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The Leap: On designing a freelance lifestyle with Jake Kahana of Caveday

Welcome to The Leap! For this IG Live series, Wethos CEO Rachel Renock sits down with entrepreneurs who took the leap toward working independently or starting their own project.

In this episode, Rachel sat down with designer and entrepreneur, Jake Kahana. Jake has had a long and fruitful career freelancing for big brands like WeWork and Johnson & Johnson, to name a few. He is also the co-founder of Caveday, which is reshaping the way the world works through guided group focus sessions. Additionally, Jake teaches workshops on emotional intelligence for corporate teams and is the creator and curator of a monthly Email Refrigerator

Watch the full interview here or read below to learn more about how Jake’s freelance career has evolved over the years, the origin and mission of Caveday, and what he envisions for the future of freelancing. 

Note: The following interview has been edited for clarity and length.

RR: Can you tell us a little bit more about your journey and how it has evolved over time?

JK: I’ve always been a creative person. I went to college thinking I was going to work at Pixar, so I studied film and animation. Then I got there and was like, oh, animation is really tedious, I’m not gonna do that. So I explored a little bit and found my way into the world of advertising. Right out of college, I was an intern at an ad agency and I did that for about seven or eight years before taking a year off to freelance and travel. I thought, “I’m done with advertising, I’m going to learn how to code.” Then I moved to New York and came back to advertising in the social impact space. 

I did that for a bit, then I got fired which led me to freelance. While I was freelancing, I started a side project called Caveday, which was events that we would run to bring people together to work in a special way. For the last six years, since Caveday’s been around, I’ve had my freelance business while building Caveday. But we just celebrated a year this month of Caveday being my full-time thing. Before, Caveday was like 10-20% of my income and now Caveday is like 90% of my income. 

RR: I know you’ve been a freelancer for a long time. And I think people wonder if freelance can be a “real” career. When did you decide that you wanted to make freelancing your career and what does that mean to you in this context?

JK: To me, “career” is sort of loaded. Like making that my career, feels like it comes with so much commitment. I’m probably gonna work for the next 40-plus years of my life. I don’t wanna say that I’m gonna freelance for the rest of my career. What I will say is this is the right direction for me now.

My understanding of careers — and at Caveday, we talk a lot about career planning — is that they’re non-linear. So much of [your] career is about, I wanted to try this and then I wanted to learn this other thing, and then I wanted to do this thing. 

And I feel like talking about freelance as your career choice, again, to me, comes with a lot of commitment and that feels really heavy. That’s a big decision instead of [saying], you know what, I’m not interested in working for someone else. I’m interested in exploring and working for myself and seeing what kind of lifestyle I can design for myself.

I think freelance as a direction, as a transition, or as a long-term choice, is right per person. For me, it was right to get me to build Caveday. And allows me to supplement my income when Caveday needs it or when I need it. I have a mortgage and two kids now, so freelance is helpful for that. And I’m sure in the next 40 years, whether I have 100% of my income be freelance or not, freelance is now something that I know that I can do, instead of thinking freelance is my career.

RR: When you’re thinking about your different businesses, how have they evolved over time in terms of revenue streams? You mentioned your income breakdown has shifted over the last year. How do you manage all of that and how do you think about revenue?

JK: My understanding of freelance was really messed up in the beginning. What I ended up doing for like the first, maybe two or three years was not freelance. I was a contractor and I didn’t even understand the difference. But what ended up happening is I started to understand that what I was aiming for was a freelance lifestyle.

A freelance lifestyle is like, I’m in control of my time, I’m in control of when I work and where I work and, and how I work. Contract work was just like, I have a job and I’m working as a part-time employee.

Freelancing is running a business. I started [realizing] that more and more. There’s a lot of sales involved. Like I have to pitch myself — this is my offering, this is what it costs, this is the scope of work, I’m writing my own contracts.

And it’s interesting because I’ve got like five or six different revenue streams. And even within those revenue streams, like with freelancing, I have three or four clients at a time. So even if I lost a client, I’m fine. If I have a slow month, I may have to do a little more business development or something. But it helped me flip the script [to see] that a full-time job can sometimes be less stable.

RR: I want to switch gears a little and talk about Caveday. Can you tell us more about how it came to be and how it’s evolved over time?

JK: Caveday started as this little side project — it was not meant to be a business. My two co-founders and I met in the summer of 2016 and we said, hey, we’re all working on side projects on the weekend, so let’s gather everyone and create a special kind of event. We were all interested in community and branding and business, so we said, I bet we can gather everyone in a way that’s more focused than a Starbucks, more fun than a library, and [offers] more community and gathering than a coworking space.

We had a co-working space donated and we said, all right, let’s call it a cave day. Like, you know, we’re gonna go into the cave for the day. It was a full day, eight and a half hours. We learned about things like body doubling and how to take breaks, how long our brain can focus before it needs a break and those kinds of things.

We designed this event and this brand as like a one-off event and we sold tickets. It was January of 2017, and we said let’s kick off the year with some focus. And we sold out. 

It really struck a nerve and quickly changed from like this [one-time] event to, we have to do this more. We were written up in Fast Company in like our second or third month as a new way of working. Companies started to reach out, and it sort of grew and evolved. 

It’s been a very iterative process. For the first year and a half, once a month we would run these all-day events. And then we started doing half days during the week. It went from in person and then we played with remote in 2018 way before the pandemic. And then when the pandemic hit, we shifted entirely remote. We started changing the price structure so that people from around the world could join. Then two years into the business, we turned it into a membership. And then we slowly added sessions. I think at the beginning of the pandemic, we had 12 sessions and now we have over 120.

People come every day to get their work done and change the way they work. Rather than think about ourselves as a productivity company, that’s like “get your shit done,” we think about it as improving your relationship to work. It’s about integrating breaks and self care, setting better boundaries, and learning how to scope your work better so that at the end of the day, you’re not like, I didn’t get enough work done so I gotta keep working. Instead, you’re like, I scoped properly, I finished my work, I can put it aside because I did enough.

RR: The pandemic generally reshaped a lot of the ways we, specifically Americans, view our lives and our work and what takes priority. How have you seen that come to life through Caveday?

JK: I think the biggest thing that struck a nerve for a lot of people — and I’m speaking very generally here — is that companies don’t care about you.

A lot of the research and reading that I’m doing is around how back in the seventies, with the introduction of consultants who work with the C-suite, [the goal was] how do we make your company more efficient?

A lot of the instruction was like, you can cut the fat. Companies started worrying about the bottom line and stock prices and focused less on people. People started getting laid off because the business performed poorly. 

Fast forward 50 years to 2020, so many people are like, I can’t believe I have to be a parent and show up at work. I can’t believe there’s no help. There’s nobody supporting what I need. There’s no mental health support. There’s no recognition of like, we’re all struggling and you still want us to write some headlines for Facebook ads that are going to people who are also struggling?

I think the biggest trend is an understanding that nobody’s looking out for me — again, speaking broadly — so I have to look out for myself. I have to find ways to generate revenue or go to my boss to ask for time off or ask for maternity or paternity leave or mental health leave. I have to advocate for myself.

RR: Last question: What do you think freelance will look like the next 10 years? What do you think will change? And what do you think will not change?

JK: I think everyone will dabble in freelance by the end of their career. This next generation of people coming out of school will likely dabble in freelance in some way over their career.

What I’d like to see in the future is the idea of a shared collective. Going away from what we talked about earlier where the company doesn’t care for me, so I gotta take care of myself. But now sort of refining that sense of, I have a group that will take care of me within the freelance world.

I love this vision of freelancers bonding together and unionizing and sharing information and helping each other out and creating collectives [because] we work better together.


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