Matthew Knight is an independent strategy partner who has spent the last decade building communities and creating tools to help freelancers work well. He built the Leapers community to support the mental health of the self-employed and recently launched Outside Perspective.
In an interview with MediaCat, he reveals what inspired him to build these communities, what struggles freelancers are facing today, and how brands can be more freelancer-friendly.
In 2017, you founded Leapers to support the mental health of the self-employed. What inspired you to build this community?
Matthew Knight
I had just handed in my resignation at a role and I had a six-month notice period where I wasn’t able to apply for other jobs. I became interested in how work was changing and how there were a lot of really old-fashioned ways of looking for new jobs and how they were all still very much permanent and 9:00 to 5:00. I was seeing a lot of people moving towards self-employment and I started writing about how work was changing on LinkedIn — but that’s not a platform for conversation. So, I started a Slack group and said, ‘Hey, if anybody else is thinking and interested about how work is changing, come and let’s carry on this conversation’. What was really interesting was that people weren’t talking about accounting platforms, operations or different ways of working in that space. It was a lot more of the emotional questions like, ‘I’m worried about asking my boss for flex because what if they say no’, or ‘I’m feeling like I’m doing this on my own, I’ve got nobody to turn to’. Within a couple of months it was obvious that people wanting to work in different ways didn’t have a support space.I was trying to signpost to resources, and it was really interesting that there was so little on our mental wellbeing and emotional wellbeing.
There was a huge amount for employees, but all of the recommendations around that were, ‘Oh, well, if you’re feeling burnt out, take some time off’, which you can’t do when you’re self-employed. There was a huge gap in good quality resources and advice. So, I decided to focus this little accidental community on taking care of yourself when you are self-employed. And then, just double down on that, work really hard to find good quality resources around mental health, speak to specialists in this area, find out what advice they were giving and what resources and research existed.
Where we found the gaps — and there were a lot of gaps at the time — we started to create new resources. We discovered that half of it was internal. It’s things that you’re in control of, like setting your own boundaries, physical health, sleep, diet or mindset shifts.
The other half is all clients: what your clients are doing or what the market is doing. This includes things like late payments, being ghosted, or not having a contract in place. Suddenly you recognisea lot of these things are not mental health issues, but business issues that affect mental health.
While the project closed last year, the research studies are still available online. Can you tell us more about the findings?
We did about five years of research, and every year we asked around 80 questions to understand how freelancers were feeling about self-employment, how aware they were coming into self-employment about mental health, and then a whole load of questions around what was affecting their mental health. We have left the research online because it’s still very much valid. I think there are a couple of findings that often come as a surprise to others when they see the data. The first one is a lot of freelancers are really underprepared for when they step into self-employment. It’s a steep learning curve and you’re not just doing the piece of work that you’re doing; you’re also the accountant, the marketing, and the sales, and you take out the trash and make the tea. You’re running a whole business; that adds a lot of complexity when you’re also trying to find work and get brilliant work done.
The second thing is that most freelancers aren’t necessarily aware of how stepping outside of employment is going to be quite different. It’s all the little micro-interactions — like saying hello to somebody at work, having a regular conversation or a mentor that you can speak to — and how beneficial they are. You don’t recognise them until they’ve gone away. You need to actively build support structures around you because they aren’t baked in.
The third thing was how much the clients you’re working with have an effect. We built a 10-point policy framework for how clients can work effectively with freelancers. Number one is around respect that those freelancers are part of your workforce. They’re not a disposable human resource that you can just discard at the project. The second point is around late payments. Financial anxiety is one of the biggest drivers around poor mental health: late payments, cash flow issues, and crucially — it’s less about the money a lot of the time — it’s about the feeling that you’ve got to chase for your money. People would be feeling awkward about asking for the money they’re owed, and they would get poor responses from clients.
There’s a huge issue around payments not being made on time and the impact that that has could be resolved easily from a process perspective overnight. The other aspect of payment is fair and transparent payments. We don’t have standardised day rates. There’s very little transparency around what is being paid and that causes all sorts of issues and imposter syndrome kicks in. People from disadvantaged backgrounds or those trying to break into the industry are getting depressed, lower day rates because they’re not charging as much as they should be.
There’s a whole other bunch of findings as well, but I think there’s a really crucial one around feedback and following up. Quite often freelancers don’t hear where their work went. If it gets an award, they might not know that it got an award until they see something in the press somewhere. They’re not told the impact of the work went on and delivered success for the client or they got additional work off the back of it. There’s very little feedback and a lot of freelancers are not allowed to share the work that they’ve done because they’re under NDA. It’s not all clients and it’s not all every project. But what’s really interesting is almost every freelancer has experienced it at some point.
You also founded the community for independent strategies, Outside Perspective, last year. How does this community help brands and strategists collaborate better?
Outside Perspective came from a very similar insight. Strategists thrive when they are learning from others. They need to be challenged and have others they can argue with. I’ve always said that the collective now for strategists is a disagreement, and I love it. I think that’s how we thrive. In an agency and client setting, you’ve got people challenging you, questioning your work and giving you input on it, it’s brilliant. But again, this is baked into employment, but not self-employment. So, we created a space where independent strategists could come together, argue a little bit, have different opinions, and learn about how self-employment is a little bit different to just working in an agency.
We have about 500 strategists in the group now. Leapers was very much open to anybody who felt that they needed help while Outside Perspective is curated — we look at your profile to check that you are working in strategy, you are self-employed, and you do have a career history. So, everybody in there gets strategy.
I wanted to have that place, like the breakout room that we had in the agency when I was part of strategy teams and running strategy. When you have 500 strategists in a room, that’s a really valuable place for businesses that want to find interesting strategists. Outside Perspective has become a single destination where anybody looking for anyone in a strategic space can come to and say, ‘We’ve got a brief, we need somebody with this type of thinking’. It’s about showing the value of independent strategy and that having a perspective from outside your organisation is so powerful, because it’s impartial, honest, and fresh. Being able to bring that in on-demand, say ‘I just need you for an hour, let’s just have a really powerful chat’ or ‘I just need you for a day to shake up our thinking a little bit’ is super powerful. We’re seeing a lot of organisations say, ‘This is brilliant, I don’t need a strategist all year round. I just need somebody to really push this project forward and have trusted people that we can keep coming back to time and time again’.
What would your advice be for brands to become more freelancer-friendly?
Recognise that your workforce is no longer just employees. It is more than people who sit in your office. Leaning into working with freelancers gives you infinite access to infinite talent. It helps you have a more diverse, robust, fluid, and flexible workforce. Embrace the fact that freelancers and independent collaborators are a superpower and a way of supercharging your work. Think about designing how you’re working with them. Don’t just bring somebody in, give them a brief and hope for the best. Freelancers are brilliant at hitting the ground running and learning what they need to do but pre-boarding and onboarding can help them be part of your team, and land a much stronger piece of work. The next thing I would say is about intentionality; think about how you want to be collaborating with others and what that looks like over the next 12 months, 18 months, or two years.
We’ve done this with a number of organisations where we set that ambition and it really focuses the mind. The final thing I would say is designing the engagement. What does onboarding look like? What does contracting look like? How do you build that talent network and how do you engage with them? How do you continue to nurture it? How can it be a two-way relationship? We’re seeing that organisations that have intentionality around working with freelancers and what it means for their business, and those investing in it as a strategic growth pillar, are seeing huge amounts of success. That’s where freelancers keep coming back — they love working with them and they’re doing better projects. It’s a win for the freelancers. It’s a win for the organisations.
Lastly, what are your plans for the future of Outside Perspective?
We’re looking to start bringing more emerging talent. Those who have stepped into freelancing, maybe straight out of university, which is increasingly popular, and are looking for mentoring or learning from others. Making more connections across the strategy community for the self-employed is a key thing. The second key thing is unlocking some of the brilliant insights in that community. We’re going to be doing these arguments on a regular basis across different themes and looking at how we can unlock interesting conversations around sectors or industry challenges. The third thing is helping organisations build their own freelancing networks from strategists.
The other project which sits outside of Outside Perspective is a platform called Freelancing Support. It is much broader and focuses on people stepping into self-employment for the first time. It’s a bit of a copilot for self-employment that helps you go from the moment you think freelancing is right for you through those first 18 months of the journey. The focus of all of this work is to help freelancers to be more sustainable. We want them to be more aware of things so they can focus on running a great business rather than getting a surprise tax bill at the end of their first year or not realising that they needed insurance or whatever it might be. That’s all we want to try and do — just make people a little bit more prepared so they can focus on doing brilliant work.
Svilena Keane, Content & Social Editor at MediaCat Magazine
Svilena is the Content & Social Media Editor at MediaCat Magazine. She has a joint bachelor’s degree from Royal Holloway University, where she studied Comparative Literature and Art History. During her time at Royal Holloway, she was also the Editor-in-Chief of the student newspaper The Founder. Since then, she has worked at a number of digital and print publications in Bulgaria and the UK, covering a wide range of topics including arts, culture, business and politics. She is also the founder of the online blog Sip of Culture and a self-published poet.
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Matthew Knight is an independent strategy partner who has spent the last decade building communities and creating tools to help freelancers work well. He built the Leapers community to support the mental health of the self-employed and recently launched Outside Perspective.
In an interview with MediaCat, he reveals what inspired him to build these communities, what struggles freelancers are facing today, and how brands can be more freelancer-friendly.
In 2017, you founded Leapers to support the mental health of the self-employed. What inspired you to build this community?
I had just handed in my resignation at a role and I had a six-month notice period where I wasn’t able to apply for other jobs. I became interested in how work was changing and how there were a lot of really old-fashioned ways of looking for new jobs and how they were all still very much permanent and 9:00 to 5:00. I was seeing a lot of people moving towards self-employment and I started writing about how work was changing on LinkedIn — but that’s not a platform for conversation. So, I started a Slack group and said, ‘Hey, if anybody else is thinking and interested about how work is changing, come and let’s carry on this conversation’. What was really interesting was that people weren’t talking about accounting platforms, operations or different ways of working in that space. It was a lot more of the emotional questions like, ‘I’m worried about asking my boss for flex because what if they say no’, or ‘I’m feeling like I’m doing this on my own, I’ve got nobody to turn to’. Within a couple of months it was obvious that people wanting to work in different ways didn’t have a support space. I was trying to signpost to resources, and it was really interesting that there was so little on our mental wellbeing and emotional wellbeing.
There was a huge amount for employees, but all of the recommendations around that were, ‘Oh, well, if you’re feeling burnt out, take some time off’, which you can’t do when you’re self-employed. There was a huge gap in good quality resources and advice. So, I decided to focus this little accidental community on taking care of yourself when you are self-employed. And then, just double down on that, work really hard to find good quality resources around mental health, speak to specialists in this area, find out what advice they were giving and what resources and research existed.
Where we found the gaps — and there were a lot of gaps at the time — we started to create new resources. We discovered that half of it was internal. It’s things that you’re in control of, like setting your own boundaries, physical health, sleep, diet or mindset shifts.
The other half is all clients: what your clients are doing or what the market is doing. This includes things like late payments, being ghosted, or not having a contract in place. Suddenly you recognise a lot of these things are not mental health issues, but business issues that affect mental health.
While the project closed last year, the research studies are still available online. Can you tell us more about the findings?
We did about five years of research, and every year we asked around 80 questions to understand how freelancers were feeling about self-employment, how aware they were coming into self-employment about mental health, and then a whole load of questions around what was affecting their mental health. We have left the research online because it’s still very much valid. I think there are a couple of findings that often come as a surprise to others when they see the data. The first one is a lot of freelancers are really underprepared for when they step into self-employment. It’s a steep learning curve and you’re not just doing the piece of work that you’re doing; you’re also the accountant, the marketing, and the sales, and you take out the trash and make the tea. You’re running a whole business; that adds a lot of complexity when you’re also trying to find work and get brilliant work done.
The second thing is that most freelancers aren’t necessarily aware of how stepping outside of employment is going to be quite different. It’s all the little micro-interactions — like saying hello to somebody at work, having a regular conversation or a mentor that you can speak to — and how beneficial they are. You don’t recognise them until they’ve gone away. You need to actively build support structures around you because they aren’t baked in.
The third thing was how much the clients you’re working with have an effect. We built a 10-point policy framework for how clients can work effectively with freelancers. Number one is around respect that those freelancers are part of your workforce. They’re not a disposable human resource that you can just discard at the project. The second point is around late payments. Financial anxiety is one of the biggest drivers around poor mental health: late payments, cash flow issues, and crucially — it’s less about the money a lot of the time — it’s about the feeling that you’ve got to chase for your money. People would be feeling awkward about asking for the money they’re owed, and they would get poor responses from clients.
There’s a huge issue around payments not being made on time and the impact that that has could be resolved easily from a process perspective overnight. The other aspect of payment is fair and transparent payments. We don’t have standardised day rates. There’s very little transparency around what is being paid and that causes all sorts of issues and imposter syndrome kicks in. People from disadvantaged backgrounds or those trying to break into the industry are getting depressed, lower day rates because they’re not charging as much as they should be.
There’s a whole other bunch of findings as well, but I think there’s a really crucial one around feedback and following up. Quite often freelancers don’t hear where their work went. If it gets an award, they might not know that it got an award until they see something in the press somewhere. They’re not told the impact of the work went on and delivered success for the client or they got additional work off the back of it. There’s very little feedback and a lot of freelancers are not allowed to share the work that they’ve done because they’re under NDA. It’s not all clients and it’s not all every project. But what’s really interesting is almost every freelancer has experienced it at some point.
You also founded the community for independent strategies, Outside Perspective, last year. How does this community help brands and strategists collaborate better?
Outside Perspective came from a very similar insight. Strategists thrive when they are learning from others. They need to be challenged and have others they can argue with. I’ve always said that the collective now for strategists is a disagreement, and I love it. I think that’s how we thrive. In an agency and client setting, you’ve got people challenging you, questioning your work and giving you input on it, it’s brilliant. But again, this is baked into employment, but not self-employment. So, we created a space where independent strategists could come together, argue a little bit, have different opinions, and learn about how self-employment is a little bit different to just working in an agency.
We have about 500 strategists in the group now. Leapers was very much open to anybody who felt that they needed help while Outside Perspective is curated — we look at your profile to check that you are working in strategy, you are self-employed, and you do have a career history. So, everybody in there gets strategy.
I wanted to have that place, like the breakout room that we had in the agency when I was part of strategy teams and running strategy. When you have 500 strategists in a room, that’s a really valuable place for businesses that want to find interesting strategists. Outside Perspective has become a single destination where anybody looking for anyone in a strategic space can come to and say, ‘We’ve got a brief, we need somebody with this type of thinking’. It’s about showing the value of independent strategy and that having a perspective from outside your organisation is so powerful, because it’s impartial, honest, and fresh. Being able to bring that in on-demand, say ‘I just need you for an hour, let’s just have a really powerful chat’ or ‘I just need you for a day to shake up our thinking a little bit’ is super powerful. We’re seeing a lot of organisations say, ‘This is brilliant, I don’t need a strategist all year round. I just need somebody to really push this project forward and have trusted people that we can keep coming back to time and time again’.
What would your advice be for brands to become more freelancer-friendly?
Recognise that your workforce is no longer just employees. It is more than people who sit in your office. Leaning into working with freelancers gives you infinite access to infinite talent. It helps you have a more diverse, robust, fluid, and flexible workforce. Embrace the fact that freelancers and independent collaborators are a superpower and a way of supercharging your work. Think about designing how you’re working with them. Don’t just bring somebody in, give them a brief and hope for the best. Freelancers are brilliant at hitting the ground running and learning what they need to do but pre-boarding and onboarding can help them be part of your team, and land a much stronger piece of work. The next thing I would say is about intentionality; think about how you want to be collaborating with others and what that looks like over the next 12 months, 18 months, or two years.
We’ve done this with a number of organisations where we set that ambition and it really focuses the mind. The final thing I would say is designing the engagement. What does onboarding look like? What does contracting look like? How do you build that talent network and how do you engage with them? How do you continue to nurture it? How can it be a two-way relationship? We’re seeing that organisations that have intentionality around working with freelancers and what it means for their business, and those investing in it as a strategic growth pillar, are seeing huge amounts of success. That’s where freelancers keep coming back — they love working with them and they’re doing better projects. It’s a win for the freelancers. It’s a win for the organisations.
Lastly, what are your plans for the future of Outside Perspective?
We’re looking to start bringing more emerging talent. Those who have stepped into freelancing, maybe straight out of university, which is increasingly popular, and are looking for mentoring or learning from others. Making more connections across the strategy community for the self-employed is a key thing. The second key thing is unlocking some of the brilliant insights in that community. We’re going to be doing these arguments on a regular basis across different themes and looking at how we can unlock interesting conversations around sectors or industry challenges. The third thing is helping organisations build their own freelancing networks from strategists.
The other project which sits outside of Outside Perspective is a platform called Freelancing Support. It is much broader and focuses on people stepping into self-employment for the first time. It’s a bit of a copilot for self-employment that helps you go from the moment you think freelancing is right for you through those first 18 months of the journey. The focus of all of this work is to help freelancers to be more sustainable. We want them to be more aware of things so they can focus on running a great business rather than getting a surprise tax bill at the end of their first year or not realising that they needed insurance or whatever it might be. That’s all we want to try and do — just make people a little bit more prepared so they can focus on doing brilliant work.
Featured image: Mikhail Nilov / Pexels