If you struggle with organization in several aspects of your life, you may have multiple, lengthy to-do lists that don't ever seem to get any shorter. The purpose of a to-do list is to help organize tasks and establish some priorities for a given time. If the lists you have written essentially scream, "Why can't I be a different person?", it may be time to take a closer look at your practice of goal-setting. Chances are, you are so hard on yourself that your to-do lists are actually a discouragement.
To-do lists full of vague or overly ambitious tasks can have the same effect. Instead of writing down massive tasks that will take years to complete, it may be helpful to jot down long-term goals ("write novel") separately for your own guidance. Another interesting consideration is whether your to-do lists would be less demanding for an employee or a child, and why you would put more effort into making them seem doable and encouraging for someone else. You probably would not put the equivalent of "Master calculus" or "Build new house" on a daily task list for another person, so why wouldn't the same standards apply to yourself?
Here are some suggestions for creating manageable to-do lists:
Nothing is ever a "snap"
Tasks that are big enough to end up on a to-do list typically take more time than we care to admit. Take the everyday example of "Paying the (xxx) bill." Unless you are one of the highly entertained Millennials depicted in bank ads (what is so funny about banking anyway?), the process of logging into a website and completing the required steps or writing a check will take considerably longer than anticipated, particularly if your password isn't recognized and you need to create a new one, but let's not go there.
Your to-do list needs to include sufficient buffers to reflect the reality of daily life. Of traffic jams, invalid passwords, and full waiting rooms. Adding a "reality buffer" to tasks on your to-do list is a useful tactic to keep you on track.
Break items taking 20 minutes or more into several steps
Items on to-do lists need to be so manageable that you can complete them in 20 minutes or less. Whenever you notice resistance and keep postponing a task, divide your work plan into more manageable chunks. Instead of writing "clean up desk" identify practical steps that will move you toward better office organization. Such steps may be "create folders," "recycle old newsletters," or "decide if printouts are needed." For emotional reasons, challenging and daunting tasks tend to stay on our to-do list much longer than "buy wine," which somehow always gets done. It can be helpful to remember the Japanese art of wabi sabi, which focuses on appreciating the beauty in our naturally imperfect world (and the fact that your mother most likely doesn't work where you do).
The to-do list format has to make sense to you
The principle of bullet-point checklists is useless for those who are not linear thinkers. If conventional lists tend to fill you with despair, try experimenting with a mind map, virtual sticky notes, or a color coding system. You may be better off using a large whiteboard or display system to arrange your thoughts. Observe how you typically take notes and use the same approach for your personal task planning.
Nothing is more discouraging than carrying around a list of unattainable goals. Usable task lists consist of steps you can successfully complete and cross off. Long-term goals can provide helpful guidance on priorities, but they can only be reached in small steps – the tasks on your to-do list. "Removing a mountain," a Chinese proverb says, "begins by carrying away small stones."