My work trip to Chicago: a photojournal

by Ashley
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Within our friend group here in Nashville, we gave each other call signs. Justin is Dough Boy (our personal baker) and they called me Spider. Now, y’all know Im an arachnophobe so in this case, I suppose I’m a little like Batman, conquering my fear by owning the name of the thing I fear. However, the reason they call me that is because I create webs of connection. Nothing brings me more joy than connecting people from near and far, matchmaking between friend groups, and bringing disparate groups of people together in one space.

And now, with my role at CNA, I get to create webs of connection for the people I work with. Can I officially add “event planner” to my LinkedIn??? 🙂

For the last 13 months, our team has been planning our internal conference, Tech Days — and I was the lead organizer 🙂 The conference is just for employees within the Technology organization of CNA (this might be called IT at other places; it includes 7 different functional areas and over 600 full-time employees + 3k contractors). This is the second time for our team to have the responsibility and as the lead organizer I reveled in the opportunity.

Tech Days 2026 has been the biggest project I’ve worked on, to date, with a budget of $1.2 million. I wish event planning could be my full-time job — it was so much fun! I am incredibly proud of the work we did on this conference. Seeing it all come together, watching everyone make connections in person, and seeing the smiles one everyone’s faces brought me so much joy. It’s a lot of work but such a joy and honor to get to work on. I hope they keep letting me do this!

I flew up on to Chicago on the Sunday before the conference and hung out with my bestie. That Monday, each Tech functional area hosted all-hands meetings to talk about 2025 accomplishments and plan for 2026. Tech Days was all day Tues and Wed, at the Sheraton Grand Riverfront, and I flew home Thursday.

Enjoy my travel journal!!

Sunday – Travel day

Check in, meet up with KP, Lincoln Park Conservatory, walk around, check out a bookstore, dinner at Blowfish, hang at her apartment for a minute, take the bus back, watch the office.

Cityscape featuring a mix of historic and modern buildings, including a tall glass skyscraper and a detailed older facade, with flags and vehicles visible along the street.
A spacious park scene with a cloudy sky, featuring grassy areas sparsely populated with trees, benches, and a large glass structure in the background.
A close-up of a Canada goose standing on the grass near a small puddle, with another goose in the background and some fallen leaves scattered around, alongside a plastic bottle.
Close-up of a vibrant purple and pink flower surrounded by green leaves in a garden setting.
Interior view of a greenhouse with a glass dome roof, featuring vibrant flowers in red and yellow hues, surrounded by lush greenery and a small water fountain.
Two smiling individuals posing for a selfie in a lush greenhouse filled with tropical plants and large palm leaves.
A serene garden scene featuring lush green plants and large leaves surrounding a calm pond, with a stone statue of a figure in the background. Pink flowers in the foreground add a pop of color to the tranquil setting.
Two smiling women posing for a selfie in a park with a city skyline in the background, featuring tall buildings and a cloudy sky.
Graffiti on pavement reading 'Death 2 ICE' in bold letters.
A colorful mural featuring a whimsical cat with large green eyes lounging on a purple float in water, with a penguin in a tuxedo standing on its head and a playful fish nearby.
A colorful mural featuring a woman with flowing hair surrounded by waves. She holds a group of animated animals, including dogs and a rabbit, all promoting an environmental message with the text 'SAVE OUR PLANET' in the background.
A woman standing inside a vintage red telephone booth with a sign that reads 'Roscoe's'. The booth is located on a city sidewalk with buildings in the background.
A brightly lit Christmas tree stands in an urban plaza at night, surrounded by tall buildings. Two pedestrians walk on the path nearby, and a ticket booth is visible to the right.
A bronze statue of Jack Brickhouse, a Hall of Fame broadcaster, is displayed prominently at night, with a large pink sculpture reading 'hope' in the background. The scene features surrounding tall buildings illuminated by city lights.
A scene from a television show featuring a man in a suit talking with two other characters in an office setting, with city skyline visible through large windows.

Monday – Departmental meetings at the home office

I like to joke that I was a personality hire since much of the value I bring to CNA Tech is my sense of whimsy. Who says work can’t be FUN?

Our team wore Hawaiian shirts to manifest warm weather for the week. We even found an Excel shirt for our boss’s boss. (My boss is in the middle.)

I brought a bunch of Hawaiian leis and pooka shell necklaces for the rest of our department. (Thanks, Aunt Leigh!!!!!)

After our all hands meeting was done for the afternoon, we headed over to the conference center to finish set up for the next day.

View from the stage of a conference setup, featuring a large screen displaying 'CMA TECHDAYS 2023' and a countdown timer. The background shows a spacious hall with round tables and chairs arranged for an event.
View from the main stage
A spacious conference hall set up for an event, featuring multiple round tables with white tablecloths, empty chairs, and a stage adorned with blue lighting and presentation screens displaying 'CMA Tech Days 2023'.
Coming together nicely!

Tuesday – Tech Days Conference (Day 1)

Up and at ’em bright and early. We have to be downstairs at 7.

And the show has begun!!!

A large conference room filled with attendees listening to a speaker on stage, with a large display screen showing the speaker's presentation.
A large audience gathered in a conference hall, watching a presentation on a stage, with speakers visible on the screen and colorful lights in the background.
A group of three individuals sitting behind a table with computers, engaging in discussion. One person is waving, wearing a red shirt, while another person is focused on their computer.
Susan, running the remote experience over Teams.
A person with pink hair and glasses with orange frames smiling at the camera, wearing a navy shirt with a badge that says 'Global Governance Risk & Control'. In the background, two people are talking and sipping drinks.
That’s our CEO behind me! Getting mic’d up for the fireside chat with our CIO.
Two people smiling for a selfie, one with pink hair and colorful glasses, and the other wearing glasses and a blue shirt, at a conference event.
My fave coworker
An indoor convention or conference setting with many attendees networking at various booths. Tables are set up with displays, and there are groups of people engaged in conversation throughout the room.
The vendor expo felt like a real vendor expo!!
A conference room with a presentation on a screen, where a speaker discusses a testing process to an audience seated at round tables.
One of the interactive game-style sessions
A large group of people seated at tables in a conference room, engaged in discussion, with a presentation screen displaying the text 'YOU TRY!' in the background.
Another interactive session — lockpicking!!
Three people interacting around a table with a Jenga-like game, one person pulling a block, another observing, and the third person preparing to take their turn.
Hanging out in the chill zone

Wednesday – Tech Days Conference (Day 2)

A smiling person with pink hair wearing orange-framed glasses and a black shirt, showcasing a lanyard with various badges and buttons, including one labeled 'Global Governance Risk & Control.'
Can you tell I stayed up way too late with my coworkers?
A group of people gathered around a table working on a jigsaw puzzle during an event, with pieces spread out and some individuals focused on fitting pieces together.
Trying to make progress on the puzzle!
A conference room with several round tables where participants are engaged in a discussion or brainstorming session. A presentation screen is visible in the background displaying content related to crowdsourcing.
An interactive problem solving session
A large audience seated in a conference room, listening to a speaker in front of a projection screen displaying content related to RansomHub enhancement operators.
One of the packed security sessions
A conference presentation in a spacious meeting room with a large audience seated at round tables, focusing on a speaker in front of a projection screen displaying a diagram related to a business process.
Talking about imposter syndrome.
A large audience attending a presentation in a conference room, with a speaker in front of a screen displaying graphs and images.
One of the most crowded sessions: Quantum Computing 101
A group of five people posing together in front of a CWA branded backdrop, smiling and dressed in professional attire.
Our team at the end of the conference.
A round table covered with a white tablecloth, featuring a puzzle with a collage of images and the text 'CNA TECHDAYS' in the center, surrounded by scattered puzzle pieces. A water bottle and a box labeled '1000 PIECE' are on the table.
This was as finished as the puzzle was gonna get.
A large group photo of over 300 attendees at a conference, standing together in a banquet hall with tables set in the background.
A large group of people gathered in a conference hall, all raising their hands in celebration. The setting features rows of chairs and tables, with attendees smiling and engaging with one another.

Having over 600 Techies together in the same place was such an incredible experience — and what an honor and pleasure to create such an event. <3 My heart is full.

Thursday – Travel day home

A panoramic view of a modern city skyline featuring tall glass skyscrapers, capturing the bustling urban landscape under a clear blue sky.
Last view from my room. Notice Navy Pier to the right?
Interior of an airplane showing a passenger's legs and hand resting on their thigh, with other seated passengers and the cabin layout visible.
Flying midday on Thursday worked out — a whole row to myself!!
Aerial view of a snow-covered landscape featuring urban development, residential neighborhoods, and open fields under a clear blue sky.
Adios, Midwest!!!

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