How do those who are organized help those who are close to them who are not? Below is a message I received, along with my answer. It might help someone else in a similar situation:

Dear Frank,

As a matter of fact we are both working. He’s in the real estate business and I’m an economist in the telecommunications sector. I’m somewhat of a compulsive organizer, with a thing for labeling up everything: boxes, folders, notebooks, envelopes, you name it. Though I’m messy here and there, I try always to develop “methods” to ease up my life and keep my things in order. Shopping lists, to-do list for traveling and so on. I like to plan ahead and make sure there’s nothing to be running for in the last minute.

My boyfriend is the opposite, and from what I’ve seen, it’s mainly because the thought of doing something complex is dreadful. He often concentrates in the small parts instead of the “whole,” and truly believes that luck is on his side and that if he does things in the last minute they will come out fine. Has never been so, but he conveniently blocks all the hardships out. He forgets routine things such as having lunch, doing laundry, paying bills and taxes and so on. Then, often the first reaction to an organizing plan, is negative. “Yes, but it won’t work for me,” “It won’t work because I’ll sure will forget to carry it/check it/write or record into it” and so on.

Currently my approach is “Yes you can!” and “Stay positive,” however I do realize that we must keep it really simple for him to get on board with the program. Thank God, once he’s sold on the idea he keeps doing it, as long as he sees the results in a fairly short time. He does have the drive, but he needs constant motivation and quick results in order to stay on, and this applies to anything: language learning, organizing methods, gym routine…

The notepad idea hit a bump in the road, since he found it tiresome to have “yet another notepad” to add to the 5 or so notebooks he randomly uses to write down things, which contribute only to the mess since he rips off the piece of paper and them misplaces it. I’ve been talking to him about a “cop-like notepad” which he could carry in his pocket and have at hand when ever he needs it to remember something.

Please, if there’s any other tip or idea you could give us, I’d be delighted to hear/read it.

Kind Regards,

(Name Omitted)

Dear Reader:

Here is what I would suggest as being essential:

A physical in-box. That is the place to just throw everything until decisions can be made on it. The mail, miscellaneous paper, etc. all goes in there. Even throw the box from the tube of toothpaste in there to serve as a reminder to put toothpaste on the grocery list. From there it’s a matter of making a decision about each item in there. Once you touch it, it can’t go back in the inbox.

Tickler files. That will hold all of the paper that he needs at some future time. For example, maybe you want to pay bills twice a month. Pick those two days. Every time a bill comes, it gets put in the tickler file for the day you want to pay them. On that day, they are all there together. Here is a chapter from a book I wrote a couple of years ago on the subject.

Something that goes with him all of the time to write down whatever he goes. That’s where something like cop-like notepad would come in. Something small enough that it would go in his pocket and be with him all the time. Here is a post that talks about what I carry. Even though I have my BlackBerry, sometimes you just need a memo pad to jot something quick. Plus, I have to have something anyway for credits cards, driver’s license, etc., so I might as well combine a memo pad with it.

Depending on the complexity of his day, the whole system could be as simple as jotting things on the pocket memo pad, one page per item. Throw them all in the in-box. Then, decide what needs to be done on future days and drop the notes in the tickler files to re-surface on the desired days. Every day, dump the notes on the desk, put them in order the way they need to be done, and there are the marching orders for the day. For things that repeat (change the air filter every month, pay the rent, etc.) put each one on a separate note and at the bottom, put instructions for when it needs to happen again. When those notes put up in the tickler files, do the task and then re-file the note.

You mentioned he has several notebooks. You might look to see what each one is for and if they could be combined into one. Even though I am very digital, I have a paper journal that goes with me to every meeting, every one-on-one conference, and is beside me when I am on the phone. Everything is chronological. I just put a date at the top of the page and take notes from calls, meetings, etc. one after the other. At the end of the day, I make decisions about what needs to be done about each of those items, and the results of those decisions go on my to-do list. Beside the item on the to-do list, I often put in parentheses the date of the notes. That way, when I start to do that particular task, I can flip back in my journal to the conversation and see my handwritten notes without ever having to recopy anything.

reQall. Here is an idea that might be appealing if your boyfriend likes technology. Check out this post: Instead of pulling a memo pad from the pocket, with reQall, he would pull out his cell phone, hit one speed-dial key, talk, and everything he said would show up in an e-mail message to him. reQall also has features that would put together a to-do list for him. There is both a free version and a subscription one. The free version gives plenty of features. If you set up a reQall account also, you could call reQall, talk, and have it “share” the message with your boyfriend so that it ends up in his e-mail. It would be like you are able to add things to his to-do list even when you are not with him.

See what you think about some of this and let me know.