How do you know if you will never find someplace to plant roots?

I've been staying with a friend in Chicago who is in a somewhat similar situation as I am. She is not American, she moved here for college (with me on the east coast) and since then has lived in two major cities (one obviously here and the other on the west coast) and at least four different apartments. She's now feeling the itch to leave Chicago for various reasons . . . but partially it is because she is bored with it and just doesn't feel at home.

You can see that we have a similar rootlessness. We had a long discussion about it and I will attempt to summarize the major points here. She also shares my fear that I will never find a place to stay for a long period of time, plant roots if you will. She has also noticed that most other people don't seem to have this problem. I myself have watched many friends be adventurous . . . and then stop, or head back to their home towns and seem to never leave again (even for vacations!). I can count on one hand the number of people I know well enough and know that they are similarly constantly moving and don't have a "home" that they are living in or aiming to live in. I initially tended to assume that there are more people out there like me, that i'm just not seeing, and that it is a side affect of our global society that provides these sorts of opportunities (perhaps forces them at times - like relocating for a job that moves HQs). I don't know that I like that construct though -  it makes me feel like a casualty of society.

Together we came up with a different hypothesis - that yes, there have always been people that stay in their same home area, and there are those that move long distances and then make roots there (ie. immigrants), but there have always been people like traveling salesmen . . . that live on the road and make their life where they are. Which is kind of how I feel - I miss people from places I have lived before, and there is a special place in my heart for the valley I grew up in, but I really haven't missed a place or a larger community in awhile - not like some of my friends who seem to mention their "homes" longingly several times a week. This construct isn't perfect either - but it makes me feel like I am a more rare personality type, rather then weird or somehow unable to find my "home."

I don't know that this conversation helped me get closer to deciding if I want to pursue Canadian citizenship - it definitely made me concerned that I will get bored with Canada and want to move on before I get through the process though. I'm also not yet ready to give up my desire to find some place to root, but conflictingly, when wanderlust strikes again I don't think I will be able to turn it down . . .