickets to the next Caveday here.

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