How did you handle your portfolio and business when starting out?
Good on ya mate, sounds like you're on the right track! I think most amateur photographers turned pro have traveled a similar path to what you're on - you've enjoyed photography as a hobby for some time, and you've probably gotten a great response to your art from friends and family. If pursuing portraiture as a profession inspires you, then it's certainly the next big step!
What you're doing is great - continue to refine your art while working with friends and family, ask for honest critiques from them as to what they most enjoyed or didn't about the shoot, any awkward moments, and what their favorite and least favorite photos are from your shoots together. Treat them just like a client, except give them carte blanche to be brutally honest. Better to learn your weaknesses before you're working with paying clients.
Then take the leap! Put your business cards and web site out there, let folks admire your art and hire you to do more of the same for their families - it's not nearly so risky or complicated as so many would like you to believe. A lot of great photographers just fall bass ackwards into the profession, just like any other career.
To actually answer your question, I got into doing paid portraiture back in high school. I bought a small digital camera to take photos of and with friends, and ended up interning with my local newspaper as a sports writer and photographer. As my photos were published and bylined in the newspaper, I had folks compliment my work and ask if I did family and senior portraits - I eventually said yes, set my prices (by completely making them up from thin air), and so began what has turned into a now 13-year career.
My day job is still with the newspaper, but my side job is owning my photography business, which I'm proud to say in 2009 earned me more with an average of four hours a week of work than my day job did in 40 - as it has every year since.
Pursuing a part-time or full-time career in portraiture is a wonderful experience, offering rewards both financial and social. If you're even asking the question here, you're probably ready for the next step - educate yourself the legalities (DBA, sales tax, etc.), set your prices and policies, and go for it - you have a real opportunity to be a blessing in your community.
Best of luck!
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