The Book Deal
Motivation and inspiration for emerging writers, helping them pave their own pathway to publishing success.
The Book Deal
Jessica Box on portfolio careers for creatives, coaching, growing your author business, content creation and social media
Jessica Box (co-founder of Matched) on portfolio careers for creatives, growing your author business, content creation and social media.
In this episode of the Book Deal podcast, Madeleine delves into the intersection of writing and business with Jessica Box, an accomplished growth executive and founder of Matched: a knowledge-sharing marketplace with 250+ vetted advisors and coaches.
Jessica shares her journey from a creative student to a tech leader, discusses the importance of storytelling in business, and offers actionable advice on managing a portfolio career, utilising social media, and avoiding burnout. The conversation also explores the evolving landscape of connection and knowledge sharing through Jessica's platform, Matched, offering invaluable insights for writers at any stage of their career.
If you would like to connect with Jessica, reach out to her at:
- Instagram: @matched.community
This week's Debut in the Spotlight is the delightful Holly Cardamone with her YA novel Summer, In Between (Hawkeye Publishing, September 2025).
00:00 Welcome to the Book Deal Podcast
00:42 Introducing Jessica Box: A Multifaceted Leader
01:14 The Intersection of Business and Writing
01:55 A Journey Through Friendship and Career
07:39 The Importance of Storytelling and Authenticity
12:08 Navigating the Tech World and Personal Growth
25:07 Building a Portfolio Career
29:46 The Guilt of Taking Time Away from Writing
30:00 Allocating Time for Tasks
30:28 The Importance of Structured Time Blocks
32:11 Introducing 'Summer in Between'
32:32 The Story of Kat and Paul
34:09 Excitement and Implementation of New Strategies
35:25 Finding Joy and Boundaries in Social Media
37:28 The Power of TikTok for Authors
40:30 The Future of AI and Social Media
46:11 Introducing the Matched Platform
48:20 Becoming a Good Coach or Trainer
52:58 Final Thoughts and Top Tips
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This is the Book Deal podcast where you will discover the inspiring stories, the authors behind your favorite books. No matter what sage of writing you are at, we've got you covered. I'm Tina Strachan. And I'm Madeleine Cleary. And join us as we pull back the curtain of published authors one deal at a time.
Madeleine Cleary:The book Deal podcast acknowledges the traditional owners, the land and waters, which it's recorded on. And pays respect to their elders past, present, and emerging. Jessica Box is an award-winning growth, executive leading product, marketing, and insights in plus$1 billion valued tech companies. She's the founder of Matched a knowledge sharing marketplace with 250 plus vetted advisors and coaches. She successfully grew Link Tree from 2 million to 45 million customers and helped Slack, Optimizely, and Braintree launch in Australia. She's also driven change for women in tech as managing Director of Girls in Tech Australia. Jessica also happens to be my best friend, and I could not be a prouder friend. See, how does Jessica's experience intersect with writing? Jessica and I have had long chats recently about the business side of. Being an author and what it means to wear many hats. With Jessica's experience, growth, and creating authentic connections in the business world, I felt it an imperative to share her excellent advice with other writers. We chat about the role of storytelling, understanding your why. Social media and content creation, coaching, how to manage your time while wearing many hats, and how to understand your own value proposition. So make sure you time box this episode into your schedule writers. It's a great one. Hello Jessica. Hi Madeleine. This is really exciting to have you on the podcast today.
Jessica Box:I'm really excited to be here, long time listener and follower of all the amazing people that have been on the podcast. It feels I've got a like slight imposter syndrome being here as someone who is, um. Not necessarily a published writer or focusing on that at the moment.
Madeleine Cleary:Wow. Well, I mean, you are, you've been to so many different book events with me as well. You're like my, my book companion when we go to different types of launches and events. And I feel like you're already part of the writing community and you are my best friend as well.
Jessica Box:And I, I have always been an avid reader. Um, so does. There's something about the study of books that I, I love and yeah, I mean, I would love to write a book one day. So
Madeleine Cleary:do you remember when we first met? Oh. I dunno if I do. Gee. Wasn't very memorable. I thought that it should be, but I remember actually, I remember this very beautiful, tall, redhead girl walking down the corridor in year seven and I thought, oh, she's confident she's going somewhere. I wanna be her friend. And so thank you for being my friend.
Jessica Box:Oh my God, that's so good. I love that. I do. I do remember you. I don't remember this specific moment because you have the best hair ever. And I remember thinking, oh my gosh, how does she have the most amazing hair? And how do you like maintain it because it's so volumous and luscious and lovely. Lovely. Um.
Madeleine Cleary:I
Jessica Box:think we connected
Madeleine Cleary:over hair. That's wonderful for those. Um, you'll have to Google it if you're listening. Um, Jess has the most beautiful red hair and we, we are always very jealous of Jess's hair. So I'm actually interested, Jess,'cause I mean, people were probably wondering why, why is, um, why is Jessica Box on the podcast and because obviously our. Podcast is to help motivate, encourage, inspiring, aspiring writers and debut writers. Um, but we've had some really good chats in the last few months, I think. And you, you provide such good advice to me about, um, in, you know, being not just an author, but I think being a, a business owner and a sole trader and, and how to present yourself and building a profile because that has been something that you've been working on for so much in the last few years. Um, so I thought it would be fantastic for you to come on and really help, I suppose, other writers who are looking at building, and this is something that you've said, and I was like, okay, we have to talk about this. Building a portfolio career, which is such an interesting term. Hmm. Yes. I guess going back to year seven, like did you ever think that. Year seven Jessica Box would be able to, what would she think about looking at your career now, how many years after? I actually don't wanna admit how many years it's been since year seven. It's probably been 20.
Jessica Box:Oh golly. Yeah, it would've been far out. Uh, I think it's, do you know, I don't think she could have conceptualized where I would be today, um, at all. And I remember, and you've had the fortunate opportunity of doing this, but I went back to Avalara, our high school, um, to speak to the year eights and year nines, and it made me really think about. What I needed to hear at that point in my, um, schooling journey to really think about not just, you know, the outcome of a specific career title per se, but the things that really l lit me up and, and my fire and like kind of following passions rather than just following like some form of, you know, I wanna be a teacher or I wanna be a doctor, et cetera. And I think back to, um, our career guidance counselor, I remember. Sitting in his room like so vividly him looking at my subjects and going, oh, okay, so you've got like science and like methods maths and like I did, you know, biology, chemistry, methods, maths. Oh, but you also have like drama and literature. Um, well, so obviously you have to be a doctor or a lawyer and I just, I remember sitting there going, I didn't really know how to respond because neither of those resonated me. I didn't with me, and I didn't really know what other options there were. What's really interesting now reflecting on, you know, if you were to see those on paper, um, it's the perfect synergy for someone who goes into tech because mm-hmm. The, the creative like, um, uh, you know, right brain side, but also with the left brain kind of analytical, strategic thinking, you know, problem solving, um, toolkit. And so I think if I was to. Like say something to my 13-year-old self, it would be just back your instincts. Because my instincts were screaming at me at the time that, oh, none of this is right. And I remember before, um, uh, the final day when, um, uni selections were due, I had, um, uh, physiotherapy as what I was gonna do up until I remember that
Nobody:I.
Madeleine Cleary:You, you are a creative at heart, Jess. You've always been creative. You've, um, you're, you're an excellent writer yourself. I remember reading your creative pieces in, in year 12 Lit. Um, your, uh, we were both massive drama nerds. Um, in year 12. Um, we were part of a very small group of drama students, um, and we loved it, and that's where we really bonded. And so I think, and you've really. Brought that creativity to the roles that you've done throughout your entire career and now as the CEO, um, and co-founder of Matched as well. Um, because I think perform there is, there is a performance element in everything that you do. Mm-hmm. And it's definitely something that writers have to think about as well. Like, I know you, 12 drama for me has held me in really good stead.
Jessica Box:Yeah. Yeah, it's, I feel like it's, um, knowing how to tell a really good story. I think it sets you in good stead regardless of what career you're in, whether it's about yourself or whether it's about a company. So, mm, I really like my whole career has been at the intersection of what I would say is tech and, um, impact. And I really have centered a lot of my decisions around what I want do and like where I wanna spend my time on how can I leave the world a better place. And I think there's so much of. Tech that is unknown when you're not deep working with engineers and product designers and all these things that, you know, I have the pleasure of working with every day, but all the decisions that I've made across my career have been, how can I do that? And I think such an important part of that is, you know, uh, being able to communicate the story behind the why. And so, um, I think when I first started my career, I didn't really. There's this concept called the Five Whys, um, by Simon Sinek. And, um, basically it takes you like one layer deeper each time, so you get to the real heart of, of the. True why? And so when we were building Match, we started with, oh, we're gonna build like a, a tech product that helps people connect, which at the surface level it's like, okay, cool, what this does nothing for. Um, and then you go a layer deeper and it's like, oh, why are people connecting? Oh, it's because they, you know, wanna be able to try, try and find true, meaningful, um, uh, authentic. Um, purpose led conversations with others and learn from each other, et cetera. And then it's like, okay, why do they wanna do that? Um, oh, it's because it's really hard to get access to the right type of information, all the right people, because, um, it's such a privileged opportunity to be able to connect with different people. And then the final ways, you know, um, you wanna unlock knowledge that you have never had. So. I get, and I'm saying this because obviously as writers and everyone listening, so much of how you tell stories is, is getting to the heart of the, the true why rather than the on the surface. And I think, um, the journey to founding match and kind of how, how we got to the true why, and I've always wanted to be an entrepreneur and start my own business. I've always dabbled in starting things myself, but this was the true. The first time that I had an idea that I put in my phone that screamed at me on a Sunday morning, and I just, it poured outta me and I went and I got to the why straight away. And I knew that it would be something that would motivate me, um, for many years to come. So I say that because it's like I had to find the story that connected with me the most, um, in order to start a business. And I think us sharing that story for Match with, um, the world is, is allowing us to really create a amazing community. So. Anyway.
Madeleine Cleary:That's so interesting. I'm, I wanna take that away.'cause I think that often writers to put things into perspective because, you know, there's, um, it's a really tough industry, the creative industry and, and often getting to the heart of why we do what we do. It holds us in really good stead. It builds resilience, I think, and it makes us truly understand our purpose and what we're contributing to. Mm. And so I think applying though that sort of layered why, why are we doing it? Why do we write, oh, well, we enjoy it, but why? Why, why? I think that's really helpful because there is so much rejection and um mm-hmm. You know, even if you've published a novel, if it's not considered a bestseller and it, you, you're, you, you get like, you know, a solid four weeks out in publicity and then some things and it, you feel a little bit flat. But I think being able to tell that and craft that narrative, I think is really, really important. And yes, storytelling is really, really important as well. In building your brand and, and that people talk about this in, in the author world about having an authentic brand, and it's often really hard to understand what that is.
Jessica Box:Yeah, and it helps, I think the, the depth of the why helps you weather the storms. Like I would say, there's been so many times where I went, okay, I am not cut out for this. I'm gonna give up. Um, and anchoring on that is it gives you a higher purpose or a higher order thinking. Um, and like, you know, rider, you've got your own, you are your own business, like you are the business. Mm-hmm. Um, so to think about it in that way, but take it a layer deeper into the true purpose. As you say, will connect you more, um, strongly to the why, but then also like to help you weather all of the, um, challenges, because of course, everyone always has challenges and setbacks.
Madeleine Cleary:Mm-hmm. So in terms of your career,'cause you've all, you were saying that tech is the perfect fit for you. Was that when you, when you were doing your performing arts degree, was that a natural thing for you to fall into tech or did it take some time?
Jessica Box:It definitely took time and I think I, and I, I'm a big fan of not saying that I, people are lucky. I think luck is, um, not, it. I think you work really hard and then you create opportunities that, um, you know, you naturally attract because of hard work. Like, I worked, I worked really, really, really hard. Um, and then I think I said yes to a lot of opportunities. And so when I was in performing outside, I mean, this was like, you know, at the start of. The iPhone coming out. I was always the person that had like the latest tech you were. Um, and I was draw, I was drawn to, I think it's just like the way it connected people, um, and the opportunities that you had to access information. Which is funny because Match is whole purposes around around that now, really. Um, uh, and yeah, I think I just also, like, I, you know, I did. Masters, which you pushed me to do. Um,'cause I finished performing arts and I was really lost and I kind of went, you know, I love this part of storytelling, but I'm super analytical that my dad is a, a very like, um, uh, analytical person. My mom's a creative. And so I'm the intersection of two of those people. And I'd lent so heavily into my creative side for so long. Um, I danced for 20 years. There was just like so much of that. Um, and then I lent. I started to lean a little bit more into my analytical side and I realized that I really loved it. Um, and the intersection of the two is tech. So, um, I like formally, uh, my kind of area of expertise, um, in tech is growth, which is, um. Effectively, how do you help a company access and, um, serve really specific subset of customers, um, which obviously lots of writers need to do, um, as you are picking their, picking, you know, um, your genre, and then also specifically the, um, you know, target audience because you can't hit everyone with Yes. What you're writing.
Madeleine Cleary:So, so that's so interesting, Jess, because, um, as creatives. We often don't think about these types of business side of being an author and the business side doesn't, isn't necessarily something that comes very naturally to authors, particularly because a lot of authors are quite introverted. Um, our preference is to stay home and. Be on our couch or on our study or wherever we write, huddled in our words. And then suddenly we are meant to have a profile We are meant to look at, you know, um, pushing our work and communicating and connecting and attending events and building something that's meaningful and authentic, whatever that means. So what advice would you say about how you, how we grow, um, our business as authors?
Jessica Box:I think it has to be anchored in, um, the authenticity, right? I think even more so now. So growth as a discipline for a long time was like paid advertising, looking at data and going, okay, how do you like target a specific subset of customers with a message? Yeah. And also
Madeleine Cleary:with no money as well. Yeah.
Jessica Box:Which you can do that. Uh, but do you know. Um, changing and I, my most recent executive role, um, before starting Match was at tre and I was the first, um, leadership hire outside of the founders. So it was a wild time. The company had no, like, was starting to generate revenue, but hadn't TA taken on what I would call like venture capital funding, which then accelerates growth. So I had gone through this stage of like just throwing a lot of money at, um, bringing in customers, which is really interesting. Obviously it works, but what's happening now in a world of AI is, um. All of the existing channels are breaking. What's been really interesting lately is, um, there's reports coming out of like businesses and companies spending 70% less on their paid advertising in the last quarter alone, um, because it's not working. So, um, and I say that because as writers, like you are generating content. Um, not only, I mean obviously you're creating, um, uh, amazing whether it's manuscripts or publishing novels, but then you have this extra layer where you need to create content to share Yeah. Your amazing manuscripts and novels. And so at TRE we worked really closely with creators, but from all different varying areas, um, whether that. Musicians who, you know, created music and then trying to disseminate, um, whether it is actual, you know, artists like, um, you know, fine artists who are then kind of, um, you know, publishing and, um, sharing their art online and then, you know, um, doing some, you know, different versions of how they, um, you know, tailor specific, um, pieces to their audience. But the reason I say that is probably breaking it down into two parts. Like you've got your craft that you. I'm so passionate about that you wanna spend all your time on, um, uh, but then you have this whole other thing is like you need to then communicate with others to sell and like be able to, um, generate revenue off the back of your art. And I think that tension is really, really strong because I would imagine you'd wanna spend most of your time just writing and, but then it's so critical to be able to, um. Build a business around yourself that is authentic to you. So my, my tip is like, get to the heart of like the, the values of what makes you, you, like you, I mean you, you know how to write and structure a really good story, but there's this kind of concept of your personal value proposition. So what is your value that you generate? Like you, for example, you obviously, um, have published your first, um, book this year. Um, but you've spent so much time prior to that. Um. Like thinking through, okay, I am an historical fiction writer. This is the area that I wanna be known for. How do I spread the message out of me as a historical fiction writer? And then naturally, when you publish a book, it fits within that view of you. Mm-hmm. And so I think what people don't do well is. Think about being really deliberate around who they are and what they wanna be known for. Um, and then testing that. So doing, you know, it getting really granular here. Oh no, we love this. This is so good.
Nobody:This is so helpful.
Jessica Box:Getting really granular, but like piece to camera. So everyone loves, there's this like, shift, getting back to the AI piece. Yeah. Um, is there's this real shift of, um, towards authenticity and trust. I think trust in particular because we're flooded with synthetic content where, um, people are. Using AI to create things. And you can tell, like it's, it's very obvious.
Madeleine Cleary:Yeah. And I'm, I'm finding that in my feed where things just don't look right and then you, you start to doubt. You're like, wait, is this AI or is this a real person?
Jessica Box:Yeah, absolutely. And it's, and so that, this happened recently, I saw Janine Alice, who's the founder of Boost. Um. Juice. Yes. Um, drinks. She, um, shared a piece to camera saying, I've started to see my own face pop up in my feed, and it's not me. Um, I am communicating with all of you to let you know that these channels are my only channels that I put myself on. So as people have influence, um, start to be kind of used in a, like, you know, whether it's chat JPT or Claude or whatever platform, um, that expands out into, I mean, it's already there in terms of. You know, name, image likeness is what I would call this, where people can take that and then go into chat gpt chat chat GPT and say, oh, create me a piece of content like Janine Dallas would, and with Janine Alice's face. And then it spits it out and so frightening. It is, it's quite frightening. Um, and the reason I say this is because it's so important that, um, people. People are connecting with authentic content right now. And the trust piece is, um, so important. So this like in-person events, in-person connection. Mm-hmm. I think we're gonna see a big flock back to that because there's this level of trust. So if you're investing in any area, it's like your piece to camera, like you as a person talking, which is really hard. I, I mean, I personally struggle with, so I, I find I have to like work myself up to it. And my co-founder, Susan and I, we've started this like, we're actually doing like quasi podcast. Style. Um, in person sessions where we talk to each other and then we turn them into little videos because
Madeleine Cleary:Oh, that's much, much better. That's actually better.'cause I find it really dif, I, I actually don't do it that, what do you call it? Piece, what is it? Piece to
Jessica Box:camera. Piece to camera. So you talk to the camera, but you talk to each other. So like we doing, but we sit in front of each other and then we have two cameras, one facing. Each, each other. Mm-hmm. Then we talk to each other so it's more authentic. It's like this, but then you stitch it together and there's like tools we call, use a platform called V that mm-hmm. Um, basically, well this is the good part of ai. It like takes our content and pulls out the best snippets, um, into like one or two minute bites. Um, so anyway, that, all of that is to say, I think there's this giant shift happening and then this concept of like. We're talking about profile, but really it's a brand. Um, uh, in our world, what's happening right now is everyone is investing really heavily in brands, um, like tech companies. It's the, the thing that you own. Because so much of what's changing is like, you actually don't own that all that much. Like you don't own your audience if you're paying for it from Meta or Instagram or et cetera. Um, but your brand is something that you own and you can communicate the message and, you know, the investment is, you know, starting to pay off for people who do that.
Madeleine Cleary:That's so interesting. I didn't actually really think about that. That you don't own your, own, your audience. If your audience is purely on Instagram or TikTok. Yeah,
Nobody:because
Madeleine Cleary:it's, it's, you are using a platform and they are on a platform.
Nobody:Yeah. But,
Madeleine Cleary:but if you are out and about in events, if you are attending and people are turning up for you, reading your book, consuming your content, providing feedback to you, that's different. Like you, you do own that more, I think.
Jessica Box:Absolutely, and like newsletters and things like that, like I really push people to do that because you've got email addresses, you've got like, you can actually communicate directly. Whereas in a social sense, you're also beholden to the algorithm. So like, I think there's something like, at the moment, only 10 to 20% of your audience. Who actually follow you will see your content. So even then, it's like a lower percentage. Um, and I've got a very funny story about owning audience. When I was at Ree, um, and it was uh, super Bowl Sunday in the us Uh, we all got up on Monday, um, morning, and Elon Musk was, had just taken over Twitter, um, and. He, uh, Twitter had shut down access to Link Tree on, um, all on on Twitter, full stop. No one could click out to a link tree link at all. Um, and so all of our creators like flooded. Um, well now called X. Still Twitter to me, but, um, uh, saying, you know, what's happening? Um, blah, blah, blah. And there was this like published piece, like in, you know, ts and Cs have been updated on, um, Twitter. Um, you know, these types of external links are not allowed anymore. Um, and so we all like, even an instant there goes your whole modus operandi, right? It wasn't even Link Tree, it was more the creators, like all their audience. They couldn't ca uh, you know, um, access their audience. Um, and so we had this, like this Monday morning in the US Sunday night, um, Monday morning in Australia, Sunday. Um, super Bowl like Elon Musk is at the Super Bowl. Um, and, um, we all get on this crisis call and then we realize quite quickly that it's gonna be. Overturned, right. Um, and you could just like, from a legal perspective, we had a general counselor who was super amazing, got on the call and basically said, yeah, no, it's gonna get overturned. So what we actually did, and this is a good lesson in like capturing moments, um, we went, okay, so we've got like high volumes of traffic coming to Link Tree, the website. To see what's going on because it's everywhere. Mm. Um, and how do we kind of like, own a really interesting narrative or voice within all of this? And so Alex, the CEO of Blink Tree, um, has a Tesla. And so, um, I was on a call and I said, how about we like get cheeky and actually just say, um, don't make me sell my Tesla at Elon Musk and. And that was what he did, and it ended up on the, uh, like a headline in the Sydney Morning Herald and a whole bunch of stuff. Um, so I say this because like the owning the audience piece is like, it's so volatile, but then you can also, like, there's ways to kind of be creative that generate a lot of like, interest in those moments as well. So,
Madeleine Cleary:well, it reminds me of when, um. Um, I can't remember if it, was it Donald Trump that just closed? Well, no, it wasn't Donald Trump. It wasn't the TikTok got banned in the US for last four days or something. Yeah. And then Donald Trump said he would overturn it. I think if he was elected
Jessica Box:the us like all the, all the execs in the US have this big sweeping, like we'll just knock everything out. And then they, and it's obviously some, a lot of it's share price. Um, but some of it, yeah.
Madeleine Cleary:But isn't it amazing that TikTok could just turn off their, their, you know, creators in the US for that? Oh, was it global or No, I think it was just in the us, wasn't it? Yeah. And then suddenly all these people on their platform is gone and, and it goes dark and you know, you don't, you don't have that control. Um, but you're right, everyone says that. Um. Newsletters and substack are really good, like creating that. I just find, um, it's really hard because, and this is something I really wanted to talk to you about. He's trying to balance where you put your energies into.
Nobody:Yeah.
Madeleine Cleary:cause you know, you, you do have so many different priorities and often for me, my substack goes to the lowest. Yeah. And so perhaps this is like a good idea that maybe to move towards, like talking about creating a portfolio career and, Hmm. One that's sustainable. Yeah, I think sustainable is probably one of the key words. Um, yeah, because, and I'll actually maybe tell us a little bit about what, what the concept is and then we can have that chat.
Jessica Box:Yeah. So, um, I would describe portfolio career as. Having a collection of things that you are passionate about and being able to monetize, um, from multiple of them. So typically you would think about full-time job as where you get your money. Mm-hmm. Um, what is changing is, um, people, while people are looking for more optionality, uh, in where they generate their income from, but they're also leaning more heavily into purpose. So obviously. Um, lots of writers and emerging writers listening to this like you are, I would imagine you're very passionate about your writing, but you also are probably in a job that sustains your life, um, or, you know, pays bills. And I think the concept of portfolio career is breaking that down into, okay, um, how do I have a collection of things that I'm passionate about and also brings in. Uh, income that I can capture value from is, is effectively what I would call that. So I've always been, and then there's another funny word for this that I would call a slasher. So as in like, I am a CEO slash a co-founder slash an advisor slash a board director slash a wife slash um, a dog mom to my dog whiskey. Um, and, and the whole concept of that is, um, being able to put. It, put all the things out there and I have my coach, um, we call these, um, wearing the hats. And so I have like a, you know, a bucket for each of my different hats and the energy that I want to, um, kind of put into, into each. And I think what happens is when you start building out something like this concept conceptually as a portfolio career, it can be really overwhelming because you think that you have to give equal energy to all the things, um, which is just not, yes, that's what I'm finding. It's really tough
Madeleine Cleary:one.'cause I mean, for writers we also wear many hats. We are. The author. Yeah. And like you said, we've got the day job, but we also do other things like we might do, like at the moment it's book week is on. So yeah. A lot of authors are out in schools. They're doing running workshops. Um, we do library events, we do speaking events and keynotes. We are attend writers festivals. Um, we run podcasts, we mm-hmm. You know, so we, we do have lots of hats. Um, and. And it is, I think, yeah, if you've got any tips on how you like Yeah. How do you avoid burnout?
Jessica Box:Yeah, so I've got, I've got two things that I've, I'm, and I will say I'm not always good at this. Like, I, I think it, it, there's periods of time, like probably right now I'm flying to Europe on Sunday and, and I've struck, I've structured exactly how I'm gonna operate the three and a half weeks so that I get downtime. So there's seven days where I'm gonna be fully offline Anyway, this is like a good lead into one of the, um. Pieces, which is time boxing. Mm-hmm. I think being really specific, and this is a, like I talk, I, and I, I'll get really detailed on this'cause I take it to the extreme. My calendar, yes. My calendar is like a series of time boxes. So when I've got a task that I need to, I think there's this like, um. Theory that like you, if you, if you don't time box, you'll just let it fill as much time as is allocated. Whereas if you put in like say a half an hour, I'm gonna spend half an hour on that, that specific time, then you either like, it gives you the correct waiting for an item. So I'll give you an example that literally after this I've got two one hour time blocks, um, for things that I need to do. One of them is like just kind of wrapping up and making sure I send out like all my last, um. Emails before I head off, and then I've gotta review a specific document for a company that I advise. And so if I like didn't put say 45 minutes in, I could just end up spending three hours on it. Mm-hmm. Um, and so it also from a cognitive load perspective means I don't have to keep creating to-do lists. So I just like map it all out at the start of the week and I go, yep. So that's my time boxing there. Um, I will say it's like so structured. Um, and so I'm, my thing is. Where I need rest or like a reset. My thing about travel is that it's the total opposite. So I love like spending time totally unstructured'cause I'm so structured in, um, like, you know, day to day.
Madeleine Cleary:Jess, you've just changed my life, I think. This is actually so useful and helpful. I am boxing because I'm just sitting here going, oh my God, this is gonna change everything for me. Because I think the problem, and particularly for me and probably for other writers, is that anything that takes us away from the writing, I feel incredibly guilty about.
Nobody:Yeah.
Madeleine Cleary:And so, and I feel, and I beat myself up about it. However, if you put scheduled time in your week or over the next, or over a couple of weeks and say, okay, I'm going to, like, I need to set aside time to read a book and prepare for an author interview. Mm. This is the allocated time that I'm gonna do, do it in. Yeah. And, and that's, and that's. Set and done, and I'm not gonna feel guilty if I can't do the writing around that because you've gone in and you've allocated it. Yeah. Like I think that's super, super helpful. And I also think that you are right about, if you don't allocate time to a task, you can just absolutely fill whatever time you have. Mm. I find that with writing, this is something Tina, my co-host has said that. She has a block. She has a one hour block in the morning for her writing. Mm. And she'll smash her writing. She will not do anything else. That's all she'll focus on. And I've started to employ that because I found with my writing, I would just, if I had three or four hours, I would just kind of pick up other things and not focus. Mm. But if you do it in like blocks and chunks, I think it's so much better and better for your focus.
Jessica Box:That's it. I was about to say, and something that you were touching on there is, it's like once it's in there, then you don't have to think about it. Mm-hmm. Because there's something to be said about ju like the juggle of all the balls. If all the balls are in the air, then you, you're thinking about'em all at the same time, rather than going, okay. I know that say on a Friday, every Friday I have one hour block where I think about social media and then I spend, I schedule my content and then I'm done. Mm-hmm. And or you have like a one hour block where you shoot your content and then those types of things. Um, because particularly when it's things that like don't give you the same energy, you wanna make sure that you're not just like, to your point, feeling guilty about like doing other things, but it's all got a specific time. The other part is like not pretending like you shouldn't be doing it, because I think, I think you can give yourself your internal monologue where it's like, oh, but like, no, I don't need to do that. But you actually do. So allocating the time means that. You know, it's got a time and a space for it to exist, rather than you feeling like, oh, well no, I shouldn't be doing that.
Holly Cardamone:Hello, my name is Holly Cardamone and I am so excited to speak to you about my upcoming debut novel. Summer in Between. Summer In Between is a young adult contemporary novel about a firecracker, bookworm and neander little surfer, and one unforgettable summer. So imagine if looking for Ellie Brandy and puberty blues had a book, baby, that's my novel, but in a little more detail. It's New Year's Day, and Kat is 17 and lives in Baters Cove, a small beach town, 90 minutes from the city. It's a town where testosterone mixes freely with casual and overt racism, and she honestly cannot wait to get out. Now, Kat has a chaotic, noisy family, including an imposing interfering nonna, two boisterous younger brothers and parents who are continually flirty with each other to the point of get a room. She has friends that she adores, but they're scattered hundreds of kilometers apart and her only contact with them for the summer is online. Kat is obsessed with her upcoming year 12 studies. She believes that they'll make or break her future. She honestly sees that the marks that she gets at the end of year 12 will be her ticket out of town. So she has a plan and that's to study hard, get into university and get out of bat's Cove. And part of her plan is to avoid the local Neanderthals, the surfers who take over the beach, including their king Paul, light wood, who is the hottest of the hot. Paul is someone who's been on cat's periphery for years. He can eat fur without a splash. He loves music and making playlists, and he's had his own hopes and dreams thwarted. Everyone loves Paul except for Kat. She's completely immune to his charms and she thinks he'd have a crack at a stop sign for. Looked at him the right way. So summer's becoming very interesting and confusing when Paul starts working for cat's Dad, a cat's house for the entire summer. So throw in a beach party or two night markets. Gelato cliff jumping into the ocean. And we have somewhere in between. Thank you so much Madeleine and Tina for the opportunity to chat to you.
Madeleine Cleary:This is so good. I'm going to implement, I'm so excited about this. This is gonna change everything and this is much more healthy, I think. And I guess you do have to allocate time to, to. Time box. Right? Like you do have to put in the effort to do that as well.
Jessica Box:Yeah. My favorite time to do that is on a Monday morning. So I do some of it on Sunday, but I'm pre, I'm like a, I'm very rigorous calendar person and I have, there's another hot tip, um, color coding, um, brings me joy that it makes my husband fearful when he looks at my calendar. But I feel like everything's got its place. So, and so I have all my personal things in there. And then each of my like advisory things like matches. You know, orange. Oh, I can send you a screenshot of what it looks like, but it's, it's all got different colors. Um, and it's helpful to me because then when I look at my calendar at a glance, I can see like where I'm allocating my time. And if I've got too much advisory on one day, I can tell my brain's gonna context switch too much. And so then I go, oh, well I need, I can't do that today. I'll move it to another day.
Madeleine Cleary:Oh, this is brilliant. I love this. I'm gonna,
Jessica Box:I'm so excited. Okay. This is great for type A people.
Madeleine Cleary:It's so, so good. And, um. I just, I I think you are, uh, spot on or too about allocating time for social media content.'cause social media, I know we just, we touched on it just before, but I, I think it's good to come back to it. Um,'cause it is like a, that's another hat that authors have to wear and not necessarily one that we're really good at. Mm. So I guess if you've got any tips about. What can we, what can we do? And we were just talking before about how we might be flipping back to more of that face-to-face in-person stuff, but I still think it's gonna play a role in future
Nobody:Yeah. For
Madeleine Cleary:creatives as well. So do you have any tips about, maybe it's coming back to what you were saying earlier about looking at the whys as well, like looking at why we do it.
Nobody:Um,
Madeleine Cleary:are we doing it to try and sell books?'cause it's probably not. Very good to sell books, but you know, is it to build connection? So how do we, how do authors get joy from social media? How do we create boundaries around social media and what, yeah, what tips do you have for us?
Jessica Box:Yes. So I think eight is connected to the five why's. And I would say my number one thing is to find your unique voice. Um, and I feel like that would resonate really well with writers.'cause it's like you've gotta find your writing voice. Yes. But you also have to find your unique social media voice and it, this one needs to be at the intersection of what you'd love and what people wanna hear. What I mean, I've never heard
Madeleine Cleary:that before. That's so good.
Jessica Box:Yeah. So what you love, but. Is obviously if you just talk about what you love, then you know, you may not find the right audience, you might not care. Yeah. But the second part is like, people act, what do people actually want to hear about? Um, and you know, I would say if, if I was picking, and there's two parts to this, it's like you can't picking a channel to start with. Like just pick one, don't try and do everything. Mm-hmm. Pick one that you're gonna focus on. And then, you know, there's this concept of habit stacking where you repeat the habit and you. Kind of bundle it in with other things. So if you're like writing at the end of writing, maybe you like wanna do a reflection on how that session went and then you share that publicly as an example. Mm-hmm. Um, and I would recommend, if you're gonna pick one, would be TikTok. Um, because there's so much opportunity for authentic content, it's also growing rapidly. You can also share your tiktoks on Instagram and it still does quite well. So that type of content. The kind of piece to camera that I was talking about where you talk at the camera, um, is what's resonating really strongly. Mm-hmm. So, um, and I think, you know, not everyone is gonna be comfortable with that because, um, you know, it takes a little bit of time to be able to feel comfortable. But I would say starting with like the interview piece, so find someone who is maybe a writer that is going on the same journey as you. And just have a, have a yap, have a conversation with each other and record it and see how it goes. Um. And yeah, I think TikTok in particular, I mean, you know, book talk in general is like such a big area, um, that people are, are resonating with. I, I feel like this year has been the biggest book week in Australia. I think there's so much happening from a connectedness to, like, storytelling at the moment that, um, finding your unique voice in that. Um, and then the specific audience that people wanna hear. I feel like that's a nice way to think about you're actually generating value for people like you are. People want to listen to you rather than it just being, I'm selling my book, it, think about it like, okay, it's, it's almost like, and this is like very, um, marketing type structures, but it's like a funnel. It is a funnel is conceptually a funnel. So you've got your audience at the top, they're like unaware of you, they don't know you. Um, and then as you. Like they typically people need to hear from you about between four to five times to then know who you are. And so the repetition is super important. Um, and the consistency. So finding something that you wanna talk about that you can be consistent with, and then hitting the same message a few times means that then people are gonna connect with you. Um, and so I think. Yeah, really allocating the time to just think about the purpose and the like, getting connected to what you're gonna say and taking it away from just selling books because people are gonna buy your books if they're connecting with you and telling, uh, and um, hearing from you. Like you would, you would know this from all the events that you've done and you share the story and then everyone's like, okay, I'm gonna, I wanna read the book.'cause the story is so amazing. That's the way to think about this. Like, don't think about it as like, oh, I've just got it. Do this post,'cause it's gonna sell me like five books. Think about it as I've got a story to share, um, and I'm gonna share it. And then the outcome from that is naturally, obviously books get sold.
Madeleine Cleary:I'm not sure, Jess, if you can see my soul dying.
Jessica Box:Yeah, I, I know that I've told you to go on TikTok before and you have not wanted to do that, but it is, it's definitely the one, I think it's, I think it's more authentic than Instagram as well. Instagram's become very, so first Facebook was very businessy and then everyone went to Instagram to become like, be all personal and then. Um, Instagram started to become businessy and everyone wanted TikTok to be all personal. So we're going through this journey of like, each channel is kind of changing. Um, chat. GPT is gonna be the next one. Um,
Madeleine Cleary:oh, like as in community, in connection on chat, GPT,
Jessica Box:it'll be the next, what I would call distribution channel. So how people, um, find you. How, how will that work? I mean, so 70 700 million people are using chat GPT per week.
Madeleine Cleary:Geez, that's insane.
Jessica Box:They haven't done this yet. Like this is what, like, so in my, in my tech circles, we're in very big in an echo chamber at the moment. Um, but yeah, so the way that Instagram and TikTok emerged, um, as channels, um, there's a similar pattern happening with chat GPT where they didn't nec they're not gonna, it's obviously not gonna be a social media channel, um, in the same way, but. Um, each person is individually browsing, um, more akin to a Google I would say, um, than a, um, than a Instagram or TikTok.
Madeleine Cleary:That, that kind of slightly frighten frightens me.'cause I know how much AI hallucinate answers and responses. So it's almost like that misinformation is really, really frightening. I actually, you know how you Google stuff and it comes up automatically with the AI response. I ignore it because I just find that a lot of the times it's wrong.
Jessica Box:It is. I, I agree with you and I think, I think Google's not, we can get all technical, but Google's not trained on the same level of data that chat GT is. So chat GT is holding things back deliberately to get to a certain level from a tech perspective. Then when they're there, I think they'll become like akin to an apple, um, where they launch apps and have. A marketplace where companies can build on top of chat GBT, so mm-hmm. Anyway, this is so
Madeleine Cleary:interesting. Um, I've actually had quite a few chats about, um, the future I suppose, of creating connections.'cause I guess what we're talking about is connection and, uh, we will talk about matched and how that's creating connections.
Nobody:Mm-hmm. Um,
Madeleine Cleary:and. You know, the way that people connect now is probably gonna be very different to the way people connect in five years and Instagram and TikTok, they're such good, you know, connection tools and I've definitely enjoyed the part of social media in connecting with other authors and readers. That's been the best part. Mm. Um, um, but, uh, you know, chatting with other people, a lot of people are saying, because AI. Is, you know, we are not sure whether content is AI generated or not.'cause I think humans still wanna connect with humans. They don't wanna connect with AI driven content. Yeah. On social media that they might be moving to platforms like Discord, where they can create groups very much about focused issue areas that they enjoy, like key issue areas that they enjoy. Yeah. It goes back to what we were saying about those in-person things, and I quite, I, I think that's quite good, but, um mm-hmm. So interested in your thoughts on that, but another thing as well, another reflection. Um, so Ally Parker, who you, you know, um, she's a friend of the podcast. Um, she was, she's been saying to me that I need to get onto TikTok. And I was talking to, we did an event last night together, and I was, it's, it's really interesting. I've done two events now with Ally in the last couple of weeks. Ally's really good on TikTok.
Nobody:Mm.
Madeleine Cleary:So for those who want a good example of, she's fantastic. Very authentic. Yeah. Um. Interestingly, a lot of the events that I attend, like, um, book events, it's attended by a certain kind of age group, I suppose, tends to be older women. Um, but when I have been going to the events with Ali, um, she attracts a younger. Audience because she's on TikTok and a lot of them are. And they said, they tell me like, oh, we, I found Ali on TikTok. Um, and so we've got now, and the positives of this is we've got this younger community reading, historical fiction, consuming this kind of content, which is different'cause I think traditionally. Tick book talkers are consuming, like romantic and fantasy and that, and romance and things like that. But now they're consuming historical fiction and they're coming together to these in-person events. They know each other, they're, they've got this nice community. They're talking about books, and that's a really positive, I think, from them.
Jessica Box:Yeah, it is. I, I fully agree. I think, um, what you're talking about is, I would say the concept of discovery and like the discovery happening, where it happens matters. And I think discovery on TikTok is so deep in community, like it's. So everyone's very open. There's no kind of like, you know, you see a lot of polish on Instagram. Um, on TikTok there's a lot of authenticity, and so people connect more deeply faster. So I am not surprised, like Ali spending time there is ge generating like a, you know, there's a bit of like cult following that happens on TikTok when, when people, when people like, see two of your videos. This comes back to this funnel that I mentioned. I think it's two or three, and then like, they follow you, then they're hooked. If someone follows you on TikTok, they're like a really high. Um, uh, a high value subscriber or person that, like, they're part of your community. So, um, yeah, it is really, it's really interesting. But to your point, I think there's. This concept of community is shifting so much. Um, and I think, yeah, we're going to have this, we're gonna have be quite binary. I think it'll be like everything happening on AI or everything happening in person. I think there's gonna be this move to people wanting to connect with a real human. Um, first. Yeah.
Madeleine Cleary:Like I'm all here for it. You know me. I like to connect people that, that's like big things. I think that's probably why we're such good friends, because we've always. Um, wanted to connect people and, and, um, maintain really good connections with people. And I think that's, you know, something that we really enjoy. So let's then talk about matched in that vein. Mm-hmm. Because, um, I wanna hear what. I know we heard about some of the whys, but tell us what your vision and goals are for matched.
Jessica Box:Yeah, so, um, matched is a knowledge sharing platform. So really what we do is, uh, we connect learners with trainers based on their goals. So, um, someone comes into match and they set a goal of, I wanna find a new role, or I wanna write a novel, or I wanna publish my first novel. Uh, and then we match. Them with the coaches, advisors, trainers, um, to help them get there. And so, uh, what that really means in practice is you can go like deep in a live one-on-one session to this point around kind of this live connection piece. Um, or you can do kind of, um, offline reviews of. Work, one of those is what I've got this morning. Um, or, you know, um, reviews of writing if you're, if you're a, um, writer. And, um, what's really amazing about that is, you know, so much of how we get access to people and, and I guess the original vision behind Match is how do we make knowledge more accessible and mm-hmm. Um, we wanna really be socioeconomic equalizer. So what that means is, regardless of your background, you can come to Match and you can find someone and connect with them. Um, where for so long, you know. Access to really experienced people is based on who you know and your networks. Um, and so really what we want match to be is you, you know, it's your own network. Your, you can build your own personal board of, of advisors, your personal community around you, um, regardless of your goals as they change over time. So say you publish a novel, um, then you've got different goals. You may be doing your second novel or, um, there's different things that you need at different points in your journey. And so we wanna be the place that people go to to access that knowledge.
Madeleine Cleary:I, I love this. And I think it's a really important thing to have, um, guidance even after you've published your book, um, because it's different to having an agent or a publisher. This is someone who is really invested in your, your long-term career as whatever you wanna be, and you can really set those standards. So I wanna talk briefly about. What it means to be a good trainer or coach, because I think it's something that a lot of authors consider offering as a service, but perhaps. Uh, to have too much imposter syndrome to say, I I can help other riders.
Jessica Box:Yes. I think it's, um, it's very normal. It's, it's like until you start doing it and it feels a little bit uncomfortable, you feel a bit like, not preachy, but like, you're kind of like, do I have the right to say this to other people? And it's like, yes, because you know, what, do you know what's really interesting about. Being a really good coach, um, you learn from that experience as much as the other person does. So I think if you go into it with that mindset of your learning of how to pass your skills onto others, then it's as valuable for you as it is for the person, um, you are supporting. And so I think what makes a really good coach is self-awareness. Um, uh, really clear understanding of where you can add value. That's something we can help with. So, um, there's sometimes, like, you know, you know that you've got a whole bunch of like skills, um, and then we call this concept, um, skill stacking. So what, what is your skill stack that you then can then communicate out? So say that, for example, would be like you. Reviews of writing, um, like certain type of words, like structural narratives, I would imagine how to think about that. Um, and then actual, just kind of live one-on-one knowledge sharing. So, you know, this podcast is a great example. There's so much like value that you are sharing on the whole journey of how you, um, uh, you know, emerging writer publish a novel the whole way through. How to get access to, um, publishers in general, other. Optional paths. Um, being able to talk to someone one-on-one about that and like personalizing it specifically, um, is really, really great. And I think we're starting to see, um, thanks a lot to you. You're our first, um, writer to sign up to match. Um, and we've now, um, literally as of next week we'll be onboarding our, our first cohort of writers, um, because exciting. Yeah, and I think it's, it's, as I mentioned, this intersection around, um, business people kind of figuring out what they wanna do next. Like, I would love to do a nonfiction, um, uh, book at some point in my journey, but I, oh, publishers,
Madeleine Cleary:if you're listening, this has a great profile, a
Jessica Box:great story to tell. Oh, I mean, I just wouldn't even know where to start. So I would be the, like a captive audience. And I think it's this self-awareness, right? Of, you know, writers don't, you may not feel like you've got. Um, the knowledge to share, but like me saying this, obviously I'm very experienced in my area, but I'm super aware that I have no knowledge in this area. So you do, you know so much about your area, so don't like discount that that's valuable to someone who, you know, has, has never touched it. And I actually have quite a lot of people message me being like, do, are there writers onm matched? Like, I'm thinking about doing a novel, blah, blah, blah. Um. So, yeah, I would say like being, just putting yourself out there and testing it out and it doesn't, if it doesn't work, it's fine. Like it's, it's like, you know, having the conversations with people, it helps you sharpen your tools as well, like understanding what's happening, um, how people think about, you know, their own narrative structures. It makes you kind of keep your tools sharp as well. Hmm.
Madeleine Cleary:This is fantastic. So are you looking at getting onboarding more riders in future?
Jessica Box:Yeah, I think we'll, um, do this first cohort and then Yeah. Where, um, we take trainer applications, um, all the time. Yep. But, um, yeah, if people wanna drop me an email or send me a message, but how do people
Madeleine Cleary:get into contact with you, Jess?
Jessica Box:Yeah. Drop me a message on the matched Insta. I think that might be. Best one, or TikTok if you really want to. But, um, um, yeah, send me message on the match Instagram, um, which is that, what's the handle for Yeah, match at at match Community. Um,
Madeleine Cleary:okay. We'll, we'll make sure it's in the show notes for everyone as well. So, um, if you wanna get into contact with Jess, it's, it's an amazing platform and Jess is an amazing woman. Mm-hmm. Um, and. Her background. We haven't even touched on all the incredible things that she has done in her career. But having a woman like Jess who's, um, been able to really craft a career in tech, it's, it's, it's not an easy thing that you've done, Jess, and I'm what, I'm probably one of the best, the most proudest friends ever. I mean, I'm the most proud of you, so
Nobody:let that catch out.
Madeleine Cleary:Well, our little year seven, um, selves, how proud would they be looking at us now? Or 20
Jessica Box:years on. That's crazy. I feel like it's, yeah, you just couldn't even dream it up. I think that's so much about like the journey, right? You just make decisions and take the opportunities as you go. Mm-hmm.
Madeleine Cleary:Exactly. I feel like there's so much more to talk about, so we might need to get you back on for a part two later down the track. Um, Jeff, because there's so much, I've just. Had so much from this. Um, we always finish though on one top tip. Um, is there something that you wanna leave all the writers, um, with, um, at the end of this, Jessica?
Jessica Box:Yeah, I think, um, we talk a lot about this kind of burnout. The, the feeling, the pressure to do everything and do it all. Um, and my tip is you can do it all, just not all at once and. Pick the sequencing. So the order, not the activity. So you don't need to chop things out. I think it's finding the right order to do the things in and saying no to some things doesn't mean that you can't bring them back down the track. And building a company is like this. Um, you know, at each stage of a company, the company looks different and you as writers are each mini companies, so it's. It's this, you know, portfolio career. But um, yeah, the sequencing is important so you can't run all the way to the finish line. We'll start at the finishing line, right? You have to start at the start and the journey is so much of how you get there. So yeah, do
Madeleine Cleary:it all. That's a great tip and it reminds me of some That was really good advice. You provided me and you, I mean, you provide me with great top tips. Always. It's very helpful to have a friend like genocide would highly recommend it. You gave me this image and you're, you're always a good storyteller, but you gave me this image of, um, the plastic place.
Tina Strachan:I was gonna say that. Yeah. Tell us about that.
Jessica Box:Yeah, so someone actually said this to me, which is a, is a very visual way of thinking about what I just said, which is, um. You if you're spinning all the plates, one of them needs to be plastic, um, which I love because obviously if they fall, the plastic one doesn't break. Um, and so find your, find your plastic plate
Madeleine Cleary:and it can be a few plastic plates perhaps as well. Yeah. In different periods of your life. Um, Jessica Box, thank you so much for joining us on the book Deal podcast. This I'm gonna take so much away from this.
Jessica Box:Thank you. It's been a joy and yeah, I'm obviously happy to help and, and speak to anyone about how they set up. Themselves as a business. So
Madeleine Cleary:yeah, please do reach out to Jess. Um, and um, yeah, we'll get you back on for part two. Thanks so much and enjoy your holiday. Thank you. I'm excited.
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