It all starts with a plan whether the goal is to become wealthy or to live cashless. Anything is possible you just have to learn to be resourceful and creative. My first step to live a cash free life for a year would be to get a job as a building superintendent this would allow me to live rent free; I'm not afraid to get my hands a little dirty. I could also become a professor in the city and live on campus. To get my desired job I would talk to people in person as well as online. To get food I would get a part time job at a supermarket where I could get food in exchange for labor. For transportation I would get a bike, a ride from a friend or plain old walking.
In regards to utilities I could go extreme and use candles, public outlets to charge my laptop and no need for a NYSE company owned gas; I would not be heating any meals. I could also move to Utah County which has some of the lowest utility costs in the nation. If I do decide to get light I would barter a service in exchange the person would pay the bill for me. The service could be walking a dog, administrative duties such as editing papers, freelance writing for a company or providing personal training to someone wanting to transform their body. This is all possible you can read about Kyle who ended up trading one red paperclip on Craigslist for a house.
In regards to clothes I could barter with friends as I do for movies and video games. I could also write to a company and offer to advertise in exchange for clothes. As I did some time ago with a supplement company by the name of Cytodyne Technologies. I used to work at a gym and while doing my extreme workouts I decided to take some meal replacement shakes and vitamins to get enough protein and save time with preparing meals. I wrote to the company and let them know that I liked the product and that I saw some nice shirts with their logo if I could have one to advertise. I sent them a picture of myself to let them know my progress. I got the shakes through a magazine by the name of ProSource. I sent the letter to the magazine company. They forwarded the letter to Cytodyne and in a few weeks I got a six month supply of meal replacements, vitamins, protein bars and shirts not only was it more than I expected ProSource ended up sending me shirts and products with their logo as well.
Now for entertainment I would borrow books and movies from the library or get all my entertainment online for free. I could also go to friends' houses for dinner in exchange I would create a board game so we could all play which I have done in the past, it is a lot of fun. When you care for people they open their doors for you, its a win-win situation.
Going without cash for a year is possible it just takes some strong networking and adapting to a new lifestyle. Sure it would be hard work but it could also be liberating. I probably could go cashless for life. Anything is possible and as long as we challenge ourselves daily we will grow and surprise our own selves. Why don't you try going cashless for a few days see what creative ways you find to evade cash.