The book...

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The first thing he wrote was Being born.

Of course, when he did it, he was a depressed teenager with too much alcohol in his system and the deep sense of loss that came after the death of Jarvis. He crossed it over a few days later, when he hadn't exactly sobered up but, at least, he was no longer sitting on the floor of his apartment, holding a kitchen knife and watching his wrists with too much interest.

As it was, he decided to turn his would be suicide note into a list of all the mistakes he had made. Tony was pretty sure that when Jarvis had given him the leather bound journal for his birthday that hadn't been his intention but Tony had learned that things rarely work as intended.

In his drunken episode he had written fifteen items in the first blank page.

Being born
Missing Jarvis' funeral
Explosion in dad's workshop
Second explosion
Ignoring Jarvis' advice
Hitting Rhodey after the time with the mittens
Sleeping with Heather Wheels
Not being good enough for dad
Not being enough for mom
Not being smarter
Being me
Starting drinking
Making dad waste time with my stupid actions
Said stupid actions
Killing myself?

It wasn't the first time he had thought about it, not really, but he always found a way to push another project first, to keep himself from doing more than thinking. But now, with the light of day and the pounding headache of a hangover, Tony decided to think about it seriously, instead of emotionally, for the first time.

He knew he was a mess. Rhodey had said it to him enough times, his father had made it clear with his disapproval and disappointment, but was he such a mess that he didn't deserve to live any more? Jarvis had always said he should be more patient and stop rushing into things...

Tony looked down at the journal and flipped the blank pages. He took a pen a scribbled a new line.

Rushing into things

Maybe there were some mistakes he could correct. In the meantime, he would write, and he would wait. Eventually he would run out of space and time.

There were things that deserved bigger letters.

Yinsen took a whole page.

Jericho
Sonic Cannon
Amplified sound paralyzer

After Afghanistan and the press conference he used a page for each letter.

W
E
A
P
O
N
S

And there were names that appeared over and over again.

Pepper
Rhodey
Happy
Dad
Mom
Obie

The last time Tony wrote Stane with a normal script and No remorse for killing him much bigger.

Sometimes he didn't have the names to write. Civilian featured heavily in the book. Sometimes he wrote the wrong ones. Natalie Rushman.

He filled four pages after his birthday party, thinking that in the end it wouldn't matter. His body would betray him before his mistakes could. One rediscovered element later, Tony couldn't stop himself from adding, in a tiny cramped script, Saving myself.

Jarvis knew, of course he did. Jarvis knew everything about him and even though Tony kept the journal carefully by hand, Jarvis kept a digital copy. Tony tried not to ask too much. He didn't want to know how many times Pepper's name was there (1072), the percentage of items done while intoxicated (61%) or how many mistakes he had left (a maximum of 659).

Sometimes Jarvis asked him to erase one line or another, but Tony only used pen and the only line scratched out had been the first. Sometimes Jarvis tried to stop him from writing something, reason with him about how it wasn't his fault.

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