Worth the effort or not?

When we bought our current home, it was needing some finishing touches. Not a lot, most of them were cosmetic needs. But they needed to be done. So a friend of mine and I repainted about half of the downstairs. Then she went back home and I lost steam and the downstairs never got finished. I repainted the half-bath. Then I painted my bedroom to cover up the hideous mural that had been left by the previous owners. We had a bonus room finished. The house was starting to come together. 

But it's taken awhile. More time then I would have liked, but isn't that the case with most things? I come to something new, either a new store, a new experience. Or maybe something bigger like a new home or job. Anything new takes some adjustment. It takes some fine tuning to get it right. To get it to the place that you feel like it's yours. 

What if it never does, though? What if I never feel that I have true ownership over the something new? What if I never feel like I'm invested? Even a small bit? Does this make the new whatever it is invalid? Or even worse, a bad choice? Is there a time limit to how long it takes to feel invested? I don't know.

Sometimes I can jump right in and make a fast connection. Some people and places just feel good to be with. But how many times do you reach out and get rejected? When do we draw the line in the sand that says I'm not going to let you hurt me any more? I think that looks different for every person. I'm still trying to figure that out for me.

Do you have answers? What has worked for you? When have you walked away? When was the effort worth the output?