Hi I’m @kayladesouzamusic , a lifelong singer-songwriter, a woman in tech, and someone who knows firsthand how hard it is to balance a career with a passion for music.
I created Five Too Nine as a community for individuals navigating that same tension — a space to share our struggles, but even more importantly, to keep our art alive.
This is for every professional who still carries a creative dream: the painter, the writer, the musician, the filmmaker, the designer.
We’re here to remind each other that creativity matters — and that your art still belongs in your life, even alongside a demanding 9-to-5.
Join us in building a community where we lift each other up, share ideas, showcase our work, and support one another’s creative journeys after the workday ends.
#FiveTooNine #ArtistryAfterHours #CreativeCommunity #ChicagoCreatives #AfterHoursArt #WorkingArtists #passionprojects
Day in my life as an entrepreneur in Chicago ✨🌆
Started the day on the grind, posted YouTube content during lunch, had my kale mango salad with my favorite Super Womb Tea, hopped on a coaching team call with @wendyamara , dinner at @lajosiechicago with my favorite person @thechi.est , packed orders for my amazing customers, and ended the night networking with creatives @five_too_nine 💻🤍
Creating, healing, connecting, and building the life I prayed for one day at a time.
What’s one thing you’re currently building for yourself this season? ✨
#ChicagoCreator #EntrepreneurLife #LatinaEntrepreneur #DayInMyLife #WomenInBusiness Chicago ContentCreator Networking SmallBusinessOwner WellnessJourney TikTokShop
Last night was a reminder of why Five Too Nine exists. ✨
A room full of people balancing careers, creativity, ideas, passions, uncertainty, ambition, and artistry — all showing up as themselves after hours.
There was something really powerful about hearing everyone share who they are beyond their job titles, what they’re building, and what they’re still becoming.
We left feeling inspired, fulfilled, and incredibly grateful to have met so many new faces. 💛
Thank you to everyone who came, shared, listened, and made space for one another. This community continues to become something really special.
See you after 5. 🌙
#FiveTooNine #ChicagoCreatives #CreativeCommunity #artistryafterhours
We’re hosting our next networking gathering on Thursday, May 14 at 6PM.
Five Too Nine is for the creatives, the corporate dreamers, the side-project builders, the “I’m more than my job title” people.
Whether you paint, write, design, build, perform, or you’re still figuring it out — this space is for you. 🎨🎙️📓
Come meet other creatives navigating life after 5PM.
Come talk about what you’re aspirations and inspirations
Leave inspired. 💛
We can’t wait to see you.
RSVP link in bio.
#FiveTooNine #ChicagoCreatives
✨ Meet our members✨ learn more about one of our founding members: @colin.mcgregor
Colin grew up in Michigan, but they bounced around to Philadelphia, Baltimore, and Buffalo before finally declaring Chicago their home in 2024. Music has always been a significant part of Colin’s life, and after they studied violin at The Juilliard School’s Pre-College program and served as associate concertmaster of the Johns Hopkins Symphony Orchestra, they became established in the Buffalo DIY scene as a member of the indie duo Girlfriend Complex.
In the blinding light of day, Colin keeps novel drug trials FDA-compliant to afford concert tickets, but songwriting is their first passion, and their primary artistic goal for 2026 is to create an album with their partner, @laurenalyssasings
✨Meet our members✨
Learn more about one of our founding members: @dana_lipson
Based in Chicago, IL, Dana is a litigation attorney by day and a long-time comedy scene regular by night. When she’s not in the weeds of motions, deadlines, and courtroom prep, you can find her chasing laughs and sharpening her skills within Chicago’s iconic comedy community. She has spent time performing, training, and collaborating at iO, The Annoyance, The Comedy Bar, and The Second City.
No longer playing the character of the exhausted and overextended law student, Dana has found a rhythm where comedy and law complement each other seamlessly: one demands precision, the other rewards play—and both require quick thinking.
If you’re into live comedy, improv, or sketch writing—or looking for recommendations on shows and classes around the city—be sure to say hello. Dana is always down to connect and swap favorites.
#fivetoonine #memberspotlight #chicagocreatives #chicagoartists
Five Too Nine is back. ✨
After a little reset, we’re hosting our next networking gathering on March 19 at 6PM at our new location:
📍 Studio 424
📍 1415 N Ashland
📍 Wicker Park
Five Too Nine is for the creatives, the corporate dreamers, the side-project builders, the “I’m more than my job title” people.
Whether you paint, write, design, build, perform, or you’re still figuring it out — this space is for you. 🎨🎙️📓
Come meet other creatives navigating life after work.
Come talk about what you’re working on.
Come leave inspired. 💛
We can’t wait to see you.
RSVP link in bio.
#FiveTooNine #ChicagoCreatives #chicagoartists #chicagomeetup #creativelife
❄️ Holiday Pause ❄️
Five Too Nine is taking a short break for the holidays.
Thank you for showing up, sharing your creativity, and making this community what it is.
We’ll be back together in January. Can’t wait to see you in the new year!
Why is it so hard to share what we create? 💭
This month at Five Too Nine, we’re diving into the courage it takes to show our work - the vulnerability of being seen, and the pride that comes with owning your art.
🎤 Show Your Work: The Vulnerability of Being Seen
🗓️ Thursday, November 20th, 2025
📍 Epiphany Center for the Arts
🕔 Doors 5:00PM | Start 6:30PM
🎟️ Free admission — RSVP in bio
Let’s talk about why sharing our art feels hard sometimes — and how we can start embracing it with confidence and community.
#FiveTooNine #ArtistryAfterHours #ChicagoCreatives
✨ Five Too Nine: October Gathering ✨
Join us Thursday, October 16, for our next community meetup — a night to share, connect, and be inspired.
This month, we’re opening the floor for members to showcase what they’ve been working on — projects, passions, and everything in between. Whether you’re polishing a short film, mixing a new track, designing your next collection, or finally finishing that script, this is your space to show it off (or just soak it in).
Come meet fellow creatives balancing ambition with artistry — because what we build after hours matters just as much as what we do from nine to five.
📅 Thursday, Oct 16
📍 Epiphany Center for the Arts
🕖 6:30PM
🎟️ RSVP link in bio
#FiveTooNine #ArtistryAfterHours #ChicagoCreatives #CommunityOverCompetition #CreativeCollective
✨ Community is at the heart of everything we do at Five Too Nine. ✨
When we gather, it’s not just about sharing ideas — it’s about leaning on each other, celebrating each other, and finding inspiration in the stories we carry.
This week, we’ll be diving into sources of inspiration — where we find them, how they sustain us, and how our community can spark new ones.
📅 Thursday, Sept 25th
📍 Epiphany Center for the Arts
⏰ 6:30PM
💡 Topic: Sources of Inspiration
🤝 Come ready to connect, share, and leave inspired
