These session notes are from the online talk “How To Grow A Resilient Freelance Business”, which was a collaboration between The Professional Freelancer and Counterflows and took place on Wednesday 27 May 2020.
Anna Codrea-Rado is a journalist, podcaster and campaigner. She writes about business, culture and tech for titles including the New York Times, Guardian and Wired. She also writes the newsletter, The Professional Freelancer about making a sustainable self-employed living and she’s the co-host of Is This Working, a podcast about the messy parts of work.
Ebony-Storm Halladay is a freelance digital marketing consultant and editorial assistant. Her clients are split evenly between writers and editors looking for editorial assistance and small businesses seeking support with building and implementing digital marketing strategies. She’s helped many freelancers streamline their workload, and identify projects to collaborate on.
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Lauren Razavi is a writer, speaker and strategist focused on the future of work and global living. She’s been a freelancer and a remote worker for more than 10 years, and has lived across 50 countries in that time. She publishes with titles like The Guardian, VICE and Wired and has managed distributed teams for clients such as Google and the Singapore Government.
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- Lauren’s book recommendation: Company Of One by Paul Jarvis
- Anna’s blog post: “What I've learned from a year of publishing a paid newsletter”
Lauren, what does a resilience freelance business look like for you?
Resilience has been a really pertinent question for me recently because the pandemic wiped out almost all of my work for the rest of the year (mainly for corporate clients). One of the big lessons for me and my business has been that I’ve not been building something that was as resilient as it could be.
In general, resilience starts with the individual, with understanding how you work and how you see your progression. It means getting to know yourself better and deciding what you want to do with that energy to build a resilient business. It’s important to be diverse and have a lot of opportunities coming your way.
I’ve had to adapt and pivot over the past couple of months. That’s led me to think differently about my work and what fulfils me, what kind of projects I want to take on and reject shaky, traditional business models. For me, a resilient business is diverse and creative. It’s looking at you as a person, as well as you as a worker.
That resonates with me a lot. The pandemic was such a shock to the system. I’ve been thinking much more about building personal and professional resilience, and I think those two things are interlinked. Ebony, what does a resilient freelance business mean to you?
I agree with Lauren on the diversity point. For me, what’s worked is having a mix of big and small contracts; having more fixed and more casual clients, knowing there are a few people who will approach me and ask for a little bit of work month-to-month on top of a few regular chunks of work.
Going into the pandemic, I was aware my business would take a hit. I knew I’d be OK if I lost around 40% of my business. I’ve probably lost a little bit more than that, but that’s made me think holistically about what I’m doing and what comes next. I think that’s resilience.
It’d be helpful if you’d each describe how you went about that reassessment of your business. How did you do it?
Before the pandemic, I knew how much I needed to make to live on. That was a number I already knew. The pandemic forced me to really face up to that number, and then to reevaluate. I looked more closely at my numbers and realised I could make it work on less that I thought.
Lauren, what about you? What was the process like when the pandemic hit? How did you reevaluate your business?
I started the year in Southeast Asia where coronavirus was on the radar a lot sooner. So by the time the business impact hit me, I’d had more time than most people in Europe to mentally prepare. I took the opportunity to really assess where the value was in my business — why my clients work with me — but also which parts of the business really make me happy. I realised I’d put too many of my eggs in one basket and stopped thinking outside the box. So lockdown really encouraged me to think creatively again and reassess things.
Obviously anyone would be hard-pressed to say they were prepared for this catastrophe, but before the pandemic, did you feel like your business was resilient? If so, what kind of things had you put in place?
I’d taken quite a lot of measures to make sure that my business was resilient over the past few years. One of the ways that I tried to accomplish that is through client retainers. Instead of working on a project by project basis with the clients as a service provider, we’d agree what we would do together over, say, 12 months. The idea behind that model was to make it a lot less about chasing up invoices for big chunks of work and worrying about cash flow. I also wanted to frame things as an ongoing relationship with my clients rather than encourage them to come to me ad hoc when they need something.
The real kick in the teeth for me there, was that all of our retainer clients were due to renew at the end of the financial year. The pandemic hit at the same moment my contracts were due to renew and pretty much all of those clients went to emergency budgets. Really unfortunate timing.
Anyway, I realised that client retainers don’t really work for me because I’m scatty and I get bored easily. So, actually, I don’t like the pressure of constant work in that way — of feeling like “this is my life now”. But I do love the collaborative relationship part of it. On a conceptual level, it’s really important to think about what you want your client relationships to look like. If a client doesn’t treat you well, is it really worth working with them in the future? The pandemic’s been an opportunity to think in that way about what you want your relationships to look like.
Anchor clients often feel like the holy grail of freelancing because of that regular income (which really helps with the fluctuation of freelancing) but I agree, ultimately it’s about that relationship building. Ebony, what were you thinking about resilience before the pandemic, or has your focus on it been sparked by the pandemic?
I’d literally just taken some action to try and diversify my business before the pandemic. I’d launched a local business collective with a cafe owner I know, looking at ways to build community and resilience on the local level. For me, it was a chance to experiment with something new and maybe launch a kind-of side hustle. It’s disheartening that, under lockdown, it hasn’t been possible to continue with that project.
Thinking about diverse income streams is priming you for that resilience mindset though. Which brings me onto my next question. How were you thinking about resilience on a personal level before? About the practice of self-resilience?
I’ve been in tune with the question of self-resilience over the past few years because I’ve struggled with depression on and off. When you hit a mental rock bottom like that, you start to think about what is meaningful to you and in your life.
That experience set me on a much better path and made for a much healthier relationship with my work. To take the time to accept that I wasn’t achieving much at points, I’m not really making stuff and putting it into the world, but I’m spending time with myself and really paying attention to what I’m doing and how it makes me feel.
For me, that’s been a crucial part of developing mental resilience: to take a step back and ask yourself some fundamental questions.
Building on that, having the time and space for creativity has been important in helping me build my resilience. Allowing myself to come away from a project if it’s just not happening and to throw myself into things when it is. I don’t think I’ve ever struggled with resilience, but sometimes I think that might be rooted in naivety! I think about it like, “It’s gonna be fine, and if it’s not fine, I’ll figure out how to make it fine.”
That can lead to burnout though. It’s important to respect yourself and your psyche. I do a lot of yoga, I work out a lot, and do the things that make me feel calm. Resilience is a physical thing for me. Resilience body wise and mind wise.
Yes, I’ve learned the same thing. So much of resilience is physical. Your emotions manifest physically in your body. The more you pay attention to that, the better off you’ll be. Next, I want to talk a bit about growth and growing a business. I know that’s a scary concept for a lot of people right now, so why is it important to think about growth at this time?
The world’s heading into another recession. There’ll be fewer opportunities trickling down from the big companies, so there’ll be fewer big opportunities for freelancers. But our reaction to that should be to think creatively.
There’s a fascinating book called “Company Of One” by Paul Jarvis that came out last year. In it, he argues that freelancers — what he calls “companies of one” — should really focus on making what they do better and optimising what they already do rather than blindly following this idea of growth in a traditional way. That understanding of growth kind of seeps down from Silicon Valley. The ambition to be a unicorn.
This whole other school of thought is emerging. It says: “I’m more of a craftsperson. I’m a maker and I want to get better at what I do.”
I think that’s a good take on growth. As an individual, you want to be able to do more interesting and exciting things, stuff that fulfils you, and that usually means getting better at what you do rather than focusing on getting more clients or commissions or whatever. We’ve all been there when you spend a week pitching and hustling, and all of a sudden everybody says yes at the same time, and you have a freak-out about how you’re going to handle it all.
In the freelance context now, growth should mean creative fuel and collaboration around everything you’re doing. Identify what inspires you and work flexibly with other freelancers to enrich yourself and grow your business. The most successful freelancers in the years ahead are going to be the ones who can build, activate and lead little networks.
When I say networks, I’m not talking about hundreds of people. I’m talking about you and four freelance mates knowing what the others do and being able to talk about it, so you’re able to cross-pollinate and work on projects together. I see that as a big part of the future. When we talk about growth, we need to avoid the trap of unicorn/Silicon Valley-type thinking. Instead, we need to think about peer-to-peer networks and small-scale collaboration.
I love that! Growth has become an almost dirty word thanks to the Silicon Valley unicorn. I love the idea of going back to a more grassroots, cooperative-style system. I suppose it’s quite literally cottage industries, where you’re working together from your kitchen table. What about you, Ebony, why do you think it’s important to think about growth?
For me, I guess I feel lucky to be doing the kind of work I’m doing and being able to work with the kind of people I get to work with. In my mind, growth is the next step when you’ve figured out how a lot of stuff works for you and an individual way of getting work done.
We’ve had a question from Lizzie. She asks: How do you manage the “speculate to accumulate” phase? Lizzie has two or three projects that she’s setting up and they won’t be generating income for a while. It’s hard to balance them with the work that pays but isn’t necessarily sustainable.
When people think about growth, many will look at developing a new revenue stream. Often that means a lot of upfront work without a lot of clear paydays. What are some tips for managing that and what are some other thoughts you have about growth in the midst of the crisis?
What fundamentally underlines my whole philosophy on freelancing, what I believe you need to do it well, is to approach the world with generosity. Sometimes you’re gonna have a lot of projects on and it’s gonna be stressful. Sometimes the projects that stress you out won’t even be your projects, they’ll be helping out a friend or whatever. But generosity is so important to business sustainability, especially during a crisis.
In practice, it means helping people out whenever you can: jumping on a call with someone if they’re having a bad day and connecting people with useful contacts before they even ask. What you accomplish by doing that — and it’s important not to do it with this result in mind, it’s just sort of the outcome you experience from it — is that you’re constantly front-of-mind for people. You’re on people’s radar. So you end up with these opportunities flowing your way. We live in the information age, the internet era — that’s how the world works now.
Whether you’re worried about attracting enough work or knowing when to go after a project that doesn’t make much money, the challenge is in designing those flows. It’s about putting as much out into the world as possible, and being generous with your time, skills and knowledge. From there, you need to have faith that even if something isn’t contributing to your wallet right now, you’re building other useful things. I guess what you’d call social capital. Being involved with things that could bring you great opportunities later on or contribute to a skillset you have other ideas about using.
It’s important not to be bogged down in these old ideas of working. We have to engage with what’s happening in the world now and what the potential is.
This question made me think about my newsletter, because that project was a lot of work over a long period of time, which was not paid until I eventually found a way to monetize it. What sustained me through that.
Yes, there is a practical element which is like Ebony said at the beginning, you need to know the number you have to bring in every month. If you have that clear in your mind, you can feel secure knowing when you've made the money to cover your bills for the month.
But then separate to that is, I love doing this thing, and even if just the process of writing this newsletter is all I get out of it, am I learning something? Am I developing a new skill? Am I growing in some other way, that isn't just financial? Of course, we all have bills to pay and you have to be thinking about finances, especially right now, but growth doesn't just mean financial growth.
What are your tips for growing in a crisis?
This stage of things is about letting yourself be free with ideas. Last week, I had a really bad creative drought, and I was just like: this is not going to happen. All those projects relied on me being creative, I accepted that they weren’t gonna happen this week. There have been other times where creativity really flows. I picked up a paintbrush and pen for the first time in maybe six months or a year at the weekend.
In terms of growth, I’m trying to pick up on those creative flows. If they're at 3am on a Sunday, that's fine. Just do it. It’s just taking advantage of those moments right now where you do feel inspired and you do want to work on something. If you are working on something that you're passionate about, and you're staying passionate about it through the crisis, that’s a really good sign. It’s hard right now.
It's so interesting to hear you talk about the painting thing. I've been doing that but with guitar. I've never played the guitar before but by learning how to play the guitar on lockdown, perhaps because it's something that’s completely divorced from my old life, it's been this important creative outlet. We've had a question from Hannah, which is a good one to ask here. Coming from a journalistic perspective, how do you find the balance between specialising and being diverse enough to be sufficiently resilient?
The number one thing is to understand the different separations that you have in your work. Everything I do revolves around the themes that I work on — the niche or the beat, whatever you want to call it. But I use my skill set a lot more widely than just writing about those things as a journalist.
This is a good time to think outside the box about what you can offer and how you work with people. If you've never tried consulting or speaking before, now is the time to do it. Specialists are in demand, just perhaps not where you've looked before. The challenging thing though is once you stop looking at what you're doing as a linear career in journalism and measuring yourself against these industry-specific milestones, you have to take a step back and think about what you're doing on another level. What's the purpose behind my writing as a journalist?
First, it's terrifying. Then it's inspiring and gets your creative juices flowing, because you're no longer restricted to looking at everything in one way, from the lens of the media industry. We're on the cusp of a completely new world of work and it's been accelerated by the pandemic. Now's a great time to step outside your comfort zone, find new areas where you can add value and achieve your goals, and look at why you write journalistic stories in the first place.
Another question we have is about the different hats we wear as freelancers, which I’d like to tackle: What are your thoughts on the importance of personal brand?
I do lots of different things: I’m a journalist, podcaster, I campaign for freelance workers’ rights, I write commercial copy, I sometimes consult, I do public speaking. I do lots of different things. But they all come back to a central theme around improving working life and making work better. Whether that is through writing a newsletter that helps freelancers make a more sustainable self-employed living or going and giving evidence to the House of Lords on fair pay for freelancers or talking on a podcast about the messy parts of work life. That’s a nice way to anchor everything. It gives you a clear mind. Pandemic notwithstanding, it gives you an influx of ideas about what to do, how to repurpose skills in new areas.
Let’s move on to talk about outsourcing. While growth can look like a lot of different things, you get to the point as a freelancer where you feel like you’ve hit full capacity in terms of what you can actually do in a day. A newsletter is one way you can scale your work, by having an audience that funds your work and continuing to grow that audience, meaning more money for the same work in the long-run. But you reach a point where you realise there’s not much value in you personally doing some of the tasks that need to be done in your business. How can outsourcing benefit you as a “company of one”?
Outsourcing tasks essentially allows you to hire people to look after the things you’re a bit shit at, and nine times out of 10, they’re probably going to do a better job than you anyway. You’ll benefit a lot from not going through the mental pain of doing the tasks that you really can’t stand. And it’s for a reasonable investment if you do the maths on it. Outsourcing can be a viable way to do more and to focus on other aspects of your business that need your attention more than something you don’t enjoy doing.
One thing to note is that, if you decide to work with other freelancers, you have flexibility there. You can work with somebody a lot one month and not very much the following month. As long as you make sure both sides are clear on expectations and what the relationship looks like, how much time someone should leave available for you, it can work really well.
A lot of people think of Tim Ferris, author of The Four-Hour Workweek, when they think of outsourcing. This idea of finding a cheap VA in India and making loads of money selling supplements or whatever. Nobody here is suggesting that’s the way to do it. Ebony can speak to this more than me, but it’s very much about establishing a relationship with somebody. Being able to trust them to do whatever it is that you need doing. That can be easier or harder depending on the task and the person — how much of a control freak you are.
I’m glad you brought up Tim Ferris because I’m reading his book now.
You look so thrilled about it!
I figured I should read it before I criticise him. I think he’s done a lot of damage to the profession of outsourcing and virtual assistants. He treats it as very transactional. He says: come up with a product, sell loads of it, outsource all the work you don’t want to do in the cheapest way possible. There’s absolutely zero relationship there. There’s no new thinking about growth there at all, like we were saying before. It’s that old model of larger profit margins as the only way. Ironically, his book is supposed to be about the opposite. I don’t think it is. Anyway, tell me about the kind of value outsourcing can add to a freelance business?
When you’re working with someone, it’s a lot like being back in the office in a way, which is ironic. We just got out and now we’re saying “give us work friends back!” If you’re working with someone who really understands the way you work and they understand the challenges you face, that person can be a great resource when you hit a creative or business block. You can pick up the phone and ask, “where should I go from here? Am I looking at this problem the right way?” Sometimes it’s having a second opinion that really helps. Outsourcing looks different for everyone. It’s a personal thing. People who are good at my kind of work understand the value of a relationship that is creative and social as well as professional.
What types of work do you do for your clients?
It really varies, but anything from managing inboxes and communications to research and reporting, putting together case studies. Sometimes people will just hit me up with transcriptions — I’ll do a couple of those a month. Often, we’ll talk through what they’re doing and I’ll be a sanity check and say “You seem stressed out about this. How can I take the pressure off? What’s the first thing that needs to happen to get this done?”
There are some parts of the writing process where people want to do their own thing. There are occasions where somebody calls me and asks if I can interview a few people on their behalf because they have too much on their plate. A note to writers considering this: you can be as picky as you like about who you work with on this in the long-term. It’s a personal relationship. If you get it right, it will work for you. Sometimes that takes time.
Lauren, how do you know you’ve reached the point where you’re ready to hand stuff over? I’ve flirted with outsourcing more for a while, and I have worked with other freelancers quite a bit in an ad-hoc way. How do you know when you’re actually ready to do it?
First off, I think it’s useful to describe how the relationship works between me and Ebony. In a nutshell:
- I notice that something in my work is causing me strain or it’s taking me ages to get it done. That’s step one of finding a task to outsource.
- Then I think about what the most important thing about the task is e.g. that I do it, or that it gets done? Or, if I break this down into its component parts, which bits are tripping me up?
- Next, I think about what the brief would look like. How would I describe how to do this well to somebody else?
- I write Ebony an email explaining my struggles and basically asking her to heal me like some sort of dodgy ashram guru.
- We agree on an experiment, a rate and a deadline to test it out and see whether it’s a shitty experience for either side (in which case, we can agree it’s not a goer).
It’s that simple. No bullshit.
I try to build that habit of thinking about tasks in micro-format into my day-to-day as much as possible. I try to make it part of the rhythm of what I’m doing to notice when I need help and act on the opportunity to seek help as often as possible. Personally, Ebony and I don’t have contracts or anything, although you can do that if you want. That’s because we’ve built a lot of trust over a long time of working together. It’s one of those situations where if I don’t pay Ebony’s invoice on time, she’s not going to get the law on me, she’s gonna send me some judgemental emojis on WhatsApp and then I’m gonna open my banking app and get it done.
I think that’s important too: not feeling like you have to act like this very big business. Bring it down to the reality level. On that point, please do what me and Anna do when we work with people: pay the people the rate they asked for, pay them within 14 days, and take the time to recommend and refer because it makes all the difference.
You have to think about it like an ecosystem that way because one freelancer might be doing something just for you and think it’s a cool thing they’d like to do more of, but unless you actually do your bit as a community member to show them that it might be possible — to refer when somebody else is struggling with the same thing — that person might never explore that area of their business.
That’s how we get stuck in these processes of the status quo way of doing things. We need to flip it and get rid of the fear. Ask ourselves what we’re actually doing here together, what we’re trying to achieve. It’s not just a bunch of individuals behind laptops struggling in silos.
There’s still this antiquated idea that as freelancers, we’re all competitors with each other, and we shouldn’t collaborate with fellow freelancers because they’re our competition. I don’t experience that in the communities I’m part of, but I’ve encountered it elsewhere.
I’ve had people think I’m crazy for running a community of freelancers and posting newsletters full of freelancing tips, because I’m helping “the enemy”, which is absolutely crazy to me. I’m here to knowledge-share with everybody, with all other freelancers, because I believe everyone should be lifted up together.
Ebony, there’s an emotional aspect to handling over your work to somebody else. You mentioned managing inboxes, for example. What’s the more emotional side of the experience of helping other people like this? I imagine it can be quite daunting.
Coming up with a structure of doing things is good. That structure doesn’t have to be particularly formal. It’s like Lauren said, my clients just hit me up and ask if I can help them with a thing, brief me and I get going. It doesn’t have to be massively formal, but deciding on how you’re going to communicate is important, otherwise you might never get around to reaching out.
The other point is to start small with some trial tasks before trying to work together closely. Choose things you’re less precious over or that aren’t urgent at first. Figure out how the relationship is going to work. It doesn’t have to be a huge deal, you don’t have to pass along something crucial.
If I can add something: Ebony and I have established this relationship and it’s really direct, honest and frank. She’s seen me in my worst moments in work and probably in life as well, but we’ve developed this relationship so we end up in a situation where Ebony actually supports my work in many ways naturally. She’s so familiar with what I’m doing and how I do it, how I think about problems, that she ends up Slacking me with useful resources or tools or ideas she’s come across. That’s part of what’s special about developing this kind of relationship and it’s definitely an antithesis to The Four-Hour Work Week approach.
This person is going to be your work agony aunt, your partner in crime. You’ve got to get along with them. If you can establish honesty and directness in your communications with the person you’re working with, it pays off, because you can go to them and say “I’m gonna experiment with you on this thing. It might not work. To be frank, it could be three months before I identify another thing you might be able to help me with.” The more open you are from the beginning, the more both sides expectations can be set. You can do it at the pace you’re comfortable with. You might find people who don’t want to do the work you have to offer, and you’ll have to keep looking. But you can find the person who is the right fit for almost anything, the more micro the task, the better in some respects.
A lot of people feel if they don’t like the work, nobody else will want it either, so it’s difficult to conceive of the idea that there’s someone out there who would happily take on that transcription, sorting your emails, whatever it might be. It’s the idea that somebody’s not going to want to do it because you don’t like doing it. So I think what you’re saying is important.
We have a question from Danielle, who asks: Do you think the future of collaboration will be the end of traditional corporate culture?
I don’t think it’s the end of corporate culture. I think that’ll keep running off into the distance somewhere. But I think people like us are going to be less affected by it. There are a lot of issues around digital presenteeism coming up and I’m refreshed to be speaking to people on the business and corporate side and freelancers and creatives who are thinking about doing things differently. Who are looking at how they manage their work, what the future of work looks like being lockdowns and COVID-19.
More broadly, I think it’s important to bear in mind that everyone from the World Economic Forum to NASA is telling us that within the next decade, two of the most crucial skills across job markets will be collaboration and creativity. As freelancers, we have this big opportunity. We’ve actually been the early adopters of doing stuff that way for a lot longer than a lot of people. We’re well-equipped for this future. I don’t think we’ll see organisational culture shift quickly, but I think we’ll see far fewer people participating in it.
Ebony, what's your take on the future of corporate culture?
I’ve got a lot of friends working remotely for the first time and there seem to be two reactions: one is they miss the structure, the other is they love it and want to do it forever. The future of work should be what works for you. If people still like to be in an office and the culture works for them, that’s their choice.
We have a question from Eliza. She wants to know about how I do working as a freelance journalist and monetising my newsletter. I feel like I could go on about that for a very long time, but briefly:
I launched a newsletter with no plan. It grew to a point where MailChimp started charging me to run it and host it on their platform. I moved to Substack, which lets you monetise a newsletter quite easily. I did that a year ago this week, and you can read my blog post about it for more details.
I do think newsletters are a good avenue for people in terms of adding an additional revenue stream and helping make their businesses more resilient, because it’s adding an extra arm.
Lauren, what is one actionable point from today's conversation that people can take away?
I’d like people to go away from today thinking about what we’re calling outsourcing, but I suppose is better described as collaborating. Involving other people in your work, whether that’s handing over tasks you don’t like or doing a bigger project with another freelancer that you respect.
My concluding point on that is just that you are probably ready to outsource something right now, and you should experiment. It doesn’t have to be all or nothing. You’re not “a freelancer who outsources” or “a freelancer who doesn’t”. Maybe you only outsource four things a year, but they’d be the biggest ballache otherwise and having them off your to-do list is a huge reward.
Ebony, what are your closing thoughts?
Do your research and figure out who you're looking for and what you need from them. Don’t be afraid to jump on a 20-minute call and exchange some ideas or share pain points. As Lauren said, it’s not all or nothing. Send someone a little task or two and figure out if it’s gonna work from there.
My closing thought is to take resilience all the way back to basics and start with yourself. Kind of what we were talking about at the beginning. Take a look at the things you're doing in your day and make sure that you're supporting your own well being, because you can’t pour from an empty jug.
Looking after yourself gives you the building blocks for a resilient business. Continuing to grow and collaborating with others and building community all feeds into a bigger ecosystem that helps everyone who is freelance.
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