It was clear from the second he sat down for his interview that Craig Gunn is the type of guy who always sees the glass half full.
He has the smile of a salesman, the laugh of a comedian, and the gift of story-telling found in any serious adventurer.
Craig’s life hasn’t been easy. Homelessness, poverty, and familial troubles have constantly blighted his prospects.
But Craig is undeterred. Beneath his jovial, fun-loving nature lie ambition, tenacity, and a thought-out plan for success.
Craig is a longtime vendor at StreetWise who can be found most days selling magazines along Milwaukee or Halsted.
“I’ve been at StreetWise on and off for five or six years,” Craig said. “I have a lot of good memories here.”
He credits StreetWise for introducing him to new friends and helping him cultivate ties with loyal customers.
Craig has had many jobs during the last few years. Some he quit; others he knew were temporary from the start. “I was for-tunate to count on StreetWise for (additional) income,” he said.
Craig currently rotates between living in shelters and his aunt’s home. He once had his own place but was evicted after coming up short on his monthly rent.
“That was the toughest challenge for me,” he said as he reflected. “Helping my relatives and friends stay in our apartments – that was a lot for me.”
Craig no longer keeps in touch with his family. Many of them moved away; others simply ended contact. But Craig has a lot of friends. He also dates.
In the meantime, he intends to read and play sports, his two favorite hobbies, he said.
When asked what his short-term goals are, Craig smiled, leaned back, and said, amidst a few hearty laughs in the background, that he aims to “make enough money to [socialize and] put food in my stomach.”
But then he deftly transitioned. Craig can easily go from being funny and lighthearted to being thoughtful and staid.
He aspires to pursue a career someday in the hopes of permanently “staying away from homelessness.”
For a pessimist, such a daunting goal would seem insuperable. But not to Craig.
“My motivation is waking up every day,” he said. “One shouldn’t give up in life. Just keep going – whether it is good or bad.”
That’s Craig in a nutshell. Articulate, animated, and ambitious, Craig has a knack for lifting up people’s spirits. Forget Bruce Jenner and Herman Cain – Craig has the makings of the next big motivational speaker!
He further proved this when he gave his case for why more people should come to StreetWise.
“People should not [be satisfied] with boredom,” he remarked. “They should come to StreetWise. They will surely accomplish something.”
Craig would know. He is living proof of it.
Sam Rothbloom, StreetWise Editorial Intern