Recap & Highlights: Chicago Planner Conference 2019

Friends. I have just come back from an incredible weekend and it has inspired me to write about it. This was the second annual Chicago Planner Conference and I was overjoyed to be asked back as a facilitator and teacher. Last year was my first planner conference EVER and I cannot recommend the experience enough.

Wait, what is a planner conference?

I had no idea these existed but a planner conference is a weekend of hundreds of planner friends who come together to share their love for all things planners, paper, pens, markers, crafty things. There are sessions that explore different art techniques, aspects of planning and time management, make and take crafts, panels featuring your favorite planner pals talking shops and hustles. And of course, a TON OF SWAG. Complete with freaking Planner Fairies (read: volunteers) making it rain TN’s, washi, and stickers.

These conferences are HUGE events that the leadership team planned for as long as it takes babies to grow, and the blood sweat and tears of all the vendors, speakers, volunteers, and sponsors. And they are VERY “people-y” as Amber Kemp said. There are a couple throughout the country that vary in intensity and size, such as Planners Go Wild, Sugary Gal Shop NYC Planner Conference, PlannerCon, etc.

SO, without further ado, here is what my experience was like this year!

Recap: Chicago Planner Conference 2019

I was so grateful to get out of the snowy tundra of Minnesota and head over to Chicago. It was a HELLISH week leading up to it but I was finally on the plane. I go to these events with just me, and I really like having the time to choose whatever I want to do outside of the conference schedule.

And apparently all I wanted to do was SHOP because I definitely made a dent in my wallet getting TN’s from Pegatina Plans and catching up with friends like Amanda (@themomlifeplanner) and perusing new Baron Fig notebooks at For Good Cause. Everyone was setting up but it was amazing to reconnect with friends. Last year I felt very out of place, by myself – and this year it just felt easier knowing a few more people.

That evening I got to meet other sponsors and speakers, and I absolutely hit it off with Felicia from Gold Mine & Coco, Ashley from Cloth & Paper, and Audrey of Things Unseen Designs. Getting to hear about their hustles and stories was inspiring since it’s more of their work but what REALLY got me was when we could bypass the polite bullshit and talk about real deal things like realities of children or the insanity of Fyre Festival and Abducted in Plain Sight. That’s what I LOVE about these things is connecting with genuine and kick ass people.

Pictured: Me and Mommy Lhey, Felicia, and Debbie

One of my personal traditions is to go to a musical during the conference weekend. Last CPC I went to Hamilton (!!!!!! I was not throwing away my shot), during SGS NYC Planner Conference, I went to see an old friend in Wicked, and this year I HAD to go see Dear Evan Hansen. As I suspected, I cried basically all of the second act.

Once I got home, I had to finalize my slides and agenda for my workshop. I KNOW – am I even a Planner????? Here’s the thing. Since I teach and train for a living, I’ve gotten used to finalizing agendas last minute when inspiration strikes lol. I swear I’m not (that) lazy.

The energy of the opening is honestly unreal. Everyone gets to sit at a table of 10-12 that’s sponsored by a shop or company, filled with goodies for each person. PLUS, people at your table might also give you table gifts in addition (it totally ranges from candy to mugs to stickers to pens- just as a “nice to meet you” treat). We got to listen to the stories and lessons of SpeckledFawns, KrissyAnneDesigns ,and Amber Kemp of Damask Love. All I have to say is I was resonating with Amber ON A SPIRITUAL LEVEL. Girl if DIY does not pan out, standup comedy will. They along with Mommy Lhey were both generous enough to give away kits and swag to EVERYONE in the ballroom like it was fricking Oprah.

After that we transitioned to workshops. I had the honor of teaching during this first block. Y’all, I have taught so many classes, so many workshops and yet I am nervous EVERY TIME. But I got to open up a dialogue about why self-care is so hard and how we keep sabotaging ourselves when we try to set boundaries. And people SHARED. The stories and things people opened up about were so raw and real and I was so grateful to Felicia, Erica of The Jewel Box, and so many others who reminded me about how much power we really have.

Photo of Jessica teaching
Me not wanting to stand in the front of the room. Photo cred: Diana @sugarygalshop

After lunch doing make & takes I also got to do a session on vision boards with Sage Greyson and then a panel on Side Hustling with the amazing women of Planner Girl Chatter and Audrey. Sometimes you just hear realness and are drawn to it – and I hope these connections carry through to the next time I get to see them.

After a closing (where I, naturally, did not win A SINGLE THING LOL), I had to save my energy before I had to hold another class. This was probably the hardest part – I actually very casually ate my dinner by myself in the lobby, recharging until I had to expend more energy. This kind of pace is not for the most introverted folks!!

We debuted a class called Cocktails & Calligraphy and IT WAS A BLAST. People were a little tired but we had fun learning brush calligraphy and joking around. Teaching this class is one of my favorite things to do. It was humbling to hear that people had such a good time and felt like they were actually able to do calligraphy for the first time ever.

AND EVEN AFTER THAT, I tried my hand at some Mommy Lhey karaoke alongside some other talented, talented people and got to place second!! I hadn’t sang on a stage in a while and it was so fun to do among some of the most supportive people I’ve met. After a mini dance party I crawled into bed at like 1:30am!

And just when you think festivities are over, I went to brunch the next day. I didn’t get a picture but it was a STUNNING setup at Pinstripes. I’m talking chocolate fountain. This was a last chance for me to chat with people and I got to talk more with MaryAnn (@marysocontraryplans), a SPITFIRE planner girl from NYC who makes me laugh and tells it straight up, and my girl from @cjayplans who is side hustling hard and gave me some amazing tips to up my tech game (thank youuuuu).

There was a snow storm coming through Chicago so thank GOODNESS we were only delayed for like 30 minutes before taking off – and I was ready to be home after somehow managing to pack all that swag into my suitcase. It’s honestly a freaking MIRACLE. So now what?

Reflections on the planner conference

After all of this, here’s what I know:

  1. I recommend planner conferences to anyone, especially if you have a pal they can go with! Save some cash now so you can throw down RIGHT when tickets go on sale. They sell out QUICK (CPC sold out in like 10 minutes – it was W I L D).
  2. This definitely takes a lot of energy! As you look at the schedule, know you need to do what you need to have fun throughout the weekend without killing yourself. Take breaks and be okay missing a few things – your energy is important!
  3. Many people go by themselves or with just one other person – people really are open to people saying HI. If there’s a Facebook group for participants, that is a really fun way to get to know who else is going, share rides, etc. Not everyone is a super extrovert – and often waiting for someone to say hello.
  4. I personally like to stay at the conference hotel. Since I’m a presenter I like being able to quick pop back to my room to drop stuff off, take a quick social rest, yaddy yada. This is a little more money but honestly I believe it is worthwhile to save on mental logistics and travel time.
  5. Save half your carryon for swag. This is not a drill. Every conference I’ve gone to I have had to give away some of the swag I got because I could not fit it in my luggage- someone had to get an extra bag to CHECK because she ran out of room!
  6. Bring a reusable bag or two to put your table gifts and other workshop swag inside (plus anything you buy!). Maybe pack a few snacks as well!
  7. You really won’t have a lot of time to plan, so don’t bring all your planner stuff! I just bullet journal so I bring my one notebook and a few pens for taking notes.
  8. Speakers, teachers, vendors are all regular people and are so easy to talk to, take pictures with, and geek out with. As one of those people myself I LOVE meeting people and doing a good ol’ selfie!
  9. Check the hotel fees. This hotel charged a daily fee for having a microwave and personal fridge, so plan accordingly if you plan on having groceries and snacks. Otherwise, plan for eating nearby, at the hotel, via an app like Grub Hub, or there was a Whole Foods near us. Often, when you check in, you have to present a card to charge for “incidentals.” This was $100 for us this time – and it was sucky for people when we found out the week of. Plan for this on your card if you can!
  10. These conferences are a SHIT TON OF WORK to plan. Be KIND to the people doing that labor of love to provide such an amazing experience for everyone. They have been thoughtful in creating the processes to sign up, choose tables, etc, so be kind and grateful
  11. The swag you get is a gift from sponsors and vendors – you might destash it, gift it, etc but whatever you do, make sure to tag them online and DO NOT SELL IT. When I couldn’t bring back a 12″x12″ scrapbook, I asked folks in the Facebook Group if anyone could use it – and someone ended up collecting them to donate to her organization that makes scrapbooks for cancer patients. General rule is don’t sell stuff you get for free.

OKAY I had a lot to say, whoops!!! Is there anything I missed? Anything you’re wondering about?! Let me know in the comments!


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