This is a post from staff writer Robert Brokamp of The Motley Fool. Robert is a Certified Financial Planner and the adviser for The Motley Fool’s Rule Your Retirement service. He contributes one new article to Get Rich Slowly every two weeks.

This post is not for those of you who have focused minds and empty “to do” lists. Nay, not for those rarefied people who go to bed knowing that they got just about everything done that they needed to, and know they will sleep the peaceful sleep of the efficient and accomplished tonight, tomorrow night, and for most nights thereafter.

This is for those of us who bring our “to do” list with us to bed every night, like a scratchy blanket. It doesn’t go away; in fact it seems to get bigger, causing us to lie there and say, “What, exactly, did I do today?”

Sleeping kitty

Cats don't let "to do" lists keep them up at night ... or during the day.

Getting stuff done is important in many aspects of your life, and financial stuff is no exception. In fact, after my many years of being a financial advisor, Certified Financial Planner, financial writer, and guy who has to do financial things, I am of the opinion that self-management is one of the most important determinants of financial success. It’s all about doing the right things as soon as possible, and limiting the wrong things as much as possible.

You know, things like opening up those retirement accounts, getting insurance before it’s needed, remembering to pay the bills, sticking to some kind of spending plan (and monitoring it), submitting reimbursement requests and other tedious paperwork, doing investment research, searching for coupons, even being known in the office or to your customers (and, in my opinion, your colleagues are your customers to some degree) as someone who can be relied upon.

Such behavior requires all kinds of things, including the ability to focus, prioritize, and be organized. Unfortunately, none of that comes naturally to me. In my brain, it’s as if someone turned on a few TVs, invited over a couple of local bands, and set free a monkey that can play the accordion. (That monkey is so dang funny – he reminds me of Weird Al.) It’s a constant fight to zero in on the most important items that are splattered all over my to-do list, and stay focused on that one task until it’s done.

As part of that struggle, I occasionally read books about organization and productivity. Recently, I read “Take Back Your Life” by Sally McGhee. I’ve re-arranged my work- and home-related regimens, and have a plan for how I’ll get stuff done (more on that later).

But I’m also adding something that I learned from my two-year effort to lose more than six percentage points of body fat and shed almost 40 pounds. I had to have a measurable goal, and had to put something on the line that was more important to me than a smaller waistline – namely, money. I made a deal with The Motley Fool’s resident fitness guru, Ben Sterling. I agreed to work out four times a week, or pay $10 for every session I skipped. Also, if I didn’t lose those six percentage points of blubber by this past September, I’d owe $200. Finally, I let Ben take a picture of me shirtless, in all my big-gut glory. If he didn’t feel I was trying hard enough, he had the right to put it up on the screen during a company meeting.

It worked.

Principles of productivity

There’s lots of good stuff in “Take Back Your Life,” but here, for me, are the key takeaways:

  • You can never get everything done. Just accept it, and focus on getting the most important things done.
  • Develop meaningful objectives, and filter your workflow through those. If a task doesn’t support a meaningful objective, then it may not be worth doing. An example of how I’ve implemented this: I’ve given up feeling guilty about not doing enough yard work, since I don’t really care about having the most manicured property in the neighborhood.
  • Put what McGhee calls “strategic next actions” on your calendar, and stick to it. Why? As McGhee writes: “Your head and your To-Do list have no boundaries; they’re limitless. Reality lies only in the calendar because it has time limits. Use it as a prioritization tool, and it will assist you to be more strategic about what you can and cannot do.” Her research suggests that something is 75 percent more likely to get done if it’s scheduled on a calendar.
  • Don’t let your email in-box control your day; get out of it. When you’re in it, be decisive. “If every time you open an email message, you make a decision about what to do with it and where to put it, you can immediately remove it from the in box and dramatically reduce your in box size.”

Now, for my new regimen. I’ve identified the behaviors that I know increase the chances that I’ll get things done. This is still a work in progress, but the current idea is that every day, I need to:

  • Get up at 6 a.m. (tough for me, since I’m a night owl).
  • Devote the first hour to uninterrupted professional reading.
  • Decide on the most important strategic next actions for the day. I also like to think of these as the “big rocks.”
  • Put them on the calendar.
  • Do the smart things: I get more work done when I close out my email (and check it once an hour), work in 30-minute spurts (using the Cool Timer software to keep me on track), and occasionally work away from my desk (in a quiet corner of Fool HQ or at one of our stand-up desks).
  • Exercise at least four times a week.
  • Every night, spend at least an hour fully engaged in an activity with my kids, beyond the usual “how was your day” discussions.
  • Review my “Night” checklist that I keep in Evernote, which includes things such as packing workout clothes and whatever else I need for the next day, as well as spend at least 15 minutes on an important house-related project and 15 minutes on a finances-related project (which, in most cases, will be related to monitoring spending).

I have a few other things, but you get the idea. And finally, the working idea for how I’ll stick to it:

  • I have a spreadsheet that has each of those items in the rows, and each day of the week in columns.
  • Every time I get one done, I mark it off.
  • I regularly meet with Nate McMahon, a wise fellow who is in charge of professional development at The Motley Fool, and will keep me accountable (well, as he said, help me keep myself accountable). For every day I don’t get two-thirds of my daily must-dos done, I owe $10. For every month in which I owed $10 on 25 percent or more of the days, I owe an additional $100.

We’re still working on the details of that last one. Nate wants to add something that makes sure I have some balance between what I do for my job, my family, and myself. We will decide on the final details by this Friday. Feel free to offer your own ideas below.

Will it work?

Looking at my plan, I do wonder if it’s sustainable. We’ll see. Maybe, after several weeks, these behaviors will become habits, and I won’t need to track them each day. But for now, the system shares a lot in common with how I was able to accomplish my fitness goal:

  1. It’s measurable and track-able.
  2. It provides short-term and long-term incentives – including rewards (being more productive) and punishments (having less money).
  3. It’s potentially embarrassing. Here’s how: In two months, I’m going to report to you, dear GRS reader, whether I’ve succeeded. It won’t involve a picture of me with my shirt off… although that would involve an extra incentive. In fact, feel free to suggest something potentially humiliating that I’d have to include in my mid-January post if I don’t follow through. Nate will be the judge.

I’ve tried various systems before. I’ve always learned a thing or two, but they still weren’t enough to get me to fundamentally change my behavior. As I try once again to cage the monkey, I am reminded of my favorite Milton Berle quote: “Too many people simply give up too easily. You have to keep the desire to forge ahead, and you have to be able to take the bruises of unsuccess. Success is just one long street fight.”