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I want to start out giving free sessions or being a free second shooter, but apparently you can't trust "free". Seems like when I charge, I get loads of people interested, but when it's free there's no one. Which sucks because I don't feel good enough to charge. I have Social Anxiety (like super charged social akwardness) that makes it even harder.
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I totally agree! People don't trust free! My friends ask me to help them with their dogs, so I of course don't charge, and they don't take the advice! I have started making them trade me. Hair cuts for training... win win!

My clients always take my advice, apparently when you pay someone $80 and hour you probably value it more.
My sister in law started doing photos on craigslist for families, cheap. She would put them all on a disk and have people do their own editing. Now she has her own little business. My brother is a marine, and she built up a good client base of military families. I have 5 other friends who are photographers and they started working for studios, hired as second shooters for professionals, or went to school and started advertising on CL. One of my friends does work for a real estate company. She self started as a hobby. She takes gorgeous pictures of homes for sale making them look homey and welcoming.

When your little ones get older maybe you could pursue it more. I know how hard it is to have a home bushiness and try and raise the kids(I failed. lol It worked for a while but both started to suffer. I had to choose, and I picked my son.). I love the pictures of your pups!