Want to Succeed as an Entrepreneur? Stop Being so Positive.

Positivity can serve to be more of a weakness than a strength.

Oh, you expected everything to go as planned? You expected this journey to be as simple and joyful as a nice frolic through a field of daisies? Wrong. This entrepreneurial pursuit is not linear. It’s more like an expedition through the Amazon filled with unknown dangers and mosquitoes that give you Lyme disease. As Elon Musk once said:

“Creating a company is a very difficult thing. A friend of mine has a saying: ‘Starting a company is like eating glass and staring into the abyss.’ You have to do lots of things you don’t like.”

I’ve historically made several attempts at building a company and I’ve solely worked as a software developer for Startups, and there is one common mistake I’ve noticed among projects that have failed versus the projects that have succeeded: “The expectation that they’ll succeed.”

This isn’t to say that you should avoid optimism like the plague. In fact, it’s a very powerful tool to help you persevere. It’s the absence of pessimism that leads to downfall. In this sense, raw positivity can serve to be your greatest weakness.

Positivity breeds expectations. Unmet expectations lead to disappointment. Disappointment leads to discouragement. Discouragement leads to giving up. Giving up leads to failure.

This is because the optimist expects greatness as a reward for his progressive actions without regard for unaccounted external circumstances — as if simply working towards a vision is enough. In turn, the optimist becomes naive and blind to the randomness reality presents. When one is naive, they become highly susceptible — emotionally and practically — to any dangers that may arise.

Beware the Black Swan Events

Coined by Nassim Taleb in his book The Black Swan, the black swan is described to be:

“a metaphor that describes an event that comes as a surprise, has a major effect, and is often inappropriately rationalized after the fact with the benefit of hindsight.”

In essence, black swans are the unpredictable unknown unknowns that pose a catastrophic danger. They creep into your workflow and sidewind you into a pit of despair. To be overly optimistic is to potentially ignore the possibilities of these random occurrences. This thus leads to huge consequences because you become blind to such calamitous events. A quote from literary critic Cyril Connoly comes to mind:

“Whom the Gods wish to destroy, they first call promising.”

Rarely anything goes as planned. That’s why being unprepared for the impact of such events may make it more likely for the foundations of your work to crumble when things do go awry. It’s for that exact reason why many projects I partook in and pursued had failed. We were so gassed up on our progress and short-term accomplishments that we became possessed with a degree of optimism that led us to ignore the possibility of future impediments. The lack of expectation for failure made my team ignore the steps needed to mitigate such events.

It’s impossible to control the future. We can’t predict the outcome of anything external to ourselves. That’s why you shouldn’t be so confident and optimistic about the results of your work. One way to draw focus away from the illusion of a bee-line path is to simply focus on the process, but another effective means that improves upon the prior solution is to simply — as the Boy Scout motto goes — be prepared.

The Wisdom of Seeing the Glass Half Empty

To become more prepared, you must anticipate such “black swan events” by first seeing them as an inevitability. You might see this as highly counter-intuitive given that we are always encouraged to see the glass half full. Self-help books and gurus drill into your head the idea that positive thinking and cheerfulness are the primary means of putting you into the driver's seat to the Valhalla of your business goals.

The harsh truth is that everything can fall apart at any given moment. Nothing is so straightforward so best believe that the road ahead will be saturated with complications. You need to march forward fully expecting that at some point, everything may turn to ash. In all likelihood, you won’t succeed in the long-term. The odds are against you.

Now, this isn’t meant to be a depressing reality used to discourage you from trying in the first place. This should simply be a reality you need to meditate upon. To the Stoics, this practice is known as Premeditatio Malorum — the premeditation of the evils and troubles that might lie ahead. One must psychologically prepare themselves for the unexpected blows of fate through negative visualization. To think negatively is to arm yourself against the trials of the future.

This is why Jeff Bezos tells his employees that it’s always “Day 1.” He goes on to say:

“‘Day Two’ is stasis. Followed by irrelevance. Followed by excruciating, painful decline. Followed by death. And that is why it is always Day One at Amazon.”

Bezos visualizes a future where Amazon might die if he were to allow himself to get too comfortable with his current success. He understands that the future isn’t written in the stars. He’s aware that kingdoms do fall no matter their size. To him, meditating upon his potential failure provides him with the motivational fuel to constantly discover ways to innovate, strategize and improve all the while staying humble.

For entrepreneurs alike, thinking with this sort of negativity is of extraordinary value, as it allows you to strategically create a plan to handle and overcome the heart-wrenching trials that the volatility of business presents. As a result, you’re better prepared for the worst to come, have reduced tension of expectation, and shield yourself from disappointment. When you decrease expectations, you can overcome obstacles with a clearer mind.

For instance, consider two entrepreneurs: The budding entrepreneur who begins his business venture with complete optimism that he’ll achieve his business goals only if he were to work hard and long enough without losing focus. Or, the entrepreneur who prepares for a disaster, sets preventative measures, trains her colleagues (if she has them) more rigorously to avoid failure, and moves towards her goal fully anticipating that her path is going to be non-linear, replete with its ups and downs?

Perhaps before you read this article, you might’ve been a sucker for the entrepreneur that puts his head down and focused entirely on his vision accompanied by none other than optimism. In reality, the second entrepreneur would have a better outcome.

She armed herself as a Spartan would in preparation for war. Going in fully expecting that she’ll fail in the process thus making her performance more tactful and relentless. When an obstacle arises, she knows exactly what to do because she is prepared for this moment. On the other hand, the first entrepreneur might be in for a rude awakening — constantly scrambling to find a way to extinguish every little fire that randomly arises.

“We must not react with injured surprise to bad things, these bad things are written into the contract of life” — Alain De Botton

Walk Away From This With a Token of Optimistic Pessimism

Now that you’ve taken a sip of the negativity kool-aid, hopefully, you see that calibrated pessimism is not a personality flaw, but a strength that’ll help you better attain your business goals.

In essence, the type of pessimism I’ve discussed is rather optimistic in its own kind of way. When you meet failure, you’re not led mentally astray and come to understand that extinguishing flames is all part of the process. When you meet good fortune, you now meet it with gratitude as it was a pleasant fruit of your persistent efforts, not because you thought you deserved it.

As William B. Irvine, author of A Guide to the Good Life: The Ancient Art of Stoic Joy, wrote:

“Negative visualization, in other words, teaches us to embrace whatever life we happen to be living and to extract every bit of delight we can from it. But it simultaneously teaches us to prepare ourselves for changes that will deprive us of the things that delight us. It teaches us, in other words, to enjoy what we have without clinging to it.”

Therefore one can conclude that as far as long-term success comes, a good place to start is by simply strategizing for failure now in order to minimize the impact of obstacles in the future. Best to be prepared than not be at all. Dare to be negative.