The Freelance Productivity ADHD Reality: How She Wrote the Book and Still Falls Apart with Sarah Townsend

Jen: Thanks so much for doing this. I’m very excited to chat with you.

Sarah Townsend: Yeah, I got imposter syndrome this morning. Overthinking. Oh my God. I can’t do this right now because I’m using, I go between different structures and different systems, and I got really hugely, hugely into Trello. And I had all these really complicated boards and it was all great. And then I just suddenly, as quickly as I started using it, I stopped choosing it and then, yeah.

Jen: I am exactly the same way. This is part of why I am so curious about this question of how do people organize their lives and how do people from all different walks of life and brain setups do this, because I am definitely all over the place. Different systems in different places, getting caught up in a system like Trello or Asana or whatever, getting really into it and then completely losing track. Yes, I completely relate and understand. And I think when I was launching this podcast, I made a lead magnet, an ebook with all of the different productivity types, to-do list types. Based in lots of research, and it was very interesting and also relieving, the opposite of imposter syndrome, to really learn about how different people are and how valid all of these different types are. So I’ll send you that ebook. You can take a look through and I think you’ll feel seen and relieved.

I like to start every interview by saying, how do you normally answer the question, what do you do?

Sarah Townsend: I am a copywriter and author. I’ve been a freelancer for 26 years, and I wrote a bestselling guide to self-employment. I’ve also written two books about language, which are essentially fun and nerdy guides to spelling.

Jen: That’s awesome. That’s a great tagline. I like your LinkedIn tagline, “from blah blah to ta-da.” Could you elaborate a little bit more on what that means?

Sarah Townsend: Of course. Most of my clients don’t come to me and ask me for copywriting services or editing services. They send me a document and say, can you work your magic on this document? So I started to think I need to spell that out into a service, a defined service, which I now call my DocuMagic Service. Clients have called me a Word Wizard many times over the years, and I thought Magic Wizard, it kind of all goes together. It just summarizes that sort of taking a strategic look at an in-depth document and transforming it into something that people actually want to read, which goes deep into the customer’s own language. Perhaps before it might have started as something that was written by four different people in four different tones of voice. And now it’s really focused on what the client needs to hear, to help them make the decision that the client wants them to make.

Jen: What are the general rules for taking something from blah blah to ta-da? What is the typical type of problem you see? And then how do you use your word magic to transform it?

Sarah Townsend: A really good question actually. Two things really stand out. I would say, first of all, the clients really often write from their own perspective. So I’m going to call them clients and readers. Clients are the people I work for. Readers are the end user of the product that I produce. The client thinks they need to reassure the reader with how many years of experience they have or how highly qualified they are. It’s not really about that. It’s more about helping the reader feel seen and helping them come to the conclusion that they can trust the client to deliver a solution to a problem that they’re feeling. A lot of it is changing the focus from being client-focused to being reader-focused, and doing that involves a lot of tweaking to the language, addressing the reader directly as “you,” for example, rather than saying something abstract and generic like “we do this for our clients,” because at that point the reader doesn’t know who the client is.

They just need to know if they can self-identify. So that’s one of the big things, sort of talking about themselves too much. But then also another thing is using language that is not focused on the reader, and perhaps treating their target audience as a group of people and feeling like they’re broadcasting their message to a group, rather than really getting super clear on who the reader is and making everything directly conversational to that reader.

Jen: I’d love to demonstrate your expertise and get some free advice. What would be some positioning language for The To Do Show, to describe it to a potential listener as intriguingly and clearly as possible?

Sarah Townsend: The difference between kind of saying, I have this podcast and I do this and I talk to people about this, it’s more like, oh hey, are you someone who uses to-do lists? This podcast is for you because you are going to learn X, Y, Z. It is just a flip in the language and the approach and the positioning, really thinking about what the reader needs to hear rather than what do you want to tell them.

Jen: That’s fantastic advice. The internet would be such a different place if everybody took that advice.

Sarah Townsend: Oh, wouldn’t it just. So would LinkedIn.

Jen: Yeah, absolutely. So you’ve been a freelance copywriter. How did you then turn that into writing a book about how to be a freelancer?

Sarah Townsend: Back in 2020, I had been freelancing for 20 years and I wrote a blog which I shared on LinkedIn about the secret confessions of a successful copywriter. I had a tagline for it at the time. It was kind of “how to go solo without going loco,” and I was so chuffed with that.

In reality, I self-published all three of my books. When I first wrote Survival Skills for Freelancers, I wanted a client of mine who was working for a mental health organization to write the foreword, and he was so supportive. He was like, this book is so needed. It’s so reassuring. It’s empathetic. It’s properly real. It’s not generic business advice. It’s what I’ve learned from 20 years of freelancing, all the mistakes that I’ve made, and here’s what I’ve learned so that you can avoid making the same mistakes and find your definition of success much more quickly than I did. He was all for writing the foreword, but because he worked for a mental health organization he was very much about positivity around mental health, and because I was using the expression “going loco,” I loved it but I had to let it go.

I just realized when the blog that I shared got so much feedback from people saying, oh my gosh, it’s so nice to actually hear reality, rather than the hustle-bro six-figure income stuff that can just alienate people and make them feel really like a failure. Rather than focusing on how successful I am, I just decided to break it down into the eight myths of self-employment. For example, going solo doesn’t mean going it alone, and too many people try to do everything themselves. So you do need support, community and connection. You need, if you can afford it, somebody to help you with the tasks that you don’t enjoy, you’re not good at, and the things that don’t make you money. So that’s just one chapter, for example. I self-published it and it has since sold in 29 countries. I’d love to get it to 30.

Jen: Wow.

Sarah Townsend: And it’s helped thousands of freelancers all around the world to grow in confidence, to set better boundaries, and to avoid burnout. Because that’s just all too common, isn’t it? Freelancers, we kind of think we can do it all. I have a special skill, in my case a special skill with writing words. Disclaimer, because I have ADHD, when I’m talking my brain’s always firing off in different directions. People might think, oh, she’s supposed to be good with words, but she’s going off at tangents. But obviously I don’t do that when I write. The book has got something like 475 star reviews on Amazon in the UK, with an average of 4.8. Even though the original book came out in 2020, there’s a brand new edition that came out in 2025, so it’s been updated. And then from that I wrote my two fun little books about spelling, which everybody loves.

Jen: That’s amazing. Congratulations. That’s very impressive. As a freelancer, you have the client work that takes so much prioritization, but you always have to be marketing yourself and your business and your skills. How does that fall on your to-do list and how do you prioritize between client work and promoting yourself?

Sarah Townsend: It’s difficult, isn’t it? Because the marketing, the social media, the admin, the accounts, all those things, that’s not the core of your business. What I found was that I spent the first however many years fighting to try and do all that stuff myself and juggling it. It’s soul destroying. You start off as a freelancer and you think, okay, words are my special skill, transforming people’s documents, writing web copy, that’s great. I’m going to be a freelance copywriter and I’m going to spend all my time doing the thing that I love doing. And if you are neurodivergent like I am, that gives me the dopamine, which gives me the motivation to do my best work. But the downside is that being a freelancer is essentially running a business, and so many people overlook that element.

As soon as you can afford to get support for the things you don’t enjoy and you’re not good at, I would do it. Because otherwise you get to the end of the week and you just think, I’ve not really done very well this week. I’ve not done much of the work that I know is me at my best. And if you are neurodivergent like me, you’ve struggled to get motivated because we are not great at focusing on the things that we don’t like doing. It’s very difficult to get motivated for those things, but very easy to get motivated for the things we love. I started outsourcing about 10 years into my business, very late to the party with that one. But it was a mindset shift. I started off thinking I can’t afford to do it, and then I realized that I couldn’t afford not to do it.

On marketing specifically, working on your business instead of in your business should be a non-negotiable, however busy you become. It’s really important to schedule time out in your weekly planner, diary, whatever you do, and actually say, okay, I’m having two hours on a Wednesday afternoon and that is on my business time. I’m not a great one for scheduling social posts or having a content plan. I am very, in everything in my life, very energy driven. The end of last year, the energy was not with me and I was struggling. I really felt like I’d lost my mojo.

The result of that was that I didn’t post on LinkedIn for something like five weeks. I know that if I do and I fight through it, anybody reading my post is going to get that. They’ll take that energy from my post. You try to hide it, but you cannot hide it. I just wait until the energy’s back with me. And then since the start of the year, I think we’re two and a half weeks into January, and I think I’ve done about 10 posts. You can tell the energy is with me.

Jen: I love that. And again, that’s one of the two Doist archetypes, and that is absolutely what I am for sure. Entirely energy based. I feel like most of my life I tried to fight against it, and in the last year really I’ve been trying to just listen to that as best as I can. I get so much better stuff done, and I’m so much less exhausted and drained.

Sarah Townsend: Leaning into that, it really does change things. Something I talk about a lot is designing your working week around what works for you. When you are freelance, you are working for yourself and we tend to forget that. We tend to fall into the patterns of what our clients dictate. When you’re freelance, as long as you get the work done to a really great standard and you deliver on time, clients don’t care what hours you work. So lean into that. For me, first thing in the morning is when I get my head down and get my writing time done. By the afternoon I am ready for a call, because calls give me energy. Build your working week around your needs and your strengths and your productivity and you’ll have a much more enjoyable time.

Jen: Absolutely. Yes, I agree very strongly. So you mentioned that the way you prioritize tasks is do, delegate, delay, or ditch. Could you walk me through that? I’ve never heard it before but I love alliteration.

Sarah Townsend: I don’t know if you are familiar with the Eisenhower Matrix. It’s like a square with four different squares within it, urgent, important, not urgent, not important. That just feels a bit corporate and businessy for me. I can’t remember where I came across this alternative. It was suggested by some neurodivergent trainer of some sort. Because they’re kind of actions rather than statements. A task is important, okay, but I want to know what action am I taking in response to this task?

So if a task comes in on my email or something like that, if it’s something I can do within about five minutes, then I will do it, get it off my plate. If it’s something I don’t really want to do, or maybe it involves a skill that isn’t necessarily one of my strongest, then I’m lucky enough to be able to outsource it to my virtual assistant. That’s the delegate bit. Delay is usually something where I think, okay, I don’t need to respond to this straight away. I will schedule it in my Outlook calendar. I’ll actually carry things forward. A friend of mine uses a bullet journal, but it’s kind of the equivalent. I’m not going to do this today, I’m going to delay it, so I’ll carry it forward a week in my schedule and it just stays there as a task with a different color coordination.

Ditch. Yeah, sometimes there are things where I think, actually I’d be better off passing this on to somebody who would be a better fit. And sometimes there are just things I need to let go of. Like, oh, I must leave feedback for this restaurant I went to. That’s the kind of task you can really easily ditch, because they permeate your working day even though they’re absolutely nothing to do with work. So that tends to be how I deal with tasks that come in.

Jen: And you’ve mentioned that your systems kind of change. What systems are you using at this moment? You’ve mentioned Outlook, but do you do written lists, Outlook calendar, a combination?

Sarah Townsend: Very hybrid. I’m kind of between systems. In the recent past I became obsessed with Trello. It takes me a long time to learn something, but when I become a bit of a power user at it, it’s like everything is controlled by Trello. I had lots of different boards with different cards within the boards. Everything was great.

Generally speaking, the way I prefer to organize my freelance business is one project at a time. Not everybody is fortunate enough to be in the position to do that, but if I can, that’s how I prefer to work. I find it takes a lot of mental energy to go from one client’s headspace to another. It’s like changing gear, but not quite so intuitive. I prefer to book work in to have one project on the go at a time. If I get ahead of myself, which I very often do, or if somebody is late sending something through, I’ll have a fallback task booked in for when the big project finishes. What happens often is that I manage to bump clients forward.

In my personal life, if I’m having a day where I’ve been doing loads of stuff and getting loads done, and then suddenly I’ll be like, dropped to the floor sobbing because I just feel like everything is too much, everything in the whole world is too much and I can’t cope with any of it. So once I’ve had a bit of a cry, usually what I’ll do is get a particular notebook and just offload everything that’s in my brain. Then the only thing that makes me start to feel better is going through and ticking those things off.

Another thing I do, which is a very specific tip, is I get a lot of thoughts while I’m driving. Oh my gosh, I need to remember to do this. What I will often do is say to my phone, remind me when I get home to do X, Y, Z, and then it pops up on a reminder on my phone. A lot of people don’t know you can do that.

It very much is a hybrid way of working. When I’m in the middle of a project I’ll have much more structured to-do lists. When I’m outside of a project, as I mentioned, I’ve got a couple of weeks in January before a really big project starts, so I’m consciously using this time to actually meet people in person, have conversations, grow my network, build relationships, and get to know more local business people. I’m not currently as to-do list bound as I usually am. There’s never been, oh, I’m stuck in one way of doing things. I’m always experimenting. But when I get into that personal sense of overwhelm, it’s only writing a physical list and going through with a pen and crossing things out that is the most satisfying.

And then when I’ve got, say, 10 of 20 things done, I’ll start a fresh page and rewrite the 10 remaining things so it’s a less messy to-do list. Write a new to-do list.

Jen: I see a lot of that too. Of all the guests I’ve had, I feel like you have the most similar brain to me, especially the to-do list brain.

Sarah Townsend: That’s so nice. Connection on the other side of the world.

Jen: Let’s see. I definitely want to address your 60 for 60 list. So yeah, you made a list of 60 things you want to do before you turn 60. Where did this idea come about? And did you make it all in one sitting or are you adding over time?

Sarah Townsend: My daughter turned 26 last year and she said, oh Mom, I’ve got a list on my phone of 30 things I want to do before I’m 30. And I turned 56 and I thought, I should do the same. I should have 60 things I want to do before I’m 60. It’s actually been really challenging to come up with 60 things. I think I’m about five off.

There have been things I’ve done and thought, ooh, that’s a win, I could add it to my 60 for 60 list retrospectively and tick it off. I’ve done that once or twice. One real example was eat a prawn. It sounds like such a ridiculous thing, but I’ve gone through my whole life being a bit, oh, well. I was vegetarian from the age of 10 and I’m still vegetarian, but I will eat fish now. I don’t like seafood though. I’m basically really picky. I’m gluten free and all that. But I went to a friend’s for dinner. She knew I was pescatarian and she made a paella and it had all these prawns.

And I said, when would be a good time for me to tell you I’ve never eaten a prawn? And she’s like, oh it’s okay, you just pick them out. I was like, nope, I’m going to motivate myself to eat a prawn by adding it to my list. So that’s what I ended up doing. Some of them are a lot harder to achieve than eating a prawn. It’s an experience I will not be repeating. I’m not a fan of prawns. They still remind me of maggots.

Jen: I’m the same as you. I became vegetarian when I was seven and then started eating seafood in my twenties. They are like the garbage men of the sea. They just eat all the grossest possible stuff. That’s crazy.

So, I’m reading through, oh, you have “watch a rugby match” on there? You’re English and you’ve never even seen a rugby match?

Sarah Townsend: Yeah, well there is more of a story behind this. I live in Gloucester, and Gloucester in the UK have a really successful rugby team. Years ago, probably about 10 years ago, I did go to a rugby match. My experience was really bad because I was sitting in a seat right next to the aisle and halfway through the match, some guy walks down the aisle, stops, and throws up all over my back. That is just the worst experience ever. I’m traumatized. I’ve kind of wiped the slate clean, quite literally, and I’ve put it back on my list. We have quite a successful women’s team as well. I think it’d be quite nice to watch a women’s game. Watch a game of rugby and just wipe that experience out of my brain would be very nice.

Jen: Okay. Well let’s get to one that’s hopefully less gross. I see you have “learn to cook quinoa.” What happened there?

Sarah Townsend: I haven’t done it, and I feel like it’s probably just like couscous, you probably just have boiling water and stir. But if I put it on the list, I’m more likely to do it. Because I’m wheat intolerant, I can’t eat couscous, but I can eat quinoa. I’m like, come on, how hard can this be?

You picked two really easy ones there. I think you need to focus on something way more dramatic, like the firewalk.

Jen: And the helicopter! Tell me about that one.

Sarah Townsend: A friend’s daughter has moved to Canada and she’s just trained as a helicopter pilot and qualified at the age of 23. I thought, well, if she can learn to fly a helicopter, I can at least go in one.

Jen: That seems reasonable. Do you have a location in mind?

Sarah Townsend: When I’ve done trips to places like New York they’re always like, oh, have this ridiculously expensive helicopter flight across the Hudson River and over Manhattan. I’ve always thought that would be absolutely amazing, but realistically I probably can’t afford to do that. I’ll probably end up flying over the Cotswolds, which is where I live. It’s a very beautiful, rural area. It wouldn’t be a sacrifice to fly over the Cotswolds.

Jen: Or you could always go to Canada and have your friend’s daughter be the pilot.

Sarah Townsend: That’s actually a good idea! I’ve got holiday ideas on the list too, because if I put it on the list, then I have to do it in the next four years. I’ve already got a few trips booked this year which are going to tick some of those off. I’m doing Annecy on a cruise with my partner in France. If you look it up on Instagram, it just looks absolutely stunning. A bit like the Italian Lakes, mountainous, with a beautiful turquoise lake, and the town itself is like a fairytale town. I’m amazed everybody doesn’t go there, but it does seem to be still relatively unknown.

The next one I’m doing is the firewalk, which is at the end of next month. I was supposed to be doing it last year. I raised £260 for charity, which is the first time I’ve ever done that in my adult life. I’ve never asked for sponsorship for anything in my adult life, so I was really chuffed with that result. Then on the day they cancelled because there was a horrendous storm and they said, we will reschedule. I thought, do not you dare reschedule for a day I can’t do. Fortunately I’ve got that coming up and I’m weirdly really looking forward to it, because they give you a kind of CBT pep talk, cognitive behavioral therapy techniques for how to be in control of your thoughts. And I think that’s not just going to help me do a firewalk, that’s going to help me in life.

Jen: Yeah, that’s really cool. Can you tell me about one of the ones you’ve already done?

Sarah Townsend: Chopping wood with an axe is the one where you found me on LinkedIn, so that’s quite cool. It was quite an easy one to take off, but I was a natural. I absolutely loved it. My friend videoed me. But I’ve actually got tendonitis in my elbow, so swinging a really heavy axe is like the worst thing I could have done. I also want to smash down a wall with a hammer. I’m not quite sure how I’m going to fulfil that one, but it feels like it would be a very satisfying thing to do.

Jen: You could post on Facebook Marketplace or something. I’m looking to smash down a wall, who has a wall that needs smashing?

Sarah Townsend: Yes! They can provide the safety equipment. I will provide the smashing.

Jen: Excellent plan. Well, my final question is, if you could see anybody’s to-do list in the whole world, whether that be a specific person or a job title, whose to-do list would you most like to see?

Sarah Townsend: Oh my gosh. Oh, that’s a question I should have prepped for. I can’t, like my brain’s gone predictably blank. I’m not even a big style magazine fan, but I reckon the editor of Vogue would be pretty cool. That would be a fairly complex setup, wouldn’t it? They’ve probably got the big whiteboards with things all over the place. Maybe because I’ve read they’re making a Devil Wears Prada follow-up film. Maybe that’s what’s in my head. There were just so many really good answers to that question.

Jen: Yes, there are. I’m also curious with anybody like that, how much of what they’re doing is delegating. How many tasks are they doing versus just thinking.

Sarah Townsend: How strategic is it? How much are they just controlling and delegating entirely? I reckon they probably don’t actually do a lot of the work themselves. They’ve just got a lot of minions running around doing all the work for them.

Jen: Yeah, I like that visual. Well, is there anything else you’d like to share?

Sarah Townsend: I was quite proud of myself for learning all the states of America. That was actually one of the ticks I’ve already done on my 60 for 60 list. It was really fun, but really hard. One of the ways I can make a task really dopamine-inducing for me is to add that element of novelty and competition. That’s what ADHD brains need, urgency, novelty, interest and competition. So that ticked two of those off and really made it easier to learn. I don’t know if I could do it on the spot now, but I’d certainly get to 48 with two left kicking myself going, what are they? Quite often it’ll be Nebraska. But yeah, that was a good one.

Jen: You know, that’s like the whole plot of one of the episodes of Friends. It’s impossible to list all 50 states.

Sarah Townsend: I was a huge Friends fan and I don’t remember that. I’m going to have to look that up.

Jen: I think it’s an early, maybe season three Thanksgiving episode, because Ross isn’t allowed to eat Thanksgiving dinner until he finishes it.

Sarah Townsend: Oh, I’ve got to look that up for sure. Well, I’ve always been absolutely shocking at geography. The next thing I taught myself after the states was all the countries of the world. There are something like 197 countries. I found this particular quiz on a website called Sporcle, which is like a quizzing website. You only have 15 minutes to type them all in. When I first started I got 14%, and then I gradually, very gradually, went from 14% up to 100%. I only had to do it once and then I could tick it off. I found Africa quite hard, but I genuinely knew nothing about geography. I always said, oh, I’m terrible at geography. And I thought, well, why don’t you do something about it?

Jen: That’s so cool. I love how diverse the categories on your 60 before 60 list are. The learning, the fun, the trying something new. It’s a very cool list.

Sarah Townsend: It’s a diverse list.

Jen: What is a cloudberry?

Sarah Townsend: They grow in Finland. They’re meant to be like probably the most expensive berries in the world and they are absolutely beautiful. I did try them when I was in Helsinki last year. I think they grow in the snow or something like that. I really need to look up more about what a cloudberry actually is rather than just having tasted one.

Jen: Well, now I want to try one. From the name alone, cloudberry, it sounds like a heavenly berry.

Sarah Townsend: Yeah, sounds like a cherub would sit on them.

Jen: Absolutely. Thank you so much for taking the time to chat with me. You’re very fun. I like your brain. Thank you for sharing. Have a great day.