Aug 27, 2017By Tom Kooy

The Dark & Uncertain Side of Entrepreneurship

Overnight success, unicorn companies, multi-billion dollar valuations. The Bentley, the 12.8m followers on Instagram, the fame and rock-star glory. We’re so quick to paint the glamourous lifestyle of the entrepreneur. We shine light on the success and believe it’s an easy road. But we fail to see the aspects of the entrepreneur’s path where the light doesn’t shine...

Overnight success, unicorn companies, multi-billion dollar valuations. The Bentley, the 12.8m followers on Instagram, the fame and rock-star glory. We’re so quick to paint the glamourous lifestyle of the entrepreneur. We shine light on the success and believe it’s an easy road. But we fail to see the aspects of the entrepreneur’s path where the light doesn’t shine, we don’t see the dark crevices that are filled with moments of depression, loneliness, times where belief and courage are at an all-time low. The stress, the lack of sleep, that feeling of going into battle when your odds are 100 to 1 to win. The gut wrenching, soul crushing moments when all feels lost.

There’s a dark side to entrepreneurship that no one talks about.

We glamourise the idea of business and it’s only when we’re all in, are we able to see the valley of death littered with failed businesses. And then we see why this game is so hard.

This isn’t some ivory tower post. I coach hugely successful serial entrepreneurs, many of whom I speak with daily and I can tell you that we all deal with this darkness. Those sleepless nights aren’t just for the newbie. Even the most seasoned and accomplished entrepreneur would be lying if they said they didn’t feel the weight of this darkness from time to time.

So wherever you are in the world, whatever part of your entrepreneurial journey you’re on, you’ll experience this darkness in one way or another. So for me, here are 4 ways I find helpful as I battle through.

Build Belief Networks

This is why you read so much about entrepreneurs surrounding themselves with the right people. You need those around you to be filled with positivity and a belief that what you are creating is not only possible but is going to be hugely profitable. You need to cut dead wood and negativity from your life if you are going to succeed.

"Whatever you do in life, surround yourself with smart people, who'll argue with you." John Wooden

The magic number (for those looking for that tangible take away) is 5. Find 5 people who you share that commonality with. Embrace one another (not in the hug way), share your successes and failures. Commit to regular structured catch ups, face to face or phone and talk. Not only will it be edifying, but it's highly probable that you will find synergy and opportunities across your businesses, which will only make them better.

You will lose friends and that’s ok. Don’t get hung up on that, if they care deeply about the journey you’re on, they’ll stick around and be there when you have the time. Everyone is always a phone call away, if they care, they’ll call.

Strategise, Plan & Prepare for Uncertainty

We hear everyone talking about this trendy acronym VUCA (Volatility, Uncertainty, Complexity & Ambiguity). So as an individual entrepreneur leading the charge in a business, you’ve got to figure out how to stop in amongst the darkness and chaos, be able to zoom out to 30,000 feet and think strategically about how to battle through these moments of uncertainty. This area requires a good few strategy sessions, but here is a quick tip guide in (a) what to look for in each of these areas and then (b) your response to help you prepare for the unknown...

"The only certainty is that nothing is certain." Pliny the Elder.


What to look for? This is where the challenge you’re facing in your business was hugely unexpected or there is instability and you don’t know how long this issue may be around for. These challenges aren’t necessarily hard to comprehend for the business owner but it’s the uncertainty of how long the volatility will go on for. For example, you run a cosmetics company that sources ingredients from overseas for your product. That overseas country experiences a coup and you can no longer get access to the ingredients you require (or price for the ingredient fluctuates substantially).

How to react? This is where scenario planning comes in and finding a willingness to build in slack. This ensures that should those events actually happen, through planning, you were somewhat prepared with 1-2months of stockpiled inventory (as an example). While expensive, it can be what would save your company.


What to look for? Where the basic causes and effects are known. Being able to change or pivot is possible but not always a guaranteed solution. Something like Amazon coming to Australia. No one quite knows how they will disrupt the food and retail landscape but the waters are quite muddied.

How to React? Data has to become your friend. Get hold of as much information as possible. In the Amazon case, build a database as to what consumers will think of Amazon Go entering the market, how will they engage with the new competitor in the Australian landscape? What impact will Amazon have on the supply chain? It’s by collecting and interpreting data, which will guide how Coles, Woolworths & IGA pivot and make structural changes to reduce the on-going uncertainty around an Amazon market entry.


What to look for? Recognising the challenge you face has many interconnected, different moving parts and variables. You see the trees but really you know you’re lost in a massive forest and require help. A great example is you’re a software company looking at regionalising your product across different countries. Each country has it’s own unique environment and many different moving variables. As such this requires a custom rollout in each region to maximise user engagement.

How to react? This is a moment to stop, consider restructuring your thinking and reach out for expertise to support growing your insight into each of the regions you are looking to rollout and the complexities that need tackling.


What to look for? To quote Donald Rumsfield. There are known knowns. These are things we know that we know. There are known unknowns. That is to say, there are things that we know we don't know. But there are also unknown unknowns. There are things we don't know we don't know. Ambiguity is the later – The unknown unknowns. There is no precedent and the future is completely unclear.

How to react? This is where ideating solutions, prototyping and experimenting is required. Testing your thoughts in the relevant markets and figuring out if your solution will deal with the ambiguity at hand. It is this design thinking and then the testing of this thinking which will guide whether what you will successfully be able to deal with those unknown unknowns.

"VUCA environments, thus become invitations for inaction. People are befuddled by the turmoil and don't act. And to succeed, you must act." General George Casey

While this is a very brief fly through. This type of strategising under a VUCA model will only further enhance your clarity and mental resolve during those times of darkness. VUCA ensures you are fortified enough within yourself to withstand the onslaught of all that being an entrepreneur comes with.

Work Hard with Structure

This is a no-brainer, but by training your brain to work hard and apply good structure to your week, you’ll find an unstoppable momentum.

This means, find daily structures that work for you. What environment, headspace and behaviours do you find support you being at your most productive? And for the opposite, what environment, headspace and behaviours block you from working at your best?

"If you built a house with your work ethic, dedication & preparation, would you trust its foundation enough to live in it?" Robert Griffen III

Figure out what works for you and stick to it. So when you do feel the darkness closing in, by getting up out of bed, putting yourself in the right environment and applying the right behaviours you’ll find this natural inclination to flip into a productive headspace that breaks the self-saboteur inside and you will work hard.

Finally, Be Clear on What you Believe.

So many people believe that entrepreneurs chase the glamour, wealth and fame. But it isn’t the desire for the superficial that gives them the courage to face the darkness. And it isn’t a hunger for some personal freedom to do whatever they like either. They face it to make impact and grow others. Their legacy is beyond themselves, it taps into a greater purpose and they see it as clearly as staring at a picture. It is that clarity of belief and purpose that makes them unstoppable.

"Our Life is what our thoughts make it." Marcus Aurelius

The Richard Branson, The Gary Vaynerchuk and the Tim Ferris’ of the world (to name a few) all have a personal entrepreneurial vision that taps them into something bigger than themselves. And for you, by finding what purpose brings you alive will provide you with a reference point to grab hold of when you catch the darkness creeping in.

Call it a North Star, Tim Ferris calls it Star Therapy or simply just call it your personal vision for your life. It will give you a perspective that will stop the darkness from crippling you, allowing you to face your challenges head on and give you an ability to break from the darkness.


To end, the entrepreneur’s journey is always filled with darkness and struggle, experiences of dramatic highs and hell-bending lows. It is quite-literally a boxing match, where every time you get up, lay a solid punch and it looks like your opponent is out for the count, a left hook comes from nowhere and before you know it, you're knocked back down and the darkness takes over.

And as anyone who is living that business glory right now will tell you, it is the choice you make in that moment of being knocked down, which determines your success. If you stay down, it's obviously over. But it's by clinging to purpose, working hard, having strong belief networks to call on and sound strategic preparation that will give you an unmatchable resolve to get back up and prepare for whatever's coming next.

So find that strength and forge ahead on your entrepreneurial journey.

Stay strong and keep smashing your goals,

All the best,