Self Observation as a tool for authentic entreprenueurship

As an entrepreneur, there’s one thing we each have to keep a watchful eye on 24/7 and that’s….ourselves!

There’s one constant in all entrepreneurial journey’s, regardless of what industry you’re in, what product you’re selling or what service you’re offering – there’s a YOU at ground level.

Like constructing a solid house, the building process begins with strong foundations without which, the integrity of the entire structure comes into question.

Too many people start out working for themselves with their eyes fixed on the wrong thing, asking themselves the wrong question – how much money will I make?

Of course, it goes without saying, that money is important and knowing how much you want or need to earn is an important metric to be aware of, but there’s a metric that too many novice entrepreneurs forget to measure and that’s their own growth and development.

It’s been said that an investment in education is an investment that guarantees a high return. So while the majority of entrepreneurs invest in the next course to learn how to create their next sales funnel, or how to trade on the stock exchange or some other technical, external skillset (which is great and necessary!), many forget to invest in their own education about themselves – their one foundational constant in their business.

Times may change, technologies may change, trends may change….but if an entrepreneur doesn’t keep up with their self-education they won’t change and may find themselves irrelevant and ill-equipped in their current entrepreneurial landscape.

Just take a look at the current impact that COVID-19 has had on small businesses and solopreneurs. Many have been left destitute and desperate because externally, so many things that were outside of their control shifted, and they hadn’t done the preparation to enable them to be flexible in relation to the circumstances, like the branches of a tree that bow and bend with each gust of wind.

In a time when their product or service becomes obsolete, an entrepreneur who’s historically taken the time to truly practice observing their own reactions and responses to external stimulus, and learning and growing from each observation is far better equipped to pivot their business, than an entrepreneur who’s business offering happens to be the current ‘flavour of the month’ but who has zero insight into themselves or their own personal development. At the drop of a hat, when the winds of change blow once more (and they will), the latter of the two entrepreneurs will not fair so well.

Many people often over-complicate personal development or personal growth activities which is why they tend to ‘leave it for tomorrow.’

But personal development is a habit, and a habit is built one tiny step at a time, one day at a time.

The practice of self observation is no different.

Self Observation Practice

So if you’re new to this practice (and even if you’re not) and you want somewhere to start with the practice of daily self observation, so that you can weather the storms that will inevitably come your way on your entrepreneurial journey, here’s a daily practice of self observation…

The purpose of this practice is to help you become more aware of how you feeling during the workday and what you accomplish on a daily basis.


Stop twice a day – midway through your work day and at the end of the day – and ask yourself the following questions. You can write your answers in a journal.

And bear in mind: The fact that you commit to doing this exercise will trigger an anticipation throughout your day, which causes you to more keenly observe yourself throughout the day.

  1. What energised me most at work today?
  2. What discouraged me most at work today?
  3. In what ways did no.1 and no.2 above affect how I spent my time? What did I accomplish?
  4. What patterns do I see emerging from what I am observing in this exercise? What action will I take about what I have observed?

Side Note: Since January 2020 our Cafinnate Crew has been sharing a weekly self observation practice in our group chat, and the learnings from these reflections for everyone involved have been huge! 

Join the Cafinnate Crew


This daily practice of self observation is an investment IN you, ABOUT you. Armed with this knowledge about yourself, as the foundation of your business, you can more confidently and effectively adapt and evolve your business, because YOU are continually adapting and evolving.

What self observation also means is that you’re really getting to know and understand yourself, perhaps in a way that you’ve never explored before. You’re learning and discovering who you really are, and what you’re really capable of, and how adaptable you are. Armed with this insight and knowledge, everything in your business carries potential of the compounding benefit. From marketing, to working with team, to new product offering – they all benefit as a result of you know you better!

Allowing your authentic self to be observed, acknowledged and acted upon diminishes comparison or obligation or any other destructive addictions of habitual limitations.

The truth is, we change. Humans are always changing, whether they realise and acknowledge it or not. Who you are now, is not who you’ll be in 5, 10 or 20 years time. Even next week, you might find that your preferences might change. Perhaps this week you like drinking lattes. Perhaps next week you prefer to drink your coffee black. Which is ‘right?’ Which is ‘true’ for you?

Both are right, both are true for you. Both choices are authentically you – if you base those decisions or preferences on feedback you receive from your practice of self observation.

So the practice of self observation allows you to stay connected to your authentic self, accepting that your authentic self evolves over time. And as you evolve, so too does your business. So in order keep your business targets, offerings and communication aligned to what’s authentic and meaningful to you, it’s time to start observing yourself.

That’s why we’re super excited about this month’s masterclass inside the Cafinnate Academy.

Awakening Your Authentic Self


This masterclass will guide you to explore and connect with your authentic self.

Authenticity is a word that’s often thrown around without regard for what it actually is or what it means.

In this masterclass Joy Activist, Jill Lambert will explain the concept and provide practical exercises and examples to help you mentally understand and physically experience what it means to be your Authentic Self.


Watch the Full Masterclass. Join the Cafinnate Crew.


Over to you…

Think back to the last 24 hours. What can you observe in your own behaviours and reactions?

And how has that impacted how you showed up in your business?

If you feel called to share, post in the comments below…




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