The Spark: Jessie McGuire on Why Fast Isn't Better, Imposter Syndrome and Dinner with Elton John

22 Apr 2026 · 24 min · 11 chapters

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In short

Jessie McGuire (Thought Matter) discusses why “fast” isn’t always better in design, the cultural pressure behind “cringe culture,” building creative confidence, and her perspective on imposter syndrome. She also shares creative rituals, fashion/personal media toxicity concerns, and a hypothetical dinner party with Elton John and Bad Bunny, plus how she’d use $150 for her mother’s birthday.

Guest background

Jessie McGuire is a branding designer and educator (teaches at Pratt). She has a master’s in branding from Debbie Millman’s branding program (graduated SVA’s first class in 2011). She’s been in the orbit of design writers like Stephen Heller.

Key claims

Design needs time for meaning; “imposter syndrome” is often externally imposed and may not reflect her own experience; social media can trigger self-doubt; young people shrink their voices due to fear of being “too earnest.”

Notable examples

Bullet journaling with many stickered notebooks; avoiding rapid design feedback cycles; her 13-year-old feeling better away from YouTube; her Instagram outfit posts making her feel “a dork” and “house wasn’t good enough”; dinner party menu blending British/Peruvian/Salvadorian influences; $150 spent on a Brooklyn dinner with her 79-year-old mother (Dolores).

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

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Reflecting on the Importance of Meaning

0:45 to 2:30

Discussion on the need for depth over speed in creative work.

“I mean, that was a big thing, wasn't it?”

Trends and Personal Preferences in Fashion

2:30 to 4:30

Jessie shares her opinions on fashion trends and personal style.

“And then if we were talking fashion, what would you say you're over?”

Creative Habits and Rituals

4:30 to 7:15

Jessie discusses her notebook habits and the importance of writing things down.

“As I mentioned before, I love talking to people.”

Challenging Imposter Syndrome

7:15 to 9:12

Jessie offers her unique perspective on imposter syndrome in the creative industry.

“appropriately, that's the wrong word, dressing in a sort of way that doesn't make me look, oh God, what kind of road am I going down?”

Cringe Culture and Creative Confidence

9:12 to 11:43

Discussion on cringe culture and its impact on creativity and expression.

“Actually on that, on that note, I was, um, I was starting to share my outfits on Instagram.”

The Role of Technology in Creative Development

11:43 to 13:05

Jessie emphasizes stepping away from technology to enhance creativity.

“I was able to be in Debbie Millman's branding program, which was co-founded by Stephen Heller.”

Influential Figures in Design

13:05 to 14:02

Jessie shares her admiration for Stephen Heller and other design heroes.

“because he just has an opinion and he's a little snarky.”

Imaginary Dinner Party with Icons

14:02 to 17:49

Jessie shares her dream dinner party guests and the significance of their music.

“I want you to delve into culture, into this is like the personal question.”

Dinner Party Details

17:50 to 18:20

Discussion about the food and ambiance of the imagined dinner party.

“We'll all stand around the piano and sing along.”

A Thought-Provoking Question

18:21 to 22:07

Jessie reflects on how she would spend $150 for her mother's birthday dinner.

“What would you do if I gave you 150 US dollars today?”
Show all 11 chapters

Legacy and Remembrance

22:08 to 23:28

Jessie poses a profound question about what we want to be remembered for.

“Not like, oh, what is history going to remember you for?”
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Transcript

Automatic transcript. May contain errors.

0:03We are back with the force of nature that is Jessie McGuire from Thought Matter. And we are just still reeling from that incredible chat on Monday, aren't we, Jessie? I mean, you covered it all, really. Yes, I feel like I was like, what is everything I just said? Hopefully it was, hopefully it made sense. Yeah, I was telling Jessie off air, I was saying, you know, it's a bit like when you've done a podcast, it's a bit like when you've had a beer, too many beers. And then the next morning, you've got that kind of, oh God, what did I say? Not that you're, you know, that's how I feel. I can only imagine other people sometimes feel that way.

0:39But you, like I was telling you, you were brilliant. We were marvellous, darling. We're at the top of our game. We're the torch bearers now.

0:49We hold the power. I mean, that was a big thing, wasn't it? In the 2020s, like getting a seat at the table. We were all saying that, let's get a seat at the table. I'm still trying to figure out where this table is and how I can get a seat at it. Yeah. I feel like I, at one point pulled the seat up too far to the table and was like, wait, I need a new table. So we all got to build our own tables. Build our own tables. That was another great thing from that. Yeah. I love it. It empowered a lot of people actually, that strange time. Anyway, now this is where we get to know you a bit more, Jessie.

1:24We've talked about all the serious, important stuff. Now we're just going to have some fun. Is that all right with you? I love it. I love fun. Good. Now, normally we allow our guests to choose the questions for the spark, but we just didn't get time, did we? This award was like a very quick announcement. So we wanted to squeeze you into the podcast season. And so I'm just going to throw some things at you and we're going to see what happens. Okay. Okay. Okay. What's a trend you're secretly over, but everyone else seems to love? Oh, uh, speed as something we should celebrate. Like, I feel like we're seeing just like, everyone wants things faster, things more efficiently.

2:04We want things to like, just move at the speed of light. I don't even know, but I, I personally, and I like to move fast, but I feel like for design, we need time to let meaning build. Like we need to not put out design systems and have 45 different reactions and hundreds of comments where people so quickly decided they liked it or didn't like it. Like, let's just like not do that. It's exhausting, exhausting. And then if we were talking fashion, what would you say you're over? You're so over. I don't even know what they're wearing in New York at the moment. Oh, fashion. Let's see. In New York, what am I over?

2:47I am over these little clog shoes that everyone was wearing. And I feel like they were like so fun and cool. And I was like, wait, what am I? Like, this is not, my foot is in like a plank. Why am I wearing this? Like, give me Adidas or Nike sneakers any day of the week. So much more comfortable. Right. over to the next question this is great I'm loving this oh what's your weirdest creative habit or ritual that you swear by oh my weirdest creative habit or rituals you know what actually um writing anything down I mean it's not a weird habit but like I have notebooks um and I have stickers on all my notebooks and I actually was just going through um in my office here I have about 20 notebooks and I have to write things down I've told my team at this point like if you're if you're talking to me and I'm not writing it down never going to happen yeah yeah yeah yeah so I've done bullet journaling I've done all like but at the end of the day if if I'm if you you know I'm really serious if I show up with a notebook that has a sticker on it if I have nothing then you know I'm not really I'm not serious oh I love it so you love stickers as well I love yes I love stickers I also feel like I love stickers on my notebooks because it helps me understand what happened at the time I was filling the notebook like this one has street vendor power I like my ice crushed and uh the constitution and I feel like that's what's happening right now see when we started this whole podcast we you were saying I'm I'm not gonna get too political and it's like don't worry because I hate getting political too we don't we try not to uh we try not to delve too much into politics but I like that what was it again ice uh i like my ice crushed i love that that's brilliant oh brilliant right there you go moving swiftly on oh what's one piece of advice you'd ban from the creative industry forever oh um i don't know if this is advice as much as um maybe this is my own personal there's so many times I meet people and I get to, I have had, again, tremendous mentors and people, but I have people who are like in coaching these days and like, do you need a coach?

5:07As I mentioned before, I love talking to people. So I'm like, oh, sure. What do you, what do you do? And what are you thinking? And I feel like I'm always told that people can help me get over imposter syndrome. Like I'm just told that all the time. And so I, there's something that I feel, and I've actually heard other people say it to young emerging designers, or I've had young people come to me. I teach at Pratt. So I've had some of my young people come to me and say, oh, somebody was telling me about this imposter syndrome. And I really, I've been thinking, and I personally feel that imposter syndrome is an external way that people see you, not internal, because I've never personally, like I, this might be a hot take, but I don't feel I've ever suffered from imposter syndrome because I've never questioned my own capabilities.

5:56I've certainly had a fear of failure. I've certainly known I showed up in rooms that people didn't expect me to show up in and that's made me feel uncomfortable. But I myself have never questioned my own ability. I've never thought that I couldn't learn my way into some room. And so I think if there's something I would really encourage to not put into somebody's mind, especially I think women and women of color, like don't ask us about imposter syndrome because most likely that's not what we're, we are thinking about. There may be structural conversations that we could be having, like opening people's imagination to thinking and seeing different ways that designers show up.

6:40But anyway, so that's, that probably wasn't your original question, but that's something that really I've been thinking a lot about recently. I love it. I love to hear how people are feeling at the moment. And I've only just discovered something today, Jessie, and you probably know it because you're on the pulse. Cringe culture. Have you heard of this? Yes. I have a 13 year old. Well, this is what I was saying. I did a sort of reel on our social media today. And I was like, if I had a daughter, she'd be able to tell me about all these kind of new cultural things that I just completely miss. I mean, I'm having a bad enough time dressing, you know, appropriately, appropriately, that's the wrong word, dressing in a sort of way that doesn't make me look, oh God, what kind of road am I going down?

7:25See what I mean? We all have to fight it. We all have to fight it. But you know what I'm trying to say. So yeah, I just learned about cringe culture today. And I think it's tragic that young people are not, you know, they're shrinking their voices because they're afraid of coming across as too earnest or like they're trying too hard. I mean, how are they going to sort of elevate their creative careers if they're not comfortable talking about themselves or going to networking events or like sharing their work, you know? Yeah, actually, so my husband's an educator, teaches in a high school, does international baccalaureate film.

8:00I have a 13-year-old, I have an eight-year-old. And we talk a lot about how to build creative confidence and whether you're eight, 13, 25, 43, 47. And I actually, yeah, whatever the ages are, I really believe that people have to step away from technology and computers because even my, my 13 year old, he's, he, he loves just making things and doing things. And he said when he sits and he crochets or he's drawing or he's like playing like a board game, he's like, he literally is like, I feel so much better than when I'm watching YouTube. And even though that's fun and it kind of entertains you. So I really think that, and I say this to my Pratt students as well, we're doing entrepreneurial class and they are always like, well, I'm going to, I'm going to Google this or chat GPT, or I'm going to look this up.

8:55And I'm like, wait, before you go to the computer, before you go and look on something like sit with your own like thoughts, sketch it out, write it out, make a list of things that are just happening. Because I do think that when you then go and look at YouTube or TikTok or you see somebody doing something different, you're like, oh, shoot, like, should I not be doing that? should I not like maybe that's not right you were talking about her clothes earlier like I will still put on my skinny jeans because I have them and they fit uh you know I've gone super baggy I mean I have those too but yeah but if I go and then I feel bad about myself like I really think that we should we should not use things that are happening on a screen to make us feel mad about ourselves.

9:42Exactly. Actually on that, on that note, I was, um, I was starting to share my outfits on Instagram. I think I was kind of like going through a phase. I've been through a very difficult health moment. So I was like, right, I'm standing upright. I'm better. I'm going to show off what I'm wearing. It's going to be fun. Um, and then I kind of put on Instagram after I hadn't been on for a couple of days and I realized all of a sudden I just felt like a dork and that my house wasn't good enough. And I'm 47 years old. So if I feel that way, what the hell is it doing to the younger generations? You know, it's quite toxic, really.

10:16Yeah. And it has been designed that way. Yes, of course it has. Yes. I mean, why the hell do I suddenly want to buy some beige cargo pants for God's sake? You know, where's that come from some algorithm somewhere told you that's what you want that's what it's getting off the yeah just going and really developing your own point of view i'm just as weak as the rest of them but at least i am self-aware jesse or so i'd like to so i like to believe same same i'm like i am i love it um oh who's your creative hero past or present and what have they taught you without even knowing it? Wow. Yeah. I feel like I have a lot of heroes, and I've been very fortunate and lucky to certainly meet a lot of my different heroes.

11:12Most recently, I have been really lucky to be in the presence of Stephen Heller. He is, and it's funny because I've gotten emails from him and I cannot not respond with, hi, Stephen Heller. Like I can't not call him Stephen Heller. But I've been really, like I said, it's been really tremendous because I've been a big fan of the Daily Heller for years and years and years. I feel like my bookshelf has like every Stephen Heller book. I was able to be in Debbie Millman's branding program, which was co-founded by Stephen Heller. And so just most recently, like I said, I got a chance to talk with him and I was invited to his class.

12:00And it was funny because I was just was with Debbie Millman, who's certainly a design hero, but Debbie Millman and I were helping critique a class. And she was like, wait, Stephen Heller, Stephen Heller didn't realize that you were in my program. And so I was, so it was just like a really kind of wonderful moment of like, you know, it is a very small world. There are these really prolific thinkers and designers and writers that I have been so lucky to just be in the orbit in and around. And it's just great when you meet folks and you have the conversation and you get to see how they teach classes or how they really see the world.

12:44And kind of in complete contrast we were talking about earlier, it has been so wonderful to meet them in person and not just through a screen, right? Not just read Stephen Heller's writing on the Daily Heller, which is great. But when you see him in person, we had a whole funny conversation about typefaces and like typefaces of the resistance. And there was just something so human about it because he just has an opinion and he's a little snarky. And so I love that. And so I think that as I continue to be really inspired by influential people, just getting to meet them and talking to them really does feel different than just reading about it or being at a distance.

13:23And they get to be inspired by you, of course. And I love how you just dropped in there just very casually. I was just with Debbie Millman. Well, yes. So yeah, in 2011, I was in her, I graduated the first class of her branding program at the School of Visual Arts. So I have a master's in branding. And so I've been very, very lucky to be in and around her orbit, which has been great. Okay, I'm going to ask you this last question before we ask you a question from the last, the previous guest. And then you've got to think of a question for the next guest because it's our lovely little chain, chain reaction that's going on.

14:01Now, you're not allowed to mention anybody from the creative industry. I want you to delve into culture, into this is like the personal question. If you could host a dinner party with two people, dead or alive, not including your best mates or anyone from the industry, who's coming and why? Put you on the spot there. I know. Anybody in, you said history? Anybody at all. It could be a pop star. It could be a politician. It could be an author, an artist, anyone. one um this could have sounds so random but like this is what's what comes to my mind I feel like I love I love music I love like so I feel like I have two musicians and one feels very current right now and um because I'm kind of suspending like time and history because they're both alive but I would host a dinner party with Elton John and Bad Bunny oh interesting oh so Elton John I know it's like it's so it's like so bizarre when I tell people this, but I when I was younger, I was obsessed.

15:08Like, I can't even tell you how obsessed I was with Elton John. I still am. I feel like you put an album on Elton John. I love. But I went I've been to so many concerts of his because when I was younger, I would beg my mother. And then I like when I got some my own income. Anyway, so I've seen him in concert many, many times. And there's just something so wonderful about his story and just him and his music. And then just now recently I've, and I probably would invite my best mate, my friend Darcy, who loves Bad Bunny at the dinner party. Like I'd invite some other people, but that would be who I right now would be so curious to hear from when it relates to like music and identity and belonging and standing in who you are and celebrating just joy.

15:51Yes. Yeah. He had a good halftime show, didn't he? So good. So good. That's a big deal over there. Are you into American football? Do you just like to enjoy watching it for the ads? No. So I actually am into football. I lived in Wisconsin for a few years when I was working at Kimberly Clark. And so it is Green Bay land. So you can't not be at a corporate company and not be into what most people are into. So I got to understand American football. I would consider myself a, what do they call it? A fair weather fan. Like I don't have like one team that I'm like really into, but at any given moment, I'm like behind probably the underdog.

16:31This season, I was very much into the Bills, heartbreak. And then the Super Bowl. Yeah, I love the Super Bowl. I feel like the ads used to be the thing I was into. Now I'm like, I can't watch anything more about technology, weight loss drugs. And it was, it was, the ads were pretty bad. That's a big thing over there at the moment. It's happening here too, as well in the UK. And And what's for dinner? What are you serving up? Well, so I did, I mean, I'm probably just going to butcher all this, but I had an opportunity to work for a UK-based company called Elmwood. So I got to know a little bit about like the cuisines.

17:10Right, I know Elmwood. Yeah. So Jonathan Sands. And so I've been to Leeds a couple of times. So there's a dish up there. I'm going to get it wrong, but it has like sausages and all kinds of things. And so I don't know why I just assume Elton John would be eating that food, but I feel like we'd have that. And then we'd have some Puerto Rican dishes. I'm Salvadorian, so I'm getting to know some of the Salvadorian dishes. So I feel like it would be a fusion of like British and the Americas served at our dinner party with a lot of really good music would be my, I guess, my dinner party. Yeah. He'll play the piano at the end, won't he?

17:51We'll all stand around the piano and sing along. Yes, like I said, I'm imagining like a lot of just like sequence and joy and piano playing and maybe some, yeah, just some amazing instruments being played. I don't know why I would be there, to be honest with you, but. You would. We both would. We're torchbearers. Elton, I know you listen to this podcast, darling. Come along and let's have a dinner together. jesse myself and a few other uh friends who was your friend again uh darcy who is uh oh darcy darcy okay all right brilliant thank you for being a good sport jesse now um on the podcast last week we had adam kurtz who is now based over in hawaii he's got two parts to his question first is okay and you know what you're the perfect next guest for this question okay Okay.

18:47What would you do if I gave you 150 US dollars today? Right. Think about that. And then the second part of the question is, because whatever you decide to do with it, he is going to post that money to you. So what's your address? Whoa, whoa, whoa, whoa, whoa. I know it's a good question, isn't it? $150? $150 US dollars, which I don't know what that translates to in British pounds. I can sort of, whilst you're thinking of your answer, I can certainly put that into the old Google. Other search engines are available. It's roughly, at today's rate,£109? pounds yeah I mean what I feel so terrible about with this question because like I I love the sentiment of like what's the money and then he gives it what I do with it and but I can't help but I got a little cynical because I was like in this late capitalistic world we live in like what can you even get for 150 dollars like I got like I got really like angry at my own brain I know I did the same I was like wait what what can you buy like I mean yeah you've got to do some good with it.

20:01You've got it. You've got it. Yeah. Here we go. So it is February 12th and it is my mother's birthday. My mother is, uh, 79 today. She is. Happy birthday. Yes. Dolores. And, um, I think I mentioned I'm an, uh, I'm an only child. I was adopted. And so my mother is the most single, most important person in my life. I feel like I do have a reoccurring dream that I forget her birthday. That's just been my whole life. I'm always like, did I forget her birthday? But today is her birthday. She is in Peru. She's with her twin sister. And so with$150, I would go and take that and we would go have a fabulous dinner in Brooklyn.

20:46And that's what I would do with my, that's what I would do with$150. Oh my goodness. Will you take a picture and send it to us? I mean, it can be private. I just want to share it with Adam and. No, absolutely. I know what my mother would order what would she get she will get an espresso martini nice and uh french fries and then some type of like dough filled pocket like a pierogi or an empanada or like some kind of like little pocket that's usually what she likes so that's what i'm gonna do with it and so adam i will i will take a picture of my beautiful 79 year old mother oh that's beautiful well thank Thank you.

21:27Thanks, Adam, for that lovely question. Right. So what is your question for the next guest, Jessie? Oh, I feel like Adam's is so like heartfelt because I was thinking about it. And, you know, with all the conversations we've been having around, like what's possible, I do think that. But as because, I mean, I know you talk to, again, amazing designers and talents. But I would want to know the next guest, what do they want to be remembered for? Yes. Like, how is history going to look back? Like, what is the thing that they really want to be? Yeah. And I know that sounds like really heavy, but I'd want to say it in a really like your wonderful optimistic voice.

22:12Not like, oh, what is history going to remember you for? But like there's so much possibility as we look into the future and it does sometimes feel heavy. But we're all like I said, we're all so talented and creative and imaginative. And so with that imagination, like what do you want to be remembered and how is history going to remember that work? And what does that mean for? Yeah. And again, I guess it could be personal family. It could be expansive. it could be it could be anything but yeah because I do think about that a lot I do think that we all we do go about our daily lives and we just do the work but there is a moment when you look back and you say like is this really what I want to be remembered for or is this really what I'm designing this life and is this really the life I want to be living in the middle of and so um there's a little reflection to that that I think is fun well it's definitely making me reflect and I'm sure it'll be like, you know, making our listeners think too.

23:09I mean, what a lovely question to end another spark. And thank you, Jessie, again, for being such a great sport and for being a brilliant guest this week. Well, Katie, thank you so much. I feel like I've been so looking forward to getting to talk with you. And thank you. Thanks to Adobe Acrobat Studio for sponsoring this episode. If you're curious about what it can do for your workflow, head to the link in the show notes to explore.

From the publisher

essie McGuire returns for The Spark, where things get a little looser and a lot more revealing.

She shares what she's tired of seeing in the creative world right now, including the obsession with speed and the pressure to react instantly to everything. It's a thoughtful take on why creativity needs time and space to breathe.

There's a brilliant moment on imposter syndrome, too. Jessie challenges the idea entirely, arguing that it's often something placed on people from the outside rather than something we truly feel within ourselves. It's a refreshing and empowering perspective.

The conversation drifts into social media, cringe culture and the pressure to present a perfect life. Jessie talks about the importance of stepping away from screens and reconnecting with your own thoughts, your own pace and your own voice.

We also get a glimpse into her personal side. From her love of notebooks and stickers to her dream dinner party with Elton John and Bad Bunny, it's full of charm and personality.

And then there's a genuinely touching moment. Asked what she'd do with $150, Jessie chooses to spend it on a meal with her mum. Simple, heartfelt and a reminder of what really matters.

She leaves us with a question for the next guest that lingers long after the episode ends. What do you want to be remembered for?

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