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Plans vs. Planning: The Churchill Principle for Real Productivity

Plans vs. Planning: The Churchill Principle for Real Productivity

Update: 2025-08-03
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“Plans are of little importance, but planning is essential”


That quote from Winston Churchill perfectly captures the dilemma we face when it comes to planning. 


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Script | 379


Hello, and welcome to episode 379 of the Your Time, Your Way Podcast. A podcast to answer all your questions about productivity, time management, self-development, and goal planning. My name is Carl Pullein, and I am your host of this show.


Planning and organising have their place. Yet, there is a danger of taking them too far and using them as an excuse or as a way to procrastinate. 


Ultimately, whatever you are planning to do will eventually need to be done. The goal, therefore, is to get to the doing part as quickly as possible. 


One of the dangers of David Allen’s Getting Things Done book, is the emphasis on organising and doing the weekly review. It’s a procrastinators heaven. An authority in the the productivity space giving you “permission” to spend two to four hours a week planning and reviewing and another large proportion of your time organising and reorganising your lists. 


Don’t get me wrong. Both planning and organising have their place and as Winston Churchill says, “planning is essential”, but it’s a thin line between helpful and unhelpful planning and organising.


In today’s episode, I will share with you some ideas that you can use to ensure that you are following some sound principles with your planning and reviewing. 


So, that means it’s time to hand you over to the Mystery Podcast Voice for this week’s question.


This week’s question comes from Sally. Sally asks, hi Carl, I’m struggling to get myself organised. I have so many things on my desk and on my computer’s desktop I don’t know where to start. I feel like all I do all day is plan what to do and tidy up my lists. How do you avoid over planning and organising? 


Hi Sally, thank you for your question.


Firstly, I must admit I have been down this road of over-planning and organising. 


I read Getting Things Done in 2009 and loved it. I ditched my Franklin Planner, the “tool” I had been using consistently for over fifteen years, bought myself a nice Quo Vadis notebook (the paper quality was better than Moleskine) and spent a whole weekend setting up the notebook as a GTD tool. 


I also printed out the GTD weekly review checklist from David Allen’s website and stuck that into the back go my planner and became a GTDer. 


It took me seven years to realise that I wasn’t getting anything significant done. I had a lot of ideas, plans and goals, yet all I seemed to be doing was reviewing, planning and doing the easy things from my context lists. 


Replying to emails was much easier than sitting down to write the first chapter of the book I wanted to write. Spending more time mind mapping the presentation I had to give on Friday seemed more important than opening up Keynote and designing the presentation. 


Yet, ironically, it was an end of year review that forced me to face up to reality and see that while I was excellent at planning and reviewing, I had become terrible at doing the work. 


And this is one of the most common problem areas I see with many of my coaching clients. The fixation on having everything perfectly organised and planned. 


You see, the problem here is not that everything is neatly organised and you have the plans to do whatever it is you want to do. The problem is nothing is being done to do those plans. 


While I was working on my recent Time-Based Productivity course, the project note I had for it was a mess. I had a lot of notes, ideas and thoughts. Yet, I maintained a strict next actions list at the top of the project note as well as links to the documents I was working on. 


It didn’t matter that below those items was a horror show of ill-thought out ideas and random thoughts. They were there in case I got stuck somewhere. What mattered was the important information was clear and at the top of the note. 


The note was designed so that the work got done. It was not designed to look pretty. 


I’ve seen clients with thirty page Word documents detailing their department’s plans for the year. It’s written in some vague management language that leaves a lot to interpretation. It’s as Winston Churchill once said of a similar document from the government’s treasury department:


“This paper, by its very length, defends itself from ever being read.”


You can spend hours going through a document like that, and nothing will ever get done. 


What matters is knowing what the department’s objectives are and what needs to be done to accomplish them. 


That does not need thirty pages. That can be summarised on one page, at most. 


If you’re working in an organisation that loves using management speak to communicate their ill-thought through ideas, one of the best ways to navigate these documents is to establish what the ultimate goal is. 


What are the targets, or in management speak “KPI’s” (Key Performance Indicators)? Once you know how you or your department will be measured, you can use your own experience and knowledge to put in place a plan to achieve those targets. 


Ultimately, your boss, and their boss, are concerned about your targets. How you achieve those targets are less important, although they should always be achieved legally, of course. 


In many ways translating these verbose annual planning documents is the role of the departmental managers. This means translating them into actionable items so that everyone in the team clearly understands what they are aiming for.


This then reduces the necessity of further planning meetings and everyone can get on and achieve the objectives. 


And this is the same for individuals. 


When we plan things out we are exploring options, considering best ways to do things and perhaps thinking of potential outcomes. 


While these exercises do have their place, they cannot replace doing the work. 


The objective, therefore, is to figure out as quickly as possible what you need to do to get the work completed. 


My wife bought me a new iron and ironing board for my birthday. I love ironing, I find it relaxing. I’ve learnt that no matter how big the pile of ironing is, the pile is not going to diminish by more planning and strategising. The only way the pile of ironing will shrink is for me to plug my iron in, set up my ironing board and get started. 


Now years of ironing has taught me to begin with the clothes that require a cooler setting and finish with clothes that require a hotter setting such as linen shirts. That’s experience, although, I remember being taught that one by my grandmother many many years ago. 


The final part of this is choosing when to do the ironing. For me, I find ironing after I’ve been sat down for a long time works best. I’m stood up and have to move around to hang my shirts up after they’re ironed. So, doing the ironing in the afternoon or early evening works best for me. 


Given that I generally do the ironing once a week, all I need to decide is when. When will I do it? That’s the only planning I need to do with something I routinely do. 


When it comes to organising, I’m always surprised how so many people have missed one of the best features of computers and technology. It’s not so you can sit and stare at a screen for hours on end. It’s the speed at which a computer can organise your files. 


You can choose to organise your files by date created, date modified, title, type of document or by size. The only thing you need to do is to put the file into a folder. 


If you were to keep things as simple as possible, two folders one for your personal life and one for your professional life would work. (And I know a lot of people who do just that and can find anything they need with the use of a keyboard shortcut or a few typed letters. 


While travelling last month, I had all my flight confirmation emails and car hire documents stored in Evernote in its own notebook. Before we set

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Plans vs. Planning: The Churchill Principle for Real Productivity

Plans vs. Planning: The Churchill Principle for Real Productivity

Carl Pullein