To color, or not to color?

I can do a lot of things pretty well.  I'm crafty.  I have an eye for home interior design. I have pretty good handwriting.

There are two things that I don't include in my list of "things I do well."  In fact, they would probably belong in a "things I can't do at all and barely struggle to grasp the basics" list.  Hair and makeup.  They're completely foreign ideas to me.  Kudos to you, girl that watches YouTube videos on contouring and experiments with different colors and types of makeup.  I wish I was you.  I don't know the difference between a lipstick and a lip stain.  I have no idea what colors look good with my skin tone.  I've had pretty much the same makeup routine since high school because I don't have a clue how to vary it.

Don't even get me started on hair.  I am so envious of you, girl that can get up each morning and do different things with your hair.  You know how to French braid?  to do a messy, but adorable updo?  to make your plain ponytail look fancy?  Teach me your ways.  I have three hairstyles:  down, pinned back and a ponytail.  That's it.  I have recently started using a lifting spray, thanks to a recommendation from my cousin.  Other than that, my hair routine is pretty basic.   The idea of changing my hairstyle gives me a slight case of the panic attacks.  I don't know what style looks best with my face shape.  I've pretty much always had the same two hairstyles....long or a bob.  I don't know how to make my hair look better when it's curled.  I had a perm once.  Can we not talk about it?  I still have emotional scars.  I highlighted my hair for a small period in high school.  That took a week's worth of convincing myself that it wouldn't be the end of the world if I put a little color in my hair.  Even so, while my hairstylist was putting the highlights in, I felt the very strong urge to throw up.  I don't do well with changes to my appearance.  You see, I don't have a very good image of myself.  My self-confidence is almost in the negative numbers and I always see the flaws in myself when I look in the mirror.  Maybe that's why I struggle with an update.  I think that, no matter what I do, it's really not going to matter.

Lately though, I've really been feeling down about myself.  I don't have many new clothes that I feel good about.  The clothes that I do have make me feel frumpy.  When I look in the mirror, all I can focus on is my acne that has decided to plague me in my adulthood.  No amount of makeup I apply will cover it and make me feel less self-conscious.  So, I've decided I need a change with my hair to hopefully pump up my self-worth.  My hair is a dark brown color.  It's very, very thin.  Has almost zero volume to it and lays flat on my head.  I'm dying for a new color.  I want to add dimension to my hair to where it doesn't seem so flat and one-dimensional.  Plus, I looked in the mirror on my way to work the other day and saw this:

GREY HAIRS!!!!!! 

I'm 28!  I'm not supposed to have grey hairs!  Curse you, dark hair and the tendency to go grey earlier!! 

So, now I'm freaking out.  I cannot have grey hairs.  Nope.  Nope. Nope.  I'm really feeling the urge to go color my hair like yesterday.

Except, read above where I explain where I'm basically illiterate when it comes to the language of beauty.  

So many colors.  So many styles.  How the heck is a girl, with basically no beauty/cosmetology sense at all, supposed to decide what to do with her hair??

Part of me is tempted to just go to my stylist, plop down in her chair and say "Do your thang."   Except 1.)  I never actually use the word "thang" in real life.  And 2.) I'm too much of a control freak for that.  

Here's where you come in, my totally awesome readers.  Help. Me. 

What you should know:  I have shoulder-ish length hair right now.  I'm working on growing it back out.  I cut it short about a year ago and loved it, but I want it long again.  I have "grass is greener when my hair is whatever my hair isn't right now" syndrome.  I have short, I want it long.  I have long, I want it short.  Oy.  

Back to the color.  I do want to stay in the brunette family.  Don't go suggesting that I go blonde because I have plenty of fun as a brunette, thankyouverymuch.  Red is off-limits.  My sister Dayna is the only redhead in the family and she rocks that shizz.  No way I could ever compete with that. 

Dayna has people come up to her often and ask what number her hair is.  God-given, baby.  I hate her a little for it.  How did my sister get awesomely unique and totally thick hair while I got what I got??

Anyway.  My original thought was to keep the dark shade of my hair and put light in it.  Kind of liking these examples: 

Really love the girl on the left.  But that seems like a big change from what I have right now.  Wuss.  Right here.

So I'm kind of gravitating towards a style that is a little more even and blends really well throughout.

Basically, I'm a chicken and I have no idea what to do with my hair.  Help??