A/N: Ah-ha! I'm finally back with an update! Sorry for the delay, but I was trying to update my other fics as well, and have been a little pressed for time lately. But thanks to everyone who reviewed, followed, or added to their favorites before, I'm always delighted to see such positive feedback! ^_^

And yes, to any of those who noticed: I changed the name. Though I liked the 'Me & My Shadow' part, I wasn't fond of the original name, but for lack of a better idea used it anyway. But then the new title came to me a little while ago, so I went ahead and changed it. Feel free to let me know which one you like better. :)

~Shikaku on Regret & Doubt~

Dear Shikamaru,

You were promoted to chunin recently. Congratulations again.

I haven't really been keeping up with this very well, huh? I started it when you were promoted to genin, and now here you are a chunin and I've only written two entries...you really are growing up fast.

But really, good job son. I'm proud of you.

You've given me something else I can lord over Choza and Inochi. Their kids didn't even make it to the final stage of the test. Plus your little stunt at the end of your match won me and Choza free drinks, I told Inochi you were going to forfeit, heh heh.

But anyway, what with all that has been going on lately, I thought this would be a good time to bring this up: Regret.

As you get older, you'll find regrets will still somehow sneak up on you, no matter how you live your life.

It may be a few simple, small things; 'I wish I had gone to that place when I still had the chance', 'I shouldn't have done that instead of that', 'If I had paid attention when he had told me the first time I wouldn't have made such a fool of myself!', and so on and so forth.

But then there are the other things, the more important things, the ones that could have altered your life in some way. 'If only I had gone on that mission instead, he wouldn't have died', 'If I had just been faster, or done something differently, nobody would have gotten hurt', 'If I hadn't said that, we'd still be friends', 'If I had told her how I felt, we might still be together right now'...these are the ones that will eat you up inside if you dwell on them, son.

Which is why you can't dwell on them.

Everybody has regrets, be they big or small, and they're lying if they tell you otherwise.

This is all especially true of us shinobi.

We, who must make split-second decisions on the battlefield. Who in an instant can end or save one's life, and who can't always foresee the consequences of those actions. Perhaps we're assigned to keep a foreign daimyo safe, and then said daimyo improves relations between our countries. Or perhaps we're commissioned to assassinate someone, who's comrades later declare a war in response.

But regardless of the outcome, we can't let our regrets dictate or ruin our lives. We must pick ourselves up and move on.

When you do make a regrettable mistake, you can learn from it without dwelling on it.

If I'm going to be honest with you, most of my regrets involve alcohol, Inochi, and Choza.

Then there was this time that had all of that, plus an ill thought-out dare involving-ah, I don't think I'd better put that in writing. The ANBU never figured out it was us, and I'd rather not leave any evidence.

This is going to sound stupid, especially now that I'm writing this to you, but I often regret how much time I spent with you as a child. I wish I could have done more, now. Maybe have been a little more patient, tought you a little more, just...simply done more.

Yet I can't dwell on any of this.

Instead, I simply acknowledge that, yes, I wish I could have done more for you as a kid, but I know now that I can't, I'm going to do what I can for now.

Then there is regret's more immediate cousin, Doubt.

Self-doubt can eat you up almost as bad as regret can. Which is why you can't let it.

Never doubt your instincts. As a ninja, I can't stress this enough. Doubting yourself will inevitably lead to failure, no matter what you're doing.

But...it is okay to have some doubts, son. Everyone does.

For instance, I highly doubt you're going to make it to adulthood without doing something stupid to embarrass yourself in public. (Sorry, your 'grand' entrance onto the chunin exam field is still fresh in my mind)

My point being: It's okay to have some doubts about yourself...but the important thing is to believe in yourself more than you doubt yourself.

Do you remember my little talk about friends? If you are ever doubting yourself or your abilities, let them help you.

I know a certain little Akamichi who's never held more doubt than belief in you.

And if that still doesn't help, and you still find you're doubting yourself...well.

Don't worry.

Your mother and I will still believe in you, and will never have any doubts or regrets when it comes to you.

(Except about the embarrassment thing. And you know, I still regret not spending as much time with you, and I'm sure Yoshino regrets dropping you...just kidding just kidding. And well your mother and I may have a little trouble believing in you if you decide to become a serial killer or a pimp or something, but don't worry our love is still unconditional, I'm sure)

(And about the above message...you're never going to get too old for me to stop messing with you.)

Your Father

A/N: I had mild writer's block on top of my time issues on this one, and it went through a lot of editing, though I think part of it was the somewhat gloomy subject. I've been looking forward to writing the next chapter though, which should be longer and more lighthearted.

This entry takes place right after the 'Sound Invasion' arc (after Shikamaru has been promoted). So when Shikaku mentions Shikamaru's 'grand entrance' still being fresh in his mind, he's talking about how Naruto 'helped' Shikamaru enter the battlefield during his chunin exam battle with Temari.