The Wise Entrepreneur

9 Dark Secrets (Mysterious Realities) of Entrepreneurship

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9 Dark Secrets Mysterious Realities of Entrepreneurship
Dark secrets of entrepreneurship

Photo by Walther Luecker on Unsplash

By the way, one of the categories of homo sapiens that are always looked at with quite some suspicion are entrepreneurs!

One of the reasons for this suspicion is the notion that entrepreneurs have quite some secrets.

Some people think entrepreneurs are superhumans. Some parents have even discouraged their children from being close to the ‘rich and manipulative’ individuals.

Do all entrepreneurs have and know these perceived secrets? Some may not – but I guess many people will still insist that they don’t quite understand entrepreneurs. Isn’t this true?

This is why my blog of today is about dark secrets of entrepreneurship!

I mean dark in the sense that little is known about them – not in the sense that they are terrible.

Why this topic? To non-entrepreneurs, I think it’s good to have an idea of some of these realities, kept hidden but true.

You never know – the article might change your opinion about entrepreneurs. They have their tribe and simply follow the rules and thinking patterns of that tribe.

To entrepreneurs, well – this can help you square up also and embrace them, and possibly find some work-arounds to manage them whenever you are.

Can we now take a look at these?

1. Some reasonable level of greed is required for entrepreneurial success. You don’t need to blame me for this. I’m writing about reality. Ok? Don’t rush to a conclusion.

Greed is simply an extreme or excessive desire for something, or to get more than you need – could be money, wealth, fame, power etc. in this case.

This may not be the primary driving factor – but could in entrepreneurship. I can hear you argue about meeting demands, serving humanity, creating value etc.

Devising strategies to beat your main competitor hands down, for market share has some element of greed. Don’t you agree with me? Any arguments?

Candidly, there is some level of greed that drives very successful entrepreneurs. Of course, the good side of this is that such entrepreneurs give a lot back to society. In this way it gets squared up somehow.

They also satisfy demand in various ways. They invest and create employment and tax with other multiplier benefits despite the apparent ‘greed’ – call it ‘drive’ if you like.

Let’s be honest. In entrepreneurship you provide value at a profit. In other words, you work every day to create and deliver value while taking away some money from another man’s pocket.

You retain some of this money. Do you just retain enough or more?

No one may assess what exactly you retain – and let’s not make this a matter of argument. Ok. It becomes a grey area if we start talking about and assessing the level of greed in this.

In entrepreneurship we talk about profit maximization, shareholder wealth maximization, scaling a business and the like. You really need to convince me that there is no element of greed in this.

I’m not even talking about some reportedly underhand things such as stealing stocks, snatching other people’s dream ideas, breaching contracts and being a controlling alpha male etc. linked to the likes of Steve Jobs, Bill Gates, Elon Musk, Ray Croc etc.

Can we proceed to my next point now?

2. Entrepreneurs often are overconfident and are slow in seeking help and trusting others. This is another thing about entrepreneurs.

Deep inside almost every entrepreneur is the thinking that they are smart, and they know it all. Sometimes it takes a big setback, catastrophic mistake or failure – to give up on that notion and provide some room to unlearn and re-learn.

Humility sometimes comes at a high cost and rather late.

This is one reason why some folks thing entrepreneurs suffer from the nasty disease of Whatifitis – in relation to the reluctance to bring in external resource and advice.

This psychological attribute of overconfidence can lead to failure of enterprises. It is even referred to as a death trap in an article by Forbes.

Despite these warnings, overconfidence is one of the dark secrets of entrepreneurship. It’s not easy to eliminate this from an entrepreneur.

I mean, you don’t need to hear an entrepreneur yap about this – but they keep it deep down in their hearts. Trust me! Of course, you can get rare exceptions.

Being a bit paranoid and not trusting other people is closely associated with this.

I have sometimes also exhibited this kind of thoughts in my small enterprise, and you don’t need to blame me. What about the big players then?

3. There is nothing for nothing in the real world – there is a price for everything. Every entrepreneur knows at the back of their minds that there is nothing for nothing in this world.

The entrepreneurship world is not the governmental or non-governmental world where sometimes you get freebies – though paid for by another person (the tax payer or donor).

Governments introduce tax syringes (Ugh!) into some people and organizations and extract money – whether they like it or not. NGO’s are more human in their approach – usually sweet-talking people and other organizations into supporting some humanitarian causes.

Not so for entrepreneurs! Forget about the donations that occasionally spring up.

Don’t be deceived in the entrepreneurial jungle. There is no free lunch.

You need to seriously (I mean very seriously) convince someone to give you a grant (even $500) or lend you money to invest in your start-up. No one puts money in a dumb idea! You need to come up with something sexy to sell – otherwise no one will give you a dime.

You need to pay something at least to that start-up employee working his or lungs out in the name of sacrificing for your business.

Your smile and sweet words about sacrifice do not pay bills. Are we together?

Don’t joke with a competitor, however friendly, because they could give you an upper cut if they had that chance.

If you are not productive (creating value) you get nothing even if you keep yourself busy.

My 7 Guidelines To Improve An Entrepreneur’s Productivity could be handy here.

Come on – do you understand?

There is nothing for nothing. Isn’t this another dark secret of entrepreneurship?

4. Success is normally a long and tough walk. Closely associated with my point about nothing-for-nothing above, is the fact that you need to be prepared for a long and tough walk.

Very few entrepreneurs get it easy. You need to make big sacrifices about money, time, relationships etc. to succeed. Rhett Power writes about this in the Newsletter.

The entrepreneurship journey is a long walk on a narrow, winding and slippery road – and you need to be prepared for this, my dear entrepreneur!

9 Dark Secrets Mysterious Realities of Entrepreneurship
Success is a long walk

I’m not scaring you. Ok. Just be ready to fail severally before you level up. Gear up to have some remorse for worse decisions, having a tough personal life and doing the donkey work for a while.

On extra workload – I vividly remember my days sitting up late every night after a very long day at work, to do accounts for a college we started with some friends. We could not afford a bursar – but we needed to understand our numbers somehow. Poor me!

There are many risks but you need to learn lessons about risk to succeed. You can read more about this in my previous articles entitled What an Entrepreneur Must Know About Business Risks and Top Lessons about Risk for an Entrepreneur – Part 1.

You need resilience to succeed.

Success and money do not come easy – and sometimes you could get emotional.

These are hard realities – but most entrepreneurs know this. They meditate about this – rarely speaking about it. The ignorant ones will learn this secret along the way.

5. Personal trials and challenges are real – and be ready to be misunderstood. Candidly, I could come up with a long list of personal trials and challenges an entrepreneur faces at different stages of the entrepreneurial journey.

Indeed, one could write a good book on this.

There are hosts of issues and likening this to a person riding a lion is a good illustration of the psychological price of entrepreneurship.

Many entrepreneurs suffer silently and mute their fears – thinking that talking about this show weakness.

Even suicidal risks have been documented in a Forbes Newsletter. This could arise from restless, depression, isolation, rejection and failure among others.

Issues to consider include loneliness, confidence crisis (despite overconfidence mentioned above), financial crisis, appearance of being selfish, insecurity, feeling stupid sometimes, watching people run away when you fail, mistrust etc.

When looking for money bankers and investors sometimes cast doubtful and prying eyes on you. It’s like you are going to take their money and escape to another continent or just die without paying back the coins.

There is a saying that you don’t demand money from the dead. This is why bankers fear sole proprietor enterprises. Don’t you agree with me? At least for a ‘corporate being’ they can proceed further within the law to demand.

Staffs watch you too – sometimes imagining you are always thinking that they are lazy. Can you imagine? I’ve read about this.

Sometimes you blindly assume that people have far bought into your vision, yet in reality they are yet to start believing in that dream you are very passionate about.

Customers and clients could think you are intruding into their personal affairs and lives in the guise of selling your products to meet their needs, etc.

Leigh Ann Betts writes about her entrepreneurial trials and tribulations, for example, but you could also listen to some podcasts on overcoming these trials – as these could be useful.

These trials are real – and form part of the dark secrets of entrepreneurship.

I hope I’m not committing a crime or sin by bringing them to the open.

6. You hire people to add value and sense – not nonsense. Again, this is another dark secret that entrepreneurs keep at the back of their mind.

In short – staffs or employees that do not add much to the enterprise are always a liability. There is so much setback and costs related to non-performing employees that entrepreneurs oftentimes scratch their heads about this silently for a while.

If an entrepreneur does not have the gut to fire immediately then he has some temporary torture on how to deal with such.

Of course, firing is the most advisable thing to do if the matter is serious – but sometimes the situation is not very straightforward. Even large businesses have sometimes turned political when it comes to this.

Sometimes some restructuring is done or abnormal conditions and situations created with the hope that the said staffs (especially executives) eventually leave on their own.

It could be a decision between kindness and reality.

An article in Forbes advises on how to fire gracefully.

Even before firing, there are some suggestions on how to handle underperforming staffs to avoid outright firing.

Are you still with me? Let me assume so.

7. Lots of things are beyond your control – but life goes on. Another dark secret entrepreneurs have is their knowledge that some things are in reality beyond their control.

Come on! Don’t mind the very brave and confident face entrepreneurs always portray even in the midst of a crisis. Sometimes big talk and grammar is used to cover a crisis.

Deep within them they have this fear of things they cannot control. Sometimes this takes away sleep but folks pretend that all is well.

These things could be a big and aggressive competitor with capacity to put on a serious fight for the market, government decisions that could cripple business operations and profitability, the knowledge that you aren’t the best in the market, etc.

Nevertheless, life must proceed.

8. Picking your poison. Entrepreneurs are oftentimes in between a rock and a hard place as far as decision making is concerned.

Sometimes the choices are very tough. It could be the decision between having food in your house or cash in the hands of your start-up employees. It could be that bad.

It might be the choice to reluctantly give up equity to continue with the business or shut down.

Picking your poison illustrates some of the tough choices.

Now, when you see an entrepreneur losing sleep over these, you can’t blame him. Can you?

Ok. Let’s now proceed to my last point about dark secrets of entrepreneurship.

9. Certain things are only in your head – and these indeed ring louder than any other thing. Without appearing like I’m trying to decode rocket science here – let me say this; it’s not easy to fully comprehend all the things that go on in an entrepreneur’s mind!

For example, data is not the sole predictor of outcomes for entrepreneurs. If you want to pick a quarrel with an aggressive and adventurous entrepreneur, try and argue along that data line only.

This is especially true for new products and services – and damn risky maneuvers.

Again, comfort with uncertainty is normal. This is one reason why some entrepreneurs argue with accountants. Accountants want some certainty. Some logic and pattern.

Take a look at 5 Entrepreneurs Who Ignored Their Advisers and Became Wildly Rich. It might make you appreciate what goes inside an entrepreneur’s brain.

We are entrepreneurs. Don’t call us crazy. One of our dark secrets is that some things only ring in our heads – and they ring loud. You need to let us follow this sound. Ok?

In making my rapid conclusion, the 9 dark secrets of entrepreneurship are very valuable for all of us to know.  Don’t you agree with me? They are the vibes of the entrepreneurial tribe.

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Have a fantabulous week ahead,

The Wise Entrepreneur



Picture of Clayton W. L. Mwaka

Clayton W. L. Mwaka

Clayton W. L. Mwaka, a Ugandan chartered accountant and motivational speaker with 24 years of diverse experience, specializes in business administration, international consultancy, and lecturing. He advocates for personal empowerment through balanced living, qualitative leadership, and paradigm shifts, aiming to unlock individual potential globally.

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