How Kaitlin Carpenter Built Creative Mornings Portland

What does it take to build a creative community that people actually want to keep coming back to?

In this episode of The Awkward Handshake, we sit down with Kaitlin Carpenter, the organizer behind Creative Mornings Portland, to talk about what it really looks like to sustain a creative community over time.

Kaitlin isn’t just hosting events—she’s curating an experience. From speakers to structure to the feeling in the room, Creative Mornings has become one of Portland’s most consistent and well-loved creative gatherings.

We talk about how she brought the chapter back to life, what it takes to keep momentum going, and why the best communities aren’t built on hype—they’re built on care.

If you’ve ever wondered how some events feel effortless while others fall flat… this episode pulls back the curtain.

In this episode, we talk about:

•  How Kaitlin relaunched Creative Mornings Portland
•  What makes a creative community feel consistent and trustworthy 
•  The role of curation in building strong events 
•  How to choose speakers that resonate with a wide audience 
•  Why structure matters more than people think 
•  The balance between creativity and sustainability 
•  What keeps people coming back month after month

Meet the Guest

Kaitlin Carpenter

Writer and creative strategist, founder of BattleCat Strategy, and organizer of Creative Mornings Portland.

Kaitlin has worked with organizations like NASA Earth Science, the U.S. Department of Justice, and Trust for the National Mall to help them connect with the right people through storytelling and strategic communication. In 2019, she relaunched the Portland chapter of Creative Mornings and has been bringing creative speakers (and donuts) to the stage ever since.

Connect with Kaitlin:

• Website
• Instagram
• LinkedIn

🎨 Want to attend a future Creative Mornings chapter? Find Portland's events and other events worldwide here: https://creativemornings.com/

Keep in touch! 

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Transcript

0:00

This is The Awkward Handshake, a podcast about networking business and what really happens in the room. We're unpacking the good, the bad, and the awkward, so you can build better connections and get paid. Let's get into it. we have an all creative episode today. You and I wanted to do this so bad, and we got Kaitlin who runs the Portland chapter of Creative Mornings. And it was just like, oh my God, she's gonna come on the podcast. I know. I ran around my apartment and I was like, she said yes. I was like, thank you for asking her to do this. Yeah, we learned in the course of doing this, how much volunteering that Kaitlin does we looked around loosely at all of the other groups that we go to, and they are largely run by volunteers. Even if somebody has like a sales funnel attached to it. You're not making really a whole lot of money from that event. So you're kind of volunteering for your own. We have certainly volunteered for our own and we really felt like Kaitlin exemplified How much volunteers run your best connection spaces? She has been running this since 2018. It's the year of 2026. That is eight years. If I have got my mental math correct and in the middle of that is COVID. Yeah, like that is a flex. Holy crap. I first met her and we go into this in, in the interview when I was starting to lead Freelancers Union, Portland chapter the amount of time that she spends on this.' cause one of her warnings to me was this will become a part-time job. Yes. And AI Portland lady said the same thing. Yes. When I asked them. And I was like, oh, good. I didn't know that's what I was getting into. so I think anybody who goes, oh, you know, it's only once a month. It can't be that bad, to make a good event. There's a lot, behind the scenes a lot. Yeah. It makes you appreciate ticketed events for what they are, because there's so much that goes into them. And to realize that a group like Creative Mornings is offering this for free. When you realize how much labor is going on behind the scenes, it's Kaitlin and a team of volunteers and a lot of generosity from speakers and sponsors who provide space for everyone to get together. I mean, it's pretty monumental and the events are so professional and beautifully hosted. They do professional video. So that you can see speakers online as well. Yep. That is not small in and of itself. The media person in me was like, don't turn this into a media episode, Mary. But I was listening to her and I was like, oh my God. That is such a huge benefit, not just to the speaker, but to the members. Yeah.'cause you can go watch all the past ones. It's, it's really cool. And then there's always volunteers on hand. They have coffee That is provided donuts. And it's just a wonderful, unique little space. If, if somebody hasn't gone, I can't recommend it enough. It's a weird little like liminal space that you step into. And for somebody like me who went to art school, it's like going back to art school when you have like like a traveling professor or like somebody who comes to talk about Their work. it's just so cool. I love that there's a lot of thoughtfulness and care huge shout out to Kaitlin. And her volunteer team. Yeah, because that thoughtfulness and care is not some magical thing that just sort of pops outta nowhere. Like those are real humans making very clear decisions and also really thinking about all of their community members in a way that is, really above and beyond All right, let's get to know Kaitlin Carpenter. She's a writer and creative strategist with an MFA from Randolph College and a BA from American University. She's helped clients including NASA Earth. The US Department of Justice and Trust for the National Mall Connect with the right people, show impact through story, and design sustainable communications without sacrificing creativity. In January, 2019, Kaitlin restarted Creative Mornings for Portland. She's been bringing creative speakers and donuts to the stage ever since. Pardon me, I got the date wrong. So she approached them in 2018, but it really started up in January, 2019. Well, really her volunteering started in 2018, if you're gonna be honest. Yes. So once again, Kaitlin, we're giving you virtual trophies. Kaitlin, thank you so much for being on the podcast. We were so excited when he said yes. Thanks. I'm really thrilled to be here. We were super excited when you said yes because you are an organizer for the Portland chapter of an international organization called Creative Mornings, and we really wanted to talk to somebody who has had this role because my co-host, Megan here, also was a chapter organizer for the Freelancers Union. we just think like, this is such an interesting angle because there are a lot of different organizations that create networking opportunities and I think sometimes people don't realize how much this comes from a network that is national or international and you have that, but you are a creative yourself. And so we wanted to start just talking about the creative part first and what you do, because there's a story in there and how it makes somebody want to become an organizer. So do you wanna tell us a little more about the things you do? Sure. So I'm a writer. That's my creative genre, I guess. A lot of the folks assume I'm like a designer 'cause that's what a lot of the people in the creative morning space are. But I write and I had no experience doing any sort of event. Production or community organizing before this. But I moved to Portland in 2017, like the week of the eclipse that was happening that fall. Oh yeah. Mm-hmm. It was just like a complete coincidence. So we like moved in our stuff and then like went up on the roof of our new apartment building, were like cool and eclipse for us. good omen, right. I was like, how lucky to have like moved in to a place where this was very visible. I'm. Always seemed to be having big life milestones when there are major things happening. Like I met my husband the day the Washington Monument got cracked in an earthquake in like the DC metro area, which is where we lived. So fast forward to 2017. I'm no longer in dc, we're in Portland. and I didn't know anyone. My plan for a year was to just go try a bunch of stuff to make myself uncomfortable, to meet new people, to try and build kind of a new network. I did that as best as I could. I mean, I went to all kinds of stuff. I went to like an event to learn how to do fancy, like fingernail art, painting. which I've never done again, but it was really cool to learn that when people are doing nail art, I was like, this is what they do. And to get a little bit better perspective of like, this is the kind of work that goes into this thing. So I did a bunch of stuff like that, of just spaces that were not necessarily my spaces, but gave me, a view into what other people were doing. but in that spring, the former, organizer of the Portland Creative Mornings chapter. Stopped doing it. She had started the chapter in 2011 and, you know, it was a ton of work to start it. She built up this really good community. I, still have so much respect for what she built and everything she did. it's an amazing foundation and she was one of, I think Portland was maybe like the. I don't know, 13th chapter or something. It was one of the very early creative mornings chapters in the world. So it had a big influence on what a lot of the other chapters around the world looked like. And so she gets a lot of credit for that. Her name is Sealy Pines. but it was time for her to move on to other stuff. It takes a lot of energy. So she stepped down and I waited all summer ' cause I had just moved here for someone else. To do this again so that I could keep going to these events and no one was doing it. And I was like, you guys, I just got here. I still don't even have any friends. I was expecting to go to these events to like make friends. but I had met a couple people at different events and making friends as an adult is hard. putting yourself out there is hard. I, despite appearances now, I'm still pretty like shy. It takes a lot of work for me to put myself out there. but kind of frequency what's the word I'm thinking of? Like recency, frequency and recency are. Kind of what you have to do to build relationships in those early stages. So I really tried to follow up with people and meet for coffees and stuff. then just harassed several people who seemed like they might maybe be a little bit interested in this, in the way that I was. I was like, this hasn't been happening. It seemed like you liked it the couple times that you were also there. And I wanna restart it. do you wanna put in the pitch with me? And, and I'll do most, you know, I'll do all the work. You don't have to do anything, I promise it'll be fine. And, so I got a couple people to do it with me, and most of them are still on the volunteer team. Um, this was in 2018 and so now we're in 2026. It's been A bunch of years. A lot of years. Yeah, a lot of years. they did end up having to do some work. Turns out I could not do it all myself. I was trying to push myself to be, exploratory and look for what I wanted to do. That was more than just doing my job, which was most of what I did when I was in DC and what part of why I wanted to move out of DC is I knew if I stayed there, most of my life would just be my job. And I was really good at my job. I'm still really good at my job. I'm a creative strategist. I do, communications and marketing strategy mostly for. Larger organizations. I've worked with NASA Earth and the National Institute of Justice and the Department of State on some like education projects for global exchange for high school students. You know, I've gotten to do some really cool things to help facilitate amazing experiences and connect brilliant people to the places that their work can make a difference. creatives can get so swept up in just doing the one thing they're good at all the time and forgetting about like the rest of the things that make them feel like a really whole person. and so that's what I was really pushing myself to explore when I moved to Portland. this was just kind of a, like a right place, right time thing of creative mornings. Needing a new host and me looking for new people and some new opportunities and these falling together in a really nice way. And then I had to learn to do a bunch of new shit, and a lot of it was paperwork, but I'm now much better at all of those things. People often think that this is my job, which is hilarious to me because if someone would pay me to do this, I would absolutely run something like this for you full time. but this is a fully volunteer, effort and I do a lot of other things in the rest of my time. Well, what kind of ROI do you get out of organizing? I've been an organizer for different kinds of organizations, alumni associations in particular. And I know the networking for yourself as an organizer hits a whole other level because you're the one directly talking with the guests and the hosts and people who don donate things and sponsor things. And I'm just wondering does it help with being a creative to be able to interface so closely with everybody here? Ooh, that's a good question. I wanted there to be a really clear line between myself. Creative mornings Portland, to make sure everyone knew that this was not about like pitching myself, especially because I was so new to Portland. It's like this is not about making any value for me. The person, the connections are not for me, the person. They're for creating value for this community that I really value and making like connections for the community of all of these creative people that I also want to meet. So I was really careful about that, especially the first few years. But the ROII do get out of it is I mean, and this is why I did it in the first place, it's still the same. I get to meet really amazing people. I get so much energy out of the events. the same thing from an event as from an idea. So, which I mean a really creative idea. Is a combination of new things and you don't get a lot of new things when you're just home by yourself, and so going into new spaces with new people, getting to hear from a creative speaker that just gets you turning the wheels even. And especially if you've been stuck on a project or you don't have a project and you wanna have a project and you just need some inspiration. no matter what you're doing, I think everyone who comes is gonna leave with some spark of energy or inspiration. And the same thing is true for me. So I think the ROI is a little hard to quantify, but is so, so meaningful to me. the relationships just the feeling honestly has been worth it a hundred percent. I hope that's true for everyone. I've been to quite a few and I can say, yeah, even, even the last one I went to a few months ago, it kind of feels like I went to art school. It feels like you're back in the school, right? And so you have that moment to kind of step outside. You've maybe not been doing as much creative work and you kind of hear somebody and it feels like they just got to go get their master's in that thing, and you're like, that's right. I could do that project that I've been thinking about, I got a DHD, so like, you're listening, but also the other part of your brain is like going through 8 million ideas and you're like, not that one. Not that one not, yes, yes. Okay. Yep. and then it's like, time to go and you're like, okay, I'm gonna run home. Where are my markers? it does create kind of a liminal space where it's almost like the Jo Bs are outside. And it's everybody who's just, you're almost like all kids again. And you are like, yeah, I do this thing with, I went to the one, uh, where he light art. And so he was doing projections on the to buildings and it was like, here's a guy who just plays with light. I mean, like, how cool is that you know, the global organization, They've done a really great job. And the organizer's name, is Tina Roth Eisenberg. She does a really great job of creating a container that doesn't have a lot of parameters. Just a few. And having just a few parameters is often all a creative person needs because you don't wanna have so many that it's like, this is for designers who do painting on four by four. You know, sometimes you need that to do like a coaster art, Gallery show or something that's highly specific. But to do something like this, we want. Parameters that everyone can kind of see themselves in, what the person might be talking about or can see how that talk might apply to their own life or their work, or their hobby or their passion. so the parameters, the motto is everyone is creative, everyone is welcome. and then the chapter I organize the only hard and fast rules that we look for in speakers are, do they have a creative story to tell? They do have to be like, in our region. and are they trying to sell something or are they giving the audience something in a generous way?'cause those are different. and even if they're talking about a specific project. that feels different than, somebody who's like here to pitch their specific. Business idea and there's a time and a place for those talks, but it isn't necessarily this space. How do you find the speakers and the spaces? Megan and I have organized a whole bunch of things, and like space is always the number one thing. Like where are we gonna have it? But then also finding your speakers who meet these kinds of requirements People will take stage time anytime you give it to them, but you're like, I don't need you to deliver a webinar in real life. Like, we, we really are gathering for something else. So how do, how do you find all of that spaces are hard. spaces for me have just gotten harder because we need kind of bigger spaces and there's like A Goldilocks problem to this of you can kind of find smaller spaces or this like medium space, but once you hit a certain number, there's just, there's nothing available in a certain price range kind of a problem. this is a free event run by volunteers, so you can imagine the budget. but we're also putting on something that. Brings in a, huge, very interested, very diverse audience. so if I can show people the value of that, that's interesting. And that can, be helpful to different types of businesses. And that's not always in a salesy way. That's also just proud of the spaces they've built or like creative companies that. Aren't bringing a lot of people into their spaces and want to be using that in a very generous way. So I also mean that of just like the community generosity and finding the places you might not always think about as hosting an event or something. And, often they're very willing. You just have to think outside of, the usual. how many people are in the creative, mornings community for Portland? I mean, our events average probably around 140 people each, if we are in a space that can fit that many. But we're often in spaces that don't fit that many, so we're usually limited to about 120 people. But I try to get us into spaces that will fit more and then, we'll, we will fill more if we have more seeds. And it fills out fast. They do. Yeah. Some of your tickets are gone. There was one that we wanted to go to and then literally like within an hour it was all gone. Gone. Which breaks my heart. It really does. It's like I wanna fit everyone all the time, but this, and this is something that. For anyone organizing an event is hard to figure out too. Especially free or low cost events. I also can't, especially if you're paying for venue space, I can't pay for a larger venue and then have like half the people cancel last minute or not show up. sometimes we are able to get like grant or sponsorship money and we are. Even if we are getting free venue space, we're renting chairs or we're paying for donuts or you know, other, there are other costs that people don't think about for a free event or any event. Even if it's like a pretty low cost event, you're like, oh, I'm just canceling my $10 ticket, and you're not thinking about if 50 people cancel a $10 ticket, that just costs a very small event, 500, maybe more dollars, that really hurts and that makes it really hard to maybe do this next time. we rent chairs for a hundred person event that's $300. If I have a bunch of those people don't come. That's really hard to be able to do that next time. And so then we have to be in a smaller space, which means not that many people can come next time. So you're really hurting the community at large. Now this is just me lecturing audiences, but, preach, please. I see both sides. It's hard. I mean, life is hard. Stuff comes up and we all need to be really. Generous with each other too, on stuff changes. like I send emails, we encourage folks to, if your plans change, like release your ticket so we can let someone on the wait list on instead. But you need to do that before, like the hour before the event where it doesn't matter, and there's always gonna be a percent of like, where that's just not possible or something comes up at work, someone gets stuck on a call, whatever, stuff happens with the kids. People have lives. I get it. We have a margin of error, but the margin of error should not be like 50% because, come on, we're all grownups or we should be. I think it's a testament to the creative mornings crowd in Portland that you do have wait lists and you are maxed out on even free tickets. Megan and I have tried to organize creatives 'cause they've come to us and they've told us. Oh, we need help networking. And we're like, great. We're gonna get you together. And getting them to commit to the day and do things where like, the creative brain is just so different than the other entrepreneurial brains that we also, work with. So we kinda made a decision where we're like, well, we're just gonna start just incorporating them in general to things instead of trying to make a curated thing. But you have a curated thing. I mean, granted, it's a global organization with chapters all over the world. but the Portland crowd is very creative and needs a lot of creative resources for creators, so I think it's amazing that the show up rate is as high for you. Like that's pretty impressive. I don't think I can take all the credit for it is all there is to it. my team has done a really good job and we've made something that is very. Predictable is a very boring word to say, but it is something you can count on. I don't think we often have misses. I think almost every single speaker we have on is amazing. They're all so, so good. And even when something small goes wrong in an event, that's not the thing that you leave thinking about, next time you come back that it's gonna be worth it. and so any event organizer, as long as you are making the thing that people are there for amazing, they'll know that next time it's worth it too. And I think integrating the creatives who can be very scattered or have a lot going on, or, you know, they're trying to go in a lot of different directions. I think finding ways. To integrate what they need into existing spaces is a good approach because then it takes off some of the burden. Spaces that other organizations are putting on that people can integrate things into, I think are a really good way around that because then you're not figuring out all the details and you're not responsible for everyone showing up, but you can coordinate the thing that you're doing really, really well. And that's the part that people will remember and that's like the part that I have to coordinate really well. Is the speaker being fucking awesome? No, just kidding. That's that's all on them. And they're great. And I can't take any credit for that either. So I just have to set a good stage for them and voila, they're amazing. How do you find them Magic, magic theory. It's the secret to everything is magic. Your website says it's all magic. And I'm here to confirm. Sometimes it's really hard to explain what you're curious about or why you're paying attention to something. Most of us just say you trust your gut or you're following your intuition. And I can't really explain it better than that, but it's a combination of that and listening to people who are smarter than me and who pay attention in spaces that are different than the spaces that I'm in and knowing to ask people who are in spaces that are different than I am. So logistically the volunteer team and I meet at least once a year to do kind of like a big planning meeting. And we look at, the way Creative Mornings works is there's a theme for each month of the year. every chapter around the world is choosing a speaker for the same theme for January. And so you'll get, 200 plus speakers. All on the theme of Ember for this month, April, 2026. And they'll be very different. the speaker for Portland is going to be someone very different from the speaker in Barcelona, where I don't think there's a chapter right now, which is crazy to me. but somebody just like LinkedIn messaged me about this. Like they were, were visiting someone in Barcelona and they just thought it was so crazy and they were so grateful. We had a chapter in Portland and anyway, which was very nice. So if you know someone in Barcelona who wants from creative warnings, I guess go nuts. Uh, but you know, all these different interpretations of this theme of ember. So pretty broad container, like I said. we look at the list of the 12 themes that are coming up and I kind of just pay attention throughout the year to people I'm seeing through like Instagram and the various, like Portland and Oregon. Media, people come through my inbox anytime someone says, I'd love to do a talk, or I know someone great, I just tell them to like, send an email. And I do mean that, it doesn't mean that everyone will end up being a speaker, but I do want everyone to be on the list. so we only have 12 spots a year and we do get tons of suggestions and so I'm not being disingenuous. It just means, you know, we have so many amazing people in this area, and I mean, everywhere the world is filled with amazing creative people. Mm-hmm. And there are lots of forums, to hear from them. And we only get to choose 12 a year. We do a little brainstorming around the themes first before we start looking at people. And that. It comes up with some interesting things too, let me give you one fun example. We were brainstorming, think it was two or three years ago. The theme was Rise, RISE. We were like, what are some portlandish thing? Like what kind of directions could we go around the word rise? Just doing some like creative. Work shopping. We were like, what about like bread? What about like, bakers was one of the directions and we ended up going that direction. Like someone did baking stuff and the speaker we ended up having was Vera Brasco. I went to that one who was amazing. Amazing. Right. hope I don't get her title wrong. she was a story director. At Leica for the Pinocchio project and some projects before that. She now does writing and illustrating of her own books. amidst all of that, she started baking like not as a job, as a hobby, so much so that she started like volunteer working for her friends at Starter Bread. Who run this like CSA bread company. So she's like very good at it. but didn't want it to be a job, didn't wanna like commodify this thing that was very interesting to her. So, we went from the word rise, which you could think of so many things. you know, someone who does hot air balloons or. I don't know, a million directions. And we wanted to do like rising, like yeast or baking and it led us to Vera, which was very fun. and then instead of donuts. Oh yes. She, she had them bring in bread. Starter bread. You can find them@starterbread.com. they're really great. I, I reached out to both of them after the talk because I was interested in working with both. They're so cool. Yeah. And I like the idea of the business model too. Going outside it literally. Yeah. You will pick it up. you get it weekly, and it'll be dropped off at locations and you go get your bread. Oh. It's like neighborhood drop off locations. Oh, I love that. It's very smart. It's very Portland that It's so Portland. I mean, it's a little, it's a little mushy gushy. It's kind of just, we meet and talk about it. It's kind of paying attention. I do also ask our past speakers often, is there anyone you've been paying attention to? Anyone you would recommend? I don't want the folks that we're looking at to just be this myopic. Thing of like, who is Kaitlin paying attention to? Because I'm a white woman in Southeast Portland, Oregon, and who I'm paying attention to or who is like coming up in my radar or like whose art is on the wall in my coffee shop is not all of who's doing amazing, incredible creative stuff in Portland. And that's not what should be represented on, the Portland Creative Mornings stage. we take that very seriously. And planning out the whole year as much as we can at a time, or at least trying to also allows us to look at, which I know this is not something every event has the ability to do, but even if you're not looking that far ahead, you can think about it sequentially. they're the kinds of diversity we usually think about. But we also try to think about industry, we're like, oh, we didn't have a lot of musicians this year. Or like, did we have any movement artists? Or, what about age? Or there are so many things you can think about and we try to cover as much as we can so that we have a true range of representation, at the event. I'm sure there are always ways we can be doing. Better, but we're always trying. I was just gonna say, the world of creativity and art is so massive. And when you're limited to 12 events per year. in art school, they were always like creative constraints. And as a student you hate it. But I remember having this teacher in my art, program she gave us this lecture one day and she's like, listen, you're gonna eventually graduate and go out and do things, and whether you do. Art full-time is your job or just is part of what you do. You are always gonna have constraints. You're gonna have constraint in your budget or in your time or in what access to resources you have or whatever. And you're gonna have to create within those constraints. So she's like learning to exercise that muscle now is my goal for you. And I always let that lesson always stuck with me. And I think that you are doing an amazing job of thinking about the diversity in the population and in art forms and in the artists themselves. that is such a monumental task to take on in a volunteer role when people are getting free tickets. So yes, they should definitely be using those tickets and showing up. And I'm just gonna plug that one more time. Please, please show up. Please show up everyone, we want you to be there. We really do. but it's such a strong community and to be able to interface with them, fill your cup as a creative, it can be very draining. Especially in the times that we are living in to be a creative and And you literally bring your mug. Yeah, I love that. Also, I like shout out to your name, take system. Oh, thank you. It's the coolest one. there are magnetic buttons. And it's just kind of like whiteboard. So you write on, And then they just get wiped off afterward that we made them a outlet. PDX, Kate Bingham and Burt's Studio. I love outlet 'cause they have a button press maker you can rent time for. That is such a great idea. And they have pronouns. Yeah, we have, yeah. We just say put your name and pronouns on them. Yep. I love the low waste name tags. We are going through so many stickers and we do lose some of the buttons'cause people forget to take them off. Yes. But I think fewer than paper name tags. And the bring the, bring your own mug and it's just very cool. It's so thoughtful. We try, that's another, Positive of being part of a global organization is there's a slack, and people do drop in, ideas and pictures and things from what they're doing at their events. honestly, I can't remember or not,'cause it's been some years since we made the button name tags. I don't know if it was our idea or if it's something we saw that someone else did, or I don't know the origin at this point. I was like, maybe we did it first and we shared and then someone else did it or maybe like someone else did it and then we made it. but it's nice that you can like, share ideas and see them spread and make other events better, that people can learn from each other's lessons. So I think whenever people can Not repeat mistakes. That's helpful. And share what they've learned. cause when, when I took up the mantle for Freelancers Union, I actually, I reached out to you And was like, can we have a coffee date?' Cause I'm gonna say yes to this thing and I don't know what the hell I'm doing. and mine was a little different than yours in that yours. it had, it had already existed and Freelancers Union did not have. A chapter in Portland at the time, and it was basically like, if you want it, you get to lead it. And then there was this whole like assessment thing to fill out of like, why do you think you should lead it? And I was like, I don't, but no one else is doing it. I learned fast. and you were kind enough to sit down and you were like, okay, here's the pros, here's the cons. you were like, this is gonna take you 20 hours a week. I hope you're, and I was like, oh no. I refuse. but you, you just kind of like, were like, here's how, to get speakers, here's how to do this. I just couldn't believe that somebody else was willing to like, sit down and tell somebody you weren't like. This is gonna bomb. I don't know why you're even doing this. You weren't like, who are you to start this thing? You were, you just took it seriously and you're like, I'm gonna tell you all the things, you know, like the pitfalls that may come, or be prepared for this. and let me know how I can help. so Kaitlin, you have a team of volunteers who volunteer with you? Yeah. Megan, you were really mostly on your own. You had your husband, Jeff, with you. Yeah. But you were mostly on your own. Yep. I'm wondering for you, Kaitlin, like how many other chapters also use volunteers and how do you, how did you decide that you were gonna do that? Everybody has at least a small group of volunteers. And, and a lot of chapters are small events. They're like maybe 20 to 30 people tops. So like, ours is one of the larger chapters in the world. Dang. Pat yourself on the back. I That's a fuck. I do. I I was like, we, we do a good job. Just a little. Listen, we're not New York, but, we do a good job, but everyone uses, has at least a small volunteer team. Yeah, I mean, having the courage, Megan, to try to start something like from scratch, and I think you did. I'm like thinking like way back to 2018 when I was feeling this out too. You did the exact same thing I did. It's like I reached out to some people I didn't know, like the Andes who ran XO xo. I was like, can you. Please have coffee with me and share a little bit about like how you thought about putting an event together and they were kind enough to do so. some things like that. Elaine and, Mary who ran, ladies Night UX for a couple years here, they're really wonderful and I had some conversations with them, but same thing of, and I, really, really believe in the. pay it forward and be generous with your time as much as you can. but people also have to be willing to, I was like, everyone can do things, but I don't think everyone will do things. And I was like, Megan, you are a will doer. you are willing to do the thing am and not everyone is. And I think that that is a huge difference. I had the same motivation that you did.'cause I I wanted to grow a network, I needed to meet all these people. And you know, I talked it over with my husband when we saw that there was this opening and he's like, you just kind of wanna be the spider at the center of the web. Like, this is how you're gonna do it, is you're gonna start this thing. And you know, Mary, you're always telling me too. You get to be peer to peer because you are now an organizer. And you get to reach out to somebody. It's not you in the audience attending someone else's event. There's just, Clout that comes with it. And I don't know, your was much bigger than mine ever was. Like, you never feel like you deserve any clout. And they're like, oh my God, I'm gonna come to this thing. And you're like, thank you so much for coming to this thing I'm very much a behind the scenes person, I feel. I'm like, I just wanna make the valuable thing and be helpful. But it's leadership. People need leaders and they appreciate when someone will do things. Yeah. And will lead. And it changes the relationship you have with people in the community and with your guests or your location sponsors. I'd say if you are gonna start something, I would get the volunteers That would've been better. it helps to have at least a couple people, who've got your back I did not have to, but you also had to run like socials at least then you had a newsletter too. Like I didn't have to do that. Yeah. Communication takes a lot of time. It does. my work is in marketing and communication, so like writing something is never daunting to me, but sometimes like that's not somebody's strong suit. And so that kind of stuff can be hard. And some of those things are not volunteers. Some of those are paid services because we do, and that's the value to the speaker. Their talk is also online and available, but that's why we pay for good videography. and we're really appreciative of them. So we're not paying the rate that like Nike would pay them. but it's not zero, but it's not zero. And it's, I hope a fun project for them. and they've been doing that with us for a long time. but yeah, it is valuable to the speakers as well that they have that, And not every speaker says yes. This might be mind blowing. Oh, But who would say no to a community like that's so active in Portland? I mean, maybe people just are magic and they don't need visibility, but are they scared? it's not everybody's thing, and I think even if I do my best job explaining what it is. A cold email is still a cold email. Yeah. And that's true. Some people just, they don't know what it is. They're busy, they have other stuff going on, and may just not interest them. Or maybe it's just not the right time. Creative Mornings is an unpaid speaking opportunity, and I fully respect that that is just not for everybody as well. fortunately we have, For several years, and also this year the annual sustaining partnership with Wacom Creative Technology Company. And part of what we use that for is to make a donation on behalf of each of our speakers. But not every chapter is able to do something like that. even with that I think is doing the bare minimum to show speakers how much we appreciate the time and energy that goes into something like this. yeah, so like it's just, it's not for everybody. I would go screaming around my apartment. I got that email. I like, oh my God. Like I One of the 12. One of 12. One of 12. She t-shirts or Yeah, I would, little merch. I would make merch. Yeah. Like an SNL like fifth host jacket. Yeah. One of 12, If I had enough money to make jackets and t-shirts. I mean, so it's not what I would be doing with it. a shadow March line, I don't think a lot of people think that way, to go find something existing and, and see if they can plug in. there was part of me that's just curious because you, plan the whole year. are you doing your planning in the summer or the fall? Like that's the weird A DHD question. It's like, but she can't do it in December. Oh yeah. Do you do it in bulk or do you do it month by month? because they do one planning session. It kind of depends. I think we tend to get the list of the upcoming year themes in like the fall, and so we start planning then, so we try to do like as much ahead as we can, If I book a speaker like fully 12 months out, people also like fall off sometimes. Yeah. And so honestly like six months out like even if we make our list of like, this is who we would like to ask for this theme. I'm not actually doing the booking of everybody 12 full months out, but usually we're starting to do our like planning in the late. Fall for the next year. The last thing I wanna say is I think the the best thing people can do for themselves is to maybe venture a little into a new Venn diagram. I do think we get pretty into specific bubbles, and that is, I think, why people enjoy creative Mornings so much, which again, theme of the day. I cannot take credit for all of this. I can take credit for stewarding this chapter, I don't know, doing a good job curating and, and supporting all of the people who have spoken at it, for the past however many fucking years it's been. Um, but we focused really, really hard on making sure people understood that creativity is not synonymous with design and, That I think just opens up so much in people's brains. And even if you're choosing to attend multiple things that can do the same thing for you of, you know, don't just get on I'm only doing this. Maybe you, you are only doing this for a while, that's okay too, but break yourself out of your rut a little bit sometimes.'cause I promise it will like blow up something in your mind for you, which will be really beautiful for whatever you're working on. I think something smaller events can do or some events can do and that we do or we try to do that not everybody does, is. use your powers for good. So we do a combination of people who like are recognizable at least a little bit, and people who are like on the upswing. Because if you're only doing people who are only recognized, that's part of what makes it feel so magical too, is after you see them, you're like, oh, now I'm seeing their work everywhere. But that's also part of how we get really cool people is they're not everywhere yet. But they're definitely going to be because they're incredible. but you have to kind of take a swing on them too. We can't only have celebrities being on stage for things. they already have a stage. I mean, I'm not saying they're boring, but it's. Boring to keep asking the people who already have a stage. we have a bit of a celebrity obsessed culture. And by celebrity I don't just mean like movie stars. I mean there are notable people in every field and, we nerd out over them and that's great. But I agree with you, the up and comers are exciting. Attention breeds attention, but don't we want something new? I am so glad we had Kaitlin on here. We needed a purely creative and creators focused episode, and this is like the perfect one. I had no idea Portland was one of the larger chapters. Yeah. In the world. I mean, maybe not surprising'cause there's so many creatives in this area, but it is not a major market like New York or la No. And I just assumed, I don't know, I thought they were all like the same size, roughly. It just didn't even occur to me. It didn't occur to me either. Did that we could be four times bigger, But then it made sense that like, oh yeah, there might be somewhere maybe only 20 or 30 people show up. What a testament to consistency. Ooh. That's like a poster child case study on consistency. we loved that there was a discussion point in this episode about using an international organization with local chapters and using that as a springboard to become a host for something. Because you and I have been hosts for all kinds of things and you have experience hosting in this capacity with Freelancers Union. I used to run the University of Michigan Alumni Association down in Los Angeles and when you have a national entity, there is something that does kind of feel like it takes the pressure off, although it's really not less work. no. But we keep talking about it. You know, if you don't have the community, then build it. And I think this is a way that's a little less intimidating in some aspects in that, if it's a known organization. They will have some power behind them to market for you so that like the people will come, basically, they put out the call, the people will come. I think a lot of people don't consider that avenue because you either don't know about all the organizations that there are because in case there isn't a chapter where you are. you don't think, oh, I should start one. Yeah, because you can't see it if it doesn't already exist in your city. or if it's in your city, kind of like Kaitlin, like it was just running along. Why does she need to be even be thinking about it until somebody wants to step down? I think it's one that gets overlooked. but sometimes the organization is over the moon that someone wants to start. A new chapter, and they will have all of the resources ready to just give you, you know, like, here's, here's your handbook. Go off, you know, and, and we'll support you in these ways. I think that it can be a really great way to not have to create everything from scratch. Mm-hmm. Although as we determined in the course of this episode and even outside of this episode, that just because you're attached to a larger entity doesn't automatically guarantee you visibility or marketing because you still have to get the word out. Like that's not magic. Just because a national organization is attached to your local chapter, sadly not. No. Getting the word out I think is the number one problem for anything, whether it's a networking group. Or your own business offers. Visibility is really a thing. Yeah. I wonder if there's any group that has a bigger budget, because a lot of times these sorts of organizations don't. Have as many resources as you would think? No. I would say that I don't think any of the organizations has as many resources as you think. I really don't because I would assume the alumni we got beaucoup books to spend. No. How interesting. And Each local club is a booster club. Oh, okay. And so your booster club raises funds for scholarship funds among other things, but you have your own bank accounts and you have a, a budget and you're like, this is what we have for this. And at least down in Los Angeles, we would get alumni members who, ' cause the Michigan Law School is a very famous law school, and so there was a lot of lawyers in the area who worked for very rich law firms. Bless to every single one of them. Past and present who hosted alumni. You know, meetings in these law firm spaces after hours. And they would go so far as to donate and order, like cater in charcuterie and drinks. Oh, and let me tell you how generous it was that they did that. Sometimes the national level will bring people to town. At least for me, being a Big 10 university, we would get, like the new football coach came and there was a huge. Fundraising luncheon with a coach and meet and greets with current and ex-athletes. A lot of them are professional, like with the NFL and they were at the lunch and so, you know, if you were a sports nut, like you're great, but that was paid for by the national level. Entirely to activate the donor base. Yeah. which is very different than the type of networking we're talking about here. But still a great example of you're not guaranteed automatic visibility in dollars just because there's a name that seems fancy. But money is finite. But if you are, you know, worried about like, well, how would I even. Make a logo, do I need to make it a business? Do like those sorts of things get taken care of. Package. If you are a branding package, working with a national or international organization, yeah, having a branding package is surprisingly, incredibly helpful. Yeah. It takes so much decision making off your plate. You're like, this is the logo. I might hate it, but here we go. You don't get any say on the tech stack. That's always the thing that everybody hates and you're like. Why do I have to use this crappy piece of tech? Yep. Like, oh, I hate this software because it's in our dusty handbook. Yeah. Mm-hmm. Mm-hmm. I think it's so interesting. You and I have tried starting things from scratch here. The smaller, more intimate ones have been much more successful. We have interviewed people, of course, the across the whole season who have started very successful things. But, starting something from scratch is heart. And I think like even if you're opening a new chapter for a national or an international organization. unless it's a chapter that already exists. Or in the case of Kaitlin, she had to reboot the Portland chapter. It's still kind of like starting from scratch. Mm-hmm. that's hard. It's hard. It's a lot of work. she gets the structure from creative mornings, from the home office, but other than that, they have a lot of freedom. With freedom comes choices and with choices comes decision fatigue. Yeah, you and I have have started, like you said, we've started things on our own and definitely there were some more, like we had to come up with does the format look like, Where are we gonna find space? even if you do the nationally, you have to find space as well, and space is the hardest thing. And certain organizations will have certain requirements. For what you can and cannot do for space. Mm-hmm. And that was where I always had my hands tied. when you and I started, you know, it was like, what are we gonna do? And thankfully for the second iteration, you know, you had a space. Mm-hmm. And that changed everything. Well change some things. Some things. I mean, this space is very finite in this studio. Yes. So we can't just have everybody, everybody come. Yeah. So then the creative constraint became like, okay, well if we're constrained by how many people will fit in a space comfortably, then that means we have to do invite only. It can't just be like this wide invitation. but we have made new friends since who do have spaces. But I love that Kaitlin brought up how she has the same problem. Yeah. It made me feel a little bit better. I felt so much better. I was like, oh, we all have the same problem. I think she solves it far more elegantly than I think we have, but it's amazing that even she runs out of space for headcount. But it is a balance of more and more people want to go to events like Creative Mornings in Portland. And Portland once again is not some huge city. It can feel large sometimes. Yeah. But it does operate like a small town and there just aren't enough really large spaces. I thought it was interesting hearing her talk about having to navigate that. Yeah. I do think though, that there are a lot of medium and small sized ones mm-hmm. That you don't even think about. That are available. To you, because you'd be surprised at the number of businesses that are like, oh yeah, yeah. You can use the backroom. You know, like you can use the restaurant, you can use the backroom. You can use, this thing, because we're not using it. I mean, this'll be a hot take, but I think eventually we're gonna have to use a lot of churches as like third spaces.'cause I mean, you're only. Using it one day of the week. So I mean, it's a lot of sick square footage. Oh, you're talking about like in the sanctuary? Oh, well, they have other places in the church too, but just like there's a lot, like it's a building that is a third space sort of. It is. That is not used a lot of the time. Like if we're running outta space in the city, you know, like I think a lot of churches have. Public information where you can rent like their basement with the kitchen and stuff like the Yeah, the activity rooms and stuff. Yeah. But yeah, if it was like in the sanctuary that's, that's, no, no. That might be a problem. But like there are a lot of, um, cafes that rent out space. Yeah. the library. The library has a huge one, has a space that you can use. Mm-hmm. Like you have to kind of think outside the box. I always think that's where it's fun to have friends who even have JOB jobs because. A lot of times they'll have like a conference room that people would love to get a couple hundred bucks for you to be in there. Yeah. Or like in the case of the alumni association, all the lawyers Yeah. Who have these firms It looks good for them to be doing, they, they kind of have to also do some community, pro bono participation, and so it counts towards that. And so, I think that we're gonna start seeing some more creative use of space in Portland because since COVID, a lot of the commercial space downtown especially, is largely gone onus in cities trying to figure out what to do with it. And wouldn't it be so nice if some of those landlords would, make them available to communities and groups? The last thing that we wanted to digest after having Kaitlin at the table with us was something so powerful that she said at the end, she said, go to all the things, just go to all the things. And then the three of us have all been to art school, so we were all like. how have you, expanded your creativity and it's never, by only staying in your discipline. So for all of our business people, you and I were talking after Kaitlin left the studio, we were like, oh my goodness, if only all of our startup community and our entrepreneur community, whatever you wanna call yourselves. if you went to some creative morning, events, instead of only going to the same things that you know, no wonder you feel constipated in your marketing or in your customer reach or in your network, like you have to cross pollinate a little bit. And for our creatives who we have also hosted in our networking event. To not only go to creative events I think people are looking for people who understand them. So they go to the things that have people like them. But what you really need is the opposite. Yes. Not like all the time, but you'd need to sprinkle it in. I think what we found too with the creatives was like went with like, and I understand again, that's a sense that's needing community and so you need that. You need somebody who also wants to talk about, you know, smack about Adobe with you. but I think new ideas come from learning new things and that kind of comes from being in a space that you're not comfortable with. It's maybe going to a marketing networking event. It's going to. I mean, there's so many like, um, diverse group events. All I could think was when you and I went to the hot sauce panel for the e-commerce group. Yeah. That was the most fun. And I was like, we do not do e-commerce and we definitely don't make hot sauce. We don't run a kitchen, but we had so many aha moments about marketing. Mm-hmm. While we were sitting in the panel session. It was so good. And everyone was so nice. creative mornings is a good one for a very diverse group of creatives. Well, I think Kaitlin brought up a really great point. I mean, talk about the thoughtfulness and care from a team of volunteers. To put on a very thoughtfully diverse group of 12, only 12 events per year in the art world. And the creative world is huge. It cannot be all designers all the time, sorry, designers. she said all different kind of artists come and talk about their work or demonstrate things to. Have some regular inspiration. Time is so valuable, especially when times are hard, like they are right now. People are emotionally and mentally exhausted and they're creatively stagnated, and instead of like only paying attention to what everyone else is doing on Instagram, why not get out in the community and go see how this person paints with light or, approaches. Movement in a different way. It will teach you something that you need to know about how you can stand out from your competition doing whatever it is that you do. Yeah, a hundred percent. What if it is not so weird, Megan? What if we're just really cutting edge? I like it. Or do you like being weird? I'm unattached. It is what it is. So some people think I am, other people don't. I like to think of it You're either collecting apocalypse skills or you're like a monk making like book of the kells and you're like trying to get as much information from as many different places to like build your library and then like beautifully illustrated, I think a lot of people just. Only like to read one section and I think you and I like to go like, let's look at the whole library and we're gonna get the reference books and we're gonna also get the romance book and we're gonna get the sci-fi book and the murder mystery book. And like we just kind of do the whole spectrum. I think that there is a sense of, Uncertainty and you have to kinda humble yourself when you're around art. Like you have to admit that you don't know everything. And I wonder if that is hard for our normal spreadsheet loving crowd of entrepreneurs. To go to a creative event. I guarantee that there are people there who need what the startup crowd is offering and startup crowd. How many times are they looking for a good designer or something? It's like, well, where do you think you're gonna find them? It's not gonna be at the giant startup happy hour where everyone's standing around crunchy in their Patagonia vest like, it's not gonna happen. Yeah, I think, I think it kind goes both ways. I think. I think people see art sometimes still as frivolous and so they shouldn't want to go to a talk about it because they are in the start of space. It is very tech, it is very forward. we have momentum, we have ideas, we are linear, we work like this. And then you see artists, and I think it's a little threatening. It's this, thing that you either can't admit that you want. Or you haven't paid attention to it in a long time. And I think it's really scary to be like, but these people are doing crazy things and they're loving it. But what would happen if I, like stepped a little bit, like things might go outta control. I have a hot take on this. Oh, okay. You can't do art without your emotion. oh, and if everything's about all money all the time and conversion rates. Mm-hmm. And your acquisition rates and your, you know, your valuation numbers. And of course there's emotions wrapped up in that. But it's different in art. Art exists because you have to feel something and you're forced to feel something. But you know, me, I've been dying on this hill 'cause. I work in media and I'm like, nobody's gonna pay attention to you if you cannot connect to your emotions and convey emotional gravity to your audience. That's why they tune in. Like people have been tuning into the awkward handshake. Yeah, they've been feeling something. They feel human again. They feel connected again and you know, they feel safe. Like it's okay for me to not know everything and try things and. to go to something like Creative Mornings and to go thank your host and to bring your, your cup so you can have your coffee. Yeah. And to not check your messages for an hour and watch somebody talk about creativity and explain it. I would bet somebody a really great lunch that you would solve some of the messaging problems and marketing problems off of something that seems absolutely, completely unrelated. Because you let your brain relax enough to have the creativity part of your brain connect the dots that it needs to connect. That no consultant can tell you. If you are the founder and you are still very deeply tied into the mission and the foundation of your company, that message has to come from you. It doesn't come from some third party, and if it does come from some third party and it happens to work for season, it's gonna expire very quickly as soon as that person walks away and you stop paying their contract and they're not there anymore. That's my hot take. That's a good one. I also had the thought that if you are just so against going to something that's not in your norm. That might be a therapy problem. Yes, you can contain multitudes. You can totally contain multitudes. I wish more of us did more often. I know the world is busy and it can be really hard when you have so many demands on. all the minutes in your day and it doesn't feel like you have time to be creative or it doesn't feel like you have time to go crunch the numbers, but if you don't eventually do both. I think that's where we see people burn out. Yeah. And as, as we have talked many times with many of the guests this season, the market is a little funky do right now. And you have to be more creative in how you approach your revenue flow. I've never left a creative morning not feeling inspired, and I do think that Kaitlin and her team of volunteers show you a side of Portland that makes you feel very proud to live here. That's it for today's episode of The Awkward Handshake. We record at Sasquatch Media Grounds in Vancouver, Washington. I'm Megan, co-founder of Fat Cap Design and creator of PDX Spellbound, and I'm Mary. Founder of Sasquatch Media Grounds and Sensible. Woo. You'll find links to everything we mentioned, guests, resources, and ways to connect with us in the show notes on your favorite podcast platform. That's also where you'll get updates on where we're headed next, and when we're inviting listeners like you to join us for guided networking in person and online. Don't be passive. Click the links. Pick better rooms. We'll see you there.