TMBA551: Transitioning from Freelancer to Running a Business

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If we had to pick one word as our greatest motivation, it’s ‘freedom’. Freedom to live life on our terms, where we want, with the people we choose.

Ali Marsland is the director of ‘The Effective English Company’.

Ali began chasing her own freedom at the age of 18, as she traveled around the world for a year before embarking on a successful career in corporate communications.

That eventually left her feeling trapped, and when the opportunity arose to become a freelancer, she decided to chase that freedom once more.

Ali joins us on this week’s podcast to describe how she ‘stair-stepped’ her way into entrepreneurship by first becoming an on-site freelancer to outsourcing work, and eventually growing her own successful agency.

See the full transcript below

Listen to this week’s show and learn:

  • How Ali’s work in the corporate world taught her skills that she is still using today. (5:29)
  • What sparked Ali’s decision to transition from freelancer to running her own business. (12:04)
  • How Ali was able to overcome her hangups about outsourcing work. (17:25)
  • What makes The Effective English Company different from more traditional businesses in their industry. (21:00)
  • How Ali’s personal values have permeated through her entire business. (22:19)


Mentioned in the episode:

Before the Exit – Our New Book
TMBA Masterminds
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Ali Marsland
The Effective English Company

Enjoyed this podcast? Check out these:

TMBA540: Are You Generating Income or Wealth?
TMBA546: Adjusting to the ‘New Normal’
TMBA548: The First 1,000 Days of Running an Agency


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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian





Full Transcript

Ali: I’ve tried to create a company that I would like to work in. If you’ve got something you’re not happy with, you have to speak up. Because I think you have to have that trust and openness and communication internally in order to be able to work well together and to deliver good service to clients.

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Dan: Welcome back to the pod. You know we have guests on for all kinds of different reasons. And today’s story really resonated with me because it’s one of those fundamental motivations of location independence. Sometimes it’s not the drive to start a business that gets us thinking about business, it’s the freedom to spend time abroad and to move freely around the world and to control our income.

This week’s story is how you can turn that motivation into a relatively reliable way to generate location independent income. Today’s founder is Ali Marsland is Founder and Director of The Effective English Company, which she describes as ‘providing an extra pair of hands for busy communications teams’.

Now, like many of us, Ali had the prospect of a pretty damn good corporate career, working as a communications professional within the National Health Service – which is, of course, the UK’s health system and is actually made up of around 400 organizations throughout the country

But, as you’ll hear, Ali decided the path she was on just wasn’t a good fit for her. And today she’s going to share how she turned her skills, contacts and knowledge of that sector into a service and then agency providing a wide range of all kinds of copywriting, editing, proof-reading and more.

I think there are lots of insights for anyone sitting out there in corporate-land thinking, ‘I wonder if I have enough momentum and a solid enough plan to take the leap’.

Added to that, she’s a passionate dragon-boater, a sport that has been mentioned more than once on this show.

So I’ll let Ali take it away …


Ali: My absolute core value is freedom. And I’ve been very focused on creating the lifestyle that I want, and developing a business that enables me to have that lifestyle. We go back to when I was 14 the travel bug bit. And I basically spent the next four years planning to then take a year off after school and literally went around the world when I was 18.

I went to university because for me, that was kind of just what everyone assumed I would do and I didn’t have a better idea. And the whole way through university, to be honest, I mean, it was okay, I didn’t do badly, I didn’t hate it, but I just never really settled. I was always on the verge of dropping out but I also was always very sensible. And I kind of, even at that age, thought, ‘Well, there’s no point, I don’t want to just drop out and then figure out what to do’. There’s no point doing that. But as soon as I figure out what I’m going to do, then I’ll drop out and do it. Well, I never figured out what I was going to do. So I ended up getting a degree.

Dan: And that degree was in?

Ali: Linguistics, so I did my degree in linguistics and obviously at the end of the course, I’m supposed to have a plan, or at least I need to decide what I’m going to do next. And at that point, I had no idea. I didn’t know what I wanted to do for work. But I was very, very clear that I did not want to just sort of step into a corporate job and I had this phobia of signing up to the corporate career path. And then waking up 20 years later, realising I hated my life.

And by that point, I knew that I did love travel. So I went to the careers library, and this was sort of 1998 so this was before the internet was a really big thing. So it was this massive big lever arch folder of ‘overseas opportunities’, and there was a sheet in there that was ‘go teach English in Sudan for two months’. Okay, that sounds like okay, I’ll do that. And then I went and looked at where is Sudan? I kind of filled in the forms and sent off for it and then find out some information afterwards. So I did it all backwards. I was like, ‘Yeah, seems like a good idea’.

Dan: And was it a good idea?

Ali: It was a good idea. Yeah. And I went for two months, stayed for a year. I enjoyed it. It was really, really interesting. I’m an okay teacher. But turns out teaching English isn’t what I want to do with my life. So I came back to the UK to figure out what came next.

Dan: It sounds like when you came back that you did join something that looked like that corporate solid path. Can you describe what you did next?

Ali: I came back from Sudan. And still at this point, I knew that I was interested in language and communication. You know, I’ve got a degree in linguistics, that has always been a theme. And, I’d always loved sort of writing and had an interest in magazines and things. So the first job that I got was working on the staff magazine for a retirement store in the UK.

They had a magazine that was produced weekly for all the staff in the store. And actually, it was a brilliant job. I loved that job. I learned loads. But it’s a weekly magazine and so by the time I’d done it, sort of for a year, I think two years cycle, it was the same stuff coming around all the time. You know, we ‘Okay, we do a feature Easter’, we do a feature on Valentine’s’ we do a feature on, you know, only the sort of annual events as a big Christmas thing. By the time you’ve gone through that process a couple of times, and you sort of running out of, you know, fresh ideas. And I always need to have a thing, something I’m working towards a project of some kind.

Dan: So what did you give yourself as that project at this moment in time when you’re starting to feel the hamster wheel effect, so to speak?

Ali: So from that one, the answer that point was I changed jobs. So I was still in kind of the corporate world at this point. Yeah. So I went, then I got a job in a PR agency, which was where I learned how to write a press release. I actually hated that job. But it did teach me lot. I think I was there for about a year. I eventually left that job without another job to go to because I hated it that much. And then I managed to find another job. I mean, I’d been applying for other things, found another job, which was a communications manager in the NHS.

Dan: And what was that like working there?

Ali: And that was great. And again, it was a really good training role for me. I was producing newsletters, I was doing the media handling, I was doing proactive and reactive media handling. I was updating the website. I was planning campaigns, I was doing everything and that job was great, but it was a long way from home. I was driving an hour and a half each day to the office. At the beginning of the day, and then again back, so I was literally driving for three hours a day to and from work. And obviously I knew that was going to be the commute when I took it. I thought, ‘Well, I can sort of stick anything for a year’. I ended up staying there about 18 months and, and then I got a secondment to a similar role in another organisation much closer to home. And that it was great just being that much closer to home. And then that contract was extended a couple of times, and then it wasn’t extended. I had no job. And I went, ah, ‘Now why am I going to do’?

Dan: What year are we?

Ali: This is 2006 now

Dan: So 2006 you get dropped? And how do you respond?

Ali: So initially I ran around and flapped and panicked a bit. And then I started talking to people close to me and sort of realized, ‘Well, I’ve been kind of thinking about maybe going self employed, like trying this freelance thing’. And so I thought, ‘Well, I’m being put in the situation now where I’ve got no job. So if I don’t try this freelance thing now, would I ever have the guts to actually leave a secure job to try it?’ I don’t know if I ever would have done it.

Dan: What was the reason you have been wanting to try it?

Ali: Travel had been a big thing for me since I was 14. And, and I think having had those few years, you know, I lived in Sudan for a year. So this in the seven years that in between when I was in the more corporate world, I was employed and I was told to have a certain number of holidays per year. And, you know, I had to book them in advance.

In practice, that meant I ended up having to book them around other people’s kids school holidays. You know, I haven’t got kids. I don’t have to plan around my own kids. Why the heck should I have to plan my life around other people’s kids? That frustrated me. And but in practice in the corporate world, that’s how it works. You work in a team. Some people are restricted around when they can take their holiday because of when their kids’ school holidays are so the other people end up having to, you know, plan around that.

I didn’t like that. I was like, ‘No, I want to be able to travel on my own terms when I want how long I want’. Money has never been a huge driver for me. I mean, you’re absolutely right what you said. I could have stayed on that career path, and I could be earning quite a lot more money. And I probably would have a flexible ish working situation, but I would not have the remote working and I would not have the travel aspect of things, and I wouldn’t be running my own business and I actually love that.

I think one of the things that I do remember very clearly around that time, obviously, it was a really big decision. There was a lot of doubt and questioning and, and I’m a big planner. And I usually have a plan A and a plan B and sometimes a plan C as well! Before I took such a big step, I needed to find a way to make it okay for myself to psychologically give myself a cushion.

What I did was I spent quite a lot of time working out very carefully how much money I actually need to live, not how much I wanted, or how much I needed to enjoy going out every weekend, what the absolute bottom line number was that I needed to pay the bills and not be out on the street. And actually, that’s what gave me loads of reassurance because nd the number that I came up with was really reassuringly low.

I thought, ‘Well, actually I can earn that much if I’m like stacking shelves in a supermarket or doing admin somewhere’. So that’s what gave me the reassurance psychologically to go for it. I thought, what as long as I can physically work, I’ll be okay. I won’t be out on the street.

And that worked pretty well for a while. But then I was like, ‘Okay, well, this is cool’. But at that time, I was working on site for clients. So I’m either working, or I’m travelling, I couldn’t do both at once. So the next step for me was to switch that around. And so I deliberately changed the way we did business, and started saying that we only work remotely.

And that was a big shift, certainly at that time, that was kind of 2012 -13. And most of my clients were NHS. So that’s the National Health Service in the UK. It’s a pretty traditional kind of audience. And so working remotely was not really very common. And that’s what sort of seven years ago in that industry. But I decided that’s what I wanted to do. So I started doing that and took a couple of years to sort of really get it completely doing that completely working remotely. But I switched out so that I could work from anywhere.

Dan: What moment did you decide to, you know, it sounds like you were, if there’s like an entrepreneurial line, you know, the freelance is just over the edge. At what moment did you decide that I shouldn’t just be a freelancer, we should build an organisation around this cash flow.

Ali: So there was kind of two steps to that for me. So 2006 was when I went freelance. So that was the first big change from being in the corporate world to actually still being very much in the corporate world but not employed. As a freelancer, I have more flexibility I have more freedom, but with travel and you know, either working or travelling.

So then the next step was switching the business to be able to do it remotely. So this was 2012. So six years and things went fine as a freelancer and I wasn’t, wasn’t sort of really making any huge waves, but I was doing fine trundling along. And but then again, I started to reach that plateau point again. And this has been a sort of cycle for me as I do something for a while, like, ‘Okay, now what?’ You know, I feel like I start to feel like I’m treading water.

And so after about six years freelancing, I was starting to feel like well, this is fine. I’m quite enjoying it. But what’s next? Basically what I’m doing is I’m exchanging my time for money. How can I grow on that? How can you develop it? I put my prices up a few times, and I basically hit the sort of market limit. So I couldn’t really put my prices up very much more, but what I could do was to start exchanging other people’s time for money.

So that was the first step. Then around 2012/13 I started outsourcing a little bit. I was still basically working as a freelancer, but it just meant I could take on a bit more work and pass them off to somebody else as well. And I switched to working remotely around the same time. So then I had about four years like that. So it’s sort of ‘freelancer and a bit’. And then 2017 really was sort of the big turning point for me when it really switched from being a freelancer who outsourced a bit to running a business.

Around that time, sort of 2016/17 going through some big changes in my life, personally, and I hit it sort of a crisis in a way I suppose. I’ve sort of Okay, just really questioning what I wanted from life. And basically almost took some time off from the business. So the business dropped right down to I was just reactive if stuff came in, I responded to it, but I didn’t do anything proactive. And you know, financially It was a terrible year. But I did the very stereotypical thing. I went off and spent a month in Bali, and then a month in Medellin.

It sounds quite, you know, stereotypical and cliched and a lot of ways but actually it was what I needed at the time. I started to find more of my right kind of people and other people who were entrepreneurial, interested in travel and figuring out their thing.

After a couple of months of that I sort of came back to ‘No Actually, I do love this business, I love communications. I basically love what I do. But I want to run it as a business now’, a real shift in mindset to, ‘Now I’m going to come back and I’m still doing the same thing. It’s still the same brand. It’s still the same company. But my role in it has changed’. And I’ve shifted now to being a business owner.

And so since then, over the last couple of years, I’ve done loads of work, looking at it now as a business. I have an operations manager and a marketing manager who are both employed. So they’re on a salary and then I have a team of freelance writers and I also have admin support as well.

Dan: A lot of us theorise on shows like this, that when you have a powerful skill set that’s valuable sometimes that can be troublesome when you’re growing a business because it’s easy to conflate the idea of business building with the skill that you execute that’s valuable. Does that kind of distinction resonate with you?

Ali: When I first started outsourcing Well, before I first started outsourcing, I was very resistant to it. Because as a freelancer I was, ‘This is me, you know. People buy by me my reputation, my personal service’. And it took me a long time to get my head around how I could possibly still sort of sell that without actually doing the work myself.

Dan: What’s the answer?

Ali: It’s a gradual process. First of all, it’s deciding to want to do it. And, and then I’ve always tried to be very open with my clients. But I think making that transition can be hard. Any business always has, you have certain clients that are with you now and clients often stay with us for quite a long time. But whenever you sign up a new client, I think that’s where you can make change. Keep your existing clients with whatever arrangement used to and I make the change for new clients.

So when new clients come in, you say, ‘This is how we work”. So when I was transitioning to working remotely, for instance, for those about 18 months, two years when I still had some on site clients, but I stopped taking any new on site clients. I decided, like we are now only working remotely, right? I didn’t want to get rid of the clients I had. But I just said that for new clients.

And similarly, when I put prices up, I do the same thing, it doesn’t mean you need to treat every client the same. If you’ve got clients who you’re used to working with a certain way they expect to receive certain treatment. Most of the time, you don’t need to change that for them. It’s always very difficult to change something when you’ve got something established. But if there’s no precedent, then you create whatever you want it to look like.

Dan: How are you getting these departments to pay you? What’s that conversation look like?

Ali: To be honest, because we work within quite a traditional industry. For the most part. Once they understand what we do and how we work, they welcome the opportunity, like every comms team that I have worked within, has more work on their ‘nice to do’ list than they’re really ever going to get around to. A lot of the time, they just don’t really know that an organisation like ours exists, because they may be used to using freelancers, but that is, you know, hiring somebody to come and sit in their office on a Tuesday or Thursday, two days a week, for instance.

And we work remotely and we work completely flexibly, which just makes it so much easier to actually outsource work to us, because it means they don’t need to sort of separate out a project. We act as an extra member of the team. So as and when they have something they need to do they can just ping us an email, ‘Oh, can you write this case study? Here’s the contact, here’s the deadline’, boom, that’s it. And it’s actually very, very easy to give us work once we’ve established that relationship.

Dan: Do you just have an hourly rate or a daily rate? Or do you propose projects to them?

Ali: So we usually just work on an hourly rate. And it depends on the client, sometimes they want a cost for a project. And I’m happy to do that. But usually, most of what we work on is quite small. And really, the way that I prefer to work is just on an hourly rate. So we work there as an extra member of the team. They send us stuff as and when they need it. Very, very simple, completely flexible.

Dan: You mentioned that you made decisions for freedom in your business. What was an example of a decision like that, that maybe the average business in your niche wouldn’t have made?

Ali: Well, in the first instance, working remotely. One of the things I say to my niche particularly is we don’t do media handling. In most communications teams that would be the point of contact when somebody in the media is writing something about that organisation, and they want a statement. The communications team will be responsible for organising that, for writing the statement and to responding to that inquiry. And, and also, if anything goes wrong in an organisation, the communications team is the one that then has to deal with the media. So they might be issuing proactive statements, but they’re basically proactively managing the media, dealing with this crisis situation.

Now, we don’t do that at all. Because I don’t want to be on call to anybody. I want to be able to be in control of my own time. And media handling by its very nature is a very responsive activity. You can charge a premium for it. You can say I only do it at certain times or whatever. But I just flat don’t do that.

Dan: Are you then like consciously sort of exploiting what makes your skillset special into this brand that you’ve built? Is that like a conscious effort to sort of externalise the values that your clients always saw in you and sort of present them in the form of a brand?

Ali: I think the answer is yes. Conscious effort? Not always that conscious. The business ethos and the brand really personifies my core values, the things that I think are important to me, flexibility is a huge thing for us. I want to have that flexibility in managing my own life. But that extends to the clients, we offer them massive flexibility by the way, we work in terms of we’re just there as a remote team. So they can just send us as much or as little as they want, as and when they want. That gives clients that flexibility. But for the team as well, you know, I have freelance writers. And we have obviously processes where we assign work to them. Everything has a deadline, but there’s loads of flexibility in terms of when they work and how they work.

The business has been entirely remote from the beginning. And it doesn’t matter where they are, doesn’t matter if they want to be sitting on the beach in a bikini. If they’re sitting at home in a bikini. I don’t care. But what I’m interested in is that they do good work on time. Things like being open and honest. And that’s something that is about the way I want to work with people. Basically, I’ve tried to create a company that I would like to work in, you know, I try to be the kind of manager that I would like to have.

When I interview people at the very beginning, in that interview process, I say them, ‘Look, openness and honesty are really important to me’. I don’t think particularly in a remote company, you can’t have a successful business unless you’ve got good communication between people. You know, I’ve got people working with me who I’ve never met and possibly never will meet. I need to be able to trust that, if you’re working for me, if there’s something that you’re not happy about, I have to trust that you’re going to say, because I don’t see you in the office. I can’t sort of pick up on body language signs or the fact that you sound a bit grumpy.That sort of thing doesn’t come across on email and text messages and things so well.

So I say, you know, I set those sort of ground rules from the beginning for the whole team. If you’ve got something you’re not happy with, you have to speak up. And I try to make sure that I then respond to anything that is raised positively and to encourage that sort of communication. Because I think you have to have that trust and openness and communication internally, in order to be able to work well together and to deliver good service to clients.

Dan: There’s a lot of people on the other side of these earbuds that want to be in the position that you’re in and have the same kinds of core motivations myself, certainly. What sort of advice do you have for them?

Ali: On the business side of things is one piece of advice that was given to me, so way back in 2006, when I was first shown struggling with his decision ‘Do I go freelance, do I make that leap and you go out self employed rather than looking for another sort of proper job?’ And, the piece of advice that I was given at that time, which has stuck with me until now is that when you’re first starting out in business, you don’t need a website. You don’t need business cards, you don’t need a brand. You don’t need a logo. You barely even need a business name. The only thing you need is clients.

Dan: How do you get those?

Ali: Get a thing that somebody wants to buy, find the people that will buy it, exchange cash.

Dan: Done deal

Ali: I would just want to encourage people to give it a go. I’ve created a life that I want to live. And it actually frustrates me when people put excuses in their own way. I’ve spoken to a lot of people over the years who sort of look at aspects of my life, and how much travelling I do or whatever else they choose to focus on. And they’ll say to me, ‘I wish I could have that, I wish I could do that’. And I’ll challenge them and say, ‘Well, you can, why don’t you?’ And a lot of the time, they’ll sort of be ‘Oh, well, boo, boo, boo, boo. Well, you know, if you want to do it, get on and do it’. If you’re just making excuses, some people do have genuine, valid reasons. And so those I’m not talking about those people, but if you actually want to do it, get on and do it. If you’re just making excuses. Stop saying you want to do it.

Dan: One final question is, I’m wondering if I can ask you to give us a sales pitch for dragon boating. This is a sport that has come up on the show a few times now. And for a lot of us like in America, we don’t know what the sport is. Could you describe what it is and where your passion for it comes from?

Ali: It’s not just in America, a lot of people don’t know what it is. And so basically, it’s a water sport. It’s a big long boat. If you think like Viking longboats, that tends to give a bit of an idea. It has a dragon’s head on the front and a tail on the back. And it has sort of benches across. So you sit in pairs and you paddle on one side. Very important thing with Dragon Boating, we are paddlers. We are not rowers.

Dan: And the difference is what?

Ali: Rowers go backwards. They can’t see where they’re going.

Dan: I see

Ali: It’s a very, very, very different motion to rowing. I’ve actually never done rowing. But we sit on a bench and we sit in pairs. We paddle in time, and we have a drummer on the front and the helm standing at the back steering. And we take it out on the water and we train and we race. It does exist all over the world. In the UK there’s a league we race all around the country. And there’s an international league as well.

Dan: Well, thanks for coming on the show. We appreciate you sharing with us today.

Ali: Hey, welcome. Good to be here. Thanks for having me.


Dan: Big ups to Ali Marsland for stopping by the show, you can check out what she’s up to over at Effective English Company dot com. Love hearing and sharing your stories.

And check out what we’re up to. Our story is over at TropicalMBA dot com. We’ll have all the links and show notes to everything mentioned in today’s episode as well as an opportunity for you to sign up for our juicy as well as an opportunity for you to sign up for our tasty newsletter. That’s right. Stay updated on everything that’s happening here at the TMBA pod and everything that’s going on below the pod so to speak. That’s it for this week. We will be back, as always, next Thursday morning. 8am Eastern Standard Time.

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