As a freelancer, staying productive, making connections, and keeping accountable are imperative. It requires a lot of personal responsibility. It’s hard, yet rewarding.

But there are also perks.

One of them is being able to work from anywhere. In Chicago, I’m fortunate to have plenty of options. When I’m feeling stir crazy or stuck, I’ll work at a local Starbucks, the Merch Mart, or the library.

But to this day nothing compares to my experience at Second Shift, a coworking space co-founded by Levi Baer and Nicole Vasquez. I stumbled on it when they hosted an open house back in March, the week of their official opening in Logan Square.

When I arrived, I was warmly greeted by Baer. He gave me a brief tour of the space, the wifi password, and I found a spot to get right to work. My day at Second Shift was one of the most energizing and productive work days I had all year.

Inspired by the experience, I asked to chat with them about their journey as entrepreneurs, what they were trying to build, and what they learned so far.

Since then, they’ve grown their community, hosted 30+ events and workshops, and were named ‘Best Coworking space of 2017’ by the Chicago Reader.

The duo is making a huge impact by helping their communities, facilitating collaboration, and providing a space for freelancers and entrepreneurs to learn and grow.

Here’s a bit of what I learned from them about accomplishing big goals, leveraging your enthusiasm, building businesses, and doing it all with a smile.

The Value of Asking Big, Hard Questions

“To accomplish great things, we must not only act, but also dream; not only plan, but also believe.” – Anatole France

Successful businesses and services are often born of solving a problem. We see problems everywhere around us. But it’s usually when something feels personally important to us that we’re compelled to try and solve it.

Asking yourself what motivates you, what work you want to do, and what sort of lifestyle you want to live is helpful for recognizing the problem you want to solve when it presents itself.

After working in the corporate world in different environments, Vasquez stumbled onto 1871, a hybrid coworking, incubator, and accelerator community of Entrepreneurs.

In an interview with Kristi Ross and Tony Batista on Bootstrapping in America, Vasquez recalls, “when I set foot in 1871, that was what changed my life. I walked in there and said, ‘what is this place’? Coming from a corporate job and being in the cubicle office, and then trying sales out, and working from your home, and from a car, I recognized there had to be a happy medium.”

Baer is cut from the same cloth.

“As I was graduating, I realized I didn’t want to work for a big company. I never liked the bureaucracy, the red tape, the ‘be a cog in the machine’ approach,” said Baer.

The process of thinking through what he didn’t want for his life and career help him better target what he wanted to chase after.

“I just want freedom and flexibility. I want to problem solve every day. I want to network and be able to have coffee with people all day and not feel like I’m not getting work done,” said Baer.

In Never Eat Alone, Keith Ferrazzi says that “the more specific you are about what you want to do, the easier it becomes to develop a strategy to accomplish it.”

When you’re specific about what you’re trying to accomplish, it strengthens your resolve for staying the course when you hit the rough patches on the road. In the beginning, when Baer and Vasquez were raising funds, sending proposals, and getting rejected by investors, it wasn’t always easy to see the way forward.

“As long as there was that little spec of light at the end of the tunnel we just kept going forward,” said Baer.

Asking the important questions up front helps reinforce trust in your plan, your purpose and your persistence for your big goals.

But accomplishing big goals seldom happens in isolation and without support.

Priceless Partnerships and Building Second Shift

Since discovering her love of coworking at 1871, Vasquez got the idea that the model could be replicated at the neighborhood level.

She worked tirelessly with the help of the community she was growing to build her own space, The Shift. This November is their 3-year anniversary.

The Second Shift is the attempt at replicating the model in the Logan Square community.

One key ingredient to making the neighborhood model work was ensuring the vibe of the new space was true to the area. Baer, a long-time Logan Square resident, community builder, and entrepreneur was the perfect partner.

“The reason we partnered is because we share the same mission and vision when it comes to our people-and-community-focused coworking space. We know each other’s strengths and so it’s easy to identify who is the best person for each task – many of our skills are complementary to each other which is wonderful,” said Vasquez.

Selecting a partner for a business venture is like choosing a roommate in college. For that relationship to thrive, it requires a few things. For starters, you hope to share some of your core values and interests. You want someone responsible that you can rely on to pay the utility bill on time. You want someone you can have a deep 3 a.m. after-bars conversation with.

nicole vasquez levi baer second shift chicago joking

Regarding their working relationship, Vasquez said of Baer, “I can start something and pass it off to him to finish, or vice versa. We both believe in NO-BS communication – so we are open, honest, and direct with each other. No passive aggressiveness, and no vagueness. It saves us time, and keeps us in good communication always.“

In a partnership, having someone you know you can rely on to deliver counts for major points. Baer and Vasquez have that with one another.

They work well together, support each other and compliment each other’s strengths. It boils down to having good people around you. Who you are as a human is going to be reflective of your business or brand. And that’s an advantage.

The Competitive Advantage of Being Yourself

In my time with Baer and Vasquez, one thing I quickly discovered was they are fun to be around. They’re personable, optimistic, and extremely open. That spirit is reflected in the air at Second Shift.

In the afternoon, I grabbed a coffee and a Kind bar from the kitchen (included with membership, by the way). That’s when I met Sean, an IT consultant turned digital marketer and a new member at Second Shift. We talked briefly, made nice, and exchanged information to keep in touch.

In Rework, David Heinemeier Hansson talks a lot about culture. He says that “You don’t create a culture. It happens. This is why new companies don’t have a culture. Culture is the by-product of consistent behavior.”

For Baer and Vasquez, they’re hyper-focused on collaboration, community building, and creating a space for people to grow their ideas and businesses. My interaction with Sean was a byproduct of that focus.

It’s not all entirely by chance, though.

One especially cool element of the community is their member wall. It’s a place where you can literally bump into each other and connect.

member wall second shift chicago

“IDEO calls these ‘casual collisions’ moments for people to literally bump into each other and get little mind melds,” said Baer.

There’s also the “What are you stuck on?” section where members can talk about their business challenges and help each other out. It’s ideal for encouraging collaboration and it creates tremendous value for their members.

The environment that’s forming is a reflection of the open, collaborative and entrepreneurial spirit of the leadership.

It’s good for the community. And it’s good business.

In a talk the duo gave at 1871 for Purpose Pitch, Vasquez said, “with every new member that joins Second Shift, their knowledge and their skills get brought into the overall community. The more we grow, the more resourceful we become. And in turn, it attracts more people to join and more external organizations want to get involved.”

And grow they have indeed.

Since their talk, Second Shift has more than 65 members. Still, with room to grow, the space is open to host events, offers mailbox memberships, and hosts open houses for interested parties get a taste of what working in a coworking space is like.

And it’s only the beginning.

Why Attitude is Everything for Entrepreneurs

Building meaningful things that last takes time. Your attitude and your approach make a big difference in whether you can survive the ups and downs.

Before our conversation wrapped up, I asked if there was any parting wisdom for people that wanted to build something of their own.

“In entrepreneurship, you have to think about how you carry yourself through all those moments. When you’re stressed out, and over budget and tired and it’s 6 a.m. or 11 p.m., and you have to send another proposal or take that call or sit in that meeting, what attitude are you gonna bring to it? Your attitude determines everything,” said Baer.

Bringing a positive attitude and a smile makes the ride manageable. Remembering that it’s work you love, despite the bumps, makes it that much more fun.

Sounds legit, right? Where do you start?

“Just do it. Whatever it is you want to do – just do it. Start now, stop thinking too much about it. Start small, document the process, and grow your idea.” said Vasquez.

Okay. Got it!


Second Shift is an award-winning, community-focused coworking space located in Logan Square in Chicago, IL. Schedule a tour and they’ll show you around.