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From hand-lettering adventures, to tutorials, to snapshots into my daily life, the Jillian Kaye Art blog has a little bit of everything.

Chicago Planner Conference 2025

I just love Paper People. They appreciate the vellum accent, the weight of cardstock, and the delicacy of washi. They pick up my sticker and know just who to send it to, they purchase a pile of postcards because, who knows!, someone they know may need a mail pick-me-up.

I just spent all weekend with Planner People and many of them fit the aforementioned category. I have never met a more enthusiastic, generous, and kind group of paper lovers. The Chicago Planner Conference was such a delight to attend — both as a vendor AND a workshop teacher!

Several months ago, I was running my booth at the St. Louis Pen Show when an email came through from Kalli at CPC asking if I’d be interested in teaching about mail art at this year’s conference. Just a few minutes into a subsequent video chat and I was totally onboard; the leadership team described the excitement and passion this group of planners has for this conference and I knew I needed to see what it was all about.

Fast forward to this past weekend as I packed my car trunk with hundreds of postcards, stickers, and stationery kits for my Envelope Art Is For Everyone workshop, eager to participate in CPC 2025! My best friends Jackie and Kara agreed to come along to help me at my vendor booth and keep me company on this short trip to Chicago from Saint Louis. Their help, guidance, and encouragement is always dear to me, but especially for an event like this where I have approximately 150 things going through my mind at once and they help me see the forest through the trees.

Approximately 600 planners attend the conference and, seeing as it is in its sixth year, there are some devoted attendees who make it a point to come every year from every corner of the US (and even someone from Canada)! I talked to so many people who said this conference in particular is so well-formatted and beloved for its organization, small size, and locality. I wholeheartedly agree; as a vendor, I felt like my investment in the weekend was well-spent thanks to their intentional sharing of my work leading up to the weekend. As a workshop teacher, I was grateful for their openness to what I wanted to teach and all the accommodations they made me for to be there. And as an attendee, I feel like the conference absolutely lived up to the hype and exceeded any expectation I had of it.

I wouldn’t consider myself a Planner… more like a lowercase planner. I have faithfully kept a paper planner since I was in middle school and I consult it daily to see I’m staying on track with my work projects, pen pals, birthdays, and appointments. My go-to has been a basic Moleskine planner I pick up at Barnes and Noble each year. However, I also rely heavily on my Google calendar to keep me a functioning adult. If I do anything extra in my paper planner, I’ll occasionally washi tape an event ticket or post-vacation photo into its pages and feel like I have my life together. I had no IDEA of the limitless possibilities and creativity that go into people’s planners. These Planners (with a capital P) are on another level and, after this weekend, I feel like I can see their ranks on the horizon.


For those who are curious, I purchased a planner at the conference that I think will be the perfect fit! It’s several steps up from my regular Moleskine planner and more along the lines of a Hobonichi Techo.

Introducing, my new baby, the Aura Estelle 2026 Weekly Essential Magnet Planner.

It has lay-flat binding, gorgeous Tomoe River paper which will be perfect for gel pen and fountain pen writing and has a gridded weekly layout with way for space for my checklists, notes, and random jottings. I’m smitten. It’s in pre-order now so I will be waiting by my mailbox for it arrive.


Speaking of mailboxes, I had the privilege of leading 70 workshop attendees in Envelope Art Is For Everyone, my workshop about making mail art! Each participant completed two pieces of envelope art and I got to share a little bit about what I create.

What an absolutely delight to have 75 minutes to wax poetic about my love of snail mail and break down mail art into easy steps to show that anyone can create beautiful envelopes with just a little effort and imagination. I loved seeing everyone’s creations and individual creativity. Each envelope looked different and that delights me to no end! Thanks to a generous sponsorship from one of my favorite brands, Sakura of America, who provided hundreds of Gelly Rolls and Pigma Brush Pens for each table to experiment with and use to decorate their envelopes.

If anyone reading this attended my workshop, thank you so much for coming! There were so many great options to choose from for Saturday workshops and I’m honored you chose to come to mine.


Being a vendor was a flavor of fun all its own: I loved the conversations I had and so enjoyed meeting people from all over the country! I got to hear all about people’s dogs, their families, their favorite fountain pens, their memories, and so much more while sharing my artwork and connecting with those I never would have been able to meet had I not vended. My girls Kara and Jackie were the Queens of the Upsell and worked hard to make sure I came home with a lot less stationery than I arrived with, God bless ‘em.

I designed a Hello From Chicago soft-touch postcard just for CPC attendees which was included in all of Swag Bags. It was a hit! I so treasure the love this postcard got, and I hope many of them are currently traversing the postal system now. I have more available and I’ll get them up on my website and Etsy soon.

So many thanks to everyone who made a purchase at my booth during CPC 2025! My bags were heavier coming home… but only because of all the swag and gifts I received during the conference, not due to my inventory. ;)


I came back to Saint Louis with an absolute treasure trove of paper, pen, stationery, washi, ink, and gifts! I was seated at Table #12 for the General Session and its sponsor was kept a surprise. Imagine my absolute joy when I arrived at the table to see all the goodies from none other than Atlas Stationers! We visited their storefront Friday afternoon before the vendor hall opened; it was a breezy but enjoyable 30 minute walk from the conference. It just so happened to be Fountain Pen Day 2025 so the store was bustling and there were special activities, freebies, and deals; an absolutely ideal first visit to this store and definitely not my last. Their sponsorship of the table included a gorgeous fountain pen, bottle of ink, high-quality lined journal, sticker book, and several more amazing goodies at each seat.

In addition to everything given to us by Atlas Stationers, every single person at the table brought tablemate gifts! I was overwhelmed, it felt like Christmas morning. Each gift was thoughtful and so, so generous. Candy, washi tapes, journals, personal items like chapstick and Liquid I.V., keychains, customized items just for CPC 2025 and SO much more. I arrived back up in our room with both arms FULL of goodies and laid them out on the bed like a Halloween candy haul. I shared everything with my friends and they each went home with a generous stash of goods for their own crafting, journaling, and planning. We are all very grateful and very spoiled. I mean it, this group was generosity personified. Everyone felt so special and appreciated.


Another highlight from the conference was teaching a room full of Planner Buddies about portraiture! It was a speedy lesson on the very basics and everyone did their best to draw their buddy while I demonstrated. Activities before my tutorial at the Planner Buddy meet-up determined five pairs of Planner Buddy winners, who all won personal portraits of themselves and as a pair! I drew everyone digitally on my iPad and printed on-the-go with my Canon Selphy wireless printer. This allowed for the winners to add their drawings into their planners and junk journals right away! This was such a fun addition to my time there and everyone was so grateful to get their portraits. Such a solid group, I can’t say enough good things about the attitudes and spirits of the attendees. They were genuinely just so happy to be there and it was infectious.


If this sounded like an absolute blast (it was!) and you’re interested in going next year, keep an eye on CPC’s website and socials for the announcements about tickets going on sale. Tickets go fast and are highly-coveted, the waitlist was deep!

Many thanks to the team of leaders and volunteers who made a conference like this possible. There were so many moving parts to track and so many decisions to make on their part, I’m in awe of this endeavor and deeply honored to have been asked to be a part of it.