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Money Mentors: Rich Hebron on What Gen-Y and the Homeless Have in Common

Rich Hebron on why Millenials and the homeless have a lot in common.Well, here’s something you don’t hear every day.

When Rich Hebron graduated from DePaul University in 2011, he had plans — and not of the full-time employment variety.

Instead of pursuing a traditional route like some of his friends, he decided to live on the streets of Chicago for four months in order to better understand the mentality of someone struggling with homelessness.

The result was a fresh perspective on what Gen-Y needs to succeed.

Rich answered my questions about his months sleeping in shelters and in bushes, plus shared his plans for Project Primetime, his Gen-Y empowerment non-profit that launched in February.

Maria: So here’s an obvious question — What inspired you to live homeless after you graduated from college?

Rich: In short, I didn’t know what I wanted to do going into my senior year of college. A friend and I went on a topic of homelessness. We began to wonder, “What if someone voluntarily became homeless for an extended period of time?” I knew I could share that knowledge with everyone else.

If you understand something more you can control it more. There’s a lot of similarities between the homeless community and our generation.

Maria: What are some of those similarities?

Rich: It’s some of the same mindset. Homeless individuals are living day to day being bystanders in their own life and feeling powerless. They are surviving, but not thriving. It’s about, “When is my next meal going to come? Where am I going to sleep?”

Our generation is surviving and not thriving. We’re stuck in this vortex I guess … My goal with Project Primetime is to help people be more confident in their decisions and be more proactive. A lot of good can come from that, a lot of innovation and new perspective.

Maria: So when you were living homeless, how exactly did that work?

Rich: My goal was to gain a general understanding of what being homeless in Chicago meant. I slept on the streets for the first month, in bushes, I’d sneak into buildings. I ate at soup kitchens. I learned a lot during the first month, but I wanted to take it to the next level to learn more. So I spent two more months in the shelter system. It was called Cornerstone, underneath the Wilson Red Line stop in Uptown. I would go to this overnight shelter called Walls in East Garfield Park. That’s where I went every night for over two months.

Maria: What were your main take-aways?

Rich: A big lesson would be, I felt this range of emotions I never felt before. One was feeling this loneliness. That was basically when I left the shelter. When I was in the shelter I could get through anything, with someone by my side. No matter what the conditions and how much it sucked, we still got through it together. When I left the shelter I did my own thing again on the streets. The day I left I thought I’d be the happiest person in the world. I walked around the corner and got on the El and headed up to Loyola … I thought I’d be the happiest person in the world, but I was the only one in the train car and the first flurries of the winter were coming down. I realized, “I’m all alone again. I’m already exhausted mentally and physically.”

I think with our generation, we’re in a not-so-ideal spot. A lot of people are struggling individually, trying to change their situation individually and what we really need to do is come together and help each other out to help our socioeconomic situation in America because we’re the future leaders, consumers and voting base. It’s in the best interest of everybody in America that we overcome these obstacles. Project Primetime’s goal is to connect people together to reduce risk and that feeling of being alone. To make that feeling of support there, to make these proactive decisions.

Maria: Do you think members of Gen-Y have any millennial traits we can actually use to our advantage?

Rich: This sounds strange, but hear me out. Our most positive trait is that we’re inexperienced. What I mean with that is, today’s world is a lot different from yesterday’s. Inexperience means rejecting the status quo, and that’s what innovation is. We’re not afraid to, it’s a very positive thing I guess. We’re not stuck in this rut for so many years.

The second most important thing is adaptability. We’ve lived in this time of rapid change, especially growing up in the first decade of the millennium. We’re used to it, it’s how we live.

Hopefully my taking a risk will inspire others to do something bold.

Do you think Rich is right about Gen-Y?

Published or updated on June 20, 2013

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About Maria LaMagna

Maria LaMagna is a recent graduate of Northwestern University where she served as editor-in-chief of the university’s award-winning daily newspaper and studied for five months in Argentina. Before joining Money Under 30, Maria worked as a reporter for CNN and the Indianapolis Business Journal. Follow Maria on Twitter @MCLaMagna.


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  1. Mike says:

    Strength in numbers! It’s not that we are not hard working, it’s just the combination of baby boomers’ irresponsibility with the “American Dream” in the buy now, pay later world…so they are retiring later in life, the mentality that we are an “entitled” and “lazy” generation before we are given the opportunity to prove ourselves as individuals, the promises we were made as children that the world is our oyster once we get our degrees and fall into our great high paying jobs (which never happened to most of us that actually got degrees to be productive in society due to the economy).

    Things are bouncing back in a big way though. I went from being jobless 2 years ago to buying a decent house for cheap! I’m a success story and I try to inspire my peers everyday. Just don’t give up the fight and remember that we can’t do it as individuals, but as a team.

  2. Foxy says:

    Great article. Very inspiring to see someone create an organization that really cares about people. There just needs to be more people like this in the world.

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