The Remote Show

Show Notes:

Jesse's links:


Jesse on LinkedIn

Mentioned on the show:

Matt Mullenweg's "5 levels of autonomy"


Tyler Sellhorn (00:02):
Hello everyone. My name is Tyler Sellhorn and welcome to another episode of The Remote Show, where we discuss everything to do with remote work, with the people who know it best. Thanks so much for listening. The Remote Show is brought to you by We Work Remotely, the largest community of remote workers in the world. With over 220,000 unique users per month, We Work Remotely is the most effective way to hire. Today we are pleased to be learning out loud with Jesse Chambers. Jesse is an entrepreneur in the digital media space. He is an accomplished executive with leadership experience at successful startups, as well as some of the largest most well-respected global media brands. In early 2019, he left San Francisco with his wife and dog and working full time from a 27 foot Airstream trailer founded WRKFRCE spelled W R K F R C E rooted in the belief that when we design our careers around our lives and not vice versa, we are more productive and more fulfilled. Jesse, tell us more about WRKFRCE and what you're trying to solve with your team.
Jesse Chambers (00:59):
Hey Tyler, it's a real pleasure to be here. I'm super excited to talk to you today. You kind of said it there reading my bio, but our main goal is really rooted in the belief that when we design our careers around our lives, not vice versa, we are happier. We are more productive. We are more fulfilled. We're better employees for the people who give us that opportunity. And so really what we want to do at WRKFRCE is to allow more businesses and professionals have that experience. The mission at WRKFRCE has changed somewhat, right? I founded the company in early 2019. So we didn't know that 50 million plus people were going to start working remotely all of a sudden. And so the tactics of how we move towards that goal have changed somewhat. Our content now is a little bit more geared towards helping people be more strategic instead of reactive as they have been during the pandemic. But at the end of the day, we feel like remote and flexible work is a path to achieving that goal of having a more well-rounded life experience that's not so dominated by the career.
Tyler Sellhorn (02:01):
Now, I know that you shared some of your learnings from having been a far-flung executive, kind of flying around traveling, leading teams all over the place. And you kind of found yourself becoming a defacto remote worker. Tell us a little bit more about your experience of recognizing that you don't actually have a headquarters as a "digital nomad" as a traveler. Can you go deep on that for us?
Jesse Chambers (02:25):
Well, it's funny because it was something that I realized that I didn't understand was happening. So, I worked for years in the Bay area. My company was based in New York and we had clients and events all across the country, all across the world. And so I was traveling a ton. I was spending at least one week per month in New York. I had two desks at two different offices in San Francisco. And so when I was in the Bay area, which was about half the time, if I needed to be in the office, I was in the office. And if I didn't need to be in the office, nobody was saying where is Jesse. In other words, I was treated like an adult and my company had gone through a couple of mergers.
Jesse Chambers (03:01):
I wasn't sure if my future was at that company or somewhere else. And so I started to look around and as I looked around, I didn't approach it from, I want to go work for X company or Y company. I really thought about what is it about work and the job that I have now that I really want to have in a new career. And when I sat down and thought about that, that was really the moment that I realized I was a remote worker. I was like, wait a minute. This is a sense of freedom and flexibility that I have really come to more than enjoy, but really sort of require professionally.
Jesse Chambers (03:31):
So armed with sort of that view, and this was in like 2017, 2018, armed with that view, I set out and started to try to find companies that work that way or to find information and communities and articles. And there really wasn't much out there. And so I was frustrated for about 30 seconds. And then I said, "Wait a minute, idiot. You know a thing or two about building digital media brands. If you wish that this existed, maybe other people would too." And so that really began the journey of coming up with the concept and ultimately founding and launching WRKFRCE.
Tyler Sellhorn (04:02):
It's so interesting to hear our experiences rhyming of looking for information, looking for the things that are going to help us be successful. It's really, really interesting to hear you say, I want to find this information. I want to know how to do this well, and I'm so grateful for organizations like We Work Remotely, like Get Lab that have been out loud with their learnings, but I'm also grateful to individuals and organizations like yourself and WRKFRCE that are building this version, right. The version that is for right now, right. That is to say, okay, we're drawing, hopefully fingers crossed here to the close of the pandemic season of remote working and that we can become, as you say, more strategic in the ways that we are going about that. I'd like to kind of pull those phases of WRKFRCE and what you guys have been creating into kind of relief. When you think about 2019 versus during the pandemic versus what you guys have on the content calendar for 2022, how do you kind of draw those contrasts or maybe there's similarities that you kind of see as a common thread throughout?
Jesse Chambers (05:11):
Yeah. I mean, you mentioned two great examples between We Work Remotely and Get Lab, and there's a whole range of other companies that have been very successful with remote work, natively, remote companies. And one of the fascinating things is, well, it's not shocking, but they document everything right. And so they were very, it was a very generous time at the beginning of the pandemic when many of those companies sort of opened their playbooks and shared them with the world who may have been struggling with a reactively remote management system.
Jesse Chambers (05:40):
One thing, just as an aside that WRKFRCE did around that time was we saw an opportunity. There was so much great information out there. There were all these playbooks from Get Labs, Index, Trello. I could go on, but they were all really dense. They were all like a minimum of 180 pages. And what we did at WRKFRCE was to write sort of the Cliffs Notes versions of those playbooks because as somebody, a founder myself, I knew that there weren't a lot of CEOs out there who had time to sit down and read 2,000 pages of remote work knowledge. And so we tried to short circuit that.
Jesse Chambers (06:12):
But to answer your question, I think that what we're seeing right now and what we've seen throughout the end of 2020, early 2021, and looking into the future, looking six months, one year, two years, five years into the future is that there's been so much acceleration. You know, people say it all the time. There's not sort of a debate about how much we've, fast-forwarded. It's a question of like, did we jump five years ahead or seven years ahead, or 10 years ahead in the adoption of remote work? I haven't heard an estimate. I just said five years. I don't think I've heard an estimate less than seven years. Right.
Jesse Chambers (06:44):
But, so we've had this change compressed into a very short period of time. And so what's happening now, as we have the ability to go back to work or go back to the office, excuse me, I should say we've been at work this whole time, is what does that mean? And what does it mean for companies? Do companies want to stay fully remote? Do companies want to stay, want to become hybrid? What does it mean to be a hybrid company? And so all of that is now going to be figured out. And I think that the interesting thing that I see is sort of the continuum of flexible options. So it's not all about just a hundred percent remote. Get Lab is great. Not every company can or should be Get Lab.
Jesse Chambers (07:28):
And there is a lot of shades of gray in between there. And one of our jokes is that we spell WRKFRCE with no O's because offices are optional. We don't say offices are evil. We say they're optional. And I think even the folks at Get Lab would argue that there are benefits to getting together in a shared space, a number of times a year. And there are benefits to having an office for some people. But I think that at the end of the day, I hope that I strongly believe that the vast majority of leaders of companies now understand that they do not need to have a co-located space and have their entire staff in an office from 9:00 AM to 5:00 PM, five days a week in order to be successful. And so how we color in the lines around that new realization and acknowledgement of a new reality is going to be really interesting. And honestly, the biggest change that I think we've seen in business in a hundred years.
Tyler Sellhorn (08:25):
Interesting. Wow. I'm just going to pull a few threads out from those comments that you just made. That WRKFRCE is trying to create the Cliff Notes to go from reactively remote to a strategic decision-making framework around the continuum of remote working. I think that's so cool to even hear you pointing back to the ways Get Lab is talking about things and what was popping off in my brain as you spoke was the way that Matt Mullenweg, the CEO of Automattic. He says he wants to see us flip the ratios of travel to homeworking in reverse to the way that you might have imagined how much time you'd be vacationing versus how much time you'd be working, like flip that around and say, "Okay, you can live wherever and work from wherever is best for you and your most productive, but then there's going to be four weeks a year instead of the four weeks of vacation, we're going to have four weeks a year where we are going to get together. And we're going to be co-located.
Tyler Sellhorn (09:28):
When you think about that continuum of remote, right? As a leader, as someone who has been a leader in an office first organization, as a leader who is leading the charge, flying the flag for office is optional kind of organizations, where do you see when you're talking to leaders and when you're thinking about as a leader yourself, how do you see that playing out for your team as we're getting ready to kind of like this fall seems to be the line of demarcation of some folks are going to be coming back into the office more than they were, or there's a few different organizations that I've seen posts on social media, hey, we're back. When you think about that, where's the continuum of remote for you? Or what do you see other people doing?
Jesse Chambers (10:13):
Well, we're a bad example because WRKFRCE is that remote first company, like first and foremost. We're going to eat that dog food all the way. And so for me, and for us, the world is opening up, right? So I'm looking forward to, I don't know if you've heard the term, Tyler, I love it. My wife hit me to it a few months ago. We know the phrase, digital nomad. I hadn't heard the term slow mad. Have you heard that one?
Tyler Sellhorn (10:33):
Yes. Yes. I happen to work with a few slow mads. Yes.
Jesse Chambers (10:35):
Nice. All right. Yeah. So I'm looking forward to getting a little bit more international and being more of a slow mad, but for me, I think you brought up Matt Mullenweg, who's sort of one of the apostles of remote work and has written one of the seminal thought pieces about the five levels of remote autonomy. I'm probably butchering that title, but it's a great article. People should go read it if they haven't already. And I see a couple of things in that continuum, in this space right now, where it's possible to go back to the office, but there is some acceptance. There is some resistance. There is some figuring out what does that mean. So the first thing is that I see a lot of companies and speaking with leaders and speaking with employees at these companies, see a lot of companies who are waving the remote work flag, but are completely stuck in level one of Matt's hierarchy.
Jesse Chambers (11:24):
What they have done is they have taken their exact schedule, their exact modes of work from the office and have moved that onto Zoom and moved that into the virtual space. And if anything, they're actually having more meetings right now because they haven't adopted any sort of asynchronous forms of communication that allow them to share information easily. And so they're very much stuck in this nine to five, eight or nine meetings on Zoom a day. And that's why you see the crazy numbers of burnout that you see in employees reporting. And I think that that then has had, and we're beginning to see the impact of this in real-time right now, this term, the great resignation. There are statistically speaking in the last two to three months, more people resigning from their jobs than we have ever seen in living memory.
Jesse Chambers (12:14):
And there's a couple of factors for that, right? It's not all just that people are resigning from jobs because their companies are not adopting the kind of flexible policies that they hoped they will. The reality is that many people probably stayed in jobs that they would have left during the pandemic for other reasons, for stability or just, it was a crazy time. And let's not rock the boat. But we are seeing this change and rooted in that change, and again, this is data-driven, this is not my theory, is certainly just wanting to move on. It was time to progress and let's go find a new job, but also certainly that companies are not offering the employees the flexibility that they now come to expect and have earned.
Jesse Chambers (12:51):
And the third thing is I think a greater sense on the part of professionals, and I say professionals as broadly as possible, in the U.S. and internationally, that it's not all about the career anymore, that maybe the pandemic has given them the need to find more balance between their careers and their lives and the need to be able to achieve more wellness in their daily life and not just have it all be about the job and the career and the corporate ladder, but that's going to have major, major impacts.
Jesse Chambers (13:21):
And the companies who number one are not offering flexibility to their employees, or number two are stuck in the Matt Mullenweg level one of remote where it's just a proxy, a worst proxy for the office, they're going to have a really, really hard time hiring and retaining talent. And the reality of change is that those who fail to adapt do not succeed. And with this much change compressed, you're going to see a lot of companies struggling. And a lot of companies really succeeding because they have adapted to the change. But it's an incredibly interesting time.
Tyler Sellhorn (13:53):
It is an interesting time. I think one of the things that is going to follow on from us moving up those levels that you described, and you did get the title, correct. I distributed works, five levels of autonomy, and we will be sure to include that article from April 2020 that Matt published. Thank you very much, Matt, for all the ways that you've worked out loud. He's in our feed further back when he talked to Matt Hollingsworth, our previous guest here on The Remote Show. So please check out Matt. He is a great resource.
Tyler Sellhorn (14:24):
But you mentioned that when we have the opportunity to fit our careers around our lives, when we have the opportunity to work in an asynchronous fashion, when we aren't shackled to a geographic area, there are opportunities such as slow mad, or nomadic life. Tell us some more about your trailer, right, and you guys working from the Airstream. I'm really curious to learn more about how you guys came to be RV people. Behind the curtain a little bit, grandfather and father owned a recreational vehicle dealership in Michigan where I grew up. So I'm very curious about your RV life.
Jesse Chambers (15:00):
Well, then you had about a hundred times as much experience in RVs as my wife and I did before we started this. So it is no exaggeration to say that before my wife and I decided to live full-time in an RV, we had not stepped foot in an RV. So that makes us either very brave or very stupid or some combination of the two. But we did rent one for a weekend before we actually made the purchase and went all in. So we weren't flying all the way upline, but it was a little bit of a leap of faith. And so, yeah, I decided to found the company. My wife owned a brick and mortar clothing store. She owned a vintage clothing store in San Francisco. She sold that. I founded what would ultimately become WRKFRCE and for a host of reasons, one of which was the fact that paying for housing in the Bay area and trying to self-finance a startup are not necessarily compatible desires.
Jesse Chambers (15:48):
But another was that we really felt like this was an opportunity for us to do something that we had always dreamed of doing, although we'd never done it, doing something that we've always dreamed of doing, but also for me to really live in the deep end of remote work and to really walk a mile in the shoes of some of the folks who would become the WRKFRCE audience and allow me to speak from a place of experience and authenticity to those folks.
Jesse Chambers (16:11):
And so it's been an amazing experience. I mean we've been living most of the time on the road. We do about eight months in the Airstream and about four months where you see me now. I'm at my family's lake house in upstate New York. I have a little shed that I've turned into an office up here, but it's been great. In the last two years, we've done 39 states. We've put about 30,000 miles on the Airstream and about 55,000 miles on our truck. And it's been a really amazing experience. Now I've been able to live and work in, as I say, in 39 states, but all kinds of places in between there. And we get our data signal from cellular signal. So that's really the only thing that limits us. With the Airstream, we are able to go for about a week without hookups, without water, electricity, all that kind of thing.
Jesse Chambers (16:52):
We have solar. And so pretty much anywhere that we can get a data signal we can live and work, which has been really amazing. I mean, I've gotten to see North America in a depth that I think few others who are not our readers have, but then saying that, one of the things I never really realized was that there are over a million people who live full time and work in an RV. There are tens of million people and you and your family know this, tens of millions of people who own RVs and spend a lot of time. And so it's been a really cool exposure to a culture that we didn't really know about, but now one that we really love.
Tyler Sellhorn (17:28):
Okay. So I'm going to run it down here, shed offices, working from an RV, slow mads, nomads, and the only requirement to be productive is a cellular connection to the internet.
Jesse Chambers (17:42):
Tyler Sellhorn (17:42):
That's the future that you guys are talking about and writing about and sharing about. And I think it is something that is already happening for many and is an opportunity for us to continue to build the future of remote working together. Okay. So you've been talking about and building an audience with people who are considering, or are already inside of building companies that are working remotely. Our audience is made up of lots of remote job seekers and also those that are seeking to hire them. Tell us, what do you hear as you're building this business, this media company, what are you hearing people say is the best way to communicate that, yeah, we are level three and above, as it relates to levels of autonomy, that we are actually doing this thing, not just letting people work sometimes here sometimes there, these many days or really treating people in that professional way that you're describing. What are the ways that we can communicate that as remote first companies or hybrid companies that really do offer flexibility?
Jesse Chambers (18:46):
Yeah. I would say two things. I would actually tack on another answer to a question he didn't ask, Tyler. But so the first is to say, as companies, right, is to be transparent with your employees, right? I think any company who says today that they've got this figured out and that they know what it's going to look like in six months or a year is going to be seen to be clearly lying through their teeth. I think it's fascinating when you see Apple announced their policy and then a large contingent of Apple employees to sign a letter saying, I don't know about that. Or you see Google or some of these other companies retract or amend their policies that they have announced within days of announcing them.
Jesse Chambers (19:26):
Those are the ones that get the press, but there are tens of thousands of other smaller companies who are going through the same thing who are hopefully listening to their employees and are being transparent about, Hey, we're going to figure this out. We're going to figure out what works best for you as our team members, for us as our company, for the long-term success of our business, and it's going to change and it's going to evolve. And so I think that the thing that companies need to be transparent about with prospective employees or with current employees is that, hey, we're doing the best we can. Here's what we're doing today. And we hope that you will give us feedback so that we can do better tomorrow. So that's the answer for the business.
Jesse Chambers (20:03):
The answer for the question that you didn't ask, Tyler, is I think another dimension to this too, is for employees who may be at a company who is not exhibiting the finest ideals of trying to manage through remote work autonomy. How do those people advocate for themselves and advocate for positive change within the business? And the advice that I would give those people is start documenting what you're doing. Start documenting your progress against your goals and sharing that and running that up the flag pole and saying, "Hey, these are my goals. I get these at the beginning of every quarter, and this is my progress against those goals. And I'm doing really well. And guess what? I've been working fully remotely for the last 10, 12 months. And you're asking me go back to the office now. I'd love to go back to the office. Here's my suggestion for that. Here's my plan for that."
Jesse Chambers (20:52):
I love the idea of the work from office Wednesday, and I hope that more people will begin to advocate for that for companies that are trying to get them to come back to the office. Say, yeah, I can't wait to come back to the office. We should have a work from office Wednesday, and that will be a dedicated time where we can do team building stuff and get together in ways that we can't do remotely or autonomously. And I think it is very important as I say, because companies who have their eyes open, who don't have their heads in the sand understand what's going on with this great resignation. And if they have any hope of hiring and retaining top talent, they'd better be listening to the talent that's within their doors. And when folks speak up and talk about how they're doing and how they're doing well and what they want, that the leadership I think will listen. I'm an optimist. And I think that if they don't listen, then maybe employees should consider joining that great resignation and go into companies who will.
Tyler Sellhorn (21:41):
Well, I think it is clear from the reaction of some of the best compensated and most perked employees on earth in Cupertino, that their reaction to the, you must be in this space this amount of time. I think that's a clarion call to the situation that there may be shoals that we're about to run aground on if we are not paying attention to the lighthouse that's telling us you need to avoid these waters.
Jesse Chambers (22:13):
And you said the word perk, right? And with Cupertino, like I think we all need to be really intentional. Flexibility is not a perk. Flexibility is a benefit and flexibility is a job requirement, I think. I think a perk is a free lunch. A perk is the ping pong table. Benefits are things like healthcare and the flexibility to allow you to work in ways that allow you to be a fuller person, a person who can be a caregiver to an aging parent, to coach your kid's baseball team, whatever it is. Flexibility and remote work, I think are a benefit. They're not a perk.
Tyler Sellhorn (22:51):
Jesse, you said it. It was not an accident that I use the word perk to describe the things that exist around the office, right? And then you drew it out, and you drew it out to say that flexibility is involved with the things that go along, right alongside compensation, right alongside benefits. How are we engaging our workforces? How are we engaging the people that work alongside us to help us achieve company goals? What is the ways that we are going to choose to attract and retain people with the ways that we are going about this work? I really appreciate you answering the question I didn't ask and providing some advice to the remote workers that are remote workers now during the pandemic and hopeful remote workers in the future. And I do think there is an emphasis on documentation. Shout out to Darren Murph and his phrase that I use often that remote work is a forcing function for intentionality, for consideration, for reflection and documentation, right?
Tyler Sellhorn (23:50):
There's a reason why there is such a strong culture in those remote first, remote only organizations towards documentation, asynchronous workflows and the rest. So speaking of giving some advice to current remote workers, hoping to stay remote, what would you say to those remote job seekers that may be, they did resign, right? And they're now seeking a job remotely. How can they demonstrate to those organizations that are hiring with a high degree of autonomy, with a high degree of flexibility, as a benefit to their workers? How can they demonstrate to those remote hiring managers that they are ready to be productive in a remote first organization?
Jesse Chambers (24:29):
Sure. Yeah. This is a question I talk to a lot of people about, and I think, the first thing I would say is highlight your experience and your success working in those ways. If you were working even a little bit at the time remotely pre pandemic, highlight your experience doing that. If you have experience managing employees, even in a not "remote work company", if you have experience managing employees in another office, guess what, that's remote work management experience. I mean, highlight that experience in your resume, call that out. And I think the documentation piece you just mentioned as a key thing, too. I think that one thing that people might overlook or might not think is as important in the hiring process or the interview process for new remote positions is your communication.
Jesse Chambers (25:13):
If you can show stellar, written communication over email, through the application process, that's going to go a long way because talk about documentation, all that is, is written communication. People use fancy words like asynchronous and talk about documentation. That's just writing stuff down. And so the more clearly you can do that and the more consistently doing that effectively is going to be something that shines through. It may not be something that the hiring manager or the executive team even is aware of, but I think that they will appreciate as they go through that process with you. And I think, another thing that might be a little bit overlooked and is something that I talk to people all the time about, about managing remote teams, often leaders or managers will ask me sort of what's my best advice or what's the best tool for managing remote teams.
Jesse Chambers (25:59):
I think that they're looking for me to tell them about some crazy new app that is going to solve all their problems. And the answer I give them often gets some strange looks, but then once we talk about it, I think they understand is set clear goals. So many companies go through the OKR process and it's a process that they engage in once a year or every six months or maybe quarterly. And I've been at companies where the attitude was sort of like, well, let's get done with these OKRs, so the executives will get off our backs and we can go back to our jobs. I think that especially in remote organizations or flexible organizations, if you have clear goals and everybody on your team and your manager knows what those goals are and how they will be judged and the timelines that they have to accomplish those goals, it doesn't matter where they are.
Jesse Chambers (26:46):
It doesn't matter if you're in the office or it doesn't matter if you're across the country or across the world, because everybody's going to have a clear line of sight on what success means for them in their role. And so I think pushing for clear deliverables and clear goals in any organization, wherever you reside across the spectrum or across Matt's five levels of remote autonomy, having clear goals is absolutely essential. And the more that employees at any level can push for that, the better their companies will perform in the future. Again, regardless of where they fall on their remote spectrum.
Tyler Sellhorn (27:18):
Jesse, that sounds like an awesome place to conclude. Thank you for continuing this conversation with me that there's no magic bullets, right. Writing stuff down effectively, right? Setting clear goals. These are things that we've known for a very long time, but are being exposed as absolute requirements for us to be effective in a remote environment. Well, thank you again. Blessings to you, Jesse. Any parting words for the audience?
Jesse Chambers (27:42):
I'll go back to it. We opened with it, right. I think that we are in a really interesting time, a once in a multi-generational period for professionals and for humanity, not to overstate it, but I really would tell anybody whether they're a leader at a company or they're a professional, they're an employee. We have an opportunity now to really seize a moment and to begin to design our careers around our lives, not vice versa. And the benefits of that can be so profound, profound in a positive way for businesses and for professionals, but also profound for us in the ability to give us a greater opportunity to live a fuller life. And I know that that sounds maybe a little woo woo, but I really believe it. And I think it's a wonderful time and I'm really excited to be going through it and to be talking with you about it, Tyler.
Tyler Sellhorn (28:31):
Yeah. Let's invite some more woo woo in our lives and our careers. Thank you very much, Jesse.
Jesse Chambers (28:36):
My pleasure, Tyler. Have a great day.
Tyler Sellhorn (28:39):
Thanks so much again for listening to the show and be sure to check out weworkremotely.com for the latest remote jobs. And if you're looking to hire a remote worker, we work remotely is the fastest and easiest way to do so. As always if you have someone we should talk to, any advice you have, or if you'd like to advertise on the podcast, please reach out to us at [email protected]. That's [email protected]. Thanks so much for listening and we'll talk to you next time.

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