I empathize, Jenni, and I find your inspiration photos very inspiring! I say go for it, and as I've been dealing with some similar pixie decisions lately, I'll offer these tips: 1) Texturizers (hair waxes, pixie pastes, gels--try several and see what you like best) can create shape when you're not quite ready to cut, creating the illusion of more length and adding that touseled airiness that is so appealing in pic #1, and which looks younger and fresher than a too-pat hairdo; 2) A bit of strategic makeup (check out Lisa Etheridge's wonderful online tutorials for great advice on eye emphasis, soft lip color, and other tricks that work so well for the models in your photos) can do wonders, so consider buying a few new products to play with; 3) Consider adding a pair of statement glasses to your nice neutral ones (take a frank and stylish friend frames-shopping with you, and try some shapes and colors that are slightly outside of your current comfort zone, but that work beautifully with your coloring, face shape, and wardrobe.) Good luck, Jenni! You have great hair from what I can see, and the color is lovely. Let it grow, and make this change work for you.