Understanding Planning

You’ve likely heard that “failing to plan is planning to fail.” This well-known saying presents an either/or scenario: either spend tine planning or head toward failure. I think it’s more nuanced than that. Yes, lack of planning is often a root cause of failure. Not all failures are due to lack of planning, though, and “The best laid plans of mice and men often go awry” (Scottish poet Robert Burns, 1785).

The right amount and the right kind of planning are key to success. There are also varying degrees of success, and success is relative. The right amount and type of planning are unique to the person. They also vary by situation. There are, however, strategies that work for everyone even if they’re individualized. Let’s look at writing as an example.

Planning in Writing

The first step in a solid writing process (meaning, it helps you reach your goals) is to plan. The other steps are write, revise, edit, and proofread. There are variations of this process depending on the discipline. For example, technical writing, novel writing, and blog writing each carries out the stages in the writing process, though they don’t always use the same terminology. They also each have a different emphasis and focus. Yet, these five basic steps lie at the heart of every good writing process.

My experience with the writing process comes through working with writers at varying levels along with my own writing endeavors. It also includes different perspectives and genres (e.g., developmental writing, freshman English, business writing, journalism, nonfiction, fiction, web content, blogs, speeches, Bible studies, and sermons). No matter the writer, perspective, or genre, planning always played an integral role. When writers struggled in areas like writing and revising, it almost always stemmed from a problem with or lack of planning.

Reflecting on Planning

If executing an idea or “plan” in writing or any other endeavor feels like wheels spinning in mud where you can’t gain any traction, reflect on your planning. Did you plan enough? Do you need to plan more? Did you research into enough depth and detail? Did you spend enough time with each part making up your whole? Did you write down your plan? Did you create an outline? Sometimes, lack of planning involves too much of a big picture view. Perhaps you spent more time in one area and neglected another, creating a lack of balance.

If you’re not a writer, consider that the writing process provides a structure adaptable to almost any project you undertake. I’ve you’ve read Comfortably Uncomfortable, you might now see that it leads you through a process of planning for your growth much like planning in writing leads you to an outline for a project.

Planning for Depth

The writing process provides a structure adaptable to any area you want to develop. Writing is thinking, after all, and we live in a culture where thinking is beginning to atrophy. The writing process provides a way to stop that decline.

The goal in planning is to decide where and how to go deeper rather being consumed by the overwhelm and overload of a too-wide life. It gives a way to actively discover rather than be passively led. Planning well allows us to stop splashing around in the shallows and discover strategies leading to a deeper life where success – in all its wondrous variety – awaits.


Sharing Comfortably Uncomfortable has been a humbling experience, and I’m grateful to all of you for supporting me in the process of creating and promoting it. You’re encouragement motivates me to keep writing and discovering more depth in my life. Thank you!