Journaling to boost your entrepreneurial mindset

When the dragons in Dragons’ Den say to the entrepreneur ‘Would you like to go and talk to the wall?’, that wall moment, for me, is like journaling. A quiet moment, to hear yourself think, untangle the data to decide what feels right and emerge clear-eyed.


Have you tried it yet to drive your entrepreneurial mindset?  

Doubtless, you’ve heard about the benefits of a journaling habit: gain clarity, generate fresh thinking, cultivate emotional balance, find your authentic business voice, and boost motivation. Many successful entrepreneurs, from Steven Bartlett to Oprah Winfrey, testify how they’ve kept a journal by their side for cultivating their mindset for success.

But let’s be honest.

Fear of the blank page is real. Knowing what to journal about, or finding the time and even believing that the words are leading somewhere can be some of the obstacles busy entrepreneurs face.

It’s time to make journaling a micro habit. Small and simple actions for mighty impact.

So, paradoxically, let’s start with that blank page and add to it a beginner’s mind!

A beginner’s mind innovates, arrives open and curious, leaving assumptions at the door! In fact, how you start something, anything, is a rich topic to journal on so that might be your first journal entry! Use this line: This is how I always start….

Journaling guidance

Before you begin this journaling experiment, write out your home-made guiding principles about what would make this work for you.

Is it setting targets or a time limit? Do you need to make a note about the kind of place that’s conducive? And what about what frame of mind is required?

See what else you can add to your guidance.

Treat your journaling habit as an experiment. Or, if you already journal and it needs a shake-up, think of this as journaling 2:0. To create a habit, much research says it takes 21 days. How many days might this habit take root for you? It’s your experiment, your rules! Confession: I don’t journal every day, but it is a habit. How do I know? Well, when I don’t do it, it can feel strange, like I’ve left something behind on a train, and things feel knotty.

Try these journaling strategies and techniques to make journaling a go-to tool to develop your entrepreneurial mindset.

Journaling techniques

Write, reflect, act.

I use this three-step process every time I sit down to journal. Why?

Because it avoids journaling as merely ‘thought dumping.’ Don’t get me wrong, one huge gain is this release, of getting what’s inside out. But there’s more to gain: we can also leverage the insights through reflection.

Here’s how:

Pull out three key words or write a one-sentence reflection from your fresh journaling. This can help bring some frame to the long text or a sense of order to your words.

And act.

Is there an action point to now note at the foot of your page? In the margins? Something to do, decide, start, or stop?

On to the mains! An appetising menu of different ways to journal, not just line after line. Using different journaling techniques is engaging and utilises different parts of the brain to bring out all your under-the-surface wisdom:

  1. Writing lists – great way to get top-of-mind thinking on the page.
  2. Letter writing – this is not to be sent but feels real and gets you to drop down into your authentic voice. What is it that you want to – need to – say if you knew no one was reading?
  3. 3rd Person – journaling from ‘I’ can become exhausting. Change it up by writing about yourself, your habits, your day using 3rd person, as if you were a fly on the wall. Not I but she/he/they.
  4. Write vertical – write the project name, the obstacle most on your mind – write the word vertically down the page. Each letter is the starting point to write a full sentence. Move onto the next letter until you work through them all. All your sentences form a snapshot of your associations, assumptions, feelings, and ideas about it. Much wisdom to reflect on there.
  5. Mind-map or one-pager – journaling doesn’t have to be long and flowing. Use other mediums – drawing, a matrix or a mind map to get ideas down fast. 
  6. What ifs – write a list of What if questions and choose the one most alive today. This question generates much fresh thinking or deeper self-knowing.

Try this one, guaranteed to crack open the path to some solutions:

 – What if the thing you’ve been avoiding holds the key somehow?

Sourcing inspiration from real life

Constantly in busy mode might make it hard to connect to feelings or thoughts when you have that quiet moment to sit and journal.

The answer?

Harvest everyday inspiration throughout your day or weekends.

  1. Resonance log

Keep a log at that back of your journal of what attracts, what resonates. Words, snippets of dialogue from your favourite podcast, words overheard on a bus or train, or heard on a TV show that resonate. Words from Insta headlines or quotes, titles of books, lines of books, images that caught your breath or you wanted to know more. A stranger you saw, a colleague or supplier you met with. Something about them that you admired, or caused you to wish something for yourself?

You might not know why these encounters caught your attention! These moments and words are all data. Data for greater self-knowledge which can develop greater self-leadership.

  1. Seven-day topics in advance

Why not brainstorm seven key topics that are top-of-mind about your business. And probe into one topic every time you journal. You might like to repeat the topic at a later date, to see what’s moved or not.

  1. Log your strengths and values

You may have used some of those assessment tools which rank your top strengths, core values or derailers. If not, do an online quiz about that now or compile your own list.

Pick one from your list to explore every time you journal.  

Use this structure:

I am more ……… when…………………    

Repeat as many times as you can in two minutes! Write out the line each time to dig deeper!

Curious, have you got this habit started?

Would love to hear how you got on and your own innovations in making the most of journaling.