As one of the few who started growing out from bald, I thought I would type down some of my experiences and advice.
I started growing my hair out after I had cut it all off due to extreme damage. I was considering bleaching my hair and a friend of mine told me to use lemon juice, "Because it's natural and gentler on the hair." I thought that made sense since I didn't know that the acid in lemon juice is very good at breaking up protein bonds. What does 80% of your hair consist of? Protein!
The result was that my hair got extremely damaged and I wasn't a patient detangler, so I damaged it even more. I was literally ripping out squirrels! It felt and looked like hay. So, I had to cut it very, very short to get rid of the damage. But I thought about it and decided that since my healthy hair was no more than a month of growth "long" I might as well just shave everything off. Just to for once in my life trying to be completely and utterly bald.
Bad things about starting over from bald/extremely short
You will have to get through all the awful growing out-stages
Hair will be all layers
People will look at you strangely
You risk sunburn on your head
You need gel or the like to keep hair out of your eyes
You will need to have your short hair cut into shape along the way or you get that icky microphone hair and that will take even longer to grow out
Good things about starting over from bald/very short
You get the chance of getting rid of all your bad hair habits
You can get to clean and moisturize your scalp as well as your skin
Hair will be too short to actually tangle so you won't get any detangling damage for a year or so
You will appreciate it more
Would I recommend it?
I don't think so. If you think about it, you'll have to realize it will take at least two years before you can even put your hair up in a pony tail. Two years… think about it. It's a long time before you're through it. Would it be worth it?
On the other hand, if your hair is or is going to be very short, why not? Consider it a once-in-a-lifetime experience in line with bungee jumping or other horrifying yet thrilling experiences.
0 to 2 months, 0 to 1 inch long hair
At this "length" you can throw away all your previous routines. I suggest that you don't use shampoo or any traditional hair products since there's so little hair to wash anyway. Threat your scalp like your facial skin: Clean, wash, tone and moisturize with your regular skin care products.
Try to take advantage of this once-in-a-lifetime chance to really spoil your scalp. Moisturize, moisturize, moisturize!
Remember that those short hairs will be your ends for lots of years. Stimulate your scalp to grow them strong.
Stock up on sunscreen! Remember that your scalp has been protected under your hair most of your life and is very sensitive. Add lots of high factor sunscreen every time you step outside the door. Use a higher factor than you use on the rest of your body - the skin on our body is used to it but your scalp is not.
Styling options: none, really. Hair will stick out straight up and not really have any possibilities. If you want to style somehow, try using leave in-conditioner designed for hair and scalp. You can use aloe vera gel, but most likely you won't need a product with a lot of hold.
Avoid harsh styling gels since it will get on your scalp.
Hair styles: none, really, but knock yourself out with scarves, bandannas, cute hats and wigs! Buy some fake hair and put under them to play around.
2 to 4 months, 1 to 2 inches long
Hair will start to lie down at this length.
Keep up with the moisturizing and sunscreen as long as you feel you can "reach" the scalp and the cream won't be stuck in your hair. Start using "real" hair products to shampoo and condition your hair. Find some designed for hair and scalp
Try measuring the hair you shed to see how fast it grows. At this length it will be very accurate because you can measure with a real ruler.
Stock up on aloe vera gel and products designed for hair and scalp.
Styling options: different styles with gel or leave in-conditioners. Aloe vera gel offer both scalp care and some hold. Try playing around with the part. It can make a huge difference to your appearance!
Avoid gelling hair down. It just looks weird at this length.
Hair styles: scarves, bandannas, cute hats and wigs. Buy some fake hair and put under them to play around.
Begin to use headbands to hold the front lengths back from your face or use small clips and claws to pin pieces back.
4 to 14 months 2 to 7 inches long
Now the hair will start to get in your eyes! It's a very annoying length and you will need to start gelling it up or sweep it to the side. Try using leave in-conditioner if you don't need as much hold as the aloe vera gel offers.
This length is great to really notice your hairs natural growth pattern. Work with its swirls instead of fighting it. This information will come very handy as it grows longer. Where does it part naturally?
If you aim for one length hair it will be too short to put up in a pony tail.
Stock up on: Lots of pretty little clips, barrettes and claw clips. Leave in-conditioner and aloe vera gel is still necessary.
Styling options: Gel up, gel to the side and lots of little clips to hold it. Try playing around with the part. It can make a huge difference to your appearance!
Avoid the dreaded "mushroom" cut (long hair on the top and short at the bottom) if you have a lot of volume in your hair!
Don't give up! This length IS very annoying, but it WILL pass. You WILL get through it and have a life of wonderful long hair.
Hair styles: Scarves, bandannas, cute hats and wigs. Buy some fake hair and put under them to play around. Begin to use headbands to hold the front lengths back from your face or use small clips and claws to pin pieces back.
Try doing little piggy tails with lots of lose hair poking out around it. High piggy tails may be able to pull hair away from your face. You can make little messy buns too at this length. Try dual high buns (aka "Mickey Mouse ears").
14 to 28 months, 6 to 14 inches long
Now the hair will be long enough to put in a pony tail! When you pony tail you can follow how more and more of the hair on the back of your head can be put up. See the "line" creep down towards your neck.
As soon as you can, stop using harsh styling products and switch to gentler leave in-products when you no longer need the strong hold.
Hair styles: Scarves, bandannas, cute hats and wigs when you feel like it. When your hair gets longer, wigs can be hard to do if you have too much hair to hide under them, so take your chances now. Use headbands to hold the front lengths back from your face or use small clips and claws to pin pieces back.
Try doing piggy tails and you can make little messy buns too at this length. I really liked the cute double buns at this length. Also do French braids to pull layers back form your face.
28 months and more, 14 inches and more
Hair will now be shoulder length or longer. Most people will consider this length "long"
You will be able to make the first "real" buns and braids
Stock up on: Inspiration to play with the length!
Styling options: Soon all styles will be possible! Look around to get inspired to play with your new length.
Avoid letting the idea that "women over 30 need to have short hair" or other similar idiotic ideas get to you!
Hair styles: Piggy tails, ponytails, braids, French braids, buns, double buns and many more.
I hope this is useful to someone!