Journaling – the leaders vital friend

Journaling – the leaders vital friend

Leadership is simple, but it is rarely easy. Simple because, in Gardner’s words it is “the ability to create a story that affects the thoughts feelings and actions of others”[1]; simple in that it’s about getting from ‘here’ to ‘there’ in any area you want to see change, but challenging in that it requires all of you to do it. Leadership is for everyone, but it also requires everything. So how do you bring everything to the task of leading? We need friends, mentors, therapists, coaches and books, but we also need ‘inner’ friends as well - friends like meditation, and the regular making of space in the day. One of the most helpful, but less spoken, friends to the leader is their journal. That simple book of empty pages with a cover that makes you want to write inside it.

Why is a journal such a crucial part of a leaders team, a leaders resourcefulness? 

 “That’s how the light gets in”

Leonard Cohen says  “there’s a crack in everything, that how the light gets in” and the leader is in constant search of light. They need to see and they need to see clearly.  When a leader writes each day in their journal they are looking for the cracks, tiny openings to give them a window into clarity. It may start by just writing the narrative of what happened yesterday, or what is going on in this phase of the leadership, but the leader is looking as they write. As they write they hear themselves talking and suddenly ‘ah ha…I hadn’t noticed that before…I keep using the word “weary”…what is it that seems so wearisome when everything is going so well right now?’

This article started in my journal. I was working hard and making sense of what is going on in our organisation right now. It’s maybe the third time in a week that I have written about the same things.  It doesn’t matter. As I write and rewrite I am organising my thoughts, putting some shape to the chaos each time, trying out whether this perspective is the most accurate way of seeing things today. Like working the piece of grit in the oyster shell, I keep on working the narrative of my leadership life to find insight, to find clarity, to find the crack of light that may illuminate where I’m feeling stuck but just cant properly name right now.

When we lived in South Africa we lived on the edge of a mountain full of vineyards. Each day that we could, we would walk up that mountain and at certain points we would stop to take in the view, to get perspective. That’s what journaling is for the leader, a walk up a mountain to get perspective on their day, this phase of their leadership journey, that meeting this morning, this oh-so-difficult decision.  When we are down in the valley of delivering our leadership each day is crowded out with so many things, so many emails, decisions, challenges, requests, tensions, conflicts.  The journal acts like a table where we begin by pouring out absolutely everything onto its surface so we can see it, just as it looks and feels in all its complex messiness. Journaling is then a process of beginning to sort through what is there and what belongs where. A good piece of leadership wisdom is “get clear and get others clear” and journaling is the place within a leaders life where they can invest in searching for clarity.

The hard work miracle

I remember a book I once read about personal and relational transformation  - it had this eye-catching subtitle - “the hard work miracle”.  Leadership is a constant search for the ‘miraculous’ in terms of breakthroughs but miracles don’t just fall off trees, they are the result of much hard work and the leaders journal is one of those places that the hard work is done. The leader can write out their questions, what’s bugging them, what they know and what they don’t know. In their journal they can write out everything they are thinking right now, they can write down what they are feeling, they can write out what they are doing. As they lay out these narratives and questions and musings they can look at what they are writing and can hunt down the patterns or spot the assumptions or note the leaps and the omissions in their logic. 

Forging wisdom out of experience

It’s one thing to get a day’s worth of experience, it’s another thing to get a day’s worth of wisdom. Wisdom is the result of processing the experiences of our leadership journey and seeking the wisdom from it.  Writing down what I did, what went well, what could have gone better, why did I react the way I did in that situation, what did I learn, is the way to find out where the wisdom lies. “If we don’t change history, then it will repeat”. This is as true for the leader as for a nation. Journaling out my history and seeing whether it achieved what I hoped it would and if it did ‘why’ did it and if it didn’t ‘why’ didn’t it.  Socrates said, “the unexamined life is not worth living” and journaling is how a leader carries out that examination. We often think of therapy as the place for serious self-examination, and it is, but what lies between todays experience and paying a therapist to process it?  Truthfully, however helpful therapy is (and it most definitely is and at times is most vital for a leader) the reality is that people aren’t in therapy for long, generally speaking. So what do we do on a day-to-day basis to live an examined life? Journal.  Journaling is open to every leader every day. 

Turning into the wind

You can be sailing along nicely in your leadership journey but you know that you are avoiding the hard things that have to be addressed. That staffing issue, that attitude issue you bumped into in someone on your team, that funding issue……you know they need to be faced but its just more comforting sailing with the wind. Journaling is a way that a leader can turn into the wind and begin to address the rough waters.  By writing down the fact that you are avoiding something and naming what it is that you are avoiding and why you want to keep on avoiding it, means that you have actually begun the process of turning the boat into the wind. Journaling helps you make the turn and it helps you stay tight on the tiller while you address rough waters. Journaling is a discipline that forces us into a process of self-reflection and a way of developing some leadership muscle.

Teasing out the threads

When your grandmother wanted to unpick your old sweater she had to start somewhere. The best place to start was looking for a strand hanging down, a loose thread. Once you pick up that loose thread then you can begin the slow process of unpicking the rest of the sweater. Journaling serves the same function. It allows us to pick up a random thought, or concern, or comment and anxiety, or intuition and to then follow it through to its conclusion.  I caught myself saying to my fellow leaders yesterday that my intuition tells me there was one-piece missing from our vision planning. A comment like that is a loose thread.  It may lead somewhere or nowhere, but writing the ‘thread’ down and then asking myself “what makes you think there’s more?” and then jotting down any random idea that comes to mind will lead me to unpick what else may be hidden. It doesn’t matter if the thread leads somewhere or nowhere, but it needs to be explored and the journal is an immediate place to begin that exploration.

Reality testing

All good leaders are realists as well as visionaries and strategists.  Regular journaling is a confrontation with reality. Starting an entry with “so what is actually going on right now?” and then naming the facts, the feelings and the behaviors that the leader sees in front of them.  “What do we know and what don’t we know” is another testing of reality.  Today I wrote out a quadrant with 4 headings – “delivery”; “sustainability”;” governance”; “opportunity”,so that I could write down the facts of what was actually going on. How many people had we actually trained since January this year? Writing down the reality is often sobering, sometimes difficult. Even noticing how hard it is to confront reality tells me that I’m in danger of avoiding the truth of a current situation and if I avoid the truth then everything that follows will be inaccurate.  Journaling is also great for reality testing our own thinking. You might start an entry with “everything seems to be coming apart right now” or “nothing seems to be moving forwards”. Journaling allows you to then reality check those statements by asking yourself in your journal “so what exactly isn’t working out?”….and then list them. What this writing down of reality achieves is it stops the leader from making conclusions based on fear or pure emotion rather than facts or evidence. Journaling is like doing one phase of CBT (Cognitive Behavioral Therapy) on yourself. 

Confronting the shadow

Every day it is likely that the leader will face unwanted or unexpected feelings. Waking up with a sense of dread that seemed to come from nowhere, for no reason; a meeting where you found yourself bored or irritated by a colleague on a subject that should have interested you greatly, a surprising roughness in the way you answered a colleagues innocent question, a fear of inadequacies.  A journal is the first place for the leader to confront themselves, to look themselves in the mirror. The one place that they can go to straight after that difficult meeting and start journaling about what they were feeling. As the leader writes, they are facing their own shadow. We all have a shadow and that shadow is never benign or innocent. That shadow is exerting as much influence through us as leaders as the nicer, more welcome parts of ourselves.  


It is clear that a leaders insecure ego can have multiple effects on the people and the organisation that they lead. Their need to lead, their need for praise, to be right, to be seen as an expert, to be loved by all, to be macho, to be conciliatory, to be the best, the first, to be seen, to be understood…..the ego is embedded in our shadow. The ego doesn’t want to be seen and most of all it doesn’t want to change. But change it must if the leader is to continue to lead with integrity. When I sat down after a talk I was giving the other evening I felt unhappy with myself, the talk I’d given and the way I’d answered some questions.  It was a prime opportunity to wake up the next day and head straight to my journal. “What was going on last night Trevor…..” I would begin to write.  Facing down my own shadow was the necessary work of that morning and that work could begin without waiting for any team or therapist…it could start right there with my journal.

A free coaching session

A coach asks questions; lots of questions. The reason for this is to raise the coachees awareness of what is going on in the situation they are exploring or the challenge they are facing. Once they have some new insight they can then create some new options for action.  The most frequently used coaching model around the world is called the TGROW model. It structures a conversation in five phases. A journal provides free coaching by using the questions on yourself. Write down each question:-

    “What is the topic you want to think through Trevor?” (T= Topic)

    “What do you need from this exploration or issue?” (G= Goal)

    “What is going on right now and what other perspectives could you get on this issue?” (R = Reality)

    “What are all the options you can think of to resolve this issue?” (O = Options)

    “What are the actual actions you are going to take?” (W = Wrap up)

Whilst having an actual coach will obviously add enormous value, especially in making sure you don’t collude with yourself, there are many issues where we can make some good progress by ourselves by self-coaching in our journal.

Freeing up the bandwidth

Computers get stuck, freeze up, or simply slow up because there is too much going on at once. Many of us experience the same feeling as a leader. Our ‘processing” bandwidth is so full that we become slow and inefficient in our thinking. Using the journal as a constant downloading process frees up our minds to work much more effectively on the main issues confronting us.

A car park for insights

A leaders reading and learning is vital. Why? Salman Rushdie said once that 

‘Those who do not have the power of the story that dominates their lives – power to retell it, rethink it, deconstruct it, joke about it and change it as times may change – truly are powerless because they cannot think new thoughts’

A leader cannot create a new story or get power over an old one using old thoughts, they need new thinking.  Where is the leader going to learn to think new thoughts if not their reading, and their learning from whatever the source? The leaders journal is like a car park for writing down those fresh thoughts. It maybe from a book, from a business magazine, from an interview you read on the Internet, from a quote someone at work used in a presentation this morning. Write them all down. And once they are written down you can return to them maybe later that day, that week or that month. Once they are written in the journal you can then journal about those insight and quotes. “That’s what Rushdie says but what do I think about what he’s saying? What new thoughts does his quote stir up for me?

What’s your story? – in search of your bigger “yes”

I started this exploration with Howard Gardner’s definition of leadership “The ability to create a story that affects the thoughts, feelings and actions of others”. A leader is someone who discerns the story they want to write in any aspect of their life (vision) and then sets about writing it (strategy) and ensures that the lives of others are positively impacted (influence).  Someone once said that the only way you can say ‘no’ to the distractions and negatives in our life is to have a bigger ‘yes’, a vision, a clear and growing picture of the story you want to write, whether that’s in your life direction, your family, your work sphere.  Journaling allows us to keep on exploring what this story is, what we want it to be, how to keep that bigger ‘yes’ fresh each day of our lives.  “Where am I heading in this project? This organisation?” or “Who am I becoming as a person?”, or “what really matters to me in my life right now – what’s my bigger story?” or “what is the legacy I want to leave”. Journaling allows us to explore and enlarge that very real story for our life.

Spend it all

The great thing about journaling is that it is entirely original – its just you, with your fresh words, today.  It is entirely unrehearsed and it’s only written for an audience of one – you; you aren’t trying to shape a talk for anyone else.  In the words of Brene Brown, when you journal, you are just writing your own “first shitty draft”, of what is going on for you right now. It’s a naked journey, its just you as you are, uncensored, as honest as you dare to be with yourself. You don’t have to spell check it, grammar check it. It can be random words, bullet points, half finished sentences – it doesn’t matter. What matters is simply doing it. Write it all down. In the words of Pulitzer Prize winning author Annie Dillard – “Spend it all”. Get it all out and then more will be given to you. That’s how it works. I wouldn’t be without it and I commend it as a vital friend to every leader every day…..or as often as you can each week. Go and buy yourself a journal and make it an integral part of your leadership….and your life.   



[1] Howard Gardner Leading Minds 1995

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