The actions that you observe in other people and yourself are just habits. If you are a natural follower, use it to your advantage and emulate somebody you think is doing a good job of being independent. I learn by watching and copying most of the time, and it seems to work for me. Find many good examples of the kind of person you would like to be and observe their actions carefully. Think about why they make certain decisions at certain times and what you would do in the same situations. Think about why you would make a different decision and what processes led you to develop this habit. Then deliberately do something different. It doesn't have to be perfect, but I think the key to any kind of meaningful change is to understand your own processes and then do something - anything - differently the next time you are in a similar situation. The fact is that you won't know what it looks like for you to be very independent until you get there, and getting there involves an evolution, not an upgrade. We are living things and we don't change in steps; we change gradually over time. You can't trade yourself in for a different model, but you can deliberately make different choices and see where it takes you. Luckily, you have the tool of self-evaluation throughout.
It all goes a little something like this:
1) Wow, that person did something I wouldn't have done. Why?
2) What would I have done in her place? Why?
3) I know that I tend to do X because of Y, but now that I am faced with this again, I am going to try that person's logic and do Z.
4) Repeat.
I think you can do this just about any second of the day. Even when you are alone. You can think of somebody you have identified as more independent than you and what they would do if they were there in your place alone. Ultimately, we could make a long list of by-yourself or with-friends activities you could try, but none of it will change the way you view your place in the world and your relationship to other people without you actually changing how your view yourself and your relationship to other people! (Don't you love circular logic?) What I mean is that what you are talking about is an internal kind of thing and you won't really achieve what you are looking for if you limit your quest to externals.
I would suggest using this thread for help in analyzing specific behaviors. For instance, why did you choose to train for a half marathon? Why does it symbolize independence for you? Where did you get the idea? When you picture yourself finishing, what else goes into that picture - what other qualities do you see in yourself that you don't possess now?
(Btw, it's nice to see you around here again. I'm not around too much myself, but I noticed.)
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"I've missed more than 9000 shots in my career. I've lost almost 300 games. Twenty-six times I've been trusted to take the game winning shot and missed. I've failed over and over and over again in my life. And that is why I succeed."
(Michael Jordan)
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