
What we’re about
Yeah, we definitely have volunteer and leadership opportunities if you're looking to get more involved. Whether you want to help organize trips, lead a local meetup, or help plan one of our co living experiences, we welcome people who are passionate and want to shape the community. We believe the best ideas come from within the group, so if you've got something in mind, we'll help you make it happen. Plus, stepping into a leadership role is a great way to grow your network and build real world experience while doing something you love.
We host all kinds of events designed for people building careers without borders. Think destination workations where you work during the day and explore a new city at night, skill sharing workshops on freelancing or remote job hunting, networking mixers with other digital nomads, and co living retreats in cool spots around the world. We also partner with real companies and entrepreneurs to bring you industry specific events like tech meetups, freelance pitch sessions, or online business masterminds so you can learn, connect, and grow professionally while living life on your own terms.
Most of our local Chicago meetups happen on weekday evenings or weekend afternoons usually Friday nights or Saturday midday so it's easy to join whether you're in a time zone aligned with the US or jumping on after work from somewhere overseas. Our online events are often scheduled with global members in mind, so we rotate times to be fair across regions. And when we travel, the schedule is built around balance: work blocks, adventure time, and meaningful connection never too packed, never too slow.
This group is open to anyone serious about combining location freedom with real income entrepreneurs, freelancers, remote employees, solopreneurs, side hustlers, and aspiring digital nomads. It doesn't matter if you're just starting out or you've been working remotely for years. If you're ready to stop dreaming about traveling the world and actually start doing it while building your career, you'll fit right in. We're all about support, not competition, and we believe diverse backgrounds make the community stronger.
If you're tired of working in isolation or scrolling through job boards that don't get what you really want, it's time to connect with people who do. Joining Chicago Knowledge And Money Associates means becoming part of a real community that helps you earn while you explore, grow your skills, and meet friends who get the lifestyle you're chasing. We're not just talking about remote work we're living it, improving it, and inviting you to build it with us. Come find your people, your momentum, and your next adventure.
Upcoming events
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Find Freedom Can You Go Remote Ready
RC9Q+CM Chicago, Chicago, IL, USEver looked at someone sipping coffee on a beach while closing deals online and thought, 'How are they really doing that?' You're not alone — and it's not a fluke. The secret? They're 'Remote Ready.'
The Remote Ready Bootcamp is your 14-day launchpad to building a real career that lets you work from anywhere — cafés in Lisbon, co-living spaces in Chiang Mai, or your favorite mountain town. Join a global community of professionals who’ve already cracked the code, with instructors currently living and thriving in Spain, Thailand, Japan, and Brazil. You’ll gain: 'step-by-step income strategies,' 'client management systems,' 'proven location-choice frameworks,' 'sustainable remote workflows,' and lifelong 'connections with like-minded go-getters.' This isn’t theory — it’s real-world tested.
Before you join, a quick readiness survey ensures we tailor everything to your goals. 🌍
📅 Spots are limited — but the journey starts with one click. Let’s build your freedom together. REGISTER HERE
You’ll get personalized onboarding details right after — and your next chapter begins.
1 attendee