Episode 138: How to work remotely from anywhere, even when you have a full-time job – with Ali Greene of Remote Works

The idea of working for a few hours each day on the beach sounds great but how realistic is it to work remotely in a full-time job? Is the reality of full-time remote work more stressful than freeing?

Ali Green was a remote worker for years before she fully transitioned to the digital nomad life and started her company which helps people and companies thrive in making work more freeing, flexible and focused.

She explains the benefits and drawbacks to remote work, how to approach your employer about transitioning into a remote position, and the surprising professions she’s seen people work remotely.

Today’s guest

Ali Greene of Remote Works

Website: Remote Works Book

Email: remoteworksbook@gmail.com

Instagram: Remote Works Book

LinkedIn: Ali Greene

Ali is the co-author of Remote Works: Managing for Freedom, Flexibility, and Focus to be released by Berrett-Koehler Publishers in early 2023.  A remote worker turned leader since 2014, she is the former Director of People at DuckDuckGo and former Head of Culture and Community at Oyster.  Ali’s mission is to empower people and companies, helping them thrive in making work (and life!) better.  She was named a “Remote Accelerator” in the 2022 Remote Influencer Report by Remote.

What you’ll learn in this episode

  • [2:06] How Ali became a remote worker and the benefits of being a digital nomad.
  • [6:37] The difference between remote work and working from home.
  • [11:34] How aspects of almost any profession can be done remotely.
  • [14:40] Surprising professions that can be done remotely.
  • [15:50] The drawbacks of working remotely.
  • [16:38] The importance of building a community as a new remote worker.
  • [20:09] Challenges for full-time remote employees.
  • [22:48] How to get spontaneous socialisation and interaction as a remote worker.
  • [28:10] How to gain influence and respect in an organisation as a remote worker.
  • [34:50] How to approach your employer about becoming fully remote.
  • [40:45] How to find companies that offer remote work positions.

Resources mentioned in this episode

Please note that some of these are affiliate links and we may get a small commission in the event that you make a purchase.  This helps us to cover our expenses and is at no additional cost to you.

Episode 138: How to work remotely from anywhere, even when you have a full-time job - with Ali Greene of Remote Works

Jeremy Cline 0:00
Working full time from home, working full time from anywhere in the world. It might sound very appealing to you. But is this something that realistically can be achieved if you're in a full-time job, especially one which is expecting its employees to spend some time in the office? Can you really enjoy the digital nomad lifestyle when you're not a consultant or a freelancer or a business owner? When you've got a nine-to-five job, can you really work your own hours from anywhere in the world? And if so, how can you make a success of it? That's what we talk about in this week's episode. I'm Jeremy Cline, and this is Change Work Life.

Hello, and welcome to Change Work Life, the podcast that's all about beating the Sunday evening blues and enjoying Mondays again. One of the lessons the COVID pandemic has taught us is just how much work can be done remotely, rather than being based in an office. Whilst some of you might prefer the office environment, for others, this opens up the possibility, not just of working from home, but of working from literally anywhere. But can you really be a digital nomad when you're in a full-time job? If so, would you actually want to be? It might offer freedom, but what about the lack of visibility with your colleagues when you're not seeing them regularly? To answer these questions and more, I'm joined this week by Ali Greene of Remote Works. With years of remote work experience, Ali recently transitioned to the digital nomad life, and she now helps people and companies thrive in making work more freeing, flexible and focused. Ali, welcome to the show.

Ali Greene 1:53
Hello, thank you so much for having me.

Jeremy Cline 1:56
Ali, why don't you start by telling us a bit more about yourself, and specifically, what has remote work enabled for you?

Ali Greene 2:04
Yes, of course. So, it's really interesting to think about my remote work journey, because I actually remember my first remote job wasn't remote at all. It was in-office job and the very first job of my career. It just so happened I was working at a start-up that was growing too fast that it couldn't find enough office space to contain all of the employees. And so, what started out as one very small, very traditional start-up office in a Chinatown office space above a Hooters, which, if you're not familiar with that brand, is a sports bar chain in the United States, expanded all over the DC area to offices throughout Chinatown, all the way over to the White House. So, eventually, I ended up working in an office building where I had lunch outside of the White House every day, and bounced around the city for meetings all of the time, until it started to rain. And then, I would pick up the phone and do my meetings with my colleagues in their respective offices. And that was my first taste of remote work, because I was like, 'Hey, we don't actually need to go to each other's different offices and waste all this time walking around Washington, DC, unless we want to.' And so, we already have the technology to allow us to work remotely, how now can we use that technology to help us with other things in our life? And so, from there, I got really antsy, and I got really frustrated that we, as humans, weren't pushing the boundaries of what work could mean. And throughout the next few years, I found myself in situation where I was able to design a work life for myself, where I ultimately was, not only working remotely, but allowed to live and work anywhere I wanted. And so, naturally, I decided to travel the world, and I worked in places like Japan, I worked in places like Cape Town and Mexico, and I did it all just spending one month in each country. And ultimately, I learned that there was a term for that called digital nomad. And when most people think of that term, they think of people working on the beach, and they think of this Instagram lifestyle. For me, it really unlocked a lot of things in my life that were a lot more meaningful. So, professionally, it was the most exciting and most challenging time of my career to be working full time and travelling full time. I felt like I had this superpower at work, because I was able to empathetically tap into what other employees were feeling. If they were feeling isolated, why were they feeling isolated? If we had communication issues at work, what were those types of communication issues? Were they because of something going on in the company culture? Was it something going on because of the fact that we were hiring diverse people from all over the world, and there were cultural issues at play? And so, I felt like, because I was travelling, and because I was personally going through all of these challenges, learning how to live in other places, I was looking through these work challenges in new lens, and I grew in my career tremendously during that time and eventually became the director of people operations at a start-up while travelling full time. And personally, it unlocks a lot of things for me as well. When I was travelling as a digital nomad, I met my partner, and I was able to figure out how to work best according to my energy styles. I was diagnosed with the chronic health issue and was able to still work and challenge myself and follow my passion and also take lots of time for rest when I needed to rest, spend more time with my family, I just got back from a three-week trip to the United States, where I was able to work and still take my nephew to baseball games. And so, all of these things meant that I was actually able to make less compromises in my life and still be able to do more. And so, for me, that is the power of remote work.

Jeremy Cline 6:04
Fantastic. And I love the idea of being able to work according to your own energy levels and managing, doing the working hours which work best for you, rather than doing the working hours which are expected of you, when you're in a traditional employer. So, since the start of the pandemic, what sort of behaviour shifts have you seen? Is it the case that people are just working from home? Or are you seeing people using the opportunity now to move to something where they are more fully remote?

Ali Greene 6:36
So, I'm seeing two things happen, and this is all based off of stories and examples in my network. So, none of this is scientific. I hope that there's a scientific study done on this. But I'm seeing two extremes happen. One is that, the past two years, people have conflated the term remote work and work from home to mean the same thing, when they dramatically do not mean the same thing. And so, I see a little bit of remote work fatigue. I tell people, even about my life, that I'm writing a book about remote work, that I've been a remote worker since 2014, and I see people's eyes glaze over, like they just don't want to talk about this anymore. They do not care. They're frustrated, they're tired, they're stressed. And they say, 'Yeah, like, okay, cool, whatever, we've been working remotely for the past two years, it's terrible. Like, we hate it. We've been stuck at our home, we've been isolated from our colleagues and our friends. We've been working too much, we're burnt out.' These are the complaints I'm hearing from people, and I have to stop them, and I have to give them a little shake and say no, what you've been doing has been working from home in a period of high trauma and high stress for many nations around the world. There's collective anxiety and collective stress that we've all faced. And I think a lot of people have used work a little bit as a crutch, because it was familiar to them, and because they felt like there was something that they could pour their energy into at home, when they didn't have the outlet to have their social community and their support system around them. And so, one, I really want to break the narrative that remote work equals working from home, they don't mean the same thing. I also want to break the narrative that working from home during the stress of the pandemic is what working from home could be like for people in the future. Working remotely, for me, just means that you have the flexibility, you have the freedom, and you have the choice to determine, not just the where you work best, because that's the most obvious thing, do you like to work in a cafe, do you like to work in a library, your house, the office, all of those are choices of remote work, but also the when you get the work done, how you get the work done, with whom you get the work done. So, your colleagues no longer have to be the colleagues only at your company, but they can be other people that bring you inspiration and creativity. And so, that's like a lesson that I think a lot of people first need to learn about remote work. The second group of people that I've been hearing from post-pandemic is the group of people that have learned that lesson, and now they're really excited about remote work, and they want to push the boundary as far as possible. But they've never done it before, and they either don't know how to do it, in terms of, well, how do I actually travel and work, travel is supposed to be for my holidays, what does that look like, how do I set up my day, how do I keep myself productive, how do I keep myself focused if I'm doing those two things, how do I do that if I'm only doing it when my partner has an office job or when my kids are in school, how do I manage the constraints; or how do I convince my company to let me do it, because my company was okay with me working from home, my company's okay with me working remotely if I come into the office every other day and check in, but my company maybe isn't okay with me working remotely if I say I want to go to Greece for the summer. So, what does that look like, how do I explain the benefits to them, how do I help them navigate things like compliance and HR policies, and that's a whole another, now you know you want to, how do you actually get to, and I think that's a very exciting time for a lot of companies that are waking up to answering those questions.

Jeremy Cline 10:43
There's a few points in there that I'd like to come on to. But before we do, I think people have realised that there's an awful lot more working from home that is possible, than perhaps had been appreciated before. But similarly, there are some professions which you can't do it remotely. I mean, you can't be a nurse working in a hospital and do that remotely, very easily at least, not with current technology as I understand it. Are there any professions or occupations which surprise people that they can be done remotely, so professions that people think that you couldn't do that remotely, but in fact, there are ways of doing it?

Ali Greene 11:33
Well, I would say with any job, even if there are in-person components, if you really analyse the job and all the tasks involved, there are remote components as well. So, take nursing or being a doctor, for example, those are jobs where there are very strong arguments that, yes, you need to be in person, you physically need to perform a surgery on somebody, and therefore need to be in a hospital with all of the tools and equipment to monitor that person. What happens after the surgery is a lot of paperwork, a lot of making sure the reporting is accurate, uploading it to the system. There is no reason that work like that, currently or in the future, to some degree couldn't be performed remotely, if the right security measures are in place to make sure that the data that's being stored and saved online is protected with things like two-factor authentication, a VPN, like a strong data security policy at the company, and teaching people how to do that. And so, even within something that's as hands on as taking care of somebody, in terms of a nurse or a doctor, there are still administrative tasks and work about work, that maybe that person would feel more comfortable doing away from the high-stress environment like the hospital, and they prefer to do that at home, where they have a little bit more quiet to reflect and analyse the notes and make sure that they're accurate. So, I would challenge the fact that, while I do think, of course, unfortunately, not everybody can have a 100% remote lifestyle or a digital nomad lifestyle, there are things that our society needs to have happened in person, there are ways to allow people to still have flexibility in their job, which is a really important distinction. But I've seen so many incredibly cool remote jobs throughout my travels. I've seen people that are professors that do all of their work and their studies remotely. I've seen people who work in the healthcare industry, not necessarily as frontline workers, but as managers, or they used to work in that, and now they coach other people on how to do that type of work, and they are able to manage teams of nurses while running that work remotely. All of the creative industries, like authors and publishers and designers, obviously, are quite easy to transition to remote. So, I think it's really about thinking what are the aspects of my job where I'm only interacting via using my phone or my laptop or a computer that could be a laptop, and how could we transition that to be a remote job.

Jeremy Cline 14:31
At the risk of putting you on the spot, what's the most surprising example of remote work that you've seen?

Ali Greene 14:37
That's a really good question. I think I was surprised meeting somebody who ran a team of nurses remotely. That was quite interesting. I was like, that's a really cool job to do, you manage the staffing and then all of that remotely. Also, someone who is able to manage the events on the ground, but the person themselves was doing everything remotely, especially things like goat yoga classes, where you have yoga and goats together, which is like very niche. And this person had like a team of people that were the yoga instructors and set up everything with the venues and managed the contracts and did all of that. We met in Kenya, and we lived and worked in Kenya, and these events were in the United States. So, that was pretty cool.

Jeremy Cline 15:31
I love those, absolutely love those examples. You've talked a lot about some of the pros of working remotely and what it can open up. What about the drawbacks, what of the things that people might want to think about before they consider taking the plunge?

Ali Greene 15:50
There obviously are drawbacks. It's a very unique lifestyle, and I think anything you do that goes against the grain comes with certain challenges, not only logistical challenges, but challenges in how you're perceived and what is accepted by your support system. And so, first and foremost, I would say, if you're wanting to take the plunge, have enough confidence to take that risk, knowing that you may not get the support you need from the people you already know, you might have to get out of your comfort zone to find a like-minded community that understand why you want to pursue a lifestyle like this.

Jeremy Cline 16:33
When you say support, support from whom?

Ali Greene 16:37
So, I think, when I first started travelling, and I said I'm going to quit my job in New York City, I'm going to work remotely and travel the world, you know, between 2014 and 2017, and my family looked at me, and they were like, 'Are you sure about that? Is that a smart choice? This sounds really fun for like a month or two, but you want to do this, and now it's been years, and it's been more years, and when are you going to stop? Haven't you gotten that out of your system yet?' And I said no, this is my lifestyle, this is something that really speaks to me, I feel very happy doing this, I feel really motivated in my work when I'm working this way, I feel very happy exploring the world in this way. And I think, at first, it was hard for my family to understand, it was hard for my friends to understand, they would call me at all hours of the day, assuming I could just talk to them whenever they wanted to chat, or every day I was home visiting to just get lunch with them whenever they could sneak away from the office to get lunch, without asking me if I was free for lunch. And I had to remind them, I'm working, I also need to check my schedule and make sure I don't have any meetings or deadlines. Just because I'm not going to an office every day does not mean that I don't have serious obligations that matter to me professionally. I'm not just hanging out at my house all day. Now, I think people understand, because of the pandemic, but at first, it was very confusing to people why I was going to a yoga class at 11 AM, why I was living in Cape Town. It just was confusing. And over time, I was able to, one, explain it to those people, and now I have amazing support from my family and friends, and they're super proud of me, but also, I was able to find digital nomad communities and other people who travel and work. And through those communities, I was able to have really great opportunities to grow my professional development skills and learn from these people with a work mindset in place and learn things about marketing and content strategies online and things like better accounting software, and just everything you want to learn, you can learn within these communities of how to run a business successfully, how to operate within your own business and champion for yourself and be a good manager remotely, as well as learn more personal development skills and just have fun with people and connect with people. And now, every few months, I will see a friend that I've met from somewhere around the world, because we intentionally plan to meet up in different cities and spend time together. So, for example, in Spain a few months ago, there were I think seven or eight people, all from different countries, all with different jobs that were spending time in between three different apartments here, and we would all work together on our different jobs during the day and then meet up for dinner and just talk about how life's going at night, and this built-in community just popped up, because we had met each other in our travels

Jeremy Cline 19:50
So, there's your interactions with other people and getting people to understand what you do and how you do it and that kind of thing, so that's one of the drawbacks. Can you touch on some other things that people might not think about that can potentially be drawbacks, or could present challenges or difficulties?

Ali Greene 20:08
I would say for full-time employees especially, if you're going to be the pioneer at your company choosing to live this lifestyle, and you don't already have a globally distributed company, learning how to manage your boundaries and how to interact very concisely, asynchronously, which means using your written communication skills, pushing back on people who ask for meetings while still being respectful, and using those moments as educational moments around things like time zones and being efficient and creating things like knowledge bases, and just best practices of how to move business to a digital-first environment becomes almost a second job for you as an employee that's already doing your tactical work. But I think it's a job that pays off for future generations of remote workers at your company, because those are challenges that need to become part of that company's cultural norms. And so, for me, it was really exciting to be able to do that one, because I was an HR director, so thinking about company culture was part of my role. But for people that maybe are software developers, that don't want to think about that, know that you might be the first person, and you are setting a cadence for other employees that are going to be asking for this at your organisation.

Jeremy Cline 21:38
One of the very interesting things that you touched on there was communication and communication with colleagues, and you talked about asynchronous communications, so using written words, something that you can send someone, and they can read it hours later or whatever. One of the things that I really noticed that I'd missed when I did go back to the office, though, was those random chit chats with my colleagues. So, it's the sorts of stuff which you just don't get on a Teams call, because you're usually phoning someone with a specific purpose, but it can be an overheard conversation, you've got Person X chatting to person Y about what was on TV last night, and you decide to join the conversation. Is this something which you just have to accept isn't going to be part of working life if you are working 100% remote? Or is there a way that you can still have that element in your working life?

Ali Greene 22:47
I love this question. So, I think that both and neither are true. Which is a terrible answer for a podcast. So, when I think about spontaneous interactions and socialisation, which I think is the basis of this question, at work, I think about it in a couple of ways. One is, how do you have spontaneous socialisation and communication with your direct colleagues and the people that work at the same company as you, and the benefit of that is it makes you feel more connected to your organisation, the benefit for the company is possibly more innovation comes out of those conversations. And so, I think having very intentional ways to help people find others in an organisation that create a network effect, based off of not only your functional skill set, so not only all the designers should know each other, but people that have the same interests, everybody who likes watching Marvel movies in the organisation should maybe know each other. How do you do that if people are remotely, and they can't have these random interactions? Well, it can still happen, it just takes a little bit of work. It doesn't have to happen in Microsoft Teams meetings or Zoom meetings, which can feel a little forced and awkward. So, you have to think a little bit outside of the box. So, one way it can happen is using messenger tools and having employee interest groups and channels, where people can share information naturally and organically through those channels, in written form or send short videos, the same way, unrelated to a company, maybe you go on to something like Reddit or Instagram and follow things that you're most interested in. But this way, you're connected to people at work that are also interested in the same thing as you. This is really cool when organisations do this, because as an employee, you're opting in, you're proactively participating with new people. And it's not people that you're interacting with when you're doing the work. And so, now, instead of only knowing the five people that are the designers on your team, you know the five people that are designers on your team and the five people that like Marvel movies, and so, you've doubled the network effect that you have at your organisation. And one of the people that knows and loves Marvel movies is an engineer with five engineers. And so, now, you know more about the engineering team, so you can get best practices around how engineers and designers can work together. And so, it becomes this very like integrated community. And it doesn't necessarily take more time, because it's just when you're taking a little bit of a coffee break, you have that 10-15 minutes in between meetings, that you can jump on something like Slack and catch up with messages, because there's no obligation to respond in any sort of time cadence. So, I love when companies are really intentional about thinking through how do we uncover who likes what in our organisation and let them spend time with each other virtually. So, that's one concept. The other concept that I really like about remote work is that, who you're having spontaneous interactions with and socialisation time doesn't have to be people you directly work with, and it can still benefit you, your morale, your engagement and the ideas that come into your company. And so, an example of that, I live in a really small town right now in Spain. And sometimes, I co-work with people, but none of them work in technology. And so, I'll go to a coffee shop, and I'll be having a coffee, doing some work with someone who teaches Pilates, for example, or runs a salon. And you would think, well, what does that have to do with remote work or HR policies and things of that nature, but hearing us all talk about our challenges at work, and hearing their perspective, I'm able to generate new ideas, I then immediately take those ideas and bring it back to my organisation and say, 'Hey, I just had a co-working session and had coffee with some of my friends locally, and here are some of their challenges, and it made me think of this challenge with our teammates and how we could approach it from this new perspective.' And so, I think that is something very important, that companies need to allow more space and time for, is how do you engage socially with people outside of your company, and what are the benefits for that for the company, and what is that circular effect of just letting people spend more time where they're interested, whether it's related to the company or not. It's a very long-winded answer to say that socialisation should come from both places.

Jeremy Cline 27:35
Clearly, if a company isn't already there, then there needs to be quite a cultural shift on the part of the company in order to implement this kind of thing. And that's almost certainly a subject of an entire podcast episode in itself. So, I don't think we'll go there just at the moment. But following on from a similar theme in this idea of visibility, one of the comments that I've heard a couple of times in my sort of profession and professional services, professionals, law, accounting, that sort of thing, is that, when it comes to promotions, in particular, partnership promotions, the feeling has been that those people who continue to go to the office and retain visibility in person are those who are more likely to achieve promotion get better known, that sort of thing. If someone has heard that, how do you prevent that from putting you off going down this fully remote working lifestyle?

Ali Greene 28:48
Yeah, I think that's a really important point. So, one, I think, if that's happening in your organisation, there's only so much you can do as the employee to change culture. That is a systemic issue from leadership and HR to be more inclusive of people regardless of where they're working. So, if I see that in organisations, one, I would stop and really question the leadership team around how they're really managing things like bias in the organisation towards people that are physically close to them. That, again, could be a whole another conversation. But what I would encourage people to do is also look at what they have control over. And so, what they have control over is, if you're not going to get visibility through things like small talk in the coffee machine, then what type of visibility will help you gain influence and respect in your organisation? And I immediately think of things that are either educational opportunities for others in the company, where you have a unique perspective, or things that will generate innovative, potentially revenue generating ideas for the company, regardless of your functional area of expertise. And those two things, I think, remote workers have an incredibly unique vantage point over office workers, that are having their same routine day in day out, and they're not seeing new things, like new ideas, new challenges, new pieces of cultural information from around the world. So, there's less noise in their environment for them to really think and judge their lived experience and relate it back to what the organisation can learn. So, an example, when I was a digital nomad back in Latin America, and I had just started travelling for the first time, I decided to take a day trip to this small town that I thought was interesting. And I bought a bus ticket online, a round trip bus ticket. And I'm from the United States, and when we tell time, we do not use military time. And so, when I was buying my bus ticket, I had assumed that I bought my bus ticket for like an 8AM departure and an 8PM return. But I actually bought an 8AM departure and an 8AM return. And I don't know why the website even let me do that, because that would be physically impossible. And so, I get to the town, I do this day trip, and I go to take the bus back, and they won't let me on the bus because I bought the wrong ticket. And when I was very upset and very emotional, and it was like, well, now I have to practice my Spanish skills, which are very bad at this stage, it was one of my very first years travelling, I need to communicate with them and tell them the mistake I made, try to get a refund, try to buy a bus ticket, it's getting late at night, it's one of the last buses back to get to my Airbnb, all of these things taught me a lot of things that an organisation, regardless of what the type of organisation is, could learn from and use. So, if you're an e-commerce organisation, and you're selling things online, the user experience for customers, how are you making things easy for them to understand, and how are you building in stop gaps into the system, so customers don't make mistakes when they buy your product. That could be something as a remote worker that I had an experience for, that was new and very eye opening for me, that someone in your office didn't have. And so, to get visibility, the next day, like the Monday, hey, how's everyone's weekend, oh, I had a terrible weekend, this thing happened to me, I got stuck on this bus, and I was thinking about user experience online, and this is something I had that could be really good for our website. Who could I talk to in the engineering team to share this feedback, because I think our website could also learn something from this. That is a new piece of visibility, where you're offering unique vantage point that's educational for the company, even though you're not there in person, that is incredibly interesting and valuable, and people will respect that. And so, it's about really sharing your travel experiences and connecting it to the company, rather than, I think a lot of people try to hide their travel experiences, and just like work is normal and try to be the best worker they can be, but when I was travelling, it was always sharing these really uncomfortable moments that I had and what I learned about it in the organisation, and how it could help the organisation in order to prove that the value of me travelling was not just for my personal happiness, which was amazing on its own, but also had a lot of value for the company.

Jeremy Cline 33:43
I love that example. It's such a simple example, but I can see, yeah, just how powerful it could be. That kind of leads nicely on to my next question, which is about how you start to have the conversations at work, if you are interested in going fully remote. Lots of places these days, they seem to be offering hybrid working. So, there's an expectation that you'll be in the office two or three days a week, and then, if you want to work from home the remaining time, then okay, that's fine. So, that's beginning to get culturally embedded. But I think the idea of going up to them and saying, 'Yeah, but now, I don't want to come into the office at all', in a lot of cases, that's going to be a slightly harder ask. So, what are some of the ways that you can approach that conversation with an employer, and in particular, what are some of the objections that you can expect to hear back, and how might you deal with those?

Ali Greene 34:50
Yes. So, I think that allowing yourself to do it in baby steps is really important for both you and the organisation. It does take a lot of practice before it feels really comfortable and second nature for you. So, while you're leaning into building this muscle, it also allows room for the organisation to get more comfortable with it. A very easy mindset shift could already be, instead of a few days in the office, a few days remote, what does that break down to percentage wise, and how can you play with that percentage within the span of a month. So, instead of looking at it at a week cadence, let's say it's 50%, let's say you say, okay, it's 50% time in the office and 50% remote. Right now, we're only looking at it at a week cadence. But what if we trial it for a month, and I do two weeks in the office and then two weeks fully remote? What would that look like, and how could I manage those expectations, where this is the project I'm working on for the two weeks I'm away, this is where I'm going, this is how I'm going to safely connect to the internet and address all of their concerns upfront, and then the trial can get bigger over time. Last time we looked at it in a month cadence, what about a quarterly cadence, that's a month and a half away from the office, a month and a half in the office. And over time, it gets the organisation more comfortable. If playing with percents doesn't feel like something genuine to you, another way to negotiate is to tack on time to pre-existing holidays. So, let's say you're going on a holiday already abroad for two weeks, and you really want to go away for a month of time. What if you physically travel away for a month, and two weeks are your holiday, and two weeks are you working, what would that look like for the organisation? How could you make that work for them? How could you make it work for you? And have a very specific plan when you go and talk to your manager or an executive at your company around. This is the project I'm going to work on while I'm away for those two weeks. This is how independent I can be when I'm tackling these tasks. And these are the types of meetings I need to have and how I'm thinking about getting them done. So, I think, by proactively laying out that project plan, it's going to be really beneficial for you in making that ask. A third recommendation I have is, instead of trying to do it fully alone, making the jump with an organisation that specialises in helping people travel and work remotely, and so there are things like co-living spaces, in Spain there's a place called Sun and Co., and they have professional development skill shares and lunch and learns as part of their accommodation package for remote workers. There's a similar company called Hacker Paradise, maybe your manager doesn't like that name, but it's the same thing. They do weekly goal setting, they do Monday networking lunches, where you get to learn about what everybody does for work, and they do Thursday talks where people do educational talks or have different themes. And so, maybe joining with other people through a programme like that would make your company more comfortable. And so, those are three very tactical suggestions I have for full-time employees looking to make the leap. I think the biggest areas of pushback right now that I hear is that there's no set policy in place yet. So, they're just looking at things at a case-by-case basis. And people are really still, there's a grey area around compliance and tax and HR rules and regulations, what happens if you get hurt while you're travelling. And for scenarios like that, there are companies that specialise in these things, so your HR team doesn't have to worry about it. If your company is interested in allowing this type of work forever, there's companies like Remote and Deel and Oyster, that are essentially EORs that help you hire and deal with compliance all over the world. And so, there's great resources that already exist, that help you navigate that. And in terms of thinking through policies otherwise, I would say just make sure that you're thinking about the policy that will help you and the employee come up with a mutually beneficial agreement. And think about that and evolve it over time.

Jeremy Cline 39:35
Just going back to the first two examples you gave, so the playing with the percentage, so rather than three days in five, call it whatever, three months in five, or whatever, and also making it part of your annual leave, so I'll be away for four weeks, I'll work for the first few weeks, and then I'll be on leave for two weeks. Both of those examples I've actually seen at my company. So, I'm just saying this to highlight the point that I have seen this in practice, yes, it can definitely work. Suppose you are interested in this lifestyle, but as you said, there's only so much that you can do as an employee in relation to the culture of your company. And you might conclude that this is just not the right place for me, because I really want to do this, I can't do it here, I'm going to have to go somewhere else. What are the best ways of finding companies that you can work for, where this is on offer, where they have this culture of, maybe it's not everyone works remotely, but it's a possibility?

Ali Greene 40:44
So, two really good resources for that, one is a job board website called Remotive.com. It was really exciting for them, they used to be Remotive.io, so that still works, but now it's Remotive.com. And they have very up to date, regular job postings from all over the world, from some of the best all remote companies that exist. I think they're an incredible resource, because they also have a newsletter that shares information about remote work and things of that nature. So, really stand out, love the work that they're doing to push forward just thinking differently about what working remotely looks like. There's also a company called Growremotely that is helping people connect to companies that are offering some sort of remote offering and really takes into consideration what the candidate's personal values are, and matches the two together. And so, that's another really great resource that I would recommend people check out. And for managers and leaders in this space, Running Remote is another very excellent community about some of the issues we've talked about today, like how do you set up a policy, how do you make sure your team has visibility, how do you make sure that things are inclusive, it's a community that I'm part of, and I just love and admire all of the people in there and how willing they are to share their examples. And so, for managers that are really already being forward thinking of how to offer that for their employees, I would recommend checking them out.

Jeremy Cline 42:27
Awesome. Well, this has been a fascinating introduction to the topic. Thank you so much for coming on and talking about it today. Where is the best place that people can find you and get in touch with you?

Ali Greene 42:40
Yeah, so I am on LinkedIn, Ali Greene, and Greene is like the colour with an extra E at the end, but I'm sure this will be in your show notes as well. So, you can connect with me personally on there. And I'm also writing a book on remote work, specifically for managers and their teams, and it's going to be a while since it comes out, because my deadline for writing is in a few days, but if you want to follow along that journey, we also share newsletters quite often with behind the scenes of working remotely and some tips, and so you can find us on remoteworksbook.com, and get in touch with us, us being me and my co-author, if you want to learn more about that.

Jeremy Cline 43:23
Fantastic. I'll put links to those in the show notes. Ali, thank you again for coming on the show.

Ali Greene 43:29
Thanks so much for having me. This was really fun.

Jeremy Cline 43:31
Okay, hope you enjoyed that interview with Ali Greene. Like so many things, one of the clear messages I got from Ali was that this doesn't necessarily have to be all or nothing all at once. It's possible to take baby steps to manage your transition to remote working, if this is something which is of interest to you. Say you're expected to be in the office three days out of every five, well, is this something that you could achieve with a five-week pattern, rather than a five-day pattern. Say you spend two weeks working from home, versus three weeks working in the office. This is something which I've seen people doing, and it seems to be working out pretty well for them. Just because your employer might have a policy doesn't mean that you can't get a little bit creative with it and see how you can tweak it so that it works well for you. It does also come down to cultural fit, and as Ali said, there are only certain things over which you have control. If you really want to work remotely full time, but it's just something that your employer is never going to agree to, no matter how much you try and how much you ask, well, maybe it's not the place for you. Maybe there's another employer who would be a bit more open to this idea. I also loved Ali's point that this could have benefits, not just for you, but for your employer as well. Again, it's a question of being creative, figuring out what the objections might be and addressing them in advance, figuring out what the benefits might be and highlighting them. We tend to get so used to the way things are done at work that we forget that sometimes you can do something a little bit differently. Ali mentioned a couple of websites there, and you'll find links to them on the show notes page for this episode at changeworklife.com/138, that's changeworklife.com/138, where there's a full transcript of the episode and a summary of everything we talked about. Also, it would be great if you could spare a couple of minutes to leave a review on Apple podcasts. With so much podcast content out there, reviews tell people that they're going to get something from listening to this particular podcast, that there's content in there that's going to be right for them. So, if you found this or any previous episodes helpful, please just take a couple of minutes to leave a review on Apple podcasts. The five-star review would, of course, be amazing, and you can do that by going to changeworklife.com/apple, that's changeworklife.com/apple. I read every single review, so yeah, please do review the show. In the meantime, there's more great content to come, so subscribe to the show if you haven't already, and I can't wait to see you in the next episode. Cheers. Bye.

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