Upon being asked the question, When you think of the word “successful,” who’s the first person who comes to mind and why?, Derek Sivers replied:

The first answer to any question isn’t much fun, because it’s just automatic. “What’s the first painting that comes to mind: Mona Lisa. Genius: Einstein. Composer: Mozart.”

This is the subject of the book “Thinking Fast and Slow” by Daniel Kahneman.

There’s the instant, unconscious, automatic thinking. Then there’s the slower, conscious, rational, deliberate thinking.

I’m really into the slower thinking. Breaking my automatic responses to the things in my life, and slowly thinking through a more deliberate response instead.

Then, for the things in life where an automatic response is useful, creating a new one consciously.

So what if you asked, “When you think of the word successful, who’s the third person who comes to mind, and why are they actually more successful than the first person that came to mind?”

In that case: first would be Richard Branson, because that’s like the stereotype – the Mona Lisa. And honestly, you might be my 2nd answer, but we can talk about that later.

My third and real answer is we can’t know, without knowing their aims.

What if Richard Branson set out to live a quiet life, but like a compulsive gambler, just can’t stop creating companies? Then that changes everything, and we can’t call him successful anymore.

---

Intuitions often don’t come from a place of wisdom, but a place of habit. They’re the narratives that have been engrained into us, day after day, until they take root in our psyche. With time, some narratives become outdated.

Recently, my housemate asked me if I would join the NBA for a year if given a contract. My intuitive response was no, because I suck at basketball and I would just embarrass myself if I played. That would also mean taking time off of medical school, which I might regret.

But then I thought about it. Being in the NBA would be awesome, because I:

1. Don’t have to play any games;
2. Can just take a leave of absence from school;
3. Will meet top athletes and coaches;
4. Can travel the world; and
5. Should make a lot of money (the average NBA salary is $7.7 million USD).

Thus, I changed my answer to a yes. My immediate response was outdated and formed by a worldview from my adolescent period: that I shouldn’t do something I suck at and that school is important.

But how do we know if our intuitions are outdated? Here’s my two cents:

Reflect. On everything. Take notice of how you react to ideas and circumstances, and see if these thoughts align with the person you are today. Once you’ve done this, filter. Anything that isn’t you or came from a previous version of you needs to quietly go. Anything you resonate with, keep.

Our automatic responses are useful – but like an organization, they need to be audited.

Are we not ever-changing, both gradually and per situation?

The interview at the start can be found on the Tim Ferriss Show #128. Highly recommended.