Hi Cordiva, This is a great question that more folks should be asking themselves. Im 38 years-old and believe that I have sorted my way through this dilemma over the past 10 years or so. I've decided that maintaining multiple personas online is unhealthy and unrealistic. Here's my advice:
1) Focus on the person you want to be. This sounds new-age kooky, but it's legit. If you are going to be embarrassed by a picture of you, think about stopping the embarrassing behavior, rather than the photograph. The older you get, the easier this gets.
2) Never post anything online that could be damaging to you professionally or personally. Avoid posting questionable content about your friends and ask them to do the same for you.
Note that this doesn't mean you should mix your professional and personal information online. On your professional blog, for instance, it's a good idea to keep personal information to a minimum; simply because the personal stuff is not interesting for most of your readers. So, it's perfectly reasonable to have personal and professional "spaces" online - but don't attempt to maintain them as separate identities. Call them what they are - different spaces targeted at different consumers - but all different facets of the same you.