GolbGuru over at Money, Matter, and More Musings recently asked me how I’m able to consistently post so much material on a daily basis and keep it as only a small part of a daily routine. The answer is fairly interesting, and it applies to many aspects of life, not just writing.

The biggest aspect of it is that I never really stop writing, though I only mechanically involve myself in writing for a small period each day. I do this by jotting down my own ideas whenever I think of them throughout the day so that when it comes time for writing (for me, usually after my son is asleep), I already have all my ideas laid out before me.

I also keep the pressure off of myself by staying very far ahead in terms of finished posts. If I were to suddenly fall off the face of the earth, as of this writing, the posting schedule of The Simple Dollar would continue for eighteen days. This enables me to enjoy little pressure to get something done right now; if I get burnt out for a bit, I can take a break for a week without any damage to the site’s momentum.

The big question that many readers would ask at this point is what about writer’s block? It is something that hits almost every blogger at some point or another – what on earth do I write about next?

The first tactic that I use is research, research, research. I read periodicals, visit other websites, and read books on personal finance without any expectation of any writing topics. This works almost every time for me; given some time, I almost always find something that gets my fingers hopping.

If that fails, I actually ask for help, but not in the obvious “ask my readers for help on the ol’ blog” way that many people do. Instead, I visit messageboards and actually ask people what sort of money questions they’re wondering about and make up a few of my own (often, they’re the topics of posts already written but not yet posted). Almost always, I’ll find a list of potential topics and at least one or two of them is enough of a nugget to get me started.

If I’m still stymied, I take a break. I don’t look at The Simple Dollar or think about it for a few days. This is where the “advance posting” really helps me out, as it uses the days where I can’t stop writing to cover the days where I can’t squeak out a word.

These three techniques have always cleared away my writer’s block. The interesting part is that most of these techniques are good ways to help yourself through anything difficult in life, from deciding whether to buy a car or a house to making a change in your own investments. Writer’s block has taught me many lessons in life, often in areas where I would least expect it.

Although I (really) like to bloviate about all sorts of personal finance topics, I keep many more thoughts on my own finances to myself. I’ve found that keeping a handwritten diary of my non-numerical financial thoughts has been invaluable (for the numbers, I use a computerized ledger).

I personally use a Moleskine daily planner for my diary-keeping needs. Each page is quite large and lined just about perfectly for my writing style, meaning I have plenty of room on a given page to fill it up with my scattered thoughts and ideas. It also fits nicely inside my jacket and also inside my briefcase, which means I can carry it with me wherever I go with ease. In fact, I often use it as a combination daily planner / diary, which means that I’ll write events in advance on that day, then use that day’s entry page as a place to collect my thoughts.

It turns out that Moleskines are often used for similar purposes, but not necessarily as a personal finance record. In fact, it has much in common with the classic tradition of the commonplace book.

So what do I write about? I simply keep the diary on me during the day and when a thought occurs that I want to remember to look at in more detail later, I jot it down. If it’s an idea that I might be able to write about on The Simple Dollar, I circle it. The thoughts are quite often broken little pieces of information, usually written in a weird shorthand that only makes sense to me, but that’s fine; it’s my diary.

I don’t restrict myself to only financial thoughts; I also use it to record upcoming dates (birthdays, etc.) and thoughts on all sorts of topics – personal issues, politics, entertainment, and so on. I generally don’t write much with each entry, just enough so that I will recall it when I reflect on my entries later.

Quite often, I’ll find later that I don’t even recall coming up with an idea, but I’ve jotted it down and it turned out to be a good one. This happens quite often (multiple times each week), and this phenomenon alone has convinced me that using such a tool is a great benefit to organizing my thoughts.

I also use the diary to record unexpected minor expenses, such as last minute gift items, an unplanned meal out with acquaintances, or a spur-of-the-moment activity. This enables me to keep track of such expenses and match them up with my budget at the end of each month.

Every few days (when I have a bit of free time), I review the last few days’ worth of entries in detail. I read through the points and investigate those points which continue to intrigue me; I also enter those noted expenses in my personal ledger. I often find that the ideas that still intrigue me when reviewing the entries lead me down paths of investigation that I would never have considered without the diary.
In short, I use this Moleskine diary to keep track of my various thoughts and use them as a record for later investigation.
It goes beyond a simple diary for me and becomes something of a memorial to my thoughts, ones that I hope will push me onward to greater things.