Planning Pitfalls | How Details Can Hinder the Process

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When I started my organizing business in 2006,  I was pretty darn sure that my way was the right way and the best way. I was very detailed and pretty rigid with my plans. Come to find out, too many details can get in the way, for both myself and my clients.
In the general planning process, we don’t start with the details. That’s saved for strategic planning, which has its own set of rules. We begin with an outline of what we want to accomplish, not the details of accomplishing it.
An outline gives us guidance and direction. Having an outline gives us some grace and freedom when it comes to planning the details.

out•line / (out′līn′)

A preliminary draft or plan, as of a project or proposal

detail / dih-teyl, dee-teyl;

an individual or minute part; an item or particular.
particulars collectively; minutiae.
attention to or treatment of a subject in individual or minute parts

Today, let’s talk about 3 more planning pitfalls.

I’ve included these 3 pitfalls together as they are very much alike, but still different. I will explain what each of them is, and then give you a solution to preventing them from happening.

1. overcomplicated /: complicated to an excessive degree


This is about making the planning process harder than it needs to be. Just like organizing, planning is a process. It doesn’t happen all at once. It’s a living, breathing process.

In this scenario, we are taking the day to create goals for the year. This will involve writing down our goals, creating a general timeline for goal completion, and an overarching outline.
However, we don’t stop there.
We make the planning process overcomplicated by deciding now would be a perfect time to outline each goal and create details for each goal.
We’ve overcomplicated the process by making what was originally a simple task into a complicated task.
Our brains just aren’t wired to complete such a difficult task in one day.


Be very specific and realistic about what you are going to accomplish in a  planning session. Then, do only that.

2. overreaching /

To reach or extend over or beyond / to miss by reaching too far or attempting too much 


When I talk about overreaching in the planning process, I am talking about creating details for something that isn’t in the near future. A 5-year plan would be a great example. It’s great to have a 5-year plan, and a 3-year plan, and a 1-year plan. But, you don’t want to make a detailed plan for either 3 years out or 5 years out. Creating the details for the next year is fine. Detailing can be so much work and we never know what’s going to happen tomorrow, let alone 3 years from now.


Plan in detail only the projects or goals you will be working on for the next 12 weeks. At the end of the 12 weeks, if you have completed your plans, then detail the next plan for the next 12 weeks. If not, review your incomplete plan and figure out what you have left to do. If you find you will still have time in the next 12 weeks for a new project, then go ahead and write down the details.  

3. overplanning /the act or instance of planning excessively


Oh overplanning, how I know all about you!
This is what I did for a long time. I had a goal or a project to complete and I found myself spending more time planning the details of the project than I actually did on the project.
That may be a little bit of an exaggeration, but it sure felt that way.
My detailed plan wasn’t working and I was beating myself up for that. I didn’t always feel like doing “A” before “B”, but it was on the calendar that way, so it must have to be that way.
I created this awesome plan that SHOULD work, and I was sticking to it, no matter what! Some call that stubborn and prideful, and they may be right 
If you find yourself in that situation, read about the Planning Pitfall | Rigidity.


This is the solution I have come up with for myself. It may work for you as well.
Instead of planning the details of what I was going to do and when I was going to do it, I created focus blocks and checklists for my repeating tasks. Things I need to do every week, or every day.
Those focus blocks go on my calendar during my weekly review and planning session. Because I am a routine oriented girl, I will be honest and tell you that these recurring focus blocks usually are on the same day and close to the same time. There are going to be times I am not able to stick with my routine. I might have an in-person organizing session, a doctor’s appointment, or, something that just came up.
We plan around this thing called life!

All of these planning pitfalls have one thing in common.

That’s the need for control.
We want and try to have control over our time, our actions, and our environment. Realistically, if you think about it, we actually don’t have much control. I know it’s hard to take, but it’s reality.
That doesn’t mean we can’t take steps to have some control over our time, our space, our goals, and our activities. That’s what the planning process is all about.
We need to plan. For all we know, we’ll be here on this earth until we are 100!

Take Action:

Do you find yourself struggling with planning? 
If so, take some time and ask yourself, am I falling into the pitfall of overcomplicating, overreaching, or overplanning?
If so, take a step back and work only on the current and upcoming projects.

If you are still having problems with planning, maybe you are experiencing other pitfalls.
Planning Pitfall 1 | Untimeliness
Planning Pitfall 2 and 3 | Winging It & Rigidity

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