by Kate Vandeveld

Because of the freelance nature of our work at WhyWhisper Collective, many of us leverage coworking spaces for community, networking, and access to office resources. We’re big believers in the growing freelance economy, and the collective impact we can make when we come together to use our skills and talents effectively.

As you may know, we’re also big supporters of social enterprise. So when freelance and social enterprise come together, we like to spread the word. This week, we had the opportunity to chat with Ben Skoda, founder of coworking space, Workshop Chicago. We’re inspired by his unique approach to developing a community for freelancers and entrepreneurs, and his belief in the growing impact of the freelance economy.

How Workshop Chicago is Building a Community -- via WhyWhisper

Here’s what he had to say:

Why did you start Workshop?

The concept for Workshop was a confluence of a few things – 1) my desire to connect quality people in Chicago, building community for remote workers and other creatives, 2) an interest in creating a multimedia platform for myself and friends to share our skill sets with the world, and 3) an attempt to see if I could start a business from the ground up and “be my own boss” (with a lot of help).


Tell us the story of Workshop's development - how did it get to where it is today?

Workshop has come a long way! We’ve gone through a lot of iteration, going back to before we had our own space. We always had a hunch that we could create something unique with the right space, the right people, a little hard work and some creativity. What we didn’t know was exactly which combination of those things would be the best route to our original vision for Workshop.

We shared the concept and got a core group of people on board. Then we started to meet and feel out what it would take to see a consistent community take shape. When we were comfortable moving ahead, we searched for spaces, and it took about 8-10 months before we signed a lease. Since we opened the doors of our space, we’ve never stopped adjusting.

We’re constantly in search of balance between building a brand, furnishing a space on a budget, developing and curating a community, finding the right group of people to manage operations and keep the creativity flowing, and most challenging of all, doing all of this while attempting to find stable revenue streams with limited resources. After a year of being in the space, we feel like we have a lot figured out, but we still have a long way to go to be a profitable business for the long-term. We’re excited about what we’ve learned, and anxious to see how people continue to utilize Workshop creatively.

How Workshop Chicago Is Building a Community -- via WhyWhisper

Co-working spaces like Workshop are so essential in supporting the growing workforce of freelancers and consultants. What has been the most rewarding part of contributing to that movement?

I’ve always been intrigued by the changing work culture, mostly because I think I fit so well into the freelance/consultant/small business culture personally. It’s been an eye-opening experience as we’ve explored ways to support the people who are trying something new, taking the plunge into entrepreneurship or pursuing a dream. It’s personally rewarding because seeing it all up close gives me faith that we can make it work – that the established vocational tracks (that never seemed to fit me) aren’t the only way. But it’s most rewarding to facilitate an environment where others have opportunities to make a new connection, get hired, collaborate, or experience a “light bulb” moment when they realize the same thing I’m realizing: “We can do this.” And we can.


How do you see the freelance movement evolving over the next 5 or so years?

I think we have the technology to make the connections it takes to be successful as a freelancer. We need to build the community, create awareness, and ultimately keep the momentum to continue to provide space so that everyone who wants to try to be their own boss has that opportunity. Going off on your own isn’t for everyone, but it took me decades to even grasp the idea that working for myself was a possibility. I’d love to live in a world where freelancing is easily accessible, and be part of a culture that supports those who want to go down that road – or at a minimum presents everyone with their realistic options. I love seeing the underdog succeed, and what we’re moving toward is the underdog being a bit more of the norm.

How Workshop Chicago Is Building a Community -- via WhyWhisper

How do you envision Workshop growing over the next 5 or so years?

Workshop could go in a few different directions, and perhaps all of them at once. We’re constantly trying to develop in a way that makes us lean and versatile, so that it’s not unrealistic that in a 24-hour period we could facilitate an active co-working community, a charity reception, a yoga class, and a support group for new entrepreneurs.

We’re looking to develop our team and systems in a way that allows us to host a full calendar, each day and night of the week, supporting the people who have invested in Workshop in a variety of ways. We plan to push the limits of what can be done in a 3,000 sq. foot loft office, and to continue to offer a soft landing for anyone leaping into a new season of their professional life.


Do you have any advice for others who are thinking about leaving the 9-5 life to work independently?

Do your homework, take calculated risks, trust those around you or find new people you can trust to help you get where you want to be. Be patient, make room for iteration and adjustments, and learn to enjoy the process more than the ultimate goal. At least those are all the things I’m working on!


If you’re interested in freelancing, or already doing it, check out our Freelancer’s Guide to 2015 for tips on how to do it right.

Are you inspired by a unique social enterprise? Tell us about them in the comments below, make an introduction via email, or let us know on Facebook, Twitter, or Instagram!