For a while I couldn't figure out why I was emotionally more attached to my iPhone-photos as opposed to the pictures I set out to take with my DSLR camera. I really wanted to like the pictures taken with my proper camera more then the ones taken with the iPhone's super small sensor and limitations. I couldn't figure out what I was doing differently. The pictures taken with my iPhone seemed to be much more interesting to look at despite being technically way inferior in comparison to what I could capture with my DSLR. The photos I took with the "big" camera seemed to constantly look a bit sterile. Obviously I knew that the person behind the camera makes all the important decisions to take a good picture and not the camera. So what was the fundamental difference?

The answer to my question was so simple that I couldn't believe that it took me so long to figure it out. The real difference between my iPhone and my DSLR photography was that my iPhone was always with me no matter what time of day it was, no matter where I went I would always have my phone with me. I wasn't planing on taking pictures like I did when I decided to take the "big" camera with me to the streets. Whenever I came across something interesting I would pull out my iPhone and take the shot as opposed to when I was heading out with my DSLR with the only goal to find something cool to shoot thus my images looked more contrived and forced. It sounds so super trivial now but this "revelation" helps me to take better pictures. When I set out to take pictures I treat my DSLR much more like my iPhone. Instead of trying to make something work I just wait until I come across something cool to shoot. Some days I come home with nothing but when I get some shots in there are usually some really good ones among them.

The conclusion of all of this is, as you've already guessed from the title, that you can't force good street photography or maybe even any type of photography.