The 7 email rule: Pitching your work to illustration clients - Kira Matthews

Summary

The Good Ship Illustration Podcast
Episode: The 7 Email Rule: Pitching Your Work to Illustration Clients – with Kira Matthews
Date: March 27, 2026

---

Episode Overview

In this engaging episode, hosts from The Good Ship Illustration chat with Kira Matthews (aka @kyrathebold), renowned as the "queen of pitching," about confidently pitching creative work to clients, especially for illustrators. The conversation explores building resilience in pitching, coping with rejection, and the power of persistent, authentic outreach—epitomized by Kira’s “7 email rule.” The discussion provides practical advice, mindset shifts, and personal anecdotes designed to empower illustrators and creatives to actively seek opportunities rather than waiting to be discovered.

---

Key Discussion Points & Insights

Kira Matthews’ Background and Pitching Journey

• Career Beginnings: Kira started in fashion styling but shifted to coaching freelancers during Covid [00:40]. She later worked at a tech startup in sales, executing nearly 1,800 cold calls and countless emails and LinkedIn messages, applying these lessons to her creative business.
• On Becoming the “Queen of Pitching”: When inbound work dried up, Kira refused to be sidelined:

  "You don't just get to disappear. You don't just get to decide that you're not having me anymore. So I went on a journey to learn how to pitch." [02:08]

Facing the Fear of Pitching

• Pitching is Scary, Even for Pros:

  "The fear didn't disappear for many years… I still get the fear now. Sometimes it’s a lot less than those early days because I send so many. Yeah, the fear is part of the process." [04:39]

• Learning from Sales Mentors: Watching experienced salespeople helped Kira claim her own space and persist, despite intimidation.

How to Approach Pitching

• Setting Intentions:

  "Intentionally going out into the world, deciding what kind of opportunities you want and who are the people in your world that can give you those opportunities." [07:29]

• Personalized Outreach: Kira emphasizes finding the right person at organizations and offering collaboration ideas directly connected to your brand and needs.

The 7 Email Rule

• Persistence Pays Off:

  "I usually recommend five to seven emails. And if they don’t reply after that, then you can give them a break for a couple of months and come back to seven emails." [09:39]

• Adding Value Each Time:

  "You’re not just saying, ‘Hey, have you seen this?’ over and over again. You’re adding something different each time... By the time they get to the end of the seven emails, they've learned a lot about you." [10:27]

• Memorable Persistence:

  "You stuck out in their mind, and now ... you are someone that they can go to when they have an opportunity." [11:09]

• Real-Life Example: It took Kira three years of follow-ups, emails, and relationship-building to land a deal with Squarespace [05:37].

Redefining Rejection & Success

• Completing the Pitch Process:

  "You're either going to get a yes, a no, or not right now. If it's just silence, the pitching process is incomplete." [08:24]

• Don’t Talk Yourself Out of Opportunities:

  "A lot of creatives make up the reason... 'Oh, they're so busy. Oh, I'm too small. Oh, my work is not good enough.' Did they say that? ... Then you need to follow up." [08:24]

• On Ghosting: Often, lack of response is about their workload and priorities—not a reflection on you.

Diversifying Outreach: Beyond Email

• Utilizing LinkedIn and Social Media:

  "Find all of those publishers on LinkedIn... follow them on Instagram. Even if they don’t follow you back, they click into the profile... It’s a great moment to stand out in their mind." [12:15]

• Physical Postcards: Nostalgic but effective, especially for publishers. Combine with digital outreach to maximize visibility.

Agency Models & Being Proactive

• New Talent Agency Approaches: Kira is building an agency model that focuses on active pitching for smaller creators rather than relying solely on commissions from inbound work [13:20].
• Agents Aren’t Magic:

  "People think having an agent is a magic thing... but even when you have an agent you have to do so much work." [18:36] "I need people to know that it’s not just waving a magic wand and I need you to be creating the content..." [19:06]

Mindset Shifts for Creatives

• Learning to Love Sales:

  "Either you learn to love sales or you get a job where you don’t have to think about sales..." [20:42]

• Pitching is a Skill, Not a Talent:

  "I taught myself how to draw. I can also teach myself how to be good at pitching... When you step into that place of curiosity... then it’s so much easier to go on that journey." [21:16]

Rejection Challenges & Building Resilience

• Rejection as Progress:

  "If you're not getting rejected every single week, then something is wrong." [25:20]

• Reframing Rejection:

  "It's not a rejection, it's the start of a conversation." [27:16]

• Real-World Example: Katie shares a story how a “no” for a public art project later turned into a “yes,” proving the importance of staying visible and engaged [32:11].
• Recommended Resource:

  "One of my favorite TED talks... is called 100 Rejections. It's about this guy who changed his life by just asking for what he wanted." [25:48]

Practical Productivity Advice

• Audit Your Actions:

  "Notice how many hours you’re spending creating content. Is that producing the rewards you want?... What are the actions that will produce the business that I want in 12 months from now?" [34:11]

---

Notable Quotes & Memorable Moments

• On Pitching:

  "I never give anyone else the chance to decide that I am not interesting. ... The only result I'm looking for is I don't mind if it's a no, but that person has to say no." — Kira [08:24]

• On Persistence:

  "If I really want it, I'm going back. I'm not gonna stop. So you might as well just work with me for pizza." — Kira [10:09]

• On Rejection:

  "If you're not getting rejected every single week, then something is wrong." — Kira [25:20]

• On Self-Promotion:

  "Nobody's mind reading. ... Even if it's just like… start with your friends or… tell your old university tutor… there are so many little micro actions that you can take." — Kira [31:37]

• Encouragement for Listeners:

  "Go out into the world. Tell them who you are and give them the opportunity to work with you." — Kira [37:05]

• On Survival After Rejection:

  "If you do get rejected, you'll notice that you do not die." — Katie [37:14] "This is the main thing. You'll be like. Life goes on. Wow. I'm still alive." — Kira [37:22]

---

Timestamps for Important Segments

• Kira Matthews’ Career & Pitching Origins: [00:40–03:04]
• Facing Pitching Fears & Building Confidence: [03:27–05:29]
• Persistence vs. Success Rate: [05:37–08:01]
• The Art of Following Up: [08:06–09:58]
• The 7 Email Rule Explained: [09:39–11:22]
• PRINT & Social Outreach (Combining Methods): [11:22–13:05]
• Agency Models and Self-Advocacy: [13:05–15:46]
• Mindset Shifts and Sales: [20:29–22:40]
• Rejection Challenge & TED Talk: [24:24–26:28]
• Stories of “No” Turning Into “Yes”: [32:11–33:32]
• Productivity, Auditing Action, and Output: [33:42–34:31]
• Final Takeaway (Do a Rejection Challenge!): [35:18–37:14]

---

Final Takeaway

Kira challenges listeners:

"If you haven't done a rejection challenge, do it... Tell the world who you are... All of those things are really clever things that your brain is trying to use to convince you to not go through the pain of rejection. Put them to the side… So go out into the world. Tell them who you are and give them the opportunity to work with you." [35:29–37:05]

And if you get rejected:

"You'll notice that you do not die." [37:14] — Katie
"Life goes on. Wow. I'm still alive." [37:22] — Kira

---

Links & Resources:

• Kira Matthews / @kyrathebold
• Recommended TED Talk: “100 Rejections”
• The Good Ship Illustration: thegoodshipillustration.com

For detailed actionable steps, practical pitching templates, and more insider wisdom, listen to the full episode!

Transcript

[A]

Sara.

[B]

So goodbye, Katie. Yeah. Thank you for agreeing to come on the Good Ship Illustration podcast. I discovered your work quite recently and I was immediately in love because you are the queen of pitching. So I'll let you introduce yourself. But that's my very short introduction.

[A]

Yeah, of course. So my name is Kyra Matthews. I'm Yairathebold on Instagram, and I am the queen of pitching. Really? Recently anointed the queen of pitching, I started my career. You are going to get the longer version. So I started my career in fashion styling. This is pre Covid, after I graduated from a fashion design degree. Then due to Covid, I had no clients. I couldn't work in fashion styling. It's so up close and personal. There's just no way you can do it remotely. I had started making content on the Internet about being a freelancer. So by the time that Covid came, I was like, oh, I'm going to turn this into a business. I'm going to become a coach. So then I spent the year learning how to coach creatives, like, listening to their challenges. And for a while, I was a mindset and manifestation coach on the Internet. Brands approached me to work with me. They wanted me to do workshops with them. They wanted me to post content. I went to New York to work with a team and do, like, in house mindset workshops with them. I had so much fun. But then In, I think 20, 22, 23, brands stopped reaching out to me. Like, they just stopped finding me. And I was like, no, I don't like this. You don't just get to disappear. You don't just get to decide that you're not having me anymore. So I went on a journey to learn how to pitch. I got a job working in a tech startup in the sales team. We were doing B2B sales, so I did about 1798 cold calls during my time in that job. I sent even more emails and LinkedIn messages and LinkedIn requests during that job. But I took everything that I learn and use it essentially in my creative business. People started asking me how I did that. I worked with, I pitched Squarespace, I pitched ganny, I pitched Papier. People started asking me how I did that. I built Pitch School, which is my course that teaches people how to pitch. And then now, 2026, when we're recording this, I'm currently building a talent agency as an extension of that because I just decided that I love pitching and I want a new challenge. So, yeah, I can see you're like, dying to dive in I see my

[B]

pen and I'm poisoning already. So many questions. So firstly, so exciting, the first stage where you were like really busy going to New York and everything. But the thing I'm most interested in is when that stopped. But instead of just crying, you actually took the bull by the horns and you were like, I'm gonna fix this. So what was your very first, like when you started pitching?

[A]

How was that?

[B]

Because I, as an illustrator, I feel like I speak for a lot of other illustrators and creatives. Pitching is terrifying and I feel like I've tried it. Maybe I could really count on one hand the times I've done a proper pitch because I'm so worried about it. And so I would love to hear, like, how did you build that muscle of pitching and not be totally terrified of it.

[A]

Okay, so even in the job that I had and I worked for that company for about a year, even within the job, I was afraid. But I guess one thing that the job gave me is that there were two other people on the sales team. One was the CEO and another one was really experienced in sales. And I worked really closely with the CEO and he was just like a G at pitching. He was like, so smart, so clever, like doing things that I didn't even know you could do in order to get what he wanted. And I think that really inspired me how he was just like, yeah, no, like I belong in that room. I'm getting in that room, I'm doing that thing. And so even though I was really scared, I think really early on I knew what would be the result at the end of this. It wasn't like I was just pitching and I didn't know what was on the line almost. One thing I will say also is that like when I was writing my first pitch, like before, when brands approached me, these are four four figure deals. Usually I'm just putting on a 60 minute workshop. So the pay compared to the amount of time I was doing for that work, I was like, oh, I'm sold, I'm in. So it's almost like I knew what I wanted. I had that vision and it was worth the fear. But I will tell you that the fear didn't disappear for many years. That was, I worked in that company from 2022 to 2023. It's 2026. I still get the fear now. Sometimes it's a lot less than those early days because I send so many. Yeah, the fear is part of the process. Process, yeah.

[B]

And do you expect to get ghosted or do you have, like, a rejection or a success rate that you monitor.

[A]

So in when I'm working on my projects, it's really interesting because this I. Okay, now that you said this to me, I'm going to track my success rate. I don't have that right now. But what I would say is there are companies that I wanted to work with so bad. I was like, I'm never going to stop emailing you. I'm never going to stop emailing you. Like, I already know we're going to work together. So, for example, Squarespace. I met the marketing team at Squarespace at an event. They were sponsoring a conference for women in business. I met the team. I was like, oh, my God, it's so nice to meet you. From me meeting them and them saying, yeah, send us some ideas to them, actually sending me a contract. It took about three years. In between those three years was multiple conversations, multiple emails I sent. Hey, what do you think about this? Is now a good time? No, now is not a good time. Try again in a couple of months. Hey, just following up. Do you want to come to my event? I'm hosting an event here. I'm doing this. I'm doing a webinar. Do you want to come watch? No, I don't want to come watch. Try again in a couple of months. So for me. So this pitching and success rate, they don't sit that well together. Because usually I'm so focused on this is happening that I'm like, I'm going to win either way. It could be now, it could be 2026, it could be 2027. I'm going to win either way. And just to define what I mean here, when I talk about a pitch, really intentionally going out into the world, deciding what kind of opportunities you want and who are the people in your world that can give you those opportunities. So for me, if I'm usually pitching things like content collaborations, I'm pitching things like paid workshops. So I'm going to the brands that also I'm going to the brands that work with creatives and tools that I use. So I have a Squarespace website, and I'm very intentionally finding the people at that organization who would be best placed to hear my ideas. I'm sending them an email. This is what I do. This is who I am. This is why I want to work with you. And I'm asking them for a response. Hey, can we talk about this? Are you open? Open to listening to my ear, to my idea. That is essentially my pitch.

[B]

I love that. Inviting a yes. Really? Aren't you?

[A]

Yes.

[B]

Yeah.

[A]

They can say no, but I would say that what a lot of people do is they think, oh, yeah, I'm going to try this pitching thing. So then they send one email, they don't get a response, and then they don't follow up.

[B]

Yes, that's exactly what happens. You're correct.

[A]

They're like, oh, I sent that email two weeks ago. They didn't reply to me, so that must mean that they are not interested in me. So I never give anyone else the. The chance to decide that I am not interesting. If somebody. The only sort of. The only result that I'm looking for is I don't mind if it's a no, but that person has to say no. I think what a lot of creatives do is that they make up the reason. Oh, they're so busy. Oh, I'm too small. Oh, my work is not good enough. That's why they haven't responded. And I will ask the people that I work with, hey, did they say that? Did they say that you were too small? No, I just. I thought that I was too small. Okay. No. Then you need to follow up. You need to follow up. You need to follow up. You're either going to get a yes, a no, or not. Right now. If it's just silence, the pitching process is incomplete.

[B]

Yeah, that's so true. And it's such a big thing, like the stories you tell yourself about what's happening. That is the thing, isn't it? So if you don't hear back and you're like, they hate me. My pitch sucked. They're laughing about me in the office, when really, they probably just have a really busy inbox and you haven't followed up.

[A]

There's so many reasons why they may not be replying. I've had clients who are pitching organizations and they send seven emails, so I usually recommend five to seven emails. And if they don't reply after that, then you can give them a break for a couple of months and come back to seven emails.

[B]

That is amazing. So you're going to send five to seven emails and then give them a rest. This is blowing my mind. Okay, we've emailed them twice. Let's stop because they're gonna hate us now. What? Okay.

[A]

Like, I. I think especially if it's a brand that, you know, has the budget to be able to pay you, I'm going back. If I really want it, I'm going back. I'm not gonna stop. So you might as well just work with Me

[B]

for pizza.

[A]

Exactly. So I had a client who sent seven emails, gave the company a break, and then the company came back because they had an opportunity come in and they were like, oh, I remembered you because you were so persistent and sent all these emails. You would be great for this. So maybe they're not emailing because they're seeing your work, but there's maybe some. There's nothing that they have available that would fit you. Now, the way that I teach people how to send seven emails is you're not just saying, hey, have you seen this? Hey, how have you seen this? Over and over again. You're adding something different each time. So even if they don't apply, they are learning so much about you in those seven emails. So by the time they get to the end of the seven emails, they've learned a lot about you. You stuck out in their mind, and now they're someone. Now you are someone that they can go to when they have an opportunity come their way that you're aligned for.

[B]

Amazing. I'm trying to think of, like, ways this could apply to illustrators, because something we talk about a lot in the picture book course is sending physical post to publishers, like, getting your work on and mailing it to them. And Helen, who's another captain of the good ship and a picture book illustrator author, she did that in her early days. Like, we just get a stack of postcards and send them. And she had this, like, relentlessness that you are, like, beaming out into the world. I feel like tenacity maybe is a better word for it. Like that level of laser focus. I'm doing this and it's just a case of, like, when are you going to give me my break? I love that so much.

[A]

I love that. Like, I think about, in any dream or goal that you're trying to achieve, pitching can play a part. So I love what you said about your colleague, like, sending all the postcards to the publishers. It's such a nice thing to receive in the post. It's such a lovely moment. But there are so many things that you can do. Like, I would find all of Those publishers on LinkedIn. Connect with them there. I would also find them if they have Instagram accounts, follow them on Instagram, because what you allow them to do is to, even if they don't follow you back, they click into the profile. They're like, who's this following me? They scroll through your feed, they might scroll through what you're posting on LinkedIn. And it's a really great moment to stand out in their mind. One thing I love about LinkedIn is that people in industries talk to each other. They say they post. Hey, I'm looking for XYZ person. Do you know anyone who. Do you have anyone you'd recommend? That's a great chance to start up a conversation with a publisher that you really want to get involved in.

[B]

Yeah, that's perfect. And for the talent agency, are you. Do you have inquiries coming in or you literally, you've got the talent and you're like, okay, I know that you would be perfect for this thing, so I'm going to go after that thing for you and pitch it. How does that work?

[A]

So it's really early days. A talent agency, it's about. It's five months old. What do I know? It's literally a baby. So what I've been doing at the moment is a founder, a creative comes to me and they're like, I want more of. I want more brand partnerships. I want to work at more conferences. Can you help me do that? So I outline a strategy of the brands that will fit well in their niche. The creator says, yeah, okay, I love that strategy. And then I essentially go out and like, pitch all of those brands and conferences. So that's how it's worked so far. The reason why I'm doing it like this is because in a couple of years ago, I had a talent agent, and traditional talent agencies work on a 20% commission, meaning that they don't get paid until you sign a contract. So if you're a very large creator, you've got a million followers across TikTok, Instagram, YouTube, it's likely you'll have a lot of inbound deals coming in. You may have things that are also reoccurring. So if a talent agency is getting 20% of everything that comes in, they're happy and they're like pitching you out. If you are a smaller creator like me, I have 5,000 followers on Instagram, and it's actually the most followers I've ever had. Like, I don't have another account with hundreds of thousands of followers. But if you're a small creator like me, you actually do have to do the legwork to get in front of the people that you really want to work with. Just because you're small doesn't mean that you don't have something valuable to offer. So when I was working with that talent agent, they just couldn't afford to do the outreach because I was such a small talent. So now I'm flipping it where I only do the outreach for my talent and they keep anything that comes inbound, which is really fun. It's an experiment. At the moment, I will say the experiment is going well. So, yeah, I'm really excited about it.

[B]

I can't wait. I'm going to stay tuned on your Instagram to hear more about that because I'm curious as to how it goes. Mainly for selfish reasons, really, because I've been running the jobs board for illustrators where.

[A]

Yeah, nice.

[B]

It's going to be changing, but in the past, for the past year, it's been. They pay a monthly subscription and then I share job opportunities and they can apply that way. But it's going to be changing soon. But, yeah, I was just curious to how you were doing that. But I'm glad to hear it's going so far. That's exciting.

[A]

Yeah, it's going really well. I'm really enjoying it. I think there's a couple of things that have happened in my life recently where I'm, like, wanting to be a bit more behind the scenes. Like, I have this desire to just write my newsletter, create a few posts and do things behind the scenes. And the talent agency is allowing me to do that, which feels really nice. I just. I will say that I am an Aries. I'm the eldest daughter. There's something in me that loves learning. If I have the potential to learn five languages, I want to do that. If I have the potential to run a 10k, I want to do that. There's something in my brain where I just want to learn everything and I want to grow and be everything. So moving into talent has been really fun for me because I'm learning with. So I'm just learning so many cool things. I'm learning about how brands work with creators and influencers, my clients within the talent agency. I've got one person who's a tech CEO. I've got one person who works in wellness. And so I get to understand just like what a whole universe of brands and organizations, like, what they're wanting from creators, budgets, how they're negotiating, how they're thinking about working with creators. So, yeah, it's. I could not be happier. I love learning. I'm in a happy place in my

[B]

language because I too, love learning. Like, I would just be happy to be left alone with a big stack of books and online courses. Oh, so good. Same.

[A]

I wish I had an unlimited budget for those kind of things. Like, unlimited. I would knock it out the park.

[B]

Yes. And actually, that's one of the really exciting things about learning more about the illustration industry. I know you mentioned, like, talent agents take 20%. So, like, little things, like a literary agent, if you write the book, the literary agent takes 15%. But if you have an illustration agency agent. Sorry, they take 40%. So being able to write your own stories and getting a literary agent over an illustration agent is such a big chunk.

[A]

I had no idea.

[B]

Yeah, nobody talks about it until you get behind the scenes and start rummaging around under the boot.

[A]

Yeah.

[B]

Under the bonnet, whatever it is.

[A]

I had no idea because I think writing a book is definitely on my bingo card for my life. Like, I have had friends that write books that have written books, and I would definitely say I don't have the bandwidth to sit down and write 90,000 words right now, but I did not know that about the literary agents taking 15%. So that's really good to know. Yeah.

[B]

So people think having an agent is a magic thing and that the goal is to get an agent and then you can just sit back and somebody will bring all the work in for you and your book or whatever it is, will be successful, all because of this magical agent. And that is. I'm pretty sure that's just never very, very rarely the case, I think.

[A]

So, like, even when you have an agent, you have to do so much work. Like, I think even when I worked as a fashion stylist, photographers, makeup artists, they want. It was like almost like this goal, let me just get an agent, and then life will be fine. I think this comes from the fact that a lot of creatives don't like selling. They don't feel comfortable selling. And also, there's this sense that the people at the top get the best opportunities, they get the most money, and so almost they are looking at an agent to circumvent the uncomfortableness of selling themselves and learning how to do that. Well, I. Within my own talent agency, I actually can't work with anyone, or at least I don't want to work with anyone who doesn't understand how the pitching process works in terms of how many. You're gonna see Me get a lot of rejections as I go out and talk to brands on your behalf. I need you to know, and I need to work with people who understand that is part of the process. It doesn't necessarily mean anything has gone wrong. This is just like the first stop in our journey together. I need people to know that, like, it's not just waving a magic wand and I need you to be creating the content. I need you to be getting in their face and connecting with them on LinkedIn and doing what you can on your end. It's. Yeah, it doesn't solve any everything. And it's definitely not for every creative out there.

[B]

No, that's such a good point. Like, it isn't for every creative. I think even being self employed and being entrepreneurial is not for everyone. And pitching is a big part of that, isn't it?

[A]

Yeah, exactly. I, even before I talked about pitching, I would talk to creatives about sales. So you might be a creative where you are. The way you make money in your business is through selling a product or selling a service for your website and doing launches. I would always say it's either you learn to love sales or you get a job where you don't have to think about sales and the money just comes to you. There really is no business without a sales function, a marketing function. They have to coexist. And I think this is why when I pivoted from the brands reaching out to me to okay, they're not reaching out to me. I need to figure this out. It's because I innately knew that I had to be in control of that part of my business. I couldn't leave it up to other people to make sure that I was getting paid. And once you step into that sense of ownership, that sense of confidence, that sense of, okay, I taught myself how to draw. I can also teach myself how to be good at pitching. I can also teach myself how to be good at sales. I learned how to make a lasagna. I'm going to go out and learn this skill as well. And when you step into that place of curiosity, knowing that people are going to say no, knowing that you're going to make mistakes and emails and things, then it's so much easier to go on that journey. And it's so rewarding. Honestly. Like when I was pitching Squarespace and they finally said yes, I got up in the living room I was working in and I was jumping, I was screaming, I was so happy. And then when I announced it to my audience, everyone was like, this is amazing. And it's so rewarding when you can do that for yourself. For me, going and getting another job really wasn't a vibe. So I was like, I'm leaning all into this adventure to see how far it can go.

[B]

Thank you for saying that because I think people forget that you do. It's a learned skill. And nobody like pops out of the womb being like, okay, I know all about marketing and let Me just hop into sales. It's not like a natural for most people, not a natural skill.

[A]

And I think the reason why it's so hard is because sales goes against our conditioned need for being polite and how we interact with humans. So I, I'm not really sending follow up emails or follow up messages to my friends that much or to strangers. But when it comes to selling my work, I'm sending a lot of follow up emails. And I think that's the thing that people really struggle with it. Go against what we've taught. We've been taught is the right way to communicate, but it's almost like you have to defrost your brain from that. I am a polite person to I want to get paid. I have something that is worth your time. Please take a minute to sit down, read this email and talk to me about it. And it's like it's a transition and it's okay that it's a bit janky and a bit uncomfortable and it doesn't fit and you feel like, oh no, they're gonna shout at me if I send another message. That's okay. I promise. You like, the best of the best sales people, the best of the best agents, all feel this. So if you are feeling this when you're sending that email, amazing. You're part of the party. Make sure you're around creatives who are also going through this so that you know you're not a weirdo and you're not doing anything wrong when the rejections come, because they will come. And just try and have as much fun as you can with it. Yes.

[B]

And that leads on beautifully to rejection challenges. So I don't know if you've ever done one of these. I did one in 2019. I called it 100 no thank yous, where I went on a mission to get 100 people to say no thank you to me. And it was so hard because I was. And I'm terrified of people saying no. But that challenge completely changed my business and I feel like I've banged on about it so much. Like I'm sick of hearing myself talk about it. But it really did change everything because I, I started applying for competitions. Not really pitching, but like seeing opportunities and being like, oh, I'm going to try out for that, or selling my work. Because at the time I was doing paintings and selling them and then I got to 30 something rejections and I was too busy to carry on doing the rejection challenge.

[A]

Oh my God.

[B]

Mostly does a lot on rejection and I've recently Seen a girl on Instagram trying to get a thousand rejections, which is incredible. She's like, what a beauty pageant and stuff. So I wanted to know, what's your opinion on the rejection challenge scene?

[A]

So I haven't done a rejection challenge, which feels strange to say, but I firmly believe that if you're not getting rejected every single week, then something is wrong. And the reason why I say that is because I think people, like, do the most they can to avoid rejection. Like, they will go weeks without trying something new, running an experiment. Like, I would say I'm really big on experimenting within my business business. So I've done lots of experiments before. But Liz Mosley, who you mentioned, I've been on her podcast also, and I love how she talks about the 100 rejections. In fact, one of my favorite TED talks for years that I would watch every single year is called 100 Rejections. It's about this guy who I think he started the whole 100 rejection things on the Internet several years ago. And it's about this guy who changed his life by just asking for what he wanted. And I watch it every single year to give me a little bit of a motivation.

[B]

Take that link out after this and watch it immediately.

[A]

It's really good.

[B]

Yeah, I suppose that maybe I'm thinking the rejection challenge doesn't. You haven't done one because you don't think you're going to get rejected. You're just following up until they work with you.

[A]

Yeah, there's no room for rejection. I also do think that I am doing a lot in my emails. I think I went through a period of doing lots of content and I think that there can be this idea that if you see someone popping up on your Instagram, you think that's all they're doing. You can't see all the things that they're doing in their emails. You can't see all of the message that messages that they've sent behind the scenes. It's almost like I'm doing a lot behind the scenes. I'm trying to get better at showing them. I love sharing, like a little dump some of the rejections I've received or the things I've pitched for this week. But honestly, for me, it feels like the fabric of my business. It feels very organic to me. And I definitely don't really think about it as a rejection. I think, oh, like, this is just for me. You've said no. Okay, we've just started the conversation because I'm like, why did you say no? It's now not a good time. Maybe you get your budgets in November, so it'll be better to come back in November. Oh, maybe you're the wrong person to ask for this. Can you direct me to who the best person I should have a conversation with? Do you know one to three people in your network that would be best for me to talk to about this? So it's almost like it's not a rejection, it's the start of a conversation. There's so much that you can discuss after somebody says no.

[B]

It's so true. And a lot of the time I've found anyway, somebody will say no, but it's not really a no, it's a not yet. And then they come back to you like a year or sometimes three years later and they're like, oh, yeah, we nearly worked together in 2021. They're just planting little seeds, aren't they?

[A]

And it's like I wrote in my newsletter today that it's the energy that you put out into the universe of wanting something and trying for it. Like sometimes it comes back exactly how you imagined it. But I think a lot of the time it comes back in ways that we can't imagine. Like, I've been rejected for things that I've asked for and then somebody else has come in and offered it to me and I don't know where they've come from. So I do just think a lot of it is energetic. And when you move from somebody who can be like passively complaining or oh, the algorithm sucks or oh, it's so unfair, nobody's booking me. Like when you move from that mindset to I'm going to create the business I want is so powerful. I just feel like people can feel it.

[B]

They can. And I think that's another thing. Like, like with manifestation and things people talk about gratitude. And that's been good a bit more recently, I feel. But it's so if you're grumpy and mourning that tiny shift of listing stuff you're grateful for and remembering, like, some people don't even have water coming out of a tap.

[A]

Like, we are so lucky. We're so lucky we have the Internet.

[B]

Like, it blows my mind to even think about it sometimes. And that can really help me go from being like, oh, this sucks. Like, I have to send emails. Like, I have emails. Like what I have.

[A]

Like, so true. Yeah, it's. I'm so with you. And one of my. Okay, so in 2021, I launched, I self published a journal. It was called the Future Self journal. And one of my favorite questions in there was to pick three wins and write down the recipe for how you created that thing. Because I think a lot of people think gratitude is amazing because it makes you realize, oh, I'm actually doing better than I think. But then a lot of people think that the things that they've achieved have just come. Like, even if somebody comes to you with an opportunity that will change your life, you had to have done something to make them come to you. Even if they, like, knock on your door and they're like, here's a million pounds, you did something. Maybe you applied to a competition, maybe you told your co workers about what you're doing on the side. Maybe you posted something on Instagram or LinkedIn and it got 10 views and you thought it was rubbish, but they actually saw it. So when you start connecting your actions, not all of your actions, some of them are not good actions to take. We can talk about that later. But some of your, like, 20 of the actions that you do in a week will lead to 80% of your results. What are those 20% actions that are creating the results that you want? And when you start connecting, oh, if I send an email, I get what I want, then you're more likely to, like, really enjoy doing those 20% actions.

[B]

That is so true. Yeah. Even things like updating your website to say you do the things that you want to do and then people see the. The website and know you do the thing. Like, I have so many. I've seen so many times illustrators be like, I can't get any work, I'm not getting commissioned. And I'm like, have you got a website? And they don't have a website. They haven't got a portfolio. They don't even say on their Instagram that they are an illustrator. I'm like, nobody's mind reading. You have to know. Yes.

[A]

Even if it's just like, your colleagues or start with your friends or, I don't know, tell your old university tutor at your university that you're starting something new and that you're wanting support or you want to be connected to other people in the industry, there is just so many little micro actions that you can take to achieve your goals. But, Katie, I have a question for you.

[B]

Okay, cool. Go for it.

[A]

When you did the rejection challenge, like, what was the favorite. What was your. What was the thing that came out of it that you were, like, most proud of?

[B]

Okay, I'll tell you. So there was a. Have you seen those sculptures that, by Wild in art. And there'll be like a load of snow dog big sculptures that people paint. So there was one in Edinburgh. It was Wally, the comic book character.

[A]

Okay.

[B]

You had to pitch your idea what you were going to paint on this sculpture. And then they had a bidding thing where businesses would pick designs they liked and like bid for them and pay for them. So anyway, I applied for this. I was going to do Flowers of Scotland. It was all very cute and everything. And they were like, oh, I'm so sorry you didn't get through. And I was like, cool. Rejection challenge. Tick got a rejection challenge. But then a month later, they were like, oh, we've got another business that wants one and they like your design. And so, so they. It raised £5,000 for this charity.

[A]

Okay.

[B]

And I got, I think I got £800 or a thousand pounds to paint my design on this sculpture. And it got on Princess street in Edinburgh where everybody could see it. And it was just the coolest thing ever, partly because it was like a tangible thing on the street and then also because it was a no that turned into an actually yes.

[A]

Yeah. I also love things where other people can see the outcome of the invisible things like you applying for that competition. Technically, no one else can see it, but then now you've painted this mural, it's like everyone can see it. And I love that.

[B]

Yeah, it's so true. And yeah, it's really important to give yourself credit for the little tiny secret behind the scenes actions, because we're all taking so many of them and we don't even realize it.

[A]

Yeah, I remember. And this is like something that is good to do. Just doing a tally of what you're spending your hours doing per week. You might be full time in your business. Just notice like how many hours you're spending scrolling or how many hours you're spending creating content. And is that producing the rewards you want? And this isn't to say that you shouldn't create content. It just means that maybe you need to change something in your flow. Maybe instead of doing like 80 Instagram content, you're doing 50 Instagram content and the other 50, you're doing something else. Like, it's. It can be quite nice to be like, to audit your time and be like, what are the actions that will produce the business that I want in 12 months from now? How can I spend more time doing that?

[B]

Yeah, that's like being more conscious of what you're doing, isn't it? And not just going on autopilot, which

[A]

I'm so guilty of, of. If I post something on LinkedIn and people find it funny, oh my God, I'll just read that post over like 45 times a day. If people are like commenting, yes, I'm like reading the post over and over again and I didn't even realize all I've done is read my post or I've just watched my own stories 79 times. So it's like, yeah, it's ridiculous. I'm just like enjoying my own content.

[B]

We all do it. It's a dopamine injection straight into the brain, literally. Oh, okay. So if you could leave illustrators listening to this one little takeaway tip or thing, what would it be? I'm putting you in this spot.

[A]

I'm sorry to do a rejection challenge, which I know is bad because I technically haven't done a rejection official challenge, but you don't need one.

[B]

You don't need one. You are living. Thank you.

[A]

I'll take that get out of jail free card. But if you haven't done a rejection challenge, do it. Even if it's just 10 days. Maybe you're going on holiday in April. Like just do a 10 day challenge. Do a 30 day challenge. Do 100 day challenge. Also watch that TED talk because I think it's all very well, you and I talking about how rejection is going to change your life. You almost have to feel your body going through it. You have to feel the terror, experience the rejection, experience the positive outcome. And then it's, now I'm a believer. Now I'm a believer in the power of rejection. So go out there, tell the world who you are. Any sort of like little excuses that your brain comes up with. I'm too small. I'm going to build a website. First, Let me post 100 pieces of content before I start pitching myself and put myself out there. All of those things are really clever things that your brain is trying to use to convince you to not go through the pain of rejection. Put them to the side. See how far you can get with your audience, the size that it is, with your website in the state that it is, I promise you, you will realize that so much of what your brain is telling you, it's fake. It's made up. You're the only one who thinks that you're not good enough. Other people actually love what you're doing and they can't do what you're doing. Even if they had 10 hours to do it, they wouldn't be able to do what you can do. So go out into the world. Tell them who you are and give them the opportunity to work with you.

[B]

Mic drop. Boom. And also, if you do get rejected, you'll notice that you do not die.

[A]

Yes. This is the main thing. This is the main thing. You'll be like. Life goes on. Wow. I'm still alive. And listen, if you want me to cheer you on, send me your rejections. I will celebrate you. Tell me what you're doing. It's all good. We've got you.

[B]

Yes. I'll put all of Kyra's links and things below in the show notes so you can find it.

[A]

But.

[B]

Yeah. This has been beautiful. I have enjoyed talking to you so much. I knew I would. This has been great.

[A]

I know. I knew this was going to be really fun.