Chase Warrington: Priorities, Abroad, Async, Retreats | Work 20XX Ep26

Jeff Frick
May 13, 2024
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Chase Warrington established travel and international experiences as his guiding priorities early in his career, recognizing the necessity of making significant trade-offs to achieve these goals. After a brief period in the corporate sector, Chase joined Doist, a fully remote company with 100 employees spread across more than 30 countries. As the Head of Operations, he has taken a holistic approach to remote work best practices and has become a prominent figure in the remote work movement, which gained momentum during the COVID-19 pandemic in 2020. Chase and his family embarked on their international living adventure and are currently residing in Valencia, Spain.

In 2021, Chase launched the "About Abroad" podcast to offer advice and insights to those interested in living abroad. The podcast covers a wide range of topics from the mundane, such as visas and taxes, to more specific themes like Van Life and obtaining dual citizenship in various countries. Chase is an active presence in the community, frequently speaking at conferences and appearing as both a host and guest on numerous podcast episodes.

Please join me in welcoming Chase Warrington to this episode of Work 20XX.

I am thrilled that Chase accepted my invitation. His mission is to streamline the path to living and working abroad, making it smoother and less complicated than when he began his international journey over a decade ago.

Episode Transcript

Chase Warrington: Priorities, Abroad, Async, Retreats | Work 20XX podcast with Jeff Frick, Ep26
English Transcript

Cold Open
You all ready Chase?
I'm ready when you guys are.
Yeah. Let's do it.
All right.

Jeff Frick:
Hey, welcome back everybody. Jeff Frick here, coming to you from the home studio for another episode of Work 20XX. And I'm really excited about this episode. Our next guest has been in this space long before it was cool, motivated by something a little bit bigger than just remote work. And so he's a top voice in this space, you hear, you see him all the time. You read his writing all the time. He's got a great podcast. So we're excited to welcome in from across the pond. I thought from Valencia, but no, he's moved to Germany, which shouldn't surprise me because the man is on the move all the time. He's Chase Warrington, the Head of Remote (now Operations) for Doist and also the host of About Abroad (Podcast). Chase, great to see you.

Chase Warrington:
Jeff, it has been a long time coming. I am super excited to be here. I've checked out the podcast before and you've had many friends and colleagues that I respect on here. So yeah, thank you for having me. It's great to see you.

Jeff Frick:
My pleasure. Thanks for accepting the invitation, because you were certainly one of the OGs in the space. So I'm really excited to have you on. But let's, do a little bit of background on, on the housekeeping. So give people kind of the 101 on Doist what your, what your day job is.

Chase Warrington:
Yeah, absolutely. So, Doist is a software company, we're predominantly known for two products that we produce One is called Todoist, which is maybe the leading task manager productivity app out there it serves over 40 million customers in 19 different languages. And, has been around for 15 years or so. And the other is Twist, which is a team communication platform built specifically for, distributed teams. I say that because we built it for ourselves. at one point when we weren't happy with some of the other tools on the market that weren't focusing on async enough for us. So, where we I say that because we're a team of about 100 people in 35 countries, we span all time zones, and we've been remote first since day one, dating back to 2009. Believe it or not. So, um the remote first-thing is, is in our DNA, and, and that's what I get to work on every day. My role as the, has been the Head of Remote for the last few years. And I'm actually just as of the time of recording, getting ready to transition into a new role as Head of Operations, which will encompass everything I was doing as head of remote, but but a bit more holistic viewpoints still focused on making distributed work work at a really high level.

Jeff Frick:
And for the folks that don't know you or are just getting to know you. You came to this because of really your passion about travel. and the fact that, you know, there wasn't a lot of remote choices ten years ago, 20 years ago. Thanks Rob Sadow and the team are helping people find them easier with the Flex Index. But you decided early on in your, like I don't wanna say career just in your life. The travel was an important part of of what you wanted to do and what you want to see, and have a slightly kind of nontraditional view of the world. I'm curious, you know, kind of, How did that come about? I know it's kind of unique because it was you and your wife. It wasn't just a solo decision that you decided to do. How did you kind of come to that, prioritization that, you know, we're going to make some trade offs because travel is important to us.

Chase Warrington:
Yeah, it's really interesting. my, the, The evolution of my viewpoint and priorities around remote work have changed over the 15 years of my career. initially it was definitely very selfishly motivated. It was like, I can't imagine sitting in a cubicle all day. I know I'm going into the business world. and whatever regard that meant at the time. And I knew that remote work was possible, even if it wasn't really popular. It just felt like this is where I'll actually get my best work done when I have a change of scenery, when I can control my day. I know I'm a self-starter enough to be able to manage my own time and energy, and, I think I'll be stifled. I don't think I'll do very well in that environment, but yeah. And then on top of that, I, I really had a desire to see the world and those, those sacrifices actually dated back to when I think on it now actually, I realize, when I was in high school, I played American football and it was like a core part of my life. And I assumed I would go on to play in college. And when I started going to visit colleges, they all said I I'd planned to study abroad. When I went to college. it was a key part of what I wanted to do. And every single coach told me, no, you won't be able to do that. you'll have to be here, you know, no season is good to go abroad. Maybe you can go do a week or two. But I wanted to do a semester, and that was that was very stifling to me at the time. I thought, like, it's a huge world. You know, I'm I'm not going to get to see any of it. I've only got these four years. Because after that I have to go into the real world. So I ended up passing up on on football scholarships to go travel instead, and just realized that this was a core part of what I had to have in my life, day to day. And that transitioned into the, into the professional world. And then, yeah, over time. I mean, this is one of the reasons why I'm so passionate about this movement is because I had to make very serious sacrifices, like huge trade offs in terms of salary, company prestige, whatever it was. I've calculated that I've cut my salary by 50% twice in my, in my career just to have more flexibility than was provided and, and as the norm at the time. And I don't think people should have to do that. so, you know, advocating for any change that I can make to, to push us in the direction of more flexibility, while still maintaining a really high standards in terms of your professional career is is something that really resonates with me now. And I've got it. I'm lucky I'm, I'm sitting where I want to be, but, I know there's a lot of people out there still, still having to fight for that. And so it's fun to be a little small part of that movement.

Jeff Frick:
Yeah, 100 people in 35 countries. I mean, what's the most concentration in any one country? That's an amazing distribution of people.

Chase Warrington:
Yeah, if you do the math, it's funny. It's like one, every third person is in a new country. Right. So it's we have very little concentration in any one place. A lot of people assume it's the US. I believe we have four or maybe five employees in the US. We actually have a pretty strong concentration in Europe. The CEO and COO and CTO are all European. So, we have a decent number of people in Portugal. We have a few people in the UK. and then it really gets very scattered from there 2 or 3 in every country.

Jeff Frick:
And what, Why did the founders go that way at the beginning? What was kind of the impetus?

Chase Warrington:
So it's funny, I think Todoist as a product was built before the company Doist existed. And Todoist was literally a side project of our CEO and founder Amir (Salihefendic) he just wanted he didn't like the to do lists that were out there. So he built as a, you know, an engineer himself. He said, I'm going to build my own. And then people started asking if they could pay for it. He ended up selling it. All of a sudden he had a company and he needed to start hiring people to service those customers. So he went on what's now Upwork, Elance at the time, hired some customer service reps to support his side project. And then as the company and product grew in popularity, the team started growing, too. And he was, you know, realizing that he had hired customer service reps from all around the world without ever having met them. in fact, one of them didn't even meet until 13 or 14 years later. and it just dawned on him, you know, there's companies out there that are operating this way. he's a bit of a traveler himself and has lived an international lifestyle and just said, you know, I think I can do this, learn from some of the best that we're doing distributed work at a high level even back then some of the early, the real real OGs and and yeah, then we decided, let's build a company around this. So it's been a fun ride.

Jeff Frick:
Yeah. Sounds a little like the Slack story, but you guys didn't get sucked up into Salesforce. so that probably worked out a little better, but it is funny how like all the side projects and all the tools that that people build internally often become, you know, the main product beyond the one that they were actually going to market with. You know, it's not that uncommon of a problem. I’m sure you've talked to Brian Elliott about it ad nauseam So let's get into some of the details about how to make, remote work successful, distributed work teams successful because you've been doing it for a long time, and the tools weren't necessarily there before. And I've listened to a number of your podcasts and a few your guests have said, you know, I know, I know this is remote and I know what it feels like when it feels bad, but what are some of the keys to doing it? To doing it really well philosophically.

Chase Warrington:
I think one of the first steps is you know, we throw this word ‘intentionality’ around all the time in this whole conversation around remote work. But I do think it's you know, it holds water because you talk to so many leaders of teams who have haphazardly gone through this transition. Right? And they've not really put a whole lot of thought and effort into the procedures and tooling and practices and rituals that the team is going to do and how those translate to the virtual first world and even for us at Doist you know having done this a really long time, the whole the whole reason that my role as Head of Remote came into existence, was because we wanted to make sure that we stayed on top of that transition time. This was a pivotal moment. There was a lot of new products and services and tools and best practices being shared from teams that were stepping into this space. And this had been a really strong part of our company DNA and a competitive advantage for us. And we didn't want to get lost in that. And so, I mean, you think about the intentionality that that our leadership team had to say, you know, we're already like pretty good at remote work. I mean, we've been doing this a long time. At least we have some experience, if nothing else. But, you know, we're going to be very intentional about making sure we stay on top of that and so making sure that our tools match what our values are, making sure that we have the right processes in place. And we're constantly evaluating these. I'm currently working on a project right now to revamp the whole way that we move product projects forward as a team, and we've had the system in place for years and we've gone through multiple iterations of it, but it has to match the way that we work predominantly asynchronously. You know, irrespective of time zones. Very much so. And it has to match the way that we work you know, so these things are like it takes a lot of intentionality to actually make it come together and work at a high level. So I do think it actually starts there.

Jeff Frick:
And then what about taking a position to be a leader in terms of communicating best practices and really being, you know, kind of an industry leader? We all know, Darren (Murph) You know, the OG of them all. And you've got a concept that you use all the time. You talk about building ‘Building in Public’ Why is that an important priority for the company versus holding it back if it's a competitive advantage? I had Jack Nilles on the other day and he said, yeah, every time we had a customer who was successful in remote work, they're like, we're not telling anybody. And you can't tell anybody either, because it's a competitive advantage that we don't want to share. So why philosophically, take the position and really publish and be public and be out there in terms of taking a leadership position.

Chase Warrington:
This ‘Build in Public’ mindset is something I've fallen in love with. The first chapter of my career was in, financial services and looking, you know somewhat corporate, I guess you would say, and looking at spreadsheets with large numbers on them and, you know, strong competition between your competitors and not a lot of building in public, I guess you would say to boil it down, and when I came over into this space and started working for Doist, I really fell in love with this concept because the root of this is that we learn from the companies before us that we're building in public. Take, you know, 37signals Basecamp, for example. We were learning a lot from them. They were writing books on this. They were, you know, sharing, blog posts and participating in interviews like this sharing what they were doing. And that helped us build our business. So I think there's something just, you know, holistically rooted in that, that we're paying it forward in a way. I also think you it's one of those situations where, like, I know for me personally, it's a selfish good deed in a lot of ways, like I I put something out there that we're doing, something we're struggling with or a failure that we had, or a success that we had. And whatever I share, I probably get 5 or 10x back in terms of feedback, questions, thought-provoking conversations that stem from that. and a lot of that we take and we, you know, build upon internally. So I think there's two sides to it, but I've, I truly have found like, I think I get way more back from building in public than I give. And so it's a fun flywheel to be caught up in.

Jeff Frick:
It's a great lesson. I mean, I'm out here in Silicon Valley and, you know, people are always thinking of startup ideas and often, you know, they want to keep it secret, keep it secret. I'm always like, listen, no one is going to do your silly startup idea, right? The difficulty in doing anything well is the execution. It's not the idea. The idea is the easy part. And so, you know the more you share your ideas with other smart people, like you said, and let them noodle on it a little bit and actually share real challenges and real questions. You might be surprised at the answers and the input and, you know getting other people's ideas because they're not going to copy your idea. There are so many pieces to the puzzle to make a successful company from an idea. It's a long way from that first thing that got written down on the napkin.

Chase Warrington:
It's actually funny, you say written down on the napkin because that's the other. Like exactly what you just said is correct. In reality, like what we when we look at our competitors, right we produce a ‘to do’ list that's done well in that space. But our biggest competitor is pen and paper. I mean, people, you know, people transitioning from writing their to-do list down on pen and paper to converting to an app. It’s not the other apps out there that are in theory our direct competitors. And so by us sharing more about how we're working, I doubt very much that we're benefiting our direct competitors as much as we are benefiting ourselves by, you know, putting our names out there in front of the people who might be the pen and paper people. So, yeah, I mean, I've met lots of people along the way that challenge this idea. Like, it's not a good use of your time. It’s not your there's no ROI on building in public. But intangibly, I strongly believe that there is.

Jeff Frick:
Oh for sure. So one of the things that you guys do, which, if anyone's paying attention, you'll see, is you guys have these great retreats and and you know, Brian Elliot, another one of our friends, loves to say that remote doesn't mean never together. You got to get together and it’s still important. So you guys get together frequently. It looks like you're always in cool, dramatic, beautiful locations. Maybe it's just the Italian light in the photography. I think in Tuscany you were recently at. So I wonder if you can share a little bit about the philosophy of how you get together and how you think about it kind of budget-wise. As I think you've mentioned, because you're not spending money on real estate, you're investing it in these retreats. So how do you think about retreats? How did that kind of come about? What's kind of the frequency and some of the logistics?

Chase Warrington:
Yeah, this is a core part of making remote work or distributed work work at a high level, in my opinion. And you mentioned Brian Elliott. It's funny, I was just briefly with him last week at Running Remote in, in Lisbon, and I gave a presentation on, that was titled ‘Remote First not Remote Only’ talking about our approach to remote work. And I cited some studies that Brian's done, as well as others such as, you know, Raj (Choudhury) from Harvard and, Annie Dean from Atlassian, basically all telling a consistent narrative that a) The teams that have adopted a virtual first distributed mindset are, almost unanimously gathering in a physical space on some level, some cadence, and b) There are tangible, like scientifically calculable, metrics that you can show that there's a positive correlation to that time, a lot of it based on connection, trust, bonds, friendships, psychological safety, these sorts of things that are that are just better developed in the co-located world. The person that wants to, you know, play devil's advocate against this would say, Well, if that's where you build those bonds, then why go through all the blood, sweat and tears to build a distributed model? when we've already got the model that “Works” in the you know, office-based environment. And so what we believe is that we can have we can in this way sort of have the best of both worlds. we can have a distributed team that allows people all the flexibility and benefits of having the freedom to choose where they live and work when it works best for them and their families. And focus on deep work and eliminate the commute and all the things that everybody that listens to this podcast already probably sees as benefits of distributed work. But then we can also bring people together in a super meaningful, and again, intentional way that serves all those other needs that aren't as easy to facilitate in the virtual world. And so we have this, you know, this great balance. We do 2 to 3 meetups per year, depending on your preference, and which team you're on. We do one all-hands meeting, which we call ‘Doist Connect’ once a year. And then about six months later we have individual team off-sites, that we call ‘Mini Retreats.’ And so every six months, at least, you have a retreat to look forward to with your team. And, upon, like, serving the team, you know, do you want more of these, less of these? It's almost unanimous that twice per year, maybe going to three times per year is the ideal number. And you rotate the location all over the world. We do, yeah so basically in each case mini retreats and Doist Connect. It's a one-week, like a five full-day experience. The Doist Connect rotates every year from location to location which so far we haven't repeated a country, since starting these back in 2015, I believe. And, you know, that could happen in the future, but most likely will never repeat a location anytime soon. And then for the mini retreats, something we've started doing over the last couple of years, we wanted to move towards standardizing these a bit more, cutting out some of the procedures and headache and workload that goes into creating them, because that's the real cost. I mean, there's a financial cost, but the real cost is in labor and distraction. So, we wanted to reduce that as much as possible. So what we did is we standardized, 15 cities. We looked at where our teammates are located. We looked at costs all these various factors, and we picked 15 cities. We built sample itineraries. We've created relationships with venues and, and facilitators and restaurants and activities and such there. And, so now we basically have like our template down for these places so teams can decide where they want to go. We facilitate the whole thing, make sure that pretty much they, you know, we're shooting for ‘retreats in two clicks’ is the goal. We're not quite there. But the idea is to make it as quickly and, painless as possible to curate these.

Jeff Frick:
So one of the things you do and you mentioned it in another podcast, is you talk about the 20, 30, 50 rule, on these retreats, so that adds up to 100. And what percentage of your time 20% - 30% - 50% Now, if I was to tell somebody, walking down the street that the categories were 1) Work, 2) R and R (Rest and Recuperation) and I’m trying to remember what the other one is 3) Activities, They would probably think that the 50% is business, you guys all got together, you don't see each other every six months. So that's what you work on. But no, it's completely flipped. You only do 20% of the time on hard business tasks. So I wonder if you could share how did you get to this 20, 30, 50? And you know, clearly there’s some experience behind why you've optimized around that kind of time allocation. When you do spend the money and effort to actually bring everybody together.

Chase Warrington:
Yeah. It's a great question. I mean, the natural inclination is to, is to do exactly what you said, like, if we're going to go through all of this effort and spend all of these resources on bringing people together, we better get some bang for our buck, right? We better produce quite a bit. And I totally get that. And to be honest, like the 20/30/50 rule is a baseline, like we want to kind of start from there, but we scale it up and down as needed. And certain off sites, require, you know, more, more time spent on work or there's an opportunity that just makes sense to tackle in that space. So we'll work from there as needed. But what we wanted to do is we we wanted to move from being, from naturally leaning into that inclination to focus a lot on work just because we're together and really force us to time box that in, to spend that time in a very meaningful way and do activities that can't be done in the virtual world. And are really designed for the co-located time together. And what we found is that you know a) we're built to be a really productive, asynchronous-first remote-first team that does really well in that environment. Like those are the type of people that we hire. Those are the way our processes are set up. We've got everything flowing in that direction. And so when we came together, we would do these, you know, early on we would do these long workshops and we would, we would try we flipped that paradigm upside down. And we did a lot of activity, but we didn't necessarily get a ton more out of it than we would have had we done it in the normal way that we work. And so we thought like, Is this the right way to invest this time? Because we've already identified that the hardest part about working, in a distributed manner is, building those connections. And that is the thing we can do best when we're together. So why wouldn't we use just these two weeks? I mean, we're talking 8 to 9, maybe ten days total per year. Why wouldn't we kind of go all in on that? And so it's not to say we don't get anything done. We do. We're really effective with the 20%. Or maybe it goes up to 30% or 40% sometimes. But you know, when we do lean into the work, we plan it out well, it’s it's optimized for the types of things we can't do the other 50 weeks out of the year, and it works really well for us. I think the other thing to mention here is like, this is like this isn't supposed to be a suggestion for others that it's the right way for them. It's just what's worked for us. And a key part of that is we are so distributed that we can really only justify getting together two, maybe three times per year if you're doing quarterly or if the cadence is a lot higher, maybe that number is different for you, maybe also like your work is more collaborative in nature. Whereas the way we've set things up, like a lot of work happens, in individual squads or teams and a lot of that can be done virtually. So I think it depends on the team though the point that I would push back on is just like really thinking through and fighting that natural inclination to think just because we're together, we have to get a lot of stuff done. Question if that's actually what's happening and if it's actually, you know, the optimized way to move forward.

Jeff Frick:
I just love that. What struck out to me, listening to that story the first time is that, you know, like you said, you've built systems and people and processes to get work done in a certain way, which is predominantly async, and not together. And so then to, to put yourselves all in a room and suddenly flip your working method and your productivity method because you're together. I mean, that's like, of course it doesn't make any sense. And the other piece too, is you just said, you know, are you really identifying the value that's happening there? Brian Elliott, when he talks about his time together with his team, he's very specific. You know, we break bread together, we volunteer together, we eat meals together. We do a lot of stuff that's not work. And I think really what it gets to that I think should be highlighted is it's this foundational building of trust and relationship that's going to enable that productivity and some of those hard conversations in difficult times down the road. So it's really foundation building more than it is. You know, let's kick out a beautiful three ring binder of all the cool $#!+ that we did here for three days.

Chase Warrington:
Yeah, you nailed it. I mean, someone came up to me recently and said, like, so is your view on a retreat, basically that it's just like a team vacation and I they're, I think their question was more like an assumption that I would agree with that. And, that's not the case. That's not what we're, we're advocating for. or suggesting at all. It's just about refocusing your time and energy on the connection bit. And there's a lot of different ways you can create connection. Probably most of all, which is like connected to the work that actually unites us. So it's certainly not an indictment on doing work together in person. It's about just using that time to do the type of work that you can't do normally, and then using the rest of the time to build out those connections in the ways that you can't do in your normal day to day. and so like those examples that, that Brian gave that you just mentioned, like, those are excellent ways to facilitate team building and, you know, build true friendships that are, that are just tough to do in our hyper async remote-first environment.

Jeff Frick:
So here's the curveball, though, is that you said that people don't have to attend, if they don't want to and there's ‘No Questions Asked’. So you've got this no questions asked attitude. It keeps coming up all over the place, which to me reflects a significant kind of ninja level degree of trust, with people. Because even though you said this is an important time we're going to build these connections, these 8 or 9 days that we're not, out of the 365, but we're not going to force you because we trust you. And, if it doesn't work for you, it doesn't work. No questions asked. Wonder if you can share that where that philosophy comes from and how it's really worked out when you do trust people that much.

Chase Warrington:
Yeah, that's a fair question. I think it's rooted in the fact that we were built as a remote-first, async-first team from the beginning and only later adopted retreats five, six years into the company being built, so Just on a pure like, human to human fairness level, it's like we hired you under these circumstances, and now we have these new set of circumstances, and we literally have people on the team who, they just have zero desire to join in on these kind of things. They're not travelers, Flying scares them to death, or they don't want to leave their families, or they have sick loved ones nearby or whatever. There's a variety of reasons. and so, you know, we just decided from the beginning, well that's not, this isn't really the core of who we are. What we do 50 weeks per year is really what dictates who we hire and the type of people we need to really surround ourselves with. So let's see this as a little bit extra. That said, I think that this is controversial for a reason. And if we're starting from scratch, maybe, you know, I'm totally like, I’ve never said this out loud or anything. It's not a fully formulated thought, but Perhaps if we were starting from scratch, that would it would be more of like a, an expectation than it would a, you know, a no questions asked sort of thing. But we do take this approach to synchronous work of all forms. I mean, again, we like we built a team that's predominantly working in an async environment. We have teammates working on opposite sides of the world. We believe in that separation. And we want people to have their their personal lives that they have full control over. So we don't even force people to attend synchronous meetings if it's not convenient for them, so much less am I going to force someone to to fly around the world to an event for a week and, you know, leave their families behind if it's not convenient for them. But I just I do think that, you know, I know I have counterparts at other companies who take a very different stance on this. And I actually get it Like I 100% see where they're coming from. but you know, if you're going to be a part of this team, you should come to these gatherings that we do. It's a core part of how we build culture and such. so I think there's a valid argument to be made there, it’s just the This is the stance we've taken and, and it's worked out fine for us. The other thing is like, we have this motto of doing everything at a world-class level at Doist so when we, you know, write code or write a blog post or service customers, we want to do it at a world-class level. And I take the same approach to our IRL strategy. Like, we want our events to be world-class events that people really look forward to coming to and they're proud to come to. So it shouldn't feel like this, like mundane meeting that you just have to go attend or. They’re experiences that you look forward to. And because of that, we have a 90% to 95% participation rate, which in this space is like really, really high, especially considering our distribution. So this isn't a problem. You know, we don't have 20% of the team opting out. And so almost everyone that can be there is there. And the few that don't, it's usually for like health or family reasons.

Jeff Frick
Yeah. And I love that when you list like all those reasons there's just so many little variables that could impact my availability for this particular week. And I think you've said in some other of your shows that, you know, maybe people miss one or miss two, but, you know, it's usually not a pattern. It's because they have some, some thing that's happening that just is preventing it. But like you said, make it attractive. So they want to go if it's possible. I want to shift gears a little bit and talk about the tooling and the tool space. You just got back from Running Remote all the, bummed I wasn’t there. Everybody else was there. But one of the things Nick Bloom likes to talk about, you know, is, as this has taken off and as it's become more mainstream, you know, there's just investment into tools, into the processes that enable remote work for a lot more than companies like yours that are new. And there's a lot more people coming into it. I wonder if you can share some of the latest that came out of Running Remote. You were just there, you know, kind of your thought on tools? Not so much competitive tools, maybe competitive tools, but more just kind of how the tooling infrastructure and, and the kind of enabling infrastructure is changing to make it easier to actually be able to execute this.

Chase Warrington:
I think this is like one of the like under the radar. I don't know if it's, maybe I would be curious to hear what you think, but it's almost like an under the radar benefit of this whole transition and explosion of, distributed work being adopted is that there's an explosion of tools that have been developed to service that market. And whether you're, you know, fully remote, like we are or you're, you know, on a hybrid team of some sort. I mean, there's tools that are developed, being developed to serve that market. And I think that's really fascinating. An example of this, like over the last year or so, we decided we've had, like many teams, you know, we've mentioned some of them today, like GitLab and Darren, for example, at GitLab, like writing the handbook that they had, the epic handbook that they have. Like we also have a company handbook. It's got around like 1,200 pages in it. We've been working on it for many years and but we had kind of hacked it together. It wasn't really like a great tool solution for all the teams and on our all the teams within the company. And we decided, like, we could we could do better than this. And like when we started to look at the market for like, okay, what are there any products out there that service this specifically? Yeah, there were like 15 of them now. There's a ton of options. And, you know, just for something very specific, like a distributed team handbook product, you know, and so, I just find this, like, really as someone who, who's wants to see this become more adopted on a wide scale. I love seeing that, there's solutions out there to, to solve those pain points. So, I'm seeing a lot in that space. I mean, there's a lot, of course, you know, connected to AI and then filtering down, I feel like AI’s sort of at the top of the, the umbrella and then filtering down from there, it's like, how do we, consolidate communication? How do we find documentation and content a lot easier? How do we filter out get to the fewest number of stakeholders and people who have to participate in any given asynchronous conversation? And then the other area that I think is really interesting is, it's like coming back to connection. There's some really interesting tools emerging to, to help support virtual connection and, strengthen tighter, deeper bonds with your async or remote first team, which is also pretty fascinating.

Jeff Frick
Yeah. We haven't talked about it much because, I don't know, maybe it's too obvious. We've been in the space too long or talking to Darren too many times, but, you know, clearly async, as a methodology and a philosophy and documentation, you know, are two of the core tenets. You talked about intentionality. I think those are the the big three words that, really set this whole thing down. and if you don't do that. So I'm just curious what happens in an emergency?

Chase Warrington:
Yeah we do. So we do have an emergency. you know, channel that you can get to get to people in a, real emergency. Basically, it's like an emergency team that's set up and with a separate Telegram space where like, notifications are turned on. And so if we need to get to people, you know, I think it's happened once or twice. in the eight years that I've been here that, you know, that needed to be used. But the truth is, with the with we're set up, I mean, we have somebody working 24 hours a day. we have people spread around all time zones. So there's, it's very rare that something happens that we, that we don't have somebody set up for, you know, to be able to handle that.

Jeff Frick:
Yeah. It's such a great when you talk about one of the other kind of unlocks is better meeting culture and doing meetings better. But you guys have like basically no meetings. You have like two hours of meetings, a work a week, which frees up, okay, just do easy math, 38 hours of productive heads down time. I mean, the productivity efficiency by not being interrupted constantly and having that as kind of a corporate standard. I mean, I can't even ask you about meetings because you guys don't even have enough meetings to have a good meeting culture.

Chase Warrington:
Yeah, we kind of suck at it, to be honest. I mean, It's funny. We're kind of terrible at meetings. it's I mean, I say that somewhat joking, but also, like, funny enough, we've mentioned Darren a few times, like a couple of years ago at Running Remote in Montreal. I sat on a panel with Darren, Stephanie Lee and Sam Fisher. All three, all four of us were somewhere in the head of remote space. And we went after the panel. We were standing backstage and we were talking about some of the pain points that we feel on our team. And I was the one like, we need more synchronicity, you know, we need more meetings. We need. And they're trying to push the number of meetings and the number of hours spent in meetings down. But an interesting conclusion we came to there was like, you know, meetings are a powerful tool. If they're used properly. But and in our case, you know, particularly at that time, we weren't using meetings enough to ever be good at hosting them. And so it was almost like, you know, an unintentional downside. We had leaned so hard into asynchronous communication that we had gotten bad at using this otherwise really powerful tool. Of course, a lot of teams go in the opposite direction and, you know, they're it's like if that tool is a hammer, they're just using the hammer for like every job, you know, and so we needed to balance that out a little bit. And I think we, we have, we’re using synchronous communication a little bit more. We're recognizing like there's, there's a great space for both synchronous and also the, that, hat bit of space in between, which is like, you know, using voice notes more and using products like Loom, for asynchronous video more. And, just providing a little bit more context than the written word can do sometimes, even if you can't actually sync up for a meeting. But, Yeah, I still would like to see us get better at the the meeting thing and without a whole lot of practice that can be tough.

Jeff Frick:
Yeah, well there's also kind of that interim thing which is like chat and IM and DM and you know, can you get something done in just a quick, you know, 15 word, exchange on a couple of IMs, which again, it's kind of tough because you get the interruption factor if you make that standard. But you know, a lot of times things can get done a lot quicker and efficiently without a meeting. Even if it is some type of synchronous or just, you know, go old school, pick up the phone and, call somebody if the time works out great.

Chase Warrington:
Crazy idea

Jeff Frick:
Yeah. But it's crazy because companies have been distributed for so long. This is not new. It's just, you know, kind of the formality of it. But, you know, I'm sure most people's teams were pretty distributed in 2019 when you actually had a team meeting, ou needed to get everybody on the phone as Kate, you know, Lister would say nine floors, nine buildings or nine time zones. You know, nobody's sitting next to the people they work with. These are all big global international organizations. Crazy.

Chase Warrington:
Yeah, that's I mean, something I found really interesting just before this call, I had, kind of I'm doing like a series of internal interviews with people about the project management system that we use to move projects forward and sprints. And we're, we're doing some revamps to that and so just talking with some people from different areas of the company about their pain points and such and, this and during this discussion with one of our engineers, she said, you know, we had been going round and round asynchronously for over a week on this technical spec that we were writing, we've been working asynchronously on this technical spec for over a week, and we've just hit a roadblock. And finally, we hopped on a call and ironed it out in an hour. The inclination is to think, "See, that's why meetings work." And that's true. That is when meetings work. But on the flip side, our modus operandi is to first go async. And nine times out of ten, this was the anomaly for her. It was the first time in many years that she had hit that point where async just wasn't working. And so that works really well for us. We start with async, and then when things aren't working, we switch to sync. You still see a lot of teams going in the opposite direction, where everything defaults to sync. But we're all still learning how to find the right balance between these. It's a moving target because the tooling changes, the situation changes. We're trying to standardize those things, but at the same time, you know, leaving room for flexibility given the situation.

Jeff Frick:
Well, not to mention when you had that meeting, everyone was so clued in to what the issues were after, however many—what period of time—exchanging ideas, and the conflicts, and what the issues were. I mean, I'm sure the level of preparedness of the people and the engagement in the issue of the people in that meeting was probably very high.

Chase Warrington:
Yes, that's it. It was 90% of the way done at that point. They hopped on for one hour, solved the whole thing and like, you know, moved on. So in either case, the work got done in a week. But instead of spending four hours a day in meetings to get there, they did it asynchronously. So I don't know, it's not all like. I think one of the things that I'm learning more and more as I get deeper into this space is it's not all or nothing. It's not remote first or office based. It's not 100% async or 100% synchronous. There's this spectrum that teams have to choose where they want to sit on that spectrum. Just being cognizant of that and building your whole infrastructure around where you've decided to sit on that spectrum is really important. And again, like we're constantly tweaking this and moving those dials to make it work best for us.

Jeff Frick:
That's great. So I want to shift gears another time and talk about your podcast, ‘About Abroad’ because you came at this really from the traveler, point of view. And, you know, you've done the van life. I think you've done a couple tours on the van, on the van life, experience and how many? Give us a quick update. I mean, you've been doing this for how many? How many episodes? How many seasons? It's amazing.

Chase Warrington:
Oh. Thank you. Yeah. Well, as a, you know, I'm a podcast host that respects the podcast host that I'm talking to, so I appreciate that. it's, a yeah, I'm in my ninth season of ‘About Abroad’ now, and I really started it as a side project, a little bit of like personal context. I'm from the U.S and I have lived like, you know, permanently in a handful of countries around the world and, most recently spent almost the last better part of the last seven years living in Spain and have been traveling around Europe for the last couple of years, spending some time, several months in different countries around Europe. So this is sort of a core part of my personal life. And, and I started ‘About Abroad’ really because I was having a ton of side conversations with people as the explosion of remote work was happening and you know, matched with my experience navigating the complexities of being an expat in different countries. Dealing with visa stuff, bureaucracy, taxes, all the, the not so fun parts that don't show up on your Instagram feed, you know, that's kind of what led to the podcast. Dealing with all those. There were lots of conversations taking place, and I thought, you know, when I started this, there wasn't a whole lot of content out there about how to do it. I mean, I was really, like, navigating it in the dark, and it was complex and challenging. And so I thought, I love having these conversations. I'm a podcast junkie and we're already having them off the air. What if we just record them and share with people, what these experiences are like, and so it sort of expanded into a whole. The space that we're talking about is kind of generally focused on global mobility. So it's not just like boring visa and bureaucracy stuff. It's also telling people's stories about how they managed to move abroad or how their, you know, traveling permanently. And a lot of it touches on remote work, which powers a large percentage of those people's stories.

Jeff Frick:
But it's so interesting, as you said, the extremes are not necessary anymore. Nick Bloom, I think in his TED Talk puts up a slide when you used to Google ‘remote work’, and there's kind of two categories of pictures and the images that would come up. When you see it, one is like the lazy slob hanging out, not getting dressed in the house, you know, a stone's throw away from the fridge, and the TV. And then the other one is the people in beautiful tropical locations with a laptop on their lap, and a nice fruity drink with an umbrella. And then, of course, the punchline is the fruity umbrella is actually a Wi-Fi antenna. It's helping the person get in. You know, it used to be a pretty extreme thing, but now, as you said, it's not necessarily so extreme. You don't have to be so extreme. You don't have to do it full time. And I'm curious, how has the paperwork in kind of the, the nasty, ugly stuff that you do have to take care of in terms of taxes and visas. And, you know, it's not the sexy stuff on Instagram, but it's the stuff to get to those, fancy Instagram pictures. So I wonder if you could share how that world has changed for people thinking about part time, a little bit, maybe a year, you know, or maybe it's an extended… You know, kind of vacation or midlife retirement, you know, to go spend a year in Tuscany or whatever.

Chase Warrington:
Yeah. It’s an awesome question because this is today's reality. That was not the reality five years ago, and much less ten years ago. It used to be extremely difficult to find a country that would want to accept you, if you weren't a citizen, or if you didn't have some sort of, like, real need to move there like work was bringing you there, marriage was bringing you there. You know, a refugee status or something like that. The options were very limited and mostly you were restricted to, you know, 90 day or 60 day tourist type visas, maybe one year, like a student visa or something. But these days, I mean, they're literally. I've talked to the people behind the scenes who are creating these digital nomad visas. They look at us like we at Doist look at users of our products. I mean, they're trying to build features and attract you to their countries. They're literally fighting over you to bring you here. And they've paved a very clear and easy path to get there. And so, you know, it's a lot easier than it used to be. And there's in a lot of cases, it's, not even a question as to whether or not you'll be approved. It's just a matter of do you check 3 or 4 boxes? You know, do you have a little bit of income to support yourself or savings? Do you have a clean background check? And, do you have a doctor that will say you're not, you know, deathly ill? And if those are the cases, then, there's a lot of countries that will accept you for a year or up to five years and even provide like a permanent path to citizenship, or permanent residency. So, yeah, it's changed a lot, with the emergence of digital nomad visas. And on the flip side, it can never be understated how painful the, the processes are, are because they're always a lot harder than they look. I'm a big advocate of hiring a professional to, to help you navigate this space. It's relatively inexpensive, Yeah, we talk about this a lot on the podcast, honestly. Like, we have individual episodes for individual digital nomad visas or countries that you might be specifically interested in, people who in our space that we've talked to a lot, Jeff, that have done that and, you know, are living abroad in Portugal or Ecuador or wherever it may be. And, so we're trying to tell their stories and explain how they navigated that space.

Jeff Frick:
Yeah. It's great. I was listening to the episode with the guy, talking about getting your Italian citizenship if you got Italian ancestry. So I’m gonna share that one with the family. And what he said it takes years and years. So let's get to be friends. But, you know, we'll get you there eventually. Well Chase, this has been great. I want to wrap kind of on the last topic, your advice for people that just feel like, you know, the standard path doesn't necessarily feel good or just doesn't fit, or I think I'm looking for something different. I love your experience of your corporate thing. When I interviewed at a Fortune, I don't know what they are Fortune 50 company and I went and it was a great interview and we went and we sat down and the guy got this little floor plan office plan out with all the desks and the cubes. And he's like, yeah, you're going to be right here. And I literally I mean, even now I just, my stomach just turned over. I'm like, I'm going to be there like? And all these little squares, you know, like I go there. And then my first job in tech at Intel, at RNB, the Robert Noyce Building main headquarters. Six foot cubes, seas of them. And then, you know, all the support columns have labels, either, you know, a letter or a number. So, Chase, you're at pole G6, the printers at A2. I'll meet you, over at Brian's desk at, you know, H4. And I just it's just like, Aahh. So for people that feel like that’s not the way, you know, I don't want to follow the pattern. You didn't, you saw a different path. You set a different priority. You made conscious trade-offs and thankfully found a partner who had aligned incentives. What do you tell people? That, hey, if it doesn't feel like the standard path is the right path, there is an alternate. You know there are alternatives and you can make it happen.

Chase Warrington:
Yeah, I think you just summarized it really well. You know, I have told many people that I've had that conversation with that in my early days of my career, I decided that was going to be my North Star, that freedom and flexibility were, you know, going to be a part of my career. And I was going to prioritize that over all else. And so, you know, that means inherently making some sacrifices and I kind of have like a little it sounds a little bit overly ambitious, and I don't think I can actually have a huge impact on this, on this goal, but it's a little bit of a goal of mine to like, make sure that people don't have to make those sacrifices and trade-offs anymore. But it may mean still that at some point you have to make some sort of sacrifice. It may mean a step back in your career trajectory, it may mean a slight pay cut. It may mean taking a job, working at something that isn't exactly aligned with what you want to do. But if you see it as one step back two steps forward, and look at the long term path, rather than, you know, instant gratification, this is what I need right now. Then I think you're setting yourself up for long-term success More ideally, like, I hope that's not the case for you. I hope you can just take the take the path forward that, you know, checks all the boxes that you want and move forward in a into a company that accepts you because the truth is, is that there's it's never been easier than it is right now. There are more options out there than there ever have been. When I found Doist, my wife found the job that I got hired at Doist for by looking at a Pinterest board. That had 75 jobs, 75 companies hiring from anywhere, and it was the only thing we had ever seen like this. And of those 75, I think 73 were engineering jobs. And, you know, I'm not an engineer. So I thought, oh, I'm kind of screwed. I looked at those two jobs, I applied for the one at Doist and I ended up getting it. But I tell that story because that was all we could find on that at that time. I can probably name you, like 75 dedicated job boards just for distributed work. Flexible work right now. So there's so many options available to you right now if you're feeling beaten down by this, I just there are positions out there. It's never been easier. And then if you're willing to make a little sacrifice if needed because that's your North Star, then I think you have, you know, you have a bright future ahead of you.

Jeff Frick:
That's great. Well, Chase, I think we'll leave it at that. That's great advice for people. And you are changing the world. You are setting the pace. You know, you're you're sharing your stories. You're out there a lot. You publish a lot, you talk a lot. You share great guests, so I think you're making an impact for sure.

Chase Warrington:
Thanks, Jeff. I appreciate it likewise. Appreciate all that you're doing. And I love listening to the guests you bring on here. So hopefully we added a little value today. And, it was a lot of fun for me, so I appreciate it.

Jeff Frick:
Great. Well, thanks for coming on I appreciate it. All right, he's Chase, I'm Jeff, you're watching Work 20XX Thanks for watching. Thanks for listening on the podcast. We'll see you next time. Take care.

Cold Close:
That was great, man.

Chase Warrington: Priorities, Abroad, Async, Retreats | Work 20XX podcast with Jeff Frick, Ep26

© Copyright 2024 Menlo Creek Media, LLC, All Rights Reserved

Chase Warrington

Head of Operations, Doist


Host , About Abroad Podcast

About Abroad on Spotify

About Abroad on Apple Podcasts 


Inspiration, Doist 

Building a Company Handbook, Doist, todoist inspiration

Productivity Methods, Doist, todoist

Doist Connect 


The GitLab Handbook, The Remote Playbook 2023, GitLab 

Atlassian Team Playbook, Atlassian 

Lessons learned: 1,000 days of distributed at Atlassian, Annie Dean, Atlassian 
Distributed work report, 2024-Jan-17

A modern work manifesto for distributed teams, Dominic Price, Atlassian

Future Forum Research, Future Forum,  Slack, Boston Consulting Group, MillerKnoll and Management Leadership for Tomorrow, featuring Brian Elliott , Sheela Subramanian, Helen Kupp, Christina Janzer, Taryn Brymn and more. 

Work from home, the Basecamp Way, Basecamp, 37signals 

The 37signals Guide to Internal Communication, Basecamp, 37signals 

The Ultimate guide to remote work, Zapier 

Automattic’s Remote Work Framework: How to Reach Autonomous & Asynchronous Nirvana, Auttomatic, 

Ideas in Action, MillerKnoll


Select Chase Appearances on other shows  

Slow Traveling Europe + Van Life with Chase Warrington from About Abroad |
Badass Digital Nomads Podcast with Kristin Wilson 

Finding Balance: Doist’s Approach to Sync vs Async Work | Chase Warrington
Flex Perspectives Podcast with Rob Sadow

Unlocking the Potential of Asynchronous Communication with Chase Warrington |
Remote First Podcast with Daphnee LaForest , Ep60, 2023-May-02

Improving the Remote Work Experience - Interview with Chase Warrington |
Cohesion Podcast with Amanda Berry by Simpplr 2023-Feb-07, Ep33

Chase Warrington (@dcwarrington) | My Latin Life Podcast #38

Are you Overvaluing Speed at Work? How to Rethink the Virtual World with an Async Mindset, Chase Warrington, Head of Remote at Doist, 116
Fellow SuperManagers Podcast 2022-Sept-07 

Episode #189: Becoming Head of Remote a Doist, Traveling Europe by Camper Van, and Hosting the “About Abroad” Podcast with Chase Warrington
The Maverick Show with Matt Bowles 

Living in Spain as an Expat or Digital Nomad With Chase Warrington, Host of the About Abroad Podcast  |
Badass Digital Nomads Podcast with Kristin Wilson, 2022-May-10

Working Remotely – Chase Warrington & Freedom Matters
By Rosalie MacMillan,,  2022-Feb-16

Navigating Remote work with Chase Warrington
As Told by Nomads with Tayo Rockson Podcast, Ep601, 2021-Dec-08

Supporting the mental health of distributed teams with Chase Warrington
Team Apart Podcast with Ryan Roghaar, 2021-May-18 

Conan Visits Intel’s Headquarters | Late Night with Conan O’Brien, Conan O’Brien, YouTube, 2020-Aug-13 

Vanlife in Europe (A Beginner’s Guide), Moving to Spain and 5 Tips for Running a Successful Remote Work Retreat with Chase Warrington from About Abroad
Zero to Travel Podcast  

Running Remote - Chase Warrington

LinkedIn Intro Post 

Speaker Profile 

Intro Video 

Promo Video 

Retreats & Offsites - IRL event strategy to support distributed teams 


Disclaimer and Disclosure 

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 © Copyright 2024 Menlo Creek Media, LLC, All Rights Reserved 


Jeff Frick
Founder and Principal,
Menlo Creek Media

Jeff Frick has helped literally tens of thousands of executives share their stories. In his latest show, Work 20XX, Jeff is sharpening the focus on the future of work, and all that it entails.