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Enjoy the Process: How Workshop Chicago Is Building a Community


Enjoy the Process: How Workshop Chicago Is Building a Community

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!  




The Freelancer’s Guide to 2015


The Freelancer’s Guide to 2015

by Kate Vandeveld

The freelance economy has grown tremendously in recent years. In fact, freelance workers are actually projected to outpace full-time workers by 2020.  And for good reason: Freelancing enables motivated and independent individuals to work for the clients whose missions inspire them, while also allowing organizations to tap into the unique skillsets that they need for particular projects.

But freelancing comes with its own unique challenges, from achieving the optimal client-freelancer relationship to keeping your finances straight. As we have quite a bit of experience in the freelance world, we thought we’d pass along some of our learnings.  Here’s our advice for freelancers who want to kick off 2015 on the right foot:

Maintain a Work-Life Balance

Making your own schedule can be incredibly liberating. As a freelancer, you are often free to work at the times when you are the most effective – early morning, late at night, or somewhere in between. The problem is, without the structure of a 9 to 5 schedule, it can become difficult to step away from work and unplug. There is always more that could be done, whether it’s clocking time on a project, researching potential clients, or honing your personal brand.


But, as with every career path, maintaining a work-life balance is essential for your success (and sanity!). It is so important to “work when you’re working, and not when you’re not.” One way to do it is to set (and adhere to) a schedule for yourself. Whether it’s based on an hourly breakdown or completing certain tasks on a given day, setting goals and limits will give you a sense of accomplishment and give you a clear sense of when it is time to sign off. If you want to do this by choosing a select number of hours to work each day or week, try using time tracking software – it will make your life a lot easier. 


Find a Co-Working Space

In chatting with other freelancers, we’ve heard the same story over and over again: At the beginning of the freelance journey, working from home is awesome. No longer do you have to adhere to a “normal” schedule; you can take breaks when you feel the need, and set up an optimal work environment for you. But after a couple of days or weeks, you may start to feel a little bit isolated or unmotivated. The joy of working from your living room is replaced by a feeling that you need to have a separate workspace, with other like-minded individuals to talk to.


Enter the co-working space. Co-working spaces are offices where individuals work on their own projects in a rented space. If you live in a big city, you’ll find that they are all over the place. Some are catered toward specific niches – tech or creative, for example – while other are open to anyone who needs a space to work. Each co-working space is a bit different, offering different set-ups – from separate offices to open floor plans with desks – and ambiance, so you should definitely do some research and visit the spots that appeal to you before making a decision. Co-working will give you the opportunity to better separate work and home when you need to, and allow you to connect with others who are doing similar or related work.

If co-working isn’t for you, be sure to create a separate spot for working within your own home. And if you want to work outside the home, but can’t find a co-working space, give your local coffee shop or bookstore a try! 


Seek Out Networking Opportunities

As a freelancer, you can secure much-needed support and inspiration by finding opportunities to connect with others who are involved in work that is relevant to your field. Without the built-in relationship-building that comes with working in an office, however, you’ll need to seek out these opportunities on your own.  Even though networking as a freelancer takes a bit more effort, it’s relatively easy to do, and will have a big impact on your career development.

Start by using online forums like to connect with other individuals in your area who are working in your field or freelancing. You can also use LinkedIn as a resource for making connections. Reach out to the people in your network who are working for organizations and businesses that you admire, and ask them to connect you with others in the space. It may seem uncomfortable at first, but more often than not, people are more than willing (and even excited!) to help you make connections with others in their networks.

Co-working spaces often provide networking opportunities as well. Before joining one, be sure to check out whether or not they have events like happy hours and workshops that will allow you to spend some non-working time with the other members. 


Stay on Top of Your Finances


Much of the time, managing finances is a little bit trickier for freelancers than they are for corporate employees. Independent contractors often have to handle their own accounting, from billing to bookkeeping to taxes, and many go into it without knowing the first thing about how to do it the right way. It might sound daunting, but there are ways to make it more manageable. Here are some tips that will make handling your finances easier:

  1. Separate your personal and business finances: This will make your life infinitely easier when tax season comes along.
  2. Select a finance day each month or quarter: Managing your finances all in one annual sitting will likely prove to be quite miserable.
  3. Use accounting apps / software: Find a software (like Freshbooks or Bench) that fits your needs, and take the time to familiarize yourself with how it works and how it can help you.
  4. Set aside a certain percentage of your income for taxes: If you aren’t working with an accountant, you can use a free tax estimator to help you decide how much to set aside for taxes.

When it comes to taxes and planning for retirement, Freelancers Union has some great tools that can help set you up for a successful year – check out their tips.


Don’t Forget About Health insurance

And last, but certainly not least, don’t forget about health insurance. When transitioning to the freelance life, it may be easy to forget about things that were previously built into your benefits package. Luckily, these days, applying for health insurance isn’t as difficult as you might think.

To get coverage, you can apply directly through, which provides a great deal of information on health coverage for the self-employed.  You can also turn to third-party sources like Freelancers Union for information about the best package for you.

However you go about it, just be sure to take care of it as soon as possible – open enrollment now ends on February 15th. If you haven’t applied by then, the only way you can get coverage for 2015 is if you qualify for a Special Enrollment Period. And if you don’t have coverage, you will be penalized at tax time at a rate that is certainly not worth it.


Whether you’re a freelancer or not, the New Year provides us all with an opportunity to start off on a better, more organized foot. Take steps to evaluate your work life, and make changes wherever you can improve.

How do you plan to set yourself up for career success this year? Let us know in the comments below, or connect with us on Facebook, Twitter, or Instagram


Freelance Resources: How to Market Your Skills Without Spending a Dime


Freelance Resources: How to Market Your Skills Without Spending a Dime

The social good network is a tightly knit, passionate community united by shared values, as well as shared goals. As such, it's a space in which a referral or introduction from a trusted source can be the defining factor in landing a partnership or a job. 

Whether you’re looking to expand the reach of your network, establish some credibility, or land a job at a company you care about, here are a few ways to market your skills without spending a dime:  

1. Give Feedback 

Social entrepreneurs and nonprofit founders tend to regularly ask friends and family for feedback and advice. They know that a few key comments on a strategy or campaign can make all the difference in the efficacy of their efforts. As such, offering feedback is a fantastic opportunity to showcase your knowledge and demonstrate your value. 

Looking for a quick and easy way to deliver your comments? Make a voice recording. Tools like EvernoteiPhone’s voice notes or Cloud Recorder  can help you create shareable voice files that succinctly demonstrate your value. After spending a couple minutes on specific feedback points, don't be afraid to throw in a sentence or two about how you might continue to be of service through freelance or contract work. 

2. Co-work

Co-working can be as official as taking part in a program like Goodnik’s in-residence program, or as casual as setting up a weekly coffee date with a friend. The most important thing to remember is that it’s about finding a good working environment for you. At WhyWhisper, we've found that working alongside people who have similar passions and values is what makes co-working most powerful. Why? Brainstorm sessions, problem-solving, and referrals will naturally occur throughout your day.

3. Sit on a Panel 

Social good networks use panels as a way to get to the heart of important issues. Seek out the ones where you can provide the most value while reaching an audience that includes prospective clients and/or partners. Prepare thoughtful and insightful commentary, and pay particular attention to connecting via social channels and email, so as to establish a relationship while you're still top of mind. Your target audience is likely to follow up with additional questions and requests to chat further. 

4. Provide Empowering Environments

Connecting people is a powerful way to demonstrate your willingness to meet the needs of others. In a world of endless meet ups and happy hours, people appreciate introductions that help them to quickly cut through the clutter. Facilitate these meetings by hosting dinners or setting up happy hours with like-minded guests. Your efforts will not go unnoticed, and your guests will be all the more likely to do the same for you in the future.

5. Know Your Own Value 

You have probably already heard that people value those who value themselves. As you establish yourself within the social good community, you will be asked for your input and advice, as well as to lend a helping hand. Carefully providing thoughtful feedback is wonderful. Finding a way to clearly  communicate the monetary value of your product or services is even better. It ensures that others in your network will think of you as a valuable colleague, and opens the door for future business. 

Do you have a helpful tip to share about networking within the social good community? Leave a comment below. We would love to hear from you!