Journey To Original Thought

Benson Mugure
14 min readAug 16, 2022

Countless philosophers and successful startup founders frequently advise us to ‘think originally’. It’s weird to think that most of us think unoriginally or in a fake way. It’s even more peculiar to call anything original in our ever increasingly complex and interconnected world. We pick up on ideas and information, actively or passively, and some trickle down into our subconscious and may emerge again veiled as a flame of creative outburst. Therefore, some of the ideas, ideals and ethics that we credit to ourselves may have never been ours to begin with. Yet it is not entirely impossible, because nothing ever really is, to independently come up with a most common idea. In his book, Sapiens, Yuval Noah Harari states that agriculture may have begun independently along fertile river valleys all over the world from Mesopotamia to the Yellow river in China. So how do you know if your ideas are original? How do you know that you have gone beyond the combined experiences of human life, which Carl Jung called the Collective Unconscious, and have begun to generate original ideas? I guess an even more important question is this: How does one start to think originally?

Paul Buchheit, the founder of Gmail and investor of JustinTV which later became Twitch, gave a talk recently reflecting on his startup experiences and gifting us with what he considers essentials of original thinking. I have outlined the key points below.

  1. I don’t know anything

Back in High School, our Deputy Principal gave us a quote which we all laughed at. The quote was: “I am the wisest man alive, for I know one thing, and that is that I know nothing. ” To his benefit, we did change his nickname from the previously boring ones to Wiseman. The quote by Socrates has many interpretations but the one I like most is that he was contemplating the vastness and infinity of knowledge that exists in the world compared with what he knew. It would seem insignificantly small, to put it bluntly.

Most of us fear knowing too little. We guess and pretend and use lots of words instead of stating the truth which is simply: We do not know. In Swahili we have the proverb Kuuliza si ujinga which means to question is not to be foolish. One who asks might be a fool for a moment but the one who doesn’t will be a fool forever. The next time you catch yourself using jargon and other means to try and cover up a lack of knowledge just use the Feynman razor and question instead of assuming and pretending. And yet this is only one half of not knowing anything. The other half is about constancy.

It takes 10, 000 hours of deliberate practice to become an expert on something. However, time and intentionality are not the only parts that exist in that equation. The system must be predictable, there must be a way to receive feedback on most recent performance, there must be a way to compare results with precedents in the past or with others’ in the present and many more factors.

Most people know this; They know they should question, they know they should remain hungry for knowledge and strive to be lifelong learners but what is unknown to most is the danger that lies in becoming an expert. Paul called it the danger of experience and expertise. You become an expert by recognizing patterns and recognizing and applying rules. To be originally creative, one has to break these rules. Yet as you work on becoming an expert, you follow them for thousands of hours and thus why experts are mostly in a prison of their own design. Jeff Bezos says that you must maintain the curiosity of a novice even as you become more proficient as an expert, for that is the sweet spot where magical innovation happens. For those thinking that one can only either be a novice or an expert to succeed, that is what we refer to as the Tyranny of the OR (a kind of false dichotomy). It is a mental fallacy that clouds judgment and impedes progress. To counter the tyranny of the OR, we must embrace the genius of the AND. The genius of the AND is not a balance. It is both X and Y, not X sometime and Y some other time. It is extreme X and extreme Y. We must become both great in depth experts in our topics but also have the curiosity and imagination associated with novices. A good example of the genius of the AND is when Jeff Bezos was asked about work-life balance. His answer, which I consider a masterpiece, is that you can never attain a work-life balance. He sees it as more of a work-life cycle. You need to be happy and satisfied at home for you to perform optimally in the workplace and vice versa. It is more of a cycle than a simple trade off of time and attention. In the same manner, successful startup founders are a dichotomy of seemingly contrasting characteristics. They might be billions but low on liquidity. They might be arrogant when it comes to ideas and humble when it comes to market-proven facts. Great companies are the same too. They pursue profits AND ideals AND impact. Not OR. Not sometimes this and the other that. One has to have both short term and long term goals and deliverables and pursue both. Let the short-term be subject to feedback and pivoting but remember to keep the long term ones constant no matter what. That’s how you remain dynamic and consistent at the same time.

The danger of experience and expertise is the reason why young founders tend to be more successful companies. I will caveat this with the fact that I mean young and heart and mind and not just in age and experience or lack thereof. Truthfully speaking, success requires a certain level of arrogance that is demanded by contrarian thinking. At some point, you have to stop listening to even those who know, for knowledge is a prison of its own kind. Do not be limited by other people’s experiences. Just because something worked before doesn’t mean it will now. Similarly, just because something has never worked doesn’t mean it never will. Technology has brought us closer, allowing for people to rent spaces (via AirBnB) half a world away in places they might never visit in their lifetime in order to donate money to Ukraine war victims. The possibilities are infinite. However, we have to remember that the best opportunities live in our collective blind spots (and they seem either bad or unimportant).

Something that might be even more dangerous than experience, is dogma and ideology. This is the reason why ideological societies are less innovative. I guess science has to kill god if progress is to be imminent. If you think that you are rational then you are already in the trap for a lot goes on underneath our consciousness both with neither our knowledge nor our permission. In terms of valuing a team (for investors) or a prospective hire/co-founder (for founders), I would suggest valuing the rate of improvement more than experience and current accomplishments.

“I am the wisest man alive, for I know one thing, and that is that I know nothing.”

Socrates

Thinking modern man

2. Kill all daemon processes

Daemons are OS background programs that perform services which are often invisible to the user. They consume memory, processor and other resources. This is the reason why computers and mobile phones work better after a reboot. In our context, daemons include doubt, anger, self-loathing, the internalized voices of our parents, media, the internet and many more.

If you catch yourself in a daemon process, take some time to find clarity of mind. Meditate, walk in nature, draw, play, read, write etc. Do not assume to know what is pulling you back for as already stated, you know nothing. Question the daemon out of existence. The stoics had such an MO for anger when insulted. They would ask one of two questions. If the said words were true, why should I be angered by the truth? If the said words were false, why should lies anger me? Thinking logically on these two are sure ways to conclude that anger due to insults is unjustified. It is a result of ego and ego is the enemy. The daemon is just a symptom.

3. Accept and move Forward (Yes and Thank You)

Even if you avoid risk all your life, life will still not go as planned. Setbacks in life and startups are inevitable. As a matter of fact, reaction to setbacks is a predictor of success. Some of the best things and ideas are rooted in some of the worst of events. When asked how founders should go about pivoting, the great entrepreneur and billionaire Peter Thiel said that no one should anticipate pivoting. Pivoting is a signal that you have done something wrong or you were wrong in your assumptions and no one plans for that. You should, however, build tenacity and be willing to accept facts. To succeed, you need such strong self-belief that it could be confused with delusion. This should, however, be caveated with a fast feedback loop that proves what is true and which assumptions are wrong. Reid Hoffman likens this loop to the OODA (Observe-Orient-Decide-Act) loop that is used in piloting.

Naval Ravikant says to work as hard as you can even if what you work on and who you work with is more important. In the startup landscape, team is slightly more important than idea because the team can always pivot. Ideas are a dime a dozen. In fact you can find a couple if you go on TiBA right now. The speed of execution and learning is essential for success. Once you decide what to work on, you must move as fast as is humanly possible be it in a team or alone. Momentum compounds and success begets success. You can get to the 90th percentile of your area of expertise by working hard or working smart. However, to get to the 99th percentile, you must do both. Focus with all your strength on your chosen path for focus is a multiplier of effort. Work stamina is actually a predictor of long term success.

The concept of Knowledge-execution gap can be used to check how much of the knowledge we are acquiring is just in time knowledge as compared to just in case knowledge. Almost everyone has this gap. There are some things that are nice to know and these are just in case knowledge which do in fact come in handy when climbing mountains, as we will see in the next point. There are also those things that we need to know to pass exams, be better friends and partners or run ventures successfully. This is the just in time information that leads to a lesser knowledge-execution gap is what one is encouraged to get more of for you to execute on them almost instantly testing their validity, relevance and usefulness.

One might ask: When will you know if you have learnt enough to execute? To be honest, I have no idea. I, however, doubt that you will ever get to that point. Execute as a means of learning and testing hypotheses for that is the way of science. Be that as it may, it might interest you to learn that there’s actually an algorithm that can help with this dilemma. It is called the explore-exploit algorithm. Exploration is the act of figuring out new stuff, of learning and adventure whereas exploitation is the stage where you execute on what you have already learnt and capitalize on it. Both these stages are very important but you can choose which one you want to be in depending on a number of factors. The first is time. Exploration needs a lot of time. You need to set aside tons of unaccountable time because you are getting into a new field and you must crawl before you can walk then run. As a rule of the thumb, explore when you have time and exploit when you don’t. You should be optimistic in exploration so that you can minimize regret, the regret of having not explored enough. You should also be thorough in exploring so that it can benefit you in your exploitation face. Remember, failures are just information that we can use to make better explore-exploit decisions in the future. The exploration stage gives long term returns in terms of memory and satisfaction whereas the exploitation stage gives the same on a short term basis. This is thus a trade-off between the long term and the short term. In his book, Algorithms to live By, Brian Christian states that: “Life is a balance between novelty and tradition, between the latest and the greatest, between taking risk and souring what we know and love.”

The concept of Knowledge-execution gap can be used to check how much of the knowledge we are acquiring is just in time knowledge as compared to just in case knowledge.

4. Choose the more interesting Path (The Path Not Taken)

Interestingness is a sign of unexplored/under-explored territory. Great startups exist in a state of productive uncertainty. Regardless of success or failure, they learn something interesting.

If you have only one definition of success then you are setting yourself up for failure. You can actually guarantee success by redefining it to mean ‘learn something interesting.’ Then you will both succeed and learn a lot. Learning should, however, be built into your day-to-day activities and not just a word that you use to justify a failed endeavour. Try and set yourself up for learning by integrating an OODA loop into your work, project, startup and even life. Start with an open ended question, make some assumptions and then test these, doubling down on what works and cutting down on what doesn’t. The easiest way to measure value and impact is numbers and that is why Nicki Minaj sure knows what she’s saying when she sings, “We made the greatest impact check the spreadsheet…”

Back when I was doing my college admissions, my college Counsellor advised us to be bold in highlighting our uniqueness. She used to say that college admissions officers admit students the way florists pick flowers for a bouquet: The more unique the better the chances of being picked. This is where contrarian thinking comes in. If we all had the same experiences then we would come to the same conclusions, right? Steve Jobs once defined the word smart using a city analogy: Guys are down there with maps trying to make sense of routes yet you can see all of it from the 80th floor of a building making connections where the rest can’t. To do this, you need different experiences than anyone else.

In life we’re always climbing mountains, moving from one challenge to another be it socially, academically or professionally. However, with a land full of mountains made possible by the internet, how do we know that we are climbing the very highest one? How do you, for instance, know that getting your undergrad degree will lead to the satisfaction that you want and increase your employability? How do you know that that relationship you are chasing will allow you to become the best version of yourself? Fortunately, this is a problem that has been pondered on before and we now know that the best way to increase the chances that you are climbing the highest mountain is to drop yourself in different landscapes then climb the highest mountain that you see. If you do this a couple of times, then chances only increase much more. So, you don’t drink nor smoke but are wondering how to network? Pay a visit to that bar. Are you all about climate change and social impact? Visit the next club meeting on making money and growing your net worth.

The most exciting things pass us by because they are hidden within plain sight. There are worlds upon worlds. This is not an invitation to do everything that can be done. This is just a suggestion to immerse yourself in unfamiliar territory every now and then and then go with the flow. The flow in this case is what you like, enjoy or completely love. That is your highest mountain in sight. Only by pursuing our genuine curiosity can we find specific knowledge. Specific knowledge is knowledge so unique to our persona that only we can replicate it. It’s like certain music or public speech, or even creativity woven into a film, a podcast, a TV or radio show or just a book, blog or software.

“We made the greatest impact check the spreadsheet…”

Nicki Minaj

5. Love What You Do

The advice being peddled everywhere is that you should do what you love. This is wrong because of a number of reasons. First, you might never find that thing that you love. Everyone is drawn to something but this is mostly when it is new and unfamiliar. Once we get used to it, the initial glow of unfamiliarity fades and it becomes a chore, a bother or an outright burden. Jeff Bezos reminds us that although we have been granted gifts and talents, we must never think that these determine our lives. Yes, to an extent, our passions choose us more than we choose them but that doesn’t necessarily mean that we have to pursue them. Our decisions, not our passions, are what determines what direction our lives will take. Another reason why you shouldn’t do what you love is that this advice assumes that what you love is fixed. When I was young, I used to love suits. Right now, I can’t stand being in one. Interests change, passions change, desires fade… Such is the nature of life. We will find ourselves, now or in the future, where we despise what is required of us. Should we then not do it so as to follow this advice? Of course not! Responsibility is part of maturity.

What we need is to change how we do what we are doing rather than changing what we are actually doing or neglecting it altogether. Being goal oriented might sound nice in theory but in reality it treats the time between now and task completion as an obstacle, a period to suffer and labour through. This is tough particularly in startups. An intrinsic approach to motivation and satisfaction ultimately increases the quality of our effort. You should do stuff to impress yourself. I know of a founder who ranks ideas based on how happy he would be if they worked, not on viability, scalability or potential. Focus on the next step rather than the end goal; Though you should keep it at the back of your mind since life and startups are long term games. You should maintain a meaningful and inspiring vision to hack the grind dull moments because a startup is just like a baby (5% cute and adorable; 95% diapers and vomit).

Just Like a Baby, a startup is 5% Cute and adorable and 95% diapers and vomit.

6. Maintain a healthy disregard for the impossible

Nothing is impossible. I doubt that is true for two reasons. First, no one has ever tried everything that can be tried to find out if one of them is impossible. And second, we can’t use the past to predict the future. The future is sooner and more peculiar than we can predict. Things that seemed, and most probably were, impossible just a couple hundred years back are now the new norm. However, to succeed, you need to maintain a healthy disregard for the impossible. This is why you should hire and spend time with rational optimists. Like Thanos, you must make yourself inevitable. Build leverage and competitive advantage so much that you are impossible to compete with. Compound yourself by letting go of small linear opportunities. This can be done by moving from zero to one every time rather than one to n, which is just copying or adding unto what already exists in the world/market.

You should have insanely great ideas in your startup that sound like you want to take over the world. Rather than succeed at something inconsequential, it is much better to fail at something awesome. Encourage doing impossible things. Impossible becomes the new normal quite quickly. Startups are machines for harnessing the fire of self interest, creating a self sustaining reaction capable of transforming the world. Economically, we don’t need more jobs, we need more Steve Jobs.

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