Jason and Tom work for the same company and take similar paths to work. But NOT the same paths. There's a walkway nearby which happens to be on both their routes to the office, but it's a perfect example of crumbling and neglected city infrastructure. For some reason Jason tempts fate and takes the walkway each day. Tom, however, refuses to and chooses to leave earlier for work so he can take the safer route.
You can see the walkway for yourself at Google Maps. The walkway runs along Hubbard avenue and crosses Rush street in the image. And if you check out the Google Street View, and look up at the walkway, well, you'll see what we're talking about! If you don't hear from Jason one of these days, you'll know why.