Why planning is everything and how to do it daily.

Day planning with Daycast
"I tell this story to illustrate the truth of the statement I heard long ago in the Army: Plans are worthless, but planning is everything."

- Dwight D. Eisenhower, 11/14/1957


If what Eisenhower said is true—if plans really are “worthless”—then why bother planning at all? How can planning be anything, let alone everything if the fruit it bears is as good as dust? Bit of a trick question there… the real fruit of planning isn’t the plan, you see. In the same way that the point of crafting a blueprint is not to have a very nice blueprint but to one day have a house where there wasn’t one before, the boon of day planning is the work we eventually produce.

It is at once humbling and empowering to realize that our careful plans accomplish nothing, but having taken the time to create them, we can accomplish a great deal. We don’t expect you to believe that on the basis of one architectural metaphor though. Allow us to break it down for you….

Why planning as everything:

As far as we can tell, medium and long-term planning at the organization and team levels is generally regarded in the business world as essential to profitable operations. Day planning at the individual level doesn’t have quite the same street cred. Managers want daily time tracked, sure. But planned? That seems to fall into the ‘whatever helps you, just get it done’ category.

We think that’s a colossal mistake.

Day planning is an essential practice for those who want to make the most of their time. Here’s why:

It stokes the fire.

By considering our projects and goals daily and sketching out a plan for making headway on them, we regularly reinvigorate our motivation. When we plan daily, we don’t fall so easily into that stale rut where we’re dragging ourselves through the motions because the gap between our efforts and a rewarding sense of progress has slowly widened to the point where everything seems vaguely pointless. Day planning helps to keep that gap narrow enough to see across.

It lightens our load.

When we don’t plan daily, projects can begin to feel like millstones around our necks, which only makes it more difficult to press on. By outlining our next steps each day, we set the weight of all that’s yet to be done down somewhere outside of our minds and unburden our cognitive resources to work unencumbered.

It keeps us engaged.

Focus isn’t a one-and-done deal. It takes regular re-calibration to stay on course. That’s where day planning comes in. By reviewing our progress and setting down our next actions, we keep our projects and goals from becoming static things we’re working toward, instead assuring that they’re dynamic growth we’re actively cultivating.

And whether we work with a team or not, planning daily spurs communication with clients, contractors, etc.—the people we need to work with in order to deliver our best. Without day planning, it’s all too easy to become so absorbed in our own efforts that we lose sight of those that depend on us and vice versa. But a daily habit of considering next steps can mitigate that natural self-absorption because it often inspires checking in with others. You’re reminded, for example, to email your designer about those icons she’s creating for your client’s website when your plan for tomorrow includes a progress report on the re-branding project.


"Plans are the documented culmination of planning. Planning, however, is an active discussion that combs all of the variables within a present situation into immediately actionable equations."

- Allen B., Software Developer


It illuminates the path.

Day planning minimizes the frequency of running into a wall and getting stuck because the process of considering where we are with our projects and what we need to do to make further progress tends to surface two things: 1) obstacles before we stumble over them and 2) alternative routes before we find ourselves in need of them.

How to plan daily:

Day planning rarely provides the instant gratification we’re so accustomed to in this 21st century. Like meditation or exercise, day planning is a habit that pays its dividends out over time. As is the case with any budding habit, it requires a bit of discipline in the beginning. But in time—the most dedicated day planners among us swear to this—you won’t have to compel yourself to do it; you’ll feel out of balance if you skip it.

1. Commit a half hour of each workday to day planning.

You may not need the entire thirty minutes every day, but by deciding at the outset to reserve them for day planning, you’ll help yourself avoid the most common obstacle to developing this skill: time. Or, rather, time’s limited quantity. “I don’t have time for that,” is such a well-worn excuse it’s see-through. You don’t have time because you don’t plan your time.

2. Bookend your days with day planning.

Don’t spend your whole half hour in one sitting. Instead, make day planning the last thing you do before going home and the first thing you do upon arrival. Plan tomorrow at the end of today, and review/adjust that plan when tomorrow begins.


"That shutdown/plan tomorrow step is a big part of getting a good sleep and not 'churning' trying to remember to do x, y or z tomorrow."

- Lauren C., CEO


3. Marry planning, not your plans.

Your workdays may never go exactly according to plan. Ours generally don’t.


But your plans will bear more fruit if you consistently take the time to create them.

4. Check your ego.

We’ve noticed two primary ways in which our egos can sour planning:

  • When we measure our days by how perfectly we executed our plans. On the one hand, this undermines planning by fostering inappropriate pride when we followed our plan to the letter and in doing so ignored opportunities to deliver greater value. On the other, it leads to harsh judgment when we deviate from our plan.

  • When we avoid planning in a bid to avoid failure. It’s not unusual for folks to try day planning and quit early on because plans make them feel like they’re committing to something they may not be able to achieve.

Our advice? As much as possible, separate your sense of self-worth from both planning and plans. It may help to adopt a flexible day planning tool, one that makes course correcting easy and doesn’t penalize you in any way when you re-route. If you feel badly when your day doesn’t go precisely according to plan, you might try an ego check or a different day planning tool. Or possibly both. (Though it could also indicate that the culture in your workplace needs help.)

Plans matter, but not as much as planning.

Eisenhower was a military man, and he was discussing the defense of the United States when he referred to planning as “everything” and plans as “worthless.” He went on to say that “... when you are planning for an emergency you must start with this one thing: the very definition of ‘emergency’ is that it is unexpected, therefore it is not going to happen the way you are planning.” Perhaps it’s fair to say that in planning our days, most of us aren’t planning for true emergencies; we’re planning for the work we do in software development, law, graphic design, marketing, IT support, etc. This is business, not war. And in business, we’d argue, our plans aren’t worthless. They give us a place to start and, at times, a perfectly good road map for the entire day.

Still, planning and work are the verbs, the essential actions we must take; plans are merely the nouns, the springboards we build and launch from anew each day. The latter matters, yes, but we can’t use plans we haven’t taken the time to create.

Top photo by Nathan Lemon