Make it Happen with Maya Middlemiss - What is the Future of Freelancing?

Looking to learn more about the future of remote work and freelancing? Look no further than this insightful interview with Ali Meehan and Maya Middlemiss. With over 23 years of experience working remotely, they share their perspectives on the benefits and challenges of being a digital nomad, the real importance of community and collaboration, and much more.

Whether you're a freelancer or considering remote work, this conversation is a must-watch. Discover how you can live and work on your own terms, no matter where you are in the world. With the rise of remote work, the possibilities are endless, and Ali and Maya offer valuable insights into how to navigate this exciting way of working.

Discover how you too can join the growing community of digital nomads and remote workers.

Connect with Maya through her Linkedin profile - https://www.linkedin.com/in/mmiddlemiss/ 

Don't forget to subscribe to our channel for more insights from Women who make it happen in business and in life.

Transcript

Well I'm back in the Make it Happen studio and today I'm delighted to be joined by Maya Middlemiss. Maya and I have quite a few things in common Maya and, I apart from both living in Spain, Maya and I have actually been working online for a very long time. So we've both been working remotely; me since 2000 and Maya a little bit longer and she's actually created a community for Digital Nomads and written a few books about the subject as well as having a podcast so I'm really excited to be talking to her let's meet Maya [Music] Hi Maya. Hello Ali it's lovely to be talking to you again. It's good to see you too it's been a long time. Please do introduce yourself to the Ladies who haven't met you before. Okay well I'm a freelance writer, journalist, podcaster um my obsessive uh key themes are the future of work and freelancing and enabling people to live and work the way they want to and where they want to. So it's a really exciting area to be working in. I live in Valencia in eastern Spain. Been in Spain for 14 years now not always in exactly the same place so I call myself a digital slomad not really that nomadic because we're here with a family and a life but yeah it's just brilliant to be able to have those choices and to see those choices opening up for more and more people now. Yeah. I love that I love that you and I have been in that type of environment for a long time but people are beginning to catch on now which is great so you offer a lot of services for people that are thinking about becoming digital Nomads as well as people that are already digital learners but learning as they go so we're going to talk a little bit about that but first of all tell me about your move to Spain? Was it something you've got planned over a long time or did it just suddenly happen? It did take quite a long time but we're going back to 2008/2009 then when lots of things were more complicated um and it's going back quite a long way now I kind of thought it would I mean some things were easier then obviously we had a freedom of movement in the EU it was a case of just rock up and and open up as a freelancer and just carry on with work so that bit was straightforward. Things like the the broadband and everything else was a nightmare um. Dealing with my employer at the time that was complicated but yeah. It was something I suppose it took us about a year end to end but we did spend some of that time just going "should we" you know not really doing anything about it. So it was it was the classic story. We went on holiday for a weekend and suddenly thought we could live here and then it so I suppose it took about a year end to end to make that happen but we haven't looked back. What would actually be your advice for people that think I could live here based on a holiday? Well yeah you probably can I mean it's obviously it's more complicated in terms of the Visas and residency now but if you if you've got a way to support yourself there's probably a way of doing it between the autonomous Visa or the new digital nomad visa. So you need to be very clear about how that's going to happen and it's it's good to be plunged into the Spanish bureaucratic procedures early on but there should be a way to make it so now and certainly even things just like the the technological environment is so much easier than it was a decade ago when we did it and you know even things like getting your paperwork done we have digital signatures now we have Broadband that works and things like that that you know it's so easy to take for granted but we certainly couldn't back in the day so if you want to make it happen then there'll be a way of doing it. Brilliant Yeah good and you've created a fantastic Community for digital nomads based on your experience which is a long experience how long have you been actually working online remotely? I've been working online remotely now for 23 years which is very easy to date because my Millennium baby was the reason I didn't want to go back to somebody else's office. I'm not sure I should call it that anymore because she's she's obviously not a baby anymore but she was the reason I started working as an employee working from home back at the turn of the Millennium and obviously that was working from home rather than working remotely. There wasn't anything remotely nomadic or mobile about it because it meant being plugged into the wall with a big grey box and it was it was some years after that that I realised we could move away from the suburbs of London and I simply wasn't going up to the parent company much anymore at that time anyway and things were becoming more decentralised and we thought we'd move out of London and by the time we looked at where we really want to be. It was more far away after that trip to Spain so we wound up here so it's it's yeah it's definitely doable and yeah sorry what was the question I've got on rambling off again. Oh it's okay I was just thinking about the community that you've created based on yeah and you're really into healthy happy home-working as well aren't you not just doing it because you can but doing it and making it healthy and having a great environment around you well it's all part of creating a lifestyle that really works for you and the healthy happy homeworking project. I started that well actually that was going to be a big book and I was planning and pitching that towards the end of 2019 because I've been doing that would have been my 20-year anniversary of working from home and I had it all pitched and outlined. I was talking to agents at the TED Talks everything because I thought I could there was nothing else I needed to learn about working from home. Then of course early 2020 the whole world changed overnight. There was much less of a market for big reminiscent bible-sized books of how to do things and what was needed was something much more actionable and tight and "help me I'm drowning" and people being forced into working from home so a lot of the big plans went out of the window. It ended up being a couple of shorter books. I call it a series because there should still be a third one one day but I've ended up um kind of diverted into other things including the Remote Work Spain Community which I set up on Facebook a couple of years ago now but that started exploding last year just because the world was unlocking and people were grasping. New potential opportunities we've got we've now got this range of Digital Nomad Visas all around the world. There are more and more opportunities for people to think about what they want and to be honest whilst I still use the branding healthy happy home-working and I've got those two books. There's been quite a shift away from working from home as a thing because people don't have to do that anymore and it's it's really important that people don't associate working remotely with being stuck indoors because we're not anymore and a lot of the problems that people associate with people with being away from the office are actually problems caused by lockdown that people were isolated they were unhealthy unhappy. They were sharing space that wasn't appropriate for work and so on and there are so many good solutions to that now we don't all have to up-sticks and be a digital nomad and wander the world with our MacBooks and our rucksacks you know there are so many different options now to be mobile, to be flexible, to be employed, to be a business owner, to be self-employed. Just the whole world of work is changing so my messaging is moving slightly away from working from home to working where you want to but without wanting to get sort of too it can get very adversarial the kind of Digital Nomads versus Expats and really it should be about individual choice and I I work from home 90 of the time I I find it much easier. I've got my my big Monitor and you know all my coloured highlighters and my books and the things I like. I'm perfectly capable of working from a small laptop like last week it was great to be at the running remote conference all week and I took my tiny laptop with me and I did get some work done on it Airbnb iffy Wi-Fi so it's possible but for me I know that working from home is the default and the fact is what's liberating about it is I can choose where that home is and what I do as soon as I log off at the end of the day I'm living where I want to be. Yeah yeah and it is fantastic the facilities we have now for working remotely or wherever you want to work from because like you you know I started in 2000 and then you had to live within 300 metres of the telephone exchange to get internet. Yeah and there was none any of these co-working spaces that have popped up everywhere um around Spain and around the world. Yeah it's brilliant a choice for having a community a physical community and you've created a fantastic online community as well to help people stay connected which is brilliant yeah we need community Well you've been doing that with Costa Women for a very long time recognising that need that we you know we If if we we turn up at an office each day we get given that Community. It's like it's almost like family you know you don't choose them unless it's your business but when when you work remotely you have to create that for yourself and it's the same with the health aspects you have to go for a walk and eat well and and practice that self-care but just like everything else to do with working remotely it's on you You haven't got a line manager looking at you saying take a lunch break or go for a walk in the sunshine and it's it's the same you know with your your social boundaries as well it shouldn't be up to work to provide you with that but a lot of people I think, I don't know what the statistics are, but people end up marrying people from work and things like that and that's not going to happen so much going forward but actually I would say that's a good thing 
Yeah yeah and thinking about that then thinking about um having to to find a community and thinking about things that you would naturally have like standing around the water cooler talking to people and having that social interaction what would be your three top tips for people that are new to this whole environment of working remotely or working from home and not and looking for that type of connection that they would normally have? I mean one of the things about moving to Spain is if you've got if you move here as a parent it's quite easy to integrate in lots of ways because you'll go into the school gate and you're meeting people there and it's similar for people that are working remotely you would sorry working in an office you would go to an office you'd make those connections you might have a relationship you might get married um but obviously that's no longer available for people. So what would be your three top tips? um That's a great question and I think I would say first of all own it and realise you need to be intentional about it otherwise you will be lonely and isolated and you know. I know some people who are extremely methodical about it who travel regularly and have to do this every six months. um I don't live like that so I can take a little bit more time putting down roots but you can think about your networks it sounds it sounds almost wrong to be strategic about friendships but if you're going to be living somewhere then you need to make an effort to get out and meet people and we're not in lockdown anymore. There's stuff going on you know if you haven't got the school gate and 30 new friends called 'Mamada' then you can go out and find people. There are there are clubs, there are activities, there are sporty things that whatever your thing is. Have a look, use the social media that we have available to us you know. Every local area has got a Facebook group stuff going on. Go and rock up and try out activities that might not be things that you would naturally be drawn to but it's a chance to meet new people go to the meet-ups go to put yourself out there a bit. Even if it doesn't feel totally comfortable at first I think that's really important so that's your local scene try to find people to connect with then use your business, your professional activities and look for ways to connect there because you will find there are communities of interest everywhere whatever your niche thing that you do, that you care about is. There'll be a podcast about it. There'll be a Facebook group. There'll be meetups about it. You might have to travel a little bit further to find your tribe but when you do it's so powerful and so energising to connect with people who care about the things that you do and this is what social media has given us is that chance to go beyond the geographic boundaries so you need both. You need your local tribes, the people to hang out with at the weekends and when you finish your work from home but never neglect your professional networks either because those are the things that will feedback directly into your work and your business actually it would just create great connection and community as well and it does spill over into real life. It was brilliant to be at running remote last week and to connect with people there who I I know really well it feels like because I've known them online for years and I've met them several times but we've never been to each other's homes or even each other's home countries in some cases. They're just people who are part of my professional tribe and it's important to nurture those relationships too. Yeah there's really great tips there I I think we we forget it's our responsibility. We're waiting for somebody else to do it for us so it's really good to have those tips from you you know about actually seizing the day and going out and doing it yourself. Did you have any business roadblocks when you started your remote working and if so how did you overcome come them um That's interesting because because of doing it for so long it just feels like another world really and it was in technologically and socially and everything else at the time I was a new mom. I was working from home in the London suburbs and it was isolating because nobody worked from home. I mean there were the the stay-at-home mums on the school run and they were the suited and booted drop them in and run to the station mums and there wasn't anybody like me and that's probably why we ended up moving away before too long so there were social roadblocks technologically and just from a work point of view I had to figure it all out myself. There was no Remote Work Spain Facebook group which you're all very welcome to join. There were there were no training resources. There were. There was very little guidance to how to manage yourself and while I was essentially an employee I was setting up a project on my own. I had no line management or accountability in that sense it was just a case of you know we'll try this for six months and I had very little sense of how to measure what I was doing, how to be productive, how to be focused and I think the resources that are available now make that so much easier. You can find accountability buddies. You can find other people working the same way you are but I had no clue about any of that so I think the roadblocks were largely structural in that sense. I couldn't there was no sort of guidebooks or or instructions uh it was like okay you want to try and make this work working from home. I was lucky enough to find somebody who would pay me to do that but they couldn't tell me how to do it. No and in the day I don't I think a lot of employers are beginning to feel more relaxed about having their team working from home. In the days when you and I were doing it, it was actually really unusual for bosses that they could trust you enough to work from home and that you wouldn't be spending the whole morning down at the coffee shop. Yeah I think there's still huge trust issues unfortunately in lots of organisations now that we're having this tension about people being summoned back to the office and you know there were lots and lots of places never wanted to go down this route um but people made it work and they made lifestyle decisions based on the fact that they could work from home and now JP Morgan or whoever's saying right no you we want you all back at your desks That's like, what you trusted me for the last three years yeah and I've been productive and effective so yeah People have have become more intentional about what they're doing and more conscious of choices I think and they're just they don't want to be locked down anymore whether that's at home or in an office yeah yeah Do you have a business role model and if so who are they and why? hat's interesting I don't have um any specific individuals that I would describe as a role models there are people whose work I always pay attention to this year. I've been geeking out a lot on Jenny Blake who wrote the book 'Free Time' and 'Pivot' but her podcast is is great as well It's got really nice production values and she's got a very melodic voice I can listen to for ages but she's very focused on uh using the concept of free time as a verb and freeing up your time to get rid of the the busy work and to automate things and so she's she's got that balance I suppose of the kind of really heart-based principle-based doing good work but also getting rid of all the unnecessary stuff to do that and I find as a solopreneur that inspires me that you don't have to grow you can develop your professionalism without scaling and hiring people. Brilliant and you've also created your own podcast haven't you? Yes uh I have a podcast which is it's not limited to Spain it's "The Future is Freelance" which um interestingly it started off as a freelance gig I was doing for a client but then ended up spinning that off independently when they didn't want to go ahead with it and I built an audience and a message around that and it seemed to me it was a bit of an inflection point earlier this year when they obviously had other priorities for their marketing budget but I realised that it was kind of you know "is the future freelance or not?" if I've been doing this thing for nearly a year and if I actually believe in it, it would be very wrong to stop it and I I really had no choice but to see if I could make it work independently. I really enjoy doing it so um you know at some point I need to find a sponsor to support it financially but at the moment I'm actually really enjoying the freedom to not be accountable editorially to anybody else just to enjoy the process to unearthing really interesting stories and guests and being able to go where I want to with it and learning about all the editing and things like that which I used to have somebody else do but it's important to know all the steps yourself anyway because you know this is the problem when you were when it is you on your own and you might have to do it yourself anyway so it's been good to learn those skills. Absolutely and that's actually interesting for my next question which was what advice would you give other women that are thinking about going freelance or working from home or working remotely um because obviously over the years you've picked up a lot of information including what you put into your two books so far um and I think for a lot of women they won't even have thought of things like having to do the technology themselves or learning, so what advice would you give? Would you go back and change anything? Well I think it's if I started from from here now it wouldn't be the same me as then so uh it's certainly things are a lot easier in many respects they're harder in others because you have so much choice in so many different directions you can go in but I think what advice would I give people I think it's definitely easier now you can start freelancing. You can start a business from next to nothing but I have a podcast episode about it called "minimum viable freelancing" in season one which is really about just try to identify that gap in the world where you can add value and you can literally bootstrap yourself into that if you have a laptop that's it you don't need to raise money. You don't need to have a big business plan. You don't need to have investors. You don't need to give away equity and an idea before you've proven it nearly everything knowledge base you can just do for yourself but you need to figure out that minimum viable hustle and then just go and test it out. It's difficult in Spain because it's not really much as we love it here and you and I've been here a long time so we do love it but it's not a culture that fosters innovation. It's hard to take risks you know you only get one shot at your autonomo discount every two or three years or whatever it is. It's it's not the easiest place to innovate and have a go but I would say just try and prove an idea in the most agile straightforward way that you can and then iterate on that once you start getting money in then you can invest in equipment and websites and services and outsourcing and things like that but try and test things in as low risk way as you can and who knows you know. Whether it's a local service, whether it's something that you can network globally, you might just have found that thing that's really you and that speaks to what you want and that thing might change. It might shift over time the world change is fast certainly in the space I work in you know a lot of my freelance workers for technology companies and they're going through a horrific flux at the moment and I have to be honest you know there are people I worked for for a long time who just basically have no freelance budget anymore. I've shifted a lot more to content creation than journalism because publications aren't using Freelancers. They're keeping things in-house as most effectively as they can and so you have to be able to be ready to shift as well and that's another reason to stay small, to stay really agile and obviously it's great if you have the kind of business where you're going to scale and hire people then that's fine but for me I feel much safer being a solopreneur and contracting with people for specific activities if if I need to. I love collaborating with other people don't get me wrong I'm not yes got to do it all myself it's not like that at all but from a business point of view it's definitely these are strange times we're in and they're going to stay strange for a while now I dare say so I'd rather keep the flexibility. That would be my advice yeah yeah yeah and I think also like you've created the um community that you have the remote working community I think a lot of particularly women feel cautious about asking for help when they come up with an idea so I think that's also a good thing to do like you mentioned earlier to actually look into some communities and ask for advice and support on that fantastic idea you've got. There'll be something out there, there'll be somebody who's figured it out who's had that same question um maybe they'll help you, maybe you'll get dozens of different answers and you have to pick through them but there is there's nothing to be gained by reinventing the wheel for sure. yeah yeah What next for you then Maya? You've mentioned that you might do another book in your series but. Yeah possibly I don't Book writing takes such a long time. It's a very focused activity. I'm you know I've got several books out there now and I mean this is this is a hard thing to say to anybody who wants to make their way as a writer but books don't pay when you're in when it comes to actually keeping the lights on Working for clients is the most effective way um we're also in a strange time in terms of the threats to a lot of content work from artificial intelligence, large language models so there's going to be it's going to be harder and harder for people to break into writing So for me yes there will probably will be more books but there will be more of other forms of content as well including the podcast, including video live keynote speaking. I think it's important for anybody who wants to specialise in content to really niche down and have a vertical where they become a thought leader and a subject matter expert as well because the general stuff will go to the chatgpt's, you know the product descriptions and so on. So for me I really want to focus on my advocacy when it comes to new ways of working. I've been doing a lot of work for the Estonian e-residency department and that's absolutely fascinating looking at the governance structures for working with our borders, There are lots of really interesting projects going on around passporting and the digital Nomad visas and even things around ways to employ people from different countries and so on that gives us that mobility and lifestyle in a way that's safe and legally compliant for the employer so those are the areas that are exciting me at the moment, where I'm looking into ways to tell those stories and bring that knowledge into the world to people who need to hear it in whatever way or form that might look like. It's all storytelling really but how the actual platform and and the media that I'll be using I don't know yet but I'll always be open to great ideas and suggestions and collaborations so let's put that out there. Brilliant well you never know who's listening who might be interested. That's why it's always great to respond to an invitation like yours and say yeah let's talk about these things now let's do it. So a quick fire round - what book have you read which made a difference to your life and why ? um Loads of books I said there's one that I tend to come back to every couple of years which is Paul Jarvis's "Company of One" which anytime I I get any mad urges to start growing or empire building or hiring people I need, I get this book out and smack myself around the head with it for the reasons that we just discussed that you know small is beautiful. You can grow, you can develop, you can become more professional. There are so many more ways to grow than building a team. Yeah good Do you have a superpower and if so what is it? A superpower well I suppose the superpower that keeps the lights on for me is storytelling yeah I've always been a Storyteller and there are so many contexts in which you can do that whether as a writer, a podcaster, a parent, a fundraiser you know If you can figure out the beginning, middle and end, the plot points, the hooks, the narratives, then you can bring any story to life for people so it's one worth cultivating. It is definitely and I think that's important to mention particularly but you mentioned artificial intelligence you know the AI is never going to tell your story so 
um we shouldn't just be scared by what's out there because it's never going to do what you can do uniquely yourself. Something you will achieve before the end of this year? 
I need to get the podcast profitable so that's my goal this year is to really build quality content there um build a good body of knowledge and find somebody who wants to sponsor it in case they're listening right now! 
We'll we'll let them know how to contact you in a minute. Would you have any advice for a younger Maya? That's a great question maybe branch out on your own earlier. I was an employee for a long time and I I really only I fell into freelancing out of lack of choice and you know it was the only way I could stay here in Spain was to to freelance because I wasn't. I know since then I've become completely unemployable I think but at the time that there were very few options available because my Spanish isn't professionally competent for the kind of work that I do so it was freelance or die So yeah I would say overcome that imposter syndrome don't wait until you have no other choice and have a bit more confidence in yourself is advice I'd love to give to a younger me or any other younger version of me that's out there listening now right. Love that and how can people contact you if they're interested in sponsoring the podcast? 
Fabulous books, well the books are all on that Big Book seller is just generally the easiest way to get hold of them. You can find me on mainly on LinkedIn and Twitter um if you find Maya Middlemiss it's me. I have this weird situation of being the only person with my name on the Internet so you can find things I've written, posted and so on, by just by searching for me but LinkedIn and Twitter are where I'm most active. If you're on Facebook then Remote Work Spain is the big community so do come along and join us there if you're in Spain. If you're dreaming about Spain, if you're a digital Nomad, if you're looking for work, come on it's a really friendly really active community so you'd be extremely welcome there and I also do a newsletter there's the website Remote Work Spain Info but I do a newsletter every week or two weeks which has jobs in it that people can do remotely from Spain so that's quite popular on the freelancing side. The podcast website is futureisfreelance.xyz so you can find links to all the episodes there. All the different players because we all do our podcasts in different ways so I have all the you can either listen to it in the browser or or hop straight into your favuorite podcast app from there so yeah I'd love to see you via any of those means just reach out and say hello because you know as Ali has proved over years and years it really is all about Community. Yeah and and for what you've said earlier it is important that we stay um educated if we're remote workers as well and your Remote Work Spain is a fantastic resource for people that want to connect both with people that are doing the same sort of things that they're doing even if it's just working remotely but also for the resources that you share in there that are really useful too So we're lucky we've got a really knowledgeable community and it's really engaged there are people there who are really willing to share and answer questions and I I mean I'd like to get some some moderation help with it one day but for now it's it's me doing it all and there is zero tolerance of any kind of and you know messing around or trolling or anything people just don't get in in the first place or they very quickly get booted out so it is a nice community so come along and there's there are no silly questions but it's good. Well thank you Maya for the chat today. It's been really interesting and really informative for people that are whatever stage they're at of their digital Nomad / remote working Journey. It's really good to see you again and be in touch again soon. Lovely it's been a great pleasure Ali thank you for having me. I really hope you enjoyed this latest recording of the Make it Happen series and I'd love you to subscribe to our podcast channel or if you're watching this on our YouTube channel just click the Subscribe button We'd love you to continue hearing and seeing more of our make it happen interviews If you're not a member of Costa Women yet but you're a woman who is living in Spain, or a woman who is thinking about moving to Spain, do come and join us at costawomen.com It's completely free to join. I look forward to sharing more "make it happen interviews" with you next time. Bye for now.