Clean-Up: The Entrepreneur’s Guide to Self-Awareness in the Digital Age

August 2, 2019
“He who knows others is wise; he who knows himself is enlightened.”
- Lao Tzu

Abu: Why do you want to be an entrepreneur?

: I want to revolutionise the education sector *and some other fluff*.

: Why do you really want to be an entrepreneur? Is it because it looks cool? Is it an itch you want to scratch? Do you want to make more money?

: *ponders for a couple of seconds* Mmmh… To be honest, it’s an itch I want to scratch. I’ve always wanted to start something of my own.

: There you go.

It was 10 October 2015 when I first met Abu Addae, the CEO and founder of Lifecheq. At the time, I was working on an ed-tech start-up called Quweza. I was feeling a little lost and demotivated about the venture and needed some guidance. 

We had a long discussion over breakfast but it was the above interaction that stood out to me. I remember it like it was yesterday because I wrote about it in my journal (thanks, Penzu, for the annual reminder). This was an eye-opener for me, as it was the first step towards being more self-aware about my ambitions.

Clean-Up Series

This is the first part to a five-part blog series called Clean-Up, where I’ll dive into the importance of self-awareness and how you can cultivate it. 

Many entrepreneurs skip this step, as it doesn’t seem as essential or fun as the other things like creating a website, pitching for funding, social media marketing, handing out business cards, writing code, etc. Self-awareness is a very broad topic and can’t be comprehensively covered in a single blog post. In this post I’m going to share the key parts that I wish I had known when I started my journey.  

Why Self-Awareness?

Self-awareness is the ability to notice and understand your habits, emotions, strengths, weaknesses, motivations, desires and reactions – and how they impact your relationships with the people around you. 

Whether you're aware of it or not, at certain points in your journey, you’ll battle with pride, vanity, self-doubt, loneliness, disappointment, greed as well as other emotions and delusions. This can lead to irrational and biased decision-making, which can destroy not just yourself, but also your relationships and the business venture that you worked so hard to create.

Being self-aware can lead to many benefits, like a clearer sense of purpose, better communication skills, an authentic personal brand, improved decision-making and stronger relationships.

When you can picture your sense of purpose.

Self-awareness isn’t a trait, divine insight or talent. It’s a skill that can be learnt with practice. To learn this skill, you need to have an innate sense of curiosity about yourself and how you respond to the environment around you.

Dr Tasha Eurich, an organisational psychologist and author of the book Insight, categorises self-awareness in two parts: 

Internal self-awareness:
This is the one most of us are quite familiar with – understanding everything that has to do with you. Remember that time when you realised that your lack of trust and perfectionism was causing you to micromanage people? That was internal self-awareness.

External self-awareness:
This is knowing how other people perceive you. As an entrepreneur, how the world perceives you or your business becomes your reality. To build the necessary relationships, you need to be empathetic – and this requires being patient and open to other people’s perspectives. Remember that time you tweeted something innocently funny, then later deleted it? Because you realised that it could be perceived in the wrong way and could ultimately hurt your brand? That’s external self-awareness.

The two types are independent. You can have a high level of internal self-awareness with a low level of external self-awareness, and vice-versa. An internally self-aware entrepreneur may be aware of their strengths and weaknesses, which in turn leads to peace of mind. However, if they don’t understand how they are perceived, it becomes difficult to act on feedback and build a product that caters to customers. 

If you’re always catering to others’ needs and desires, you may lose yourself and become less authentic, and this can have a direct impact on the venture that you are working on. Self-neglect is as dangerous as self-delusion. To be effective in your relationship-building and other business dealings, you need a balance between the two levels of awareness. 

Many online personality quizzes, like the enneagram test, promise to give a good overview of your personality and how you interact with other people. However, the results from these tools and assessments can be inaccurate due to one culprit that hinders most people on the road to self-knowledge: The ego.

You vs Your Ego

The ego is an elusive character that’s entrenched within yourself. It’s the collection of ideas you have about your personality, talents and abilities that make up your public image. More often than not, this image is usually an illusion created to cope in this world where most people tend to put their best foot forward on social media.

We take up traits of people we consider heroes, even though they don’t align with who we really are. Anyone who threatens this illusion we’ve created of ourselves is easy to perceive as an enemy. This is why most egotistical people are constantly fighting with other people online. A fragile sense of self is often under threat and few things make you more fragile than an inflated ego.

Your ego rushing to fight someone on the timeline.

In his book, Ego is the Enemy, Ryan Holiday explores the negative aspects of the ego and its effects on several historical and contemporary figures.

“The ego we see most commonly goes by a more casual definition: An unhealthy belief in our own importance. Arrogance. Self-centered ambition… It’s that petulant child inside every person, the one that chooses getting his or her way over anything or anyone else. The need to be better than, more than, recognised for, far past any reasonable utility — that’s ego. It’s the sense of superiority and certainty that exceeds the bounds of confidence and talent.”

Ultimately, your ego fuels your desire to elevate your social status. While this can give you the confidence to be more bold and daring, it can be a distraction in many ways. 

For example:

Your ego wants to raise funding because that looks great in a press release.

Your ego wants to hire people you don’t even need because how else will they know that you’re doing well?

Your ego is more concerned with looking successful than actually being successful. #WhileTheySleep #WeAllHaveTheSame24Hours

Your ego makes it difficult for you to say “no” to every idea, project or initiative that comes your way, because FOMO.

FOMO Loading...

Your ego keeps asking ‘why is this happening to me? I don't deserve this! How can I turn this around and prove to everyone that I’m as great as I think I am?’

Your ego can’t wait to mention whom you know and what title you’ve bestowed upon yourself.

You ego fuels anxiety because it makes you more concerned about keeping up with appearances.

Your ego can make you waste your life doing things you don’t like to get things you don’t really want to prove yourself to people you don’t respect. All in return for elevated social status.

An inflated ego can be your enemy because it leads you to:

  • Have a sense of entitlement.

  • Create unrealistic expectations.

  • Become dependent on external validation.

  • Lose touch with reality.

  • View constructive criticism as a personal attack.

We’re all guilty of these things at varying degrees. We use social media to talk about how great we are, the many books we’ve read, the kilometres we’ve run, the successful people we know, the money we make and many other achievements to signal some form of success.

There’s definitely nothing wrong with celebrating your achievements; that’s an important part of the journey. You worked hard for these milestones and you should go all out! Give yourself a high-five right now for being awesome!

High Five!

However, the tricky part is that the lines are easily blurred between celebrating who you are in public and the unhealthy habit of signalling for society’s approval and validation. As an entrepreneur, it’s even harder to draw the line because signalling success can, in some instances, bear fruit for your business. We all have an ego and we all need validation in one form or the other. What’s important is understanding how this can make or break us.

We Don’t Operate in a Vacuum

Back when I worked as an investment analyst, our investment philosophy emphasised the fact that companies don’t operate in a vacuum. An analysis of a company’s financials isn’t enough to determine whether you have a good buying opportunity or not. You also need an understanding of macro-economic trends, as they create great investment opportunities.

How does this apply to our ego? Well, because we live in a society governed by the forces of supply and demand. Since the beginning of time, humans have always been attracted to shiny things. That Instagram celebrity posting all the rented cars, fake watches and borrowed cash has a perceived higher social status, regardless of how the material items are attained. Since perception is reality, they’ll attract the attention and exposure to opportunities that can increase the chances of acquiring those items. 

Is this sustainable? Nope. Does it lead to a happier life? Double nope. You’ll have to continuously keep up with appearances and live your life according to an external yardstick that you have no control over. As Holiday highlights in Ego is the Enemy, an unchecked ego has led many historical figures to an unhappy life.

Trying to keep up with appearances like...

Your goal, however, should not be to eliminate the ego completely, but rather, to have a healthy dose of it – just enough to navigate this rigorous path you’ve chosen. You just need to become aware of how it can get in the way of your decision-making and not let it damage the relationships around you. To keep your ego in check, you need to be honest with yourself at all times.

When you have a healthy dose of ego to keep you afloat.

Keep it Real with Yourself

“Sometimes one must choose to be silent, or be silenced. But if a truth cannot be spoken, it must at least be known. Even if you dare not speak truth to others, never lie to yourself.”

- Frances Hardinge

How many people have you heard say they produce their best work under pressure? I've sat on many interview panels and I hear this mentioned all the time. However, the truth of that matter is that most people buckle under pressure and when it happens, their mental health is negatively impacted and their relationships are strained, which in turn affects their work.


When you’re under pressure, there is usually a hard deadline that you can’t afford to miss. This means that if the task is not completed, there will be consequences. If you’re a student, you need to submit that assignment; otherwise, you risk failing the course. As an entrepreneur, you need to submit that proposal; otherwise, someone else will be given that opportunity. If you’re me, you need to finish this post or else you’ll miss your self-imposed deadline to publish a blog post. 

That doesn’t mean you produce your best work under pressure. It just means you don’t have room to procrastinate when you have conditions that force you to do your work. 

This is a common lie we tell ourselves, amongst many others. Without taking time to actually interrogate yourself and reflect on your experiences, it’s easy to live your life thinking you have qualities that don’t exist.

Do you love your job as a whole or do you just like the praise that comes with the title?

Is this business really your passion? Or do you just want an extra income?

Is your employee/co-founder living up to your expectations or are you just avoiding the uncomfortable process of letting them go?

Are those people really haters or are you just avoiding their (constructive) criticism?

Are you really offended or are you acting out of insecurity?

Are KFC Zinger Wings really delicious? I mean, the answer is always yes, but you catch my drift.

What you need to understand is that there’s no wrong answer to these questions. It’s okay to just want to make an extra income. It’s okay to just want to do things because you think they make you look cool. It’s okay to work at a job you don’t like if that’s your only option. It’s okay to build things for short-term gain with no long-term strategy. 

Working on projects you’re not passionate about for short-term gain is not a sustainable strategy as you won’t have the motivation to persist when you hit roadblocks. But that doesn’t mean you shouldn’t work on that project if you want to. The key thing is for you to be aware of your intentions and understand and accept the trade-offs of your choices.

Being honest with yourself will help you combat the many cognitive biases you have to deal with as an entrepreneur. It will help you understand what’s driving your subconscious behaviour. To draw insight from your experiences or intentions, you need to reflect on them by asking yourself the right questions.

The Right Questions

“Insight doesn’t come from success or failure but rather from reflection.”

Shane Parrish

The process of introspection requires you to interrogate your experiences and how you interpret them. When thinking about business processes, we’re always encouraged to start with “why?”. On the surface, it makes sense to ask “why do you do the things you do?” You need to build a strong foundation for your motives and “why?” questions do exactly that.

However, most “why?” questions do more harm than good when it comes to introspection.

“Why?” carries emotionally charged assumptions which can turn you into a victim who cannot objectively see the situation for what it is. If you ask yourself “why am I angry?”, you’ve already assumed that the emotion you are feeling is anger. 

If you ask yourself, “what am I feeling right now?”, you give yourself a chance to name the emotion and deal with it as opposed to just experiencing it. 

If you ask yourself, “why do I hate my job?”, you’re reinforcing the idea that your job isn’t suitable to you and the main solution would be to move on to another one. However, asking yourself what you hate about your job is a more productive approach, as it pushes you to explicitly list out the things you hate and could possibly change.

What questions will keep you open to discovering new information that can be negative or in conflict of our existing beliefs. Why questions have the exact opposite effect.”

- Dr Tasha Eurich

When you encounter a problem or negative experience, asking “why?” can lead to rumination. Psychologist, Susan Nolen-Hoeksema described rumination as the tendency to repetitively think about the causes, situational factors and consequences of one’s negative emotional experience.

When you think you're getting somewhere...

Rumination can masquerade as self-reflection, but falling down this rabbit hole is counterproductive and can cause anxiety, and anxiety interferes with problem solving. We ruminate most when we analyse situations where we feel our abilities fell short. To avoid rumination, it’s important not to be too harsh on yourself and to let go of unattainable goals. Instead, focus on what’s within reach.

Be Kind to Yourself

Ultimately, the goal of becoming more self-aware is self-acceptance. You have to make peace with the reality of whom you are before considering the changes you need to make in order to become whom you want to be.

In the book, The Courage to be Disliked by Ichiro Kishimi and Fumitake Koga, it is emphasised that it is not self-affirmation we should be concerned with, but self-acceptance. Self-affirmation is making suggestions to yourself even when something is beyond your ability. Self-acceptance is accepting your shortcomings and figuring out how to improve. 

One example given in the book is when you get 60% in your exam and you’re not too happy with your performance. Self-affirmation is telling yourself that you were unlucky and that next time you will get 100%. By contrast, self-acceptance is accepting that you’re a 60% person and proceeding to figure out what needs to change to become a 100% person. Without self-acceptance, self-awareness becomes an unpleasant process which prevents you from living a happy and fulfilling life. Appreciate who you are at every step of the journey.

When that self-acceptance kicks in.

While you shouldn’t delude yourself, keep in mind that we tend to talk in much harsher tones to ourselves than we would with other people. Your internal dialogue should always leave you hopeful, motivated and optimistic about the future. To avoid judging and overly criticising yourself, ask if you would say those harsh things to someone you love. Chances are the answer would be no. Always view yourself from the third-person and give yourself constructive feedback, which will progressively develop the self-confidence you need to mould a healthy self-image.

It’s Not Easy

Assuming you don’t become a monk and isolate yourself from the rest of the world, it’s nearly impossible to get to a point where you’re entirely self-aware. Constant exposure to the internet, amongst other mediums of communication, means that we’re constantly fed new information on a daily basis. We are complex, multivariate individuals, with urges, goals, interests and ideas that evolve. This makes it impossible to accurately predict and know how you will respond to every situation you encounter in your lifetime. However, being self-aware can give you a fairly good idea of the actions inspired by the emotions that have been triggered by your experiences.

The core of self-awareness is cultivating the ability to manage what takes up your energy as an entrepreneur. Once you discard all the unnecessary clutter, how do you then get the most out of the essentials? That’s the next phase of the clean-up process – time management.

Recommended Reading list:

  1. The Courage to Be Disliked - Ichiro Kishimi, Fumitake Koga
  2. Ego is the Enemy - Ryan Holiday
  3. Insight - Tasha Eurich
  4. The Entrepreneur’s Guide to Keeping Your Sh*t Together - Sherry Walling, Rob Walling
  5. A Guide to the Good Life - William B. Irvine


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If you would like to read more about my background, check out my
Origins Story.

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