How is your "I love me Book" set up?

Mine starts with an ERB, followed by the stuff, in order, that you see in your iPERMS so that someone reviewing my record will see everything in order with my iPERMS.

That being said, I only have a physical book for someone to look over. My REAL record of stuff is saved digitally to the cloud. I despise paper products, I only use it because CSMs generally won't look at my board file without a physical copy of stuff.

I kept mine pretty basic. Awards, Schools, Promotions, ERB, Civilian Education and my Bio. What I did add was a CD with a digital copy of just about everything thing else I could think of.

I categorized mine for various reasons. One of those was in case I needed documents of a particular category, say evaluations, for an employer. I kept my last three NCOERs and group them together. From the categories I go in order of precedence then date.

Chronologically; civilian and military alike.

For doing a digital version of your I Love Me Book I'd recommend using DropBox/Google Drive.

Personally I have 2 books: 1 with all of my Awards/ certs in chronological order. The other, photocopies of the aforementioned awards/certs and everything else organized ERB, HS/College, NCOERs, Awards, Certs, Property. I keep the 2nd in my locker at work so I can dig it out and make photocopies whenever but the DropBox makes working from home easy.

I have my CIV Resume at the front then my orders in order by date then PT card, Army drivers licence, then BCT cert, AIT cert, then any army schools that i attended then any online courses and then i add all other stuff to the back. like transcripts from my colleges and civilian awards or certs.

Mine is a pretty full 4" binder organized into the following sections:
1. Personal info: Birth cert, HS diploma, EPSQ copy, physical, etc.
2. NCOERs
3. Training certificates and military ed. diplomas
4. Awards and commendations
5. Civilian ed transcripts
6. Misc.

I have found this method to be good for me. At home, I have a file box filled with paperwork from my USAR and NCARNG service, copies of orders, and enlitment/reenlistment documents. It doesn't really matter how you organize everything, as long as you keep it somehow.

I have a 3-ring binder organized into several categories, which are then organized by date.

I. Promotion Warrants
II. MOS Schools, Certifications
III. Professional Military Education
IV. Awards
V. Civilian Education
VI. Misc.
VII. Master Brief Sheet, followed by past Fitness Reports
VIII. Original orders

If I have a graduation picture, it goes behind the corresponding certificate.

I also have friends who simply organize everything by rank, e.g. the promotion warrant, followed by everything they have from that rank.

You would have to ask my Daughter how she did it. Got one several years ago from her and it is pretty cool. I sent her a lot of pictures and what I got back was pretty impressive. I wouldn't know where to begin editing down 21 years.