Episode 237 - Creating Your Own Community with Jessie Kwak
May 7, 2024
"What trips people up so often is the flip side of ego, which is just you thinking about yourself and worrying about what people are thinking about you, when really everyone's thinking about themselves and not about you." —Jessie Kwak
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Jessie Kwak discusses CREATING YOUR OWN COMMUNITY. Our conversation was triggered by the fact that Jessie recently hosted the first Author Alchemy Summit, and I wanted to find out what had made her decide to dive into this huge community-building undertaking. But even if organizing your own conference isn’t on your bucket list, the best practices she shares are generalizable to all sorts of other big projects that might be on your wish list: testing your commitment to a major undertaking, the importance of engaging a team of helpers, the challenge of delegation, battling imposter syndrome, gathering supporters and offering them opportunities (rather than asking for favors), achieving balance with the rest of your work, the importance of avoiding task-switching, and following the flow of your energy. I also think that hearing about what is involved in being a conference organizer can help us be better (and more empathetic) conference attendees, but Jessie also offers some great practical tips for us as attendees, including how to find the conferences that best meet our goals and networking for introverts.
If one of those topics piques your interest, you can easily jump to that section on YouTube by clicking on the flagged timestamps in the description.
If one of those topics piques your interest, you can easily jump to that section on YouTube by clicking on the flagged timestamps in the description.
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Jessie Kwak is an author and business book ghostwriter living in Portland, Oregon. When she’s not writing, she can be found sewing, mountain biking, or out exploring new worlds both at home and abroad. She is the author of a supernatural thriller, two series of space scoundrel sci-fi crime novels, and a handful of productivity books including From Chaos to Creativity and From Big Idea to Book.
Links
Jessie's Links:
https://www.jessiekwak.com/
https://www.instagram.com/kwakjessie/
https://bsky.app/profile/kwakjessie.bsky.social
https://www.youtube.com/channel/UC29MGqlb0BZ7eDOxcd0-ENA
Jessie's Previous Podcast Appearances:
Episode 132 - From Big Idea to Book with Jessie Kwak
Episode 179 - Is Freelance Copywriting for You? with Jessie Kwak
Companion Episodes:
Episode 155 - The Benefits (and Costs) of Membership with Roland Denzel
Inbetweenisode 116 - Creating Community, Content, and Creative Energy with Jeff Elkins
Episode 039 - Building a Writer Community with Connie Johnson Hambley
Matty's Links:
Affiliate links
Events
https://www.jessiekwak.com/
https://www.instagram.com/kwakjessie/
https://bsky.app/profile/kwakjessie.bsky.social
https://www.youtube.com/channel/UC29MGqlb0BZ7eDOxcd0-ENA
Jessie's Previous Podcast Appearances:
Episode 132 - From Big Idea to Book with Jessie Kwak
Episode 179 - Is Freelance Copywriting for You? with Jessie Kwak
Companion Episodes:
Episode 155 - The Benefits (and Costs) of Membership with Roland Denzel
Inbetweenisode 116 - Creating Community, Content, and Creative Energy with Jeff Elkins
Episode 039 - Building a Writer Community with Connie Johnson Hambley
Matty's Links:
Affiliate links
Events
I hope you enjoyed my conversation with Jessie! Are you thinking about organizing a conference of your own now? If not, which of her tips are you going to apply to another major undertaking you’re considering or are working on now?
Please post your comments on YouTube--and I'd love it if you would subscribe while you're there!
Are you getting value from the podcast? Consider supporting me on Patreon or through Buy Me a Coffee!
AI-generated Summary
The episode features a conversation between Matty Dalrymple, the host of The Indy Author Podcast, and Jessie Kwak, an author and conference organizer. Jessie discusses her experiences in organizing the Author Alchemy Summit, a conference focused on the business side of writing, particularly on connecting directly with readers. The summit was described as a small, intimate gathering in Portland, Oregon, designed to foster community and networking among writers.
Jessie's motivation for organizing her own conference stemmed from her dissatisfaction with existing events, which she found either too large and impersonal or too narrowly focused on craft rather than business. She aimed to fill this gap with a conference that balanced community, networking, and educational content, specifically tailored to authors interested in the business aspects of their career.
One key theme of the conversation is the importance of understanding your goals when selecting or creating a conference. Jessie emphasizes that knowing what you want to get out of a conference can guide you in choosing or organizing one that meets your needs. This clarity of purpose helps in creating a focused and valuable experience for attendees.
Jessie shares the challenges she faced in organizing the summit, including dealing with imposter syndrome, the difficulty of delegation, and the intricacies of marketing and logistics. She underscores the value of community support and feedback in refining her ideas and gaining the confidence to proceed. Jessie's narrative illustrates the iterative process of organizing a successful event, highlighting how each conversation and piece of feedback helped her to refine her vision and execution.
The discussion also touches on the practical aspects of conference organization, like the selection of speakers and sponsors. Jessie's approach to gathering speakers was rooted in her existing network, prioritizing individuals likely to contribute meaningfully to the conference theme. She candidly discusses her struggle with approaching sponsors, eventually realizing that she was offering valuable advertising opportunities rather than merely seeking financial support.
Balancing the demands of organizing the conference with her other professional responsibilities was another significant challenge. Jessie's strategy involved focused blocks of time dedicated to different tasks, which helped manage her workload and maintain productivity. This approach also helped her manage the psychological demands of switching between tasks and roles.
Networking for introverts is highlighted, with Jessie sharing strategies to create an environment conducive to natural, comfortable interactions. She stresses the importance of structured yet relaxed settings that encourage engagement among attendees.
In conclusion, the conversation encapsulates the multifaceted nature of organizing a conference, from conceptualization to execution. It reflects on the personal growth and community building inherent in such endeavors, offering insights and advice for others considering similar projects. Jessie’s experiences illustrate the complexities of creating an event that balances educational content with networking opportunities, all while managing the logistical and emotional challenges involved.
Jessie's motivation for organizing her own conference stemmed from her dissatisfaction with existing events, which she found either too large and impersonal or too narrowly focused on craft rather than business. She aimed to fill this gap with a conference that balanced community, networking, and educational content, specifically tailored to authors interested in the business aspects of their career.
One key theme of the conversation is the importance of understanding your goals when selecting or creating a conference. Jessie emphasizes that knowing what you want to get out of a conference can guide you in choosing or organizing one that meets your needs. This clarity of purpose helps in creating a focused and valuable experience for attendees.
Jessie shares the challenges she faced in organizing the summit, including dealing with imposter syndrome, the difficulty of delegation, and the intricacies of marketing and logistics. She underscores the value of community support and feedback in refining her ideas and gaining the confidence to proceed. Jessie's narrative illustrates the iterative process of organizing a successful event, highlighting how each conversation and piece of feedback helped her to refine her vision and execution.
The discussion also touches on the practical aspects of conference organization, like the selection of speakers and sponsors. Jessie's approach to gathering speakers was rooted in her existing network, prioritizing individuals likely to contribute meaningfully to the conference theme. She candidly discusses her struggle with approaching sponsors, eventually realizing that she was offering valuable advertising opportunities rather than merely seeking financial support.
Balancing the demands of organizing the conference with her other professional responsibilities was another significant challenge. Jessie's strategy involved focused blocks of time dedicated to different tasks, which helped manage her workload and maintain productivity. This approach also helped her manage the psychological demands of switching between tasks and roles.
Networking for introverts is highlighted, with Jessie sharing strategies to create an environment conducive to natural, comfortable interactions. She stresses the importance of structured yet relaxed settings that encourage engagement among attendees.
In conclusion, the conversation encapsulates the multifaceted nature of organizing a conference, from conceptualization to execution. It reflects on the personal growth and community building inherent in such endeavors, offering insights and advice for others considering similar projects. Jessie’s experiences illustrate the complexities of creating an event that balances educational content with networking opportunities, all while managing the logistical and emotional challenges involved.
Transcript
Matty: Hello, and welcome to The Indy Author Podcast. Today, my guest is Jessie Kwak. Hey Jessie, how are you doing?
Jessie: Hey, I'm doing great.
Matty: I am pleased to have you back and to give our listeners and viewers a little bit of background on you, Jessie Kwak is an author and business book ghostwriter living in Portland, Oregon. When she’s not writing, she can be found sewing, mountain biking, or out exploring new worlds both at home and abroad. She is the author of a supernatural thriller, two series of space scoundrel sci-fi crime novels, and a handful of productivity books including “From Chaos to Creativity” and “From Big Idea to Book.” In fact, Jessie was a guest back in episode 132, talking about "From Big Idea to Book." She has also been on episode 179, "Is Freelance Copywriting for You?"
And to that biography, we can now add Conference Organizer. That's what we're going to be talking about today. We're going to be talking about creating your own community. I had two reasons behind inviting Jessie here. One was that I think it would be interesting for conference attendees to see what goes into creating a conference. But I also think that this whole idea of taking that step to create your own community is really generalizable beyond the specifics of conferences. So we're going to be covering both those aspects, some that are more conference organizational specific, and some that are more generalizable to creating one's own community in general.
The background of Jessie's conference, the Author Alchemy Summit
Matty: So, Jessie, let's start with a description of the conference that you organized.
Jessie: Yeah, the Author Alchemy Summit was held here in Portland, Oregon about three weeks ago from when we're recording this. It was the end of February. It was a small, kind of intimate conference. There were about 60 people there, including speakers and staff. The focus was entirely on the business of writing, specifically on how to connect directly with your readers. I used that question as a focal point because we could have talked about anything from ads to newsletters to craft. I thought, if we have a single track of programming in a small community, we really need a focus. To me, connecting directly with your readers is a question that many authors are trying to figure out these days.
What made Jessie decide to organize a new conference?
Matty: What made you decide to start your own conference versus looking through the available suite of conferences for one you could attend as an attendee?
Jessie: Yeah, I attend a lot of conferences and I really enjoy it. I love the community, I love networking, and I've been to a lot of the bigger ones. I've been to 20 Books in Vegas, which is, of course, probably about the biggest conference you can get into as a writer. Then I've been to some very small ones, like local writing retreats or craft-focused critique group sorts of things. I didn't find a lot that was really in this middle ground, under a hundred people, really focused tightly on networking and community as well as having a high level of educational content. It's been very hard for me to find one that's so business focused.
A lot of conferences, at least in the Pacific Northwest, tend to be more focused on craft and writing, or they're very genre-oriented, like we have some great local sci-fi cons and horror cons. But as far as something that was of that size, focused on community and really on the business aspect, there just wasn't anything like that in the Pacific Northwest.
How can attendees find the conferences that best meet their goals?
Matty: This is a good opportunity to talk about how conference attendees can benefit from this conversation. When you were researching conferences, you were looking for what you just described and weren't finding it. When people are looking for conferences that are a good match for what they want, do you have any transferable advice?
Jessie: Knowing what your goal is the first step. Are you looking to pitch to agents? You won't find that at an indie conference; you'll want to look for a more traditionally focused conference. Are you looking for a wide variety of topics? You won't find that at a small conference, but you might not find as much networking opportunity at a bigger conference as you would at a smaller one. So, know your goals, and then talk to people who have attended in the past. That's a great way to get an idea of whether a conference is for you, whether it's going to be valuable for your genre or career path, whether you're indie or traditional.
What is the vibe like? Some conferences have been around for a while and can be a little hard to break into as a new person. Everyone already knows each other, and it's hard to know who to talk to. Talking to past attendees can be really valuable to get a sense of the vibe.
Testing your commitment to a big undertaking
Matty: Let's talk through the logistics of setting this up. Describe how you went from not finding what you needed to deciding to put on a show.
Jessie: I tapped into my network and started asking anyone I knew who had conference organizing experience to talk me through the steps and try to talk me out of it. I wanted to be talked out of it. I'd say, "Let me tell you my idea, and please poke as many holes as you can in it." I hoped to leave these conversations relieved that I didn't have to organize a conference and could just keep writing my books. But with every conversation, I kept clarifying my idea and thinking, "No, this sounds great; this sounds doable, actually."
And in the end, after talking to enough people, I decided to put down a payment on this event space. Once I did that, I was committed.
Matty: Yeah, I think that's obviously generalizable advice. Anytime you're considering a big leap that's going to require a lot of time, money, effort, or any significant resource, it's a good idea to go to knowledgeable people and ask them to talk you out of it. Going in with the mindset to be persuaded not to do it can be revealing. For certain personalities, the first reason not to proceed might deter them. But this process can really solidify your commitment if you decide to go ahead.
So, what was it like to take that step where you were completely committed?
Jessie: Oh, it was scary. The hardest part was just getting to the point where I was ready to sign the contract. I had to be mindful of potential pitfalls in the contract. Fortunately, I had a local friend who organizes a more traditional writers conference, and I asked them to review the hotel contract to ensure there were no hidden clauses. That was incredibly valuable and confidence-building. But once I paid the deposit, I felt like I had to learn how to market a conference. So, it was very much a process of building the conference as I went along.
Engaging a team of helpers
Matty: And obviously, you weren't doing this on your own. You've mentioned tapping into experts. Did it boil down to you being the sole organizer and consulting experts, or did you assemble a more active team of helpers?
Jessie: Essentially, I was the sole organizer seeking expertise. My husband contributed quite a bit, especially toward the end. He was also my sounding board throughout the process, but he acted as the logistic coordinator during the event, which allowed me to focus on networking, moderating panels, and taking care of the speakers. If someone had a question about the schedule, Rob was there to handle it, which was great.
Another person I brought onto my team was my next-door neighbor, Lydia, who managed the catering for us. She's very organized and considerate, paying attention to details like allergies and dietary restrictions. When I asked her to be the catering director, she accepted, and a few days later, she came over with spreadsheets and a Pinterest board full of ideas for food presentation. I knew then that I had chosen the right person.
The challenge of delegation
Matty: It seems like you lucked into two good helpers there. Did delegating that kind of work come naturally to you, or was it something you struggled with?
Jessie: Delegating is really hard for me, especially in this case because I often didn't know what I needed. People would ask, "What can I help you with?" and I didn't know what to tell them since I was figuring things out as I went. For the second event in 2025, it'll be easier to delegate because I now understand the tasks involved in each project. But the first time around, it was very difficult to delegate when I was still feeling my way through the process.
Matty: There are analogies here for a writer getting ready to publish a book; they have to understand book cover design or the editorial world. You've got to get your feet wet to fully understand what's involved and what you can and cannot comfortably delegate.
Jessie: Exactly, once you've played around with something for a bit, you can decide what you no longer need to do yourself, like updating a website, and can hire a virtual assistant. But until you've done it once, you don't know how to explain it to someone else. Once you do, and you find yourself repeating the task, that's the time to delegate.
Battling imposter syndrome
Matty: Were there any parts in the planning process that were more or less difficult than you expected?
Jessie: Setting up the schedule was emotionally fraught for me. I had a great lineup of speakers, but deciding on the panels and schedule was tough. I suffered from imposter syndrome, questioning my authority to make these decisions. I mentioned this to my husband, and he reminded me that as the conference organizer, I am indeed the one to make these decisions. That helped, but it still took me a while to finalize the schedule because I was caught up in my own doubts for some time.
Matty: Yeah, I can imagine for any of these big endeavors, like organizing a conference, it would be helpful for people to rehearse ahead of time. For instance, "I'm going to be talking to this big-name author, and then I will have to tell them, ask them, or insist on something." Do I feel comfortable about that? Both intellectually comfortable — I guess I am the organizer — and also psychically comfortable, just like what you were saying.
Jessie: Yeah, I read something the other day in a newsletter from a copywriter whose newsletter I subscribe to. He was talking about how ego can really get in your way of putting yourself out there. Normally, we think of ego in terms of, "I think I'm so great," which is more of the hubris side of ego. But he said what often trips people up is the flip side of ego, which is you thinking about yourself and worrying about what people think of you, when really everyone is thinking about themselves and not about you. So when you're going to a conference, many people worry, "What will I say if somebody asks me this?" or "What will people think about this?" Honestly, nobody's really thinking that much about you. I was so tripped up on my own ego, worrying about what people would think of my decisions when, in reality, people were just excited about the conference. They weren't concerned about the specifics of my decision-making.
Matty: Where does she get off?
Jessie: Yeah.
Gathering speakers
Matty: I was also curious about how you ended up with the speakers. In other situations, there might be two ways of going about it. One is "I've developed this network of people who know a lot about X, and I'd love to get them together to do a conference about X." The other is "I want to do a conference about X, and now I'm looking among my network of people to see who could contribute to that." Does one of those sound more like what you did for your conference?
Jessie: My approach was definitely more the first one. I looked at my network and thought about who I could ask that would probably say yes or at least entertain the idea. So, I started with whom I knew, compiled those people, and then built the conference around them. One thing I will do differently next year is think more about the schedule and the topics I want to cover and then find the people to fill those roles. Now that I've established this event, I can point to it and say, "Here, I did this thing, here are some rave reviews. Would you like to come?" Some people have reached out, saying, "Oh, I'd love to be invited next year," which is a really great place to be in. But yes, I definitely started with who I knew that might say yes.
Matty: And did you have to adjust your ego in order to approach those people you wanted to involve?
Jessie: Oh my gosh, yes. That was one of the scariest parts — that and emailing sponsors to ask about sponsorships. I would put off those emails for hours, even days. I'd be in cold sweats just thinking about emailing someone to invite them to my conference. Again, like you said, that was my ego getting in the way, making me worry about what they would think of the invitation.
And my husband's in sales, so he was just like, "People get these kinds of requests a lot. They move on and don't think about you again. They're not upset with you." He was like, "Why are you so worried about asking sponsors for money? That's what they do."
Matty: Did you have to take a different approach between organizations you were requesting sponsorships from and speakers you were expressing interest in as speakers?
Offering opportunities (not asking for favors)
Jessie: Definitely, I think the sponsorship was harder for me because it was straight-up asking for money. I'm thinking, "Who am I, what am I offering you?" But with the speakers, I felt a bit more like I was inviting them to an opportunity, and we were all going to get something out of it. I had to adjust my mindset with sponsors as well because I wasn't asking for a handout; I was selling advertising. Once I reframed it as selling advertising instead of asking for money, it felt very different, and that's what helped me get over that hurdle.
Matty: Yeah, that's clearly very generalizable. I know promotional work isn't super comfortable for anyone, but if you think of it as getting what you have to offer in front of people who could benefit from it, it not only makes it easier to see the value on both sides but also helps you identify your target audience. If you're mentally preparing a pitch and can't clearly define the benefit to them, then maybe you're not pitching to the right group. The same goes for presenting your book to an audience; if it feels like a mismatch, then it might actually be one.
Jessie: Right, whether it's a partnership or a book sale, it should be about the benefit to your audience, not asking for favors. People get hung up because they feel like they're asking for favors when they're not. You're a business owner providing a service. That service is entertaining and educational books. If your message isn't resonating with your audience, there's a mismatch. It's not about begging more; it's about selling. It's a mindset shift.
Achieving balance with a huge project
Matty: One thing people can empathize with is what happens when you take on a huge project and you don't have 20 spare hours a week. You're having to balance this with everything else on your plate. How did you do that, especially since you have a ghostwriting, copywriting business, and you're doing work for yourself and others?
Jessie: Yeah, that was tough to balance. I definitely didn't get as much writing done last year as I wanted to, which... Yeah. So, that was something I had to ask myself from time to time, especially when I had an injury last year and had a rough patch. I knew going back to things, I only had room for one project. Was it organizing this conference? People would understand if I called it off. Or was it writing the next book in my series? The value of bringing all these people together and doing something for the community, which supported me during that rough patch, won out over finishing the book. So, I didn't do it all. It's been a year since I finished my last book, and I'm still on act two of my current one. It's about setting priorities and figuring out what is the most important draw for you and why it is so valuable.
Avoid task-switching
Jessie: But in terms of actual productivity and balance, I tried to focus. I'd be like, "Okay, today is a conference day. Tomorrow, I'll work on this one client project." I work better when I'm not bouncing around and instead focusing on one project at a time. So, with the conference, I'd segment it out by days, as much as I could. For example, I only took meetings on Tuesdays and worked on my fiction on Fridays, setting myself that schedule.
Matty: I'm definitely a proponent of avoiding task-switching as much as possible. Looking back at my corporate life, I realize how inefficient it is to switch tasks every 15 minutes. Once I started working for myself and could segment my time as I wanted, I became much more efficient. Now, I'm always experimenting with the perfect duration for chunks of time. Is it an hour? Half a day? A whole day? A week? I'm currently juggling a nonfiction book I didn't plan to have take up all my time, but I got into a situation where the words were coming easily. Every morning, I would get my tea and think, "Do I go back to my fiction book, which I'm excited about, or do I continue with this nonfiction because it's flowing easily?" Those decisions about how to allocate and then chunk out time are crucial. As you said, today might be just for conference stuff, but tomorrow will be for fiction writing.
Jessie: Yeah, to your point about following the flow of your energy, that's one of the most productive things you can do, especially if you have control over your schedule and don't have to switch tasks abruptly. While I set myself schedules, aside from only taking meetings one or two days a week, I keep things flexible. If I wake up brimming with ideas for essays for my newsletter, I prioritize writing them. It's most efficient to let the words out when they're eager to come. Following the energy flow is key, but it's also important to balance that. Sometimes I might neglect emails while riding that energy wave, so I have to remind myself to dedicate time to clearing my inbox.
Networking for introverts
Matty: Another thing I know you planned carefully for your conference was emphasizing community building for a group that included many introverts. How did you make the environment comfortable for them?
Jessie: Networking for introverts is a topic I'm often asked about. I'm an introvert but have trained myself to network effectively. I understand it can be daunting for people who are new to networking or introverted. At the conference, I wanted to foster an environment where conversations could spark naturally. We had a happy hour before the conference where people could socialize and pick up their packets. I had a few outgoing individuals tasked with engaging anyone who was alone, and I did a lot of that myself. My husband and Lydia handled logistics, so I could focus on mingling and introducing attendees to each other, facilitating connections based on common interests.
For meals, I know how isolating it can be to look for someone to lunch with at a conference. To avoid this, we catered breakfast and lunch right in the event space.
Jessie: People could show up early, grab a bagel or yogurt, and often they'd sit in the same place at the table, getting a chance to talk with their tablemates or meet someone new. After the breakout sessions before lunch, discussions could continue over food, which was ready to go. This eliminated the need for attendees to figure out where to go for lunch or deal with reservations. Making meals convenient and in the event space was critical.
Matty: There are two lessons here beyond conferences. One is finding helpers to manage logistics, allowing you to focus on strategic aspects like introductions and pairing people up. This is similar to indie authors delegating tasks like book cover design to professionals so they can focus on their strengths. The second lesson is the importance of experience. Just as you have to read a lot of books to write one, attending many conferences gives you insights into organizing your own. If you hadn't had those experiences as an attendee, you wouldn't know what to consider for your conference.
Jessie: Right. When I started organizing, I asked everyone I knew who had organized a conference. I quizzed people about their conference experiences and sent out surveys. When someone joined the marketing list for the conference, they received a survey about their preferences and experiences at other conferences. I continually sought other people's experiences. As writers, especially in fiction, we provide readers with new experiences and perspectives. Similarly, if you're unfamiliar with something, like finding an editor or writing a certain character, there are many resources available. You can tap into your network, email experts, or follow them for insights. There are ways to learn how to do something if you listen and seek out information.
Matty: I wanted to circle back to the idea of community. You went into this with a robust community, as evidenced by your ability to tap into them for speakers and attendees, and now you probably have an even bigger network. Do you have any tips for capitalizing on that expanded community for your own benefit and for the benefit of the new people in your community? Maybe it's paving the way for the next conference or helping out in other ways. Are there tips you can share about how to keep those relationships vital after an event?
Jessie: One of the things people often don't do after an event is follow up with the people they met. You might exchange business cards or emails, but many don't send that follow-up email. I often tell people at conferences, if you ever have questions or want to chat, I'm happy to Zoom with you, and very few actually take me up on that offer. We tend to get home from an event and think everyone is busy or they were just being polite. My advice for expanding your community after an event is to actually follow up. Take people at their word. If they say they’d love to meet for coffee or answer questions via email, take advantage of it. Email them.
Matty: That’s great advice. You and I, along with some other attendees of 20 Books, have kept in touch, which has been very valuable to me for a number of reasons. So, I'm a big fan of that. Jessie, thank you so much for sharing all those perspectives. Please let the listeners and viewers know where they can find out more about you, your upcoming conference, and everything else you do online.
Jessie: Thank you so much, this has been a great conversation. You can find more about me at jessiekwak.com. That's J-E-S-S-I-E-K-W-A-K.com. That will have links to the Author Alchemy Summit website. The dates for next year are now set: February 14th through 16th, 2025.
Matty: Great, thank you so much.
Jessie: Thank you. Appreciate it.
Jessie: Hey, I'm doing great.
Matty: I am pleased to have you back and to give our listeners and viewers a little bit of background on you, Jessie Kwak is an author and business book ghostwriter living in Portland, Oregon. When she’s not writing, she can be found sewing, mountain biking, or out exploring new worlds both at home and abroad. She is the author of a supernatural thriller, two series of space scoundrel sci-fi crime novels, and a handful of productivity books including “From Chaos to Creativity” and “From Big Idea to Book.” In fact, Jessie was a guest back in episode 132, talking about "From Big Idea to Book." She has also been on episode 179, "Is Freelance Copywriting for You?"
And to that biography, we can now add Conference Organizer. That's what we're going to be talking about today. We're going to be talking about creating your own community. I had two reasons behind inviting Jessie here. One was that I think it would be interesting for conference attendees to see what goes into creating a conference. But I also think that this whole idea of taking that step to create your own community is really generalizable beyond the specifics of conferences. So we're going to be covering both those aspects, some that are more conference organizational specific, and some that are more generalizable to creating one's own community in general.
The background of Jessie's conference, the Author Alchemy Summit
Matty: So, Jessie, let's start with a description of the conference that you organized.
Jessie: Yeah, the Author Alchemy Summit was held here in Portland, Oregon about three weeks ago from when we're recording this. It was the end of February. It was a small, kind of intimate conference. There were about 60 people there, including speakers and staff. The focus was entirely on the business of writing, specifically on how to connect directly with your readers. I used that question as a focal point because we could have talked about anything from ads to newsletters to craft. I thought, if we have a single track of programming in a small community, we really need a focus. To me, connecting directly with your readers is a question that many authors are trying to figure out these days.
What made Jessie decide to organize a new conference?
Matty: What made you decide to start your own conference versus looking through the available suite of conferences for one you could attend as an attendee?
Jessie: Yeah, I attend a lot of conferences and I really enjoy it. I love the community, I love networking, and I've been to a lot of the bigger ones. I've been to 20 Books in Vegas, which is, of course, probably about the biggest conference you can get into as a writer. Then I've been to some very small ones, like local writing retreats or craft-focused critique group sorts of things. I didn't find a lot that was really in this middle ground, under a hundred people, really focused tightly on networking and community as well as having a high level of educational content. It's been very hard for me to find one that's so business focused.
A lot of conferences, at least in the Pacific Northwest, tend to be more focused on craft and writing, or they're very genre-oriented, like we have some great local sci-fi cons and horror cons. But as far as something that was of that size, focused on community and really on the business aspect, there just wasn't anything like that in the Pacific Northwest.
How can attendees find the conferences that best meet their goals?
Matty: This is a good opportunity to talk about how conference attendees can benefit from this conversation. When you were researching conferences, you were looking for what you just described and weren't finding it. When people are looking for conferences that are a good match for what they want, do you have any transferable advice?
Jessie: Knowing what your goal is the first step. Are you looking to pitch to agents? You won't find that at an indie conference; you'll want to look for a more traditionally focused conference. Are you looking for a wide variety of topics? You won't find that at a small conference, but you might not find as much networking opportunity at a bigger conference as you would at a smaller one. So, know your goals, and then talk to people who have attended in the past. That's a great way to get an idea of whether a conference is for you, whether it's going to be valuable for your genre or career path, whether you're indie or traditional.
What is the vibe like? Some conferences have been around for a while and can be a little hard to break into as a new person. Everyone already knows each other, and it's hard to know who to talk to. Talking to past attendees can be really valuable to get a sense of the vibe.
Testing your commitment to a big undertaking
Matty: Let's talk through the logistics of setting this up. Describe how you went from not finding what you needed to deciding to put on a show.
Jessie: I tapped into my network and started asking anyone I knew who had conference organizing experience to talk me through the steps and try to talk me out of it. I wanted to be talked out of it. I'd say, "Let me tell you my idea, and please poke as many holes as you can in it." I hoped to leave these conversations relieved that I didn't have to organize a conference and could just keep writing my books. But with every conversation, I kept clarifying my idea and thinking, "No, this sounds great; this sounds doable, actually."
And in the end, after talking to enough people, I decided to put down a payment on this event space. Once I did that, I was committed.
Matty: Yeah, I think that's obviously generalizable advice. Anytime you're considering a big leap that's going to require a lot of time, money, effort, or any significant resource, it's a good idea to go to knowledgeable people and ask them to talk you out of it. Going in with the mindset to be persuaded not to do it can be revealing. For certain personalities, the first reason not to proceed might deter them. But this process can really solidify your commitment if you decide to go ahead.
So, what was it like to take that step where you were completely committed?
Jessie: Oh, it was scary. The hardest part was just getting to the point where I was ready to sign the contract. I had to be mindful of potential pitfalls in the contract. Fortunately, I had a local friend who organizes a more traditional writers conference, and I asked them to review the hotel contract to ensure there were no hidden clauses. That was incredibly valuable and confidence-building. But once I paid the deposit, I felt like I had to learn how to market a conference. So, it was very much a process of building the conference as I went along.
Engaging a team of helpers
Matty: And obviously, you weren't doing this on your own. You've mentioned tapping into experts. Did it boil down to you being the sole organizer and consulting experts, or did you assemble a more active team of helpers?
Jessie: Essentially, I was the sole organizer seeking expertise. My husband contributed quite a bit, especially toward the end. He was also my sounding board throughout the process, but he acted as the logistic coordinator during the event, which allowed me to focus on networking, moderating panels, and taking care of the speakers. If someone had a question about the schedule, Rob was there to handle it, which was great.
Another person I brought onto my team was my next-door neighbor, Lydia, who managed the catering for us. She's very organized and considerate, paying attention to details like allergies and dietary restrictions. When I asked her to be the catering director, she accepted, and a few days later, she came over with spreadsheets and a Pinterest board full of ideas for food presentation. I knew then that I had chosen the right person.
The challenge of delegation
Matty: It seems like you lucked into two good helpers there. Did delegating that kind of work come naturally to you, or was it something you struggled with?
Jessie: Delegating is really hard for me, especially in this case because I often didn't know what I needed. People would ask, "What can I help you with?" and I didn't know what to tell them since I was figuring things out as I went. For the second event in 2025, it'll be easier to delegate because I now understand the tasks involved in each project. But the first time around, it was very difficult to delegate when I was still feeling my way through the process.
Matty: There are analogies here for a writer getting ready to publish a book; they have to understand book cover design or the editorial world. You've got to get your feet wet to fully understand what's involved and what you can and cannot comfortably delegate.
Jessie: Exactly, once you've played around with something for a bit, you can decide what you no longer need to do yourself, like updating a website, and can hire a virtual assistant. But until you've done it once, you don't know how to explain it to someone else. Once you do, and you find yourself repeating the task, that's the time to delegate.
Battling imposter syndrome
Matty: Were there any parts in the planning process that were more or less difficult than you expected?
Jessie: Setting up the schedule was emotionally fraught for me. I had a great lineup of speakers, but deciding on the panels and schedule was tough. I suffered from imposter syndrome, questioning my authority to make these decisions. I mentioned this to my husband, and he reminded me that as the conference organizer, I am indeed the one to make these decisions. That helped, but it still took me a while to finalize the schedule because I was caught up in my own doubts for some time.
Matty: Yeah, I can imagine for any of these big endeavors, like organizing a conference, it would be helpful for people to rehearse ahead of time. For instance, "I'm going to be talking to this big-name author, and then I will have to tell them, ask them, or insist on something." Do I feel comfortable about that? Both intellectually comfortable — I guess I am the organizer — and also psychically comfortable, just like what you were saying.
Jessie: Yeah, I read something the other day in a newsletter from a copywriter whose newsletter I subscribe to. He was talking about how ego can really get in your way of putting yourself out there. Normally, we think of ego in terms of, "I think I'm so great," which is more of the hubris side of ego. But he said what often trips people up is the flip side of ego, which is you thinking about yourself and worrying about what people think of you, when really everyone is thinking about themselves and not about you. So when you're going to a conference, many people worry, "What will I say if somebody asks me this?" or "What will people think about this?" Honestly, nobody's really thinking that much about you. I was so tripped up on my own ego, worrying about what people would think of my decisions when, in reality, people were just excited about the conference. They weren't concerned about the specifics of my decision-making.
Matty: Where does she get off?
Jessie: Yeah.
Gathering speakers
Matty: I was also curious about how you ended up with the speakers. In other situations, there might be two ways of going about it. One is "I've developed this network of people who know a lot about X, and I'd love to get them together to do a conference about X." The other is "I want to do a conference about X, and now I'm looking among my network of people to see who could contribute to that." Does one of those sound more like what you did for your conference?
Jessie: My approach was definitely more the first one. I looked at my network and thought about who I could ask that would probably say yes or at least entertain the idea. So, I started with whom I knew, compiled those people, and then built the conference around them. One thing I will do differently next year is think more about the schedule and the topics I want to cover and then find the people to fill those roles. Now that I've established this event, I can point to it and say, "Here, I did this thing, here are some rave reviews. Would you like to come?" Some people have reached out, saying, "Oh, I'd love to be invited next year," which is a really great place to be in. But yes, I definitely started with who I knew that might say yes.
Matty: And did you have to adjust your ego in order to approach those people you wanted to involve?
Jessie: Oh my gosh, yes. That was one of the scariest parts — that and emailing sponsors to ask about sponsorships. I would put off those emails for hours, even days. I'd be in cold sweats just thinking about emailing someone to invite them to my conference. Again, like you said, that was my ego getting in the way, making me worry about what they would think of the invitation.
And my husband's in sales, so he was just like, "People get these kinds of requests a lot. They move on and don't think about you again. They're not upset with you." He was like, "Why are you so worried about asking sponsors for money? That's what they do."
Matty: Did you have to take a different approach between organizations you were requesting sponsorships from and speakers you were expressing interest in as speakers?
Offering opportunities (not asking for favors)
Jessie: Definitely, I think the sponsorship was harder for me because it was straight-up asking for money. I'm thinking, "Who am I, what am I offering you?" But with the speakers, I felt a bit more like I was inviting them to an opportunity, and we were all going to get something out of it. I had to adjust my mindset with sponsors as well because I wasn't asking for a handout; I was selling advertising. Once I reframed it as selling advertising instead of asking for money, it felt very different, and that's what helped me get over that hurdle.
Matty: Yeah, that's clearly very generalizable. I know promotional work isn't super comfortable for anyone, but if you think of it as getting what you have to offer in front of people who could benefit from it, it not only makes it easier to see the value on both sides but also helps you identify your target audience. If you're mentally preparing a pitch and can't clearly define the benefit to them, then maybe you're not pitching to the right group. The same goes for presenting your book to an audience; if it feels like a mismatch, then it might actually be one.
Jessie: Right, whether it's a partnership or a book sale, it should be about the benefit to your audience, not asking for favors. People get hung up because they feel like they're asking for favors when they're not. You're a business owner providing a service. That service is entertaining and educational books. If your message isn't resonating with your audience, there's a mismatch. It's not about begging more; it's about selling. It's a mindset shift.
Achieving balance with a huge project
Matty: One thing people can empathize with is what happens when you take on a huge project and you don't have 20 spare hours a week. You're having to balance this with everything else on your plate. How did you do that, especially since you have a ghostwriting, copywriting business, and you're doing work for yourself and others?
Jessie: Yeah, that was tough to balance. I definitely didn't get as much writing done last year as I wanted to, which... Yeah. So, that was something I had to ask myself from time to time, especially when I had an injury last year and had a rough patch. I knew going back to things, I only had room for one project. Was it organizing this conference? People would understand if I called it off. Or was it writing the next book in my series? The value of bringing all these people together and doing something for the community, which supported me during that rough patch, won out over finishing the book. So, I didn't do it all. It's been a year since I finished my last book, and I'm still on act two of my current one. It's about setting priorities and figuring out what is the most important draw for you and why it is so valuable.
Avoid task-switching
Jessie: But in terms of actual productivity and balance, I tried to focus. I'd be like, "Okay, today is a conference day. Tomorrow, I'll work on this one client project." I work better when I'm not bouncing around and instead focusing on one project at a time. So, with the conference, I'd segment it out by days, as much as I could. For example, I only took meetings on Tuesdays and worked on my fiction on Fridays, setting myself that schedule.
Matty: I'm definitely a proponent of avoiding task-switching as much as possible. Looking back at my corporate life, I realize how inefficient it is to switch tasks every 15 minutes. Once I started working for myself and could segment my time as I wanted, I became much more efficient. Now, I'm always experimenting with the perfect duration for chunks of time. Is it an hour? Half a day? A whole day? A week? I'm currently juggling a nonfiction book I didn't plan to have take up all my time, but I got into a situation where the words were coming easily. Every morning, I would get my tea and think, "Do I go back to my fiction book, which I'm excited about, or do I continue with this nonfiction because it's flowing easily?" Those decisions about how to allocate and then chunk out time are crucial. As you said, today might be just for conference stuff, but tomorrow will be for fiction writing.
Jessie: Yeah, to your point about following the flow of your energy, that's one of the most productive things you can do, especially if you have control over your schedule and don't have to switch tasks abruptly. While I set myself schedules, aside from only taking meetings one or two days a week, I keep things flexible. If I wake up brimming with ideas for essays for my newsletter, I prioritize writing them. It's most efficient to let the words out when they're eager to come. Following the energy flow is key, but it's also important to balance that. Sometimes I might neglect emails while riding that energy wave, so I have to remind myself to dedicate time to clearing my inbox.
Networking for introverts
Matty: Another thing I know you planned carefully for your conference was emphasizing community building for a group that included many introverts. How did you make the environment comfortable for them?
Jessie: Networking for introverts is a topic I'm often asked about. I'm an introvert but have trained myself to network effectively. I understand it can be daunting for people who are new to networking or introverted. At the conference, I wanted to foster an environment where conversations could spark naturally. We had a happy hour before the conference where people could socialize and pick up their packets. I had a few outgoing individuals tasked with engaging anyone who was alone, and I did a lot of that myself. My husband and Lydia handled logistics, so I could focus on mingling and introducing attendees to each other, facilitating connections based on common interests.
For meals, I know how isolating it can be to look for someone to lunch with at a conference. To avoid this, we catered breakfast and lunch right in the event space.
Jessie: People could show up early, grab a bagel or yogurt, and often they'd sit in the same place at the table, getting a chance to talk with their tablemates or meet someone new. After the breakout sessions before lunch, discussions could continue over food, which was ready to go. This eliminated the need for attendees to figure out where to go for lunch or deal with reservations. Making meals convenient and in the event space was critical.
Matty: There are two lessons here beyond conferences. One is finding helpers to manage logistics, allowing you to focus on strategic aspects like introductions and pairing people up. This is similar to indie authors delegating tasks like book cover design to professionals so they can focus on their strengths. The second lesson is the importance of experience. Just as you have to read a lot of books to write one, attending many conferences gives you insights into organizing your own. If you hadn't had those experiences as an attendee, you wouldn't know what to consider for your conference.
Jessie: Right. When I started organizing, I asked everyone I knew who had organized a conference. I quizzed people about their conference experiences and sent out surveys. When someone joined the marketing list for the conference, they received a survey about their preferences and experiences at other conferences. I continually sought other people's experiences. As writers, especially in fiction, we provide readers with new experiences and perspectives. Similarly, if you're unfamiliar with something, like finding an editor or writing a certain character, there are many resources available. You can tap into your network, email experts, or follow them for insights. There are ways to learn how to do something if you listen and seek out information.
Matty: I wanted to circle back to the idea of community. You went into this with a robust community, as evidenced by your ability to tap into them for speakers and attendees, and now you probably have an even bigger network. Do you have any tips for capitalizing on that expanded community for your own benefit and for the benefit of the new people in your community? Maybe it's paving the way for the next conference or helping out in other ways. Are there tips you can share about how to keep those relationships vital after an event?
Jessie: One of the things people often don't do after an event is follow up with the people they met. You might exchange business cards or emails, but many don't send that follow-up email. I often tell people at conferences, if you ever have questions or want to chat, I'm happy to Zoom with you, and very few actually take me up on that offer. We tend to get home from an event and think everyone is busy or they were just being polite. My advice for expanding your community after an event is to actually follow up. Take people at their word. If they say they’d love to meet for coffee or answer questions via email, take advantage of it. Email them.
Matty: That’s great advice. You and I, along with some other attendees of 20 Books, have kept in touch, which has been very valuable to me for a number of reasons. So, I'm a big fan of that. Jessie, thank you so much for sharing all those perspectives. Please let the listeners and viewers know where they can find out more about you, your upcoming conference, and everything else you do online.
Jessie: Thank you so much, this has been a great conversation. You can find more about me at jessiekwak.com. That's J-E-S-S-I-E-K-W-A-K.com. That will have links to the Author Alchemy Summit website. The dates for next year are now set: February 14th through 16th, 2025.
Matty: Great, thank you so much.
Jessie: Thank you. Appreciate it.