In my case, it is easier to be open with people I hardly know. All my fiends and family do have strong opinions and outdated views of myself. Talking to a stranger who is willing to listen is easier and deeper.
What I found personally tricky is to advertise my professional hedge as a mobile dev.
I have received lots of resume of freelancer to help me on projects, and it is always quite difficult to know how professional and experienced they really are. Any blog or contributions to open communities (stackoverflow, github etc.) are very useful.