Why Entrepreneurial Careers Are The Answer

This post goes into what an entrepreneurial career is, why they’re worth pursuing ahead of conventional careers, and the key pillars underlying them. It‘s written from a philosophical perspective, with the aim of giving you an understanding of how you can cultivate an entrepreneurial career, and the sync they have with living a fulfilling life.


When creating a life that’s meaningful, lived on your own terms, and has you achieving all that you could — there’s no better career path to choose than one that’s entrepreneurial.

Before diving into why that is, it’s worth exploring what the hell entrepreneurial actually means.

What’s interesting about the word is that it’s an adjective; and so is a matter of perspective, making its meaning subjective. That’s in contrast to the noun “entrepreneur”, which the dictionary defines as:

“a person who organises and operates a business, taking a greater than normal financial risk to do so”.

Seems reasonable. Boiled down, it’s “someone who creates a business” — since the greater financial risk is inherent in that process.

So then — what is an “entrepreneurial career”?

There’s more to it than only “someone who creates and runs a business”; though that’s certainly a huge part of these careers. No — whether your career is entrepreneurial or not is a matter of shared perception that hinges on your mindset and narrative, rather than a tangible definition. You know intuitively when you have an entrepreneurial career — no tangible definition is required.

And the people around you will also intuitively recognise when you’re on an entrepreneurial career path; because they’ve been raised in the same culture as you and so share your perceptions of an entrepreneurial career.

But while we can’t define entrepreneurial, there are two intangible and non-definable, yet immensely powerful forces that underpin every person’s entrepreneurial career. These are mindset and narrative. Since they’re rather philosophical in nature, by simply understanding their importance you’ll be halfway towards creating an entrepreneurial career for yourself. So they’re worth delving into:


The mindset underpinning an entrepreneurial career is one that ‘rightfully fears failure, but takes action anyway.

Sounds a lot like bravery, no?

In contrast to “stupidity” where people don’t fear failure and take action. Which is why the popular Silicon Valley catchphrase of “don’t fear failure” is naive — it’s stupid to not fear failure when there are significant negative consequences related to that failure. Bravery is feeling the fear, and then taking action anyway; as you recognise that fear comes from being aware of the risks involved and that this will help you make the right decisions.

It’s the ability to see your failures not as good things, but still as opportunities to learn fast. It’s understanding that in order to create the most value in the world, you must tread the line between order and chaos; that is, to conceive of the thing you can do that is on the edge of what you are capable of, but not over it.

By doing this continuously — taking action that has you with one foot in what you know and are capable of (order), and one foot in what you don’t know and has risk-reward (chaos), you will create the most value in the world:

An entrepreneurial mindset implies that you take action that has one foot in what you know, and one in the unknown. So you’re not taking excessive risk (too far towards chaos) but also aren’t being too cautious.

By seeing this action at the edge of what you’re capable of as a one-off, you could fail and get bad returns or succeed for high returns. But this doesn’t reflect the real world. Instead, the actions in your career are iterative — you will have many chances to succeed and fail — and taking this approach will lead to the highest realisation of your potential.


If you continuously take action at your edge in your career, you will get the fastest learning from your failures, and will also extract the most value each time you succeed.

These failures and successes feed into each other; you learn from your failures, and what you learn increases the breadth of your capabilities, which, in turn, creates greater value when you do succeed.

Through an entrepreneurial mindset, you’re realising your potential faster than you could anywhere else, and creating the most value.


The other big intangible underlying “entrepreneurial” is owning your personal narrative. Everyone has a narrative; it’s how you view your actions in the context of what you’ve done, and where you want to go in life. For example, two people are laying bricks together. In one person’s view, they’re laying bricks and earning their pay cheque. But to the other person, they’re creating the beginnings of a cathedral.

Most people don’t take the time to understand and tailor their narrative. Instead they make choices without a clear direction in life, which gives space for others influences to shape their life choices and ultimately leads to creating a life that those other influences want for you, rather than what you yourself want.

But in taking ownership of your narrative, you know the direction in which to apply your entrepreneurial mindset — because you’re aware of where you’re headed and why. This has an immense effect on your degree of autonomy, as you’ll be taking actions in sync with what you find meaningful rather than what others find useful. It’ll also raise your ability to persevere through hard times, since the actions you’ll be taking will be intrinsically motivating to you by definition of being in sync with your narrative.

When taking ownership of your narrative, it’s necessary not to fall into the trap that many of our generation do — in seeing an emotional state like happiness as a goal.

Instead, your narrative should be aimed at what you find meaningful. This will give significance to your past actions and also give direction to your future choices.

Pursue Your Meaning, Not Your Happiness

Happiness is not an aim. It’s a “state of being”– a choice you make at each moment. It doesn’t have any bearing on what you have and who you could be; because you could simply decide right now to be happy — and then your life is devoid of any point on the horizon to aim at. Worse still, there’ll be lots of difficult moments in your life, especially if you’re pursuing something truly hard and risky like entrepreneurship. In this case, “happiness as a life aim” paradoxically only serves to make you more unhappy, as you become more aware of your continuous failure to be happy when the inevitable many difficult moments come your way.

Instead, choose to pursue something meaningful in your career . That way each inevitable setback from the entrepreneurial path will be seen as a way to learn and move towards your “point on the horizon”.

It will also act as a barometer by which to make your career decisions, by giving you a clear direction and strength of conviction behind the risks you’ll take. It’s this increased focus, and perceived significance behind your actions, that will lead you achieving so much more and being more fulfilled while doing so.

Maslow updated his hierarchy of needs before death to include “transcendence”. Notice that the two highest needs are deeply related to pursuing what is meaningful to you, and owning your narrative.


The right mindset moves you to create the most value in the world, and to realise your potential.

Owning your narrative orients your choices towards what is meaningful to you, giving autonomy and focus.

Having both of these powerful intangibles in place are the building blocks of any entrepreneurial career — so it’s worth cultivating both.

It means you will make the most impact you can in what you find meaningful; realising your full potential in the process.

It’s easiest to illustrate the need for both of them in being entrepreneurial by removing one of them and seeing what happens:

Mindset Without Narrative

When someone doesn’t take ownership of their narrative, but still has the right mindset, they will take action and develop fast, but in directions that aren’t in their control.

A person without owning their narrative faces many choices on where to apply their entrepreneurial mindset. But has no way of making a decision on which one to select in a coherent way — meaning they will develop fast in taking action at the edge of what they’re capable of, but in the direction established for them by someone else. In not owning their narrative, their choices will be directed by a combination of things; society’s conventions, family expectations, and employer priorities to name a few of the most common factors. This leads to highly capable and driven people achieving lots in their careers, but feeling empty on the inside.

It’s a common story we can see playing out in society today; a young professional who went to a top university, aced their extracurricular activities and degree, and then — unsure of what to do in their careers and without owning their narrative — they jump into the graduate scheme of a corporate. After some years, they’re earning a good salary, may have become a homeowner and may even be married. Yet, they can’t shake the feeling that “there’s got to be more to life than this”. They distract themselves with surface level things; going out, planning holidays, tackling “to do” lists, buying things and more. But the feeling only grows; that something is missing in their lives.

In having the right mindset but not owning a narrative, those people are paying a heavy price. They’re not heading towards something meaningful, and have less time to do so; they sacrifice the impact they could have had on the world and the fulfilment they could have attained; fated to wonder at what could have been until they finally decide to own their narrative.

Narrative Without Mindset

This one’s obvious. For those who own their narrative and understand what’s meaningful to them — they simply won’t manifest their potential or impact the world as they could unless they cultivate the mindset that balances what they’re capable of with the risks of the unknown. They may feel they’re taking the safer route in their choices; but in fact they’re taking the guaranteed route only to not achieving all that they could.

Bringing It All Back To Entrepreneurial Careers

On a practical note to end, what types of careers lend themselves to being entrepreneurial? There are a few, but three in particular spring to mind:

  • founding a company
  • freelancing
  • working in early stage startups

Founding a company gives you the chance to create your vision, and gather together those people who share your vision. It’s the best opportunity to make that vision on your own terms too, all under the imaginary concept of a “company” which removes your personal risk from the venture.

Freelancing gives you the opportunity to work on what you want, where you want and with who you want; achieving state of flow in the work you love while also being tremendously autonomous.

Working in startups makes it possible to join someone else in creating a vision that is closely aligned to your own, while fast tracking your learning by taking on huge responsibility in an environment highly exposed to chaos.

In Conclusion

The purpose of this post was to explore the concept of what makes a career entrepreneurial, and why those types of careers are the best place to realise your potential and manifest your meaning.

To be entrepreneurial is something that does not need to be defined; it is simply recognised in yourself, in others, and by others. There are two intangibles underlying it that I can discern — mindset and narrative.

You will, I hope, know if you have the right mindset and narrative in place to be entrepreneurial from reading this post; and will see the importance of cultivating them both if you don’t.

Thank you for reading; if you disagree with or would like to discuss further any parts of what I’ve written, I’d love to have an open-minded chat with you — just email harry@nomad.academy and we can take it from there :)

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