Challenging Conventional Wisdom: Why Success Stories Can’t Always Guide Your Path

The problem with the advice we find online is that it often comes from a position of success. Rarely do we hear advice from the weary or defeated. If they do give advice, we just don’t listen, why would you? Would you take directions from a blind person? It’s same the reason why the book: “What I Learned Losing a Million Dollars” is not on the New York Best Seller List, but in reality, it’s from these folks that the most can be gained from, not to follow what they did but to know the pitfalls of the exact journey we are on. People who do succeed have completely different points of view from when they were starting off, and the advice they give come from a place of recall rather than from a fresh perspective compared to people who have ingrained experiences of loss.

Can You Remember Dinner?
Let’s do a simple exercise: can you recall how each day of last week felt? How did Monday feel? How did Tuesday feel, and so on? Pause for a bit. If you’re like me, or any other regular person, it would be hard to articulate how the past week has been to its details let alone the minute details of each day, it would be easy to remember the high or low points but not the average. That’s how the brain works, it only remembers things that are worth remembering, and mashes everything else in between.

This however, is not a conscious decision, your brain decides what is worth remembering, if you spilled your coffee in front of your co-workers and embarrassed yourself, your brain goes “Hmm that looks like something I should remember” when in fact you wished that had never happened and it would be erased completely from memory. We aren’t truly in control of what goes stored in our brains and how much detail we can recall from past experiences, why then do we almost always listen to advice from people who made their success 10–20 years ago?

The big CEOs, successful entrepreneurs, and athletes remember the highlights, they remembered when they were struggling or how all they thought about was to push through the uncertainties, but the meat of their experiences, the averages of their day-to-day would have been lost and most of the time it’s in the mundane where the magic happens. They would also have overlooked how luck had played a part in their lives and ultimately in their successes.

In the book “Stumbling on Happiness”, the author discusses about happiness is subjective and that there is no way for one person to convey the same exact feeling of happiness to another person. For example, you can rate your happiness of eating an ice cream a seven out of ten, but your seven could be completely on a different scale as someone who is say on their death bed or from a war-torn country.

He further states that although we have different scales it does not mean any of them are valid or invalid, it’s just that we have a completely different frame of reference. The author continues that the only way we can share our internal dialogue or emotions is by getting the perspective of someone with similar conditions. The key word being similar, because it’s practically impossible to have someone have the same exact conditions as you, even if you had a biological twin, they would have a completely different standpoint as you.

In other words, the people who are in the midst of doing what you are doing have advices that are more invaluable to you rather than from people who’d already done it long in the past.

If that is truly the case, what advices would I make to someone who is also trying to become an entreprenuer coming from the regular 9–5 job?

Buy time when possible
We’ve all heard the cliche, “time is the most valuable thing can spend on”, the reason cliches survives is because there is so much lesson usually packed in them that each interpretation of it passes the test of time. We all have 24 hours in a day regardless of what our standing in life is. What is not obvious is the perception of time can differ from person to person, and it is possible to slow time down based on your frame of mind.

Have you ever experienced that feeling when you’re on a week-long vacation in a tropical island and, before you know it, the vacation is over and you’re left wondering, “Where did the time go?” Or perhaps on a Monday morning, when you find yourself bombarded with back-to-back meetings, making it feel like you’ve been in the office for 16 hours instead of just 8? Our brains translates time differently depending on the context. We can all have 24 hours in a day, but yours can feel shorter or longer depending on what you are doing.

When you can, buy time. Buy a year off from work to allow yourself to pursue that dream. When I say buy time, save enough that when you do take time off you are not constantly thinking about the running bills at home. Sort out your finances and avoid the temporary vacations. When you are on your time off for a longer period of time, time will slow down exponentially. I’m on my 5th week of being a nomad, and my family back home has been constantly messaging me about how I’m doing, to them it feels like I’ve been gone for so long, but the constant change and feeling of not having to be anywhere at any given time has slowed time for me significantly, to them it has been more than a month, but to me it feels like I’ve been traveling for 6 months alone with my thoughts and being able to produce my best work yet.

Always Play the Infinite Game
I first heard the term “infinite game” from Simon Sinek, infinite games are things that will compound in the future regardless of what happens, and essentially that is the only way to win the game. One good metric to understand if you are playing an infinite game is if you multiply whatever you are doing by 10 years. What happens in 10 years if I keep doing what I’m doing? If I kept watching television for 10 years what happens, will that pay dividends? If not, it’s probably best to minimize or stop doing it completely. If I kept reading books for 10 years, what can happen?

If I practice speaking for 10 years, what can happen? This is all subject to personal interpretation because not all form of media or activity is equal. I can read books for 10 years but if the books I read are all nonsense, then it could amount to nothing. In anything you do give it further thought, if I kept doing this is this going to pay me dividends in the future, would I learn an invaluable lesson that will help me later on? “Rome wasn’t built in a day” so play infinite games.

Expose Yourself to as Many Black Swan Events as Possible
Finally, this is one of my favorites: immerse yourself in as many Black Swan events as possible. In other words, embrace the concept of Serendipity Events, as explained by Nassim Taleb in his book “The Black Swan: The Impact of the Highly Improbable”.

Never underestimate the power of being in the right place at the right time. Take Bill Gates, for example. One of the main reasons he was able to build Microsoft was because, when he was younger, he studied on a campus that provided him with free access to a personal computer. He would spend most of his time with it. Imagine, Bill Gates the founder of Microsoft not having access to a free computer when he was a child, do you think he would’ve been able to build his empire then?

A journalist once asked former president Barrack Obama, if he hadn’t married Michelle, who would be the first lady, he then responded that Michelle would still the first lady, it would be a different president altogether, attributing much of his success to his lovely wife.

The success stories today are littered with serendipity events of people just meeting the right people at the right time, or just being in certain locations at a given time that ultimately propelled their endeavors. Never underestimate what can happen in a day or a year, it only takes one event to change your whole entire life.

In order for you to be positioned to be in these types of events you have to be willing to put yourself out there, be vulnerable, and be open. Nothing will ever happen if you stay cooped up all day in your room or at your house wondering why nothing interesting ever happens. Help serendipity find you. Nassim Taleb suggests using a litmus test to determine if serendipity is likely to occur. According to him, if you can predict every detail of your day with absolute certainty, there is probably a minimal chance for serendipitous events to take place.