Outlook from the Inside Out: Step 1

The first step in taking on my Outlook problem is asking "What is Holding You Back?" Morgenstern suggests 3 possible answers:

1. Technical Errors:  Simple mechanical mistakes in the organizing system
2. External Realities:  Limitations beyond your control (transitions, no more room, job cuts)
3. Psychological Obstacles:  What's inside you that leads you to gravitate toward disorganization.

As I examine my overflowing inbox and never-ending overdue task list, I see obstacles in all 3 categories.  A (non-exhaustive) list:

Technical Errors: 
I'm not using my folders in any kind of effective way.  I keep everything I remotely want to remember in the inbox because I'm afraid it will be lost forever anywhere else, because....
My system of flagging emails for follow up has become meaningless since the list of overdue items is so long it is ridiculous.
My organization system was designed for a development office that was just me; my own system is holding me back from delegating effectively with my new staff member.

External Realities:

Donations from individuals, foundations, and businesses are 70% of our organization's revenue. Growing as an organization requires increasing donation revenue.  Grant proposals have become more complex and have more expansive requirements for outcomes and reporting.  So even maintaining the same number of grants takes much more time; growing our funding base happens on top of that. Responsibilities beyond the scope of development have been added. I have, gratefully, been able to add one other person to work on development, but it only addresses a portion of the need.

Psychological Obstacles:
I'm not surprised to find some accurate descriptions of myself here. Obstacles that resonate are the need for perfection (waiting to have time to do the job perfectly), fear of success/fear of failure (letting disorganization hold you back for fear of what might happen without that excuse), and unclear goals and priorities (taking on too much and feeling scattered in a million directions).

Organization is not my savior, just a tool to help me.  Those psychological obstacles are outward reflections of a deeper state of my heart: putting my trust in perfection, desiring to be in control of my own life completely, and lack of trust in God and His goodness. That is a life's work-in-progress.

The encouraging part of answering the question "What is holding you back?" is that I can experience relief for some of my stress points by simply learning some new skills and processes.  Some realities are beyond my control, so I need to organize what I can and not get burdened down by what I can't.  And, thankfully, there's help for my heart, so I don't need to be afraid of addressing those psychological obstacles.

Step 2:  Analyze and Strategize