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Courtesy of Rosie Quasarano/ Cup and Spoon

Cup and Spoon will open in Humboldt Park this spring.

Wicker Park startup says quit your job

by Maranda Bodas
Feb 12, 2014


Maranda Bodas/MEDILL

Jennifer Philbrook works out of Free Range Office. Philbrook quit her job this month to launch Stitch Method, a brand consulting firm.

Liane Jackson, founder of Wicker Park’s Free Range Office, wants people to quit their jobs or at least give them the tools to do so.

Free Range Office caters to entrepreneurs and freelancers by providing affordable and lease-free desk space and mentorship. On Thursday, the space is hosting a workshop called "Quit Your Job Boot Camp" to provide future small-business owners with the tools necessary to leave their jobs and join Chicago's startup community.

“So many people who are employed feel trapped,” Jackson said. “They want to be their own boss and we want to give them a road map to do that.”

Carolyn Ou, founder of Sandbox Consulting in Chicago, will join seven speakers at Thursday’s event, doling out advice on everything from financial planning to health and wellness practices. “We will give them a dose of reality,” she said. “We call it a boot camp because people will either move forward with their plans or take the idea of owning a small business off the table.”

The small business sector is growing across the U.S. According to the Small Business Administration, the number of small businesses across the country has increased 49 percent since 1982 and small enterprises provide 55 percent of all domestic jobs. The expanding startup-sector gained steam after Great Recession hit in 2007-2008 and many people were forced to get creative when they lost their jobs.

Rosie Quasarano, 32, became one of 23 million small-business owners across the country when she quit her job at an advertising firm in October to launch Cup and Spoon, a pop-up coffee shop that will open its first brick-and-mortar location in Humboldt Park this spring.

Quasarano said that timing is crucial. “Feel it out and make sure it is the right time to do it,” she said. “It is the combination of being prepared but also being willing to take the risk.”

Planning will be a cornerstone of Thursday’s event. Khloe Karova, an independent financial analyst, will help budding entrepreneurs answer the tough question: Can I afford to take the risk?

“There are people who are very good at planning. Those are the people that are most likely going to be successful,” Karova said. “You need to have the discipline, process and planning.”

According to Karova, plotting a road map is just a small part of the equation. “You have to get people to invest in you and build a network,” she said. “You need to figure out how to regularly problem solve with other people and get creative.”

During the past three years, Chicago has made a big push to attract and keep small businesses in the city. The number of co-working spaces has quadrupled to meet the demand for flexible workspace, and the city invested more than $2 million in technology innovation with the launch of 1871, a tech startup community in the Merchandise Mart.

“If the Chicago economy is going to thrive, small businesses are going to be a big part of it,” said Elliot Richardson, CEO of Chicago’s Small Business Advocacy Council.