My Advice? Be Skeptical of Advice

The protagonist in the picture above is working his way through the proverbial minefield of life. It will take careful navigational skills and good decision making to make it to his desired destination.

On the perimeter, a host of well-intentioned people are eagerly offering advice, each based upon his or her unique life experiences, talents, and biases. The protagonist, willing to listen and adhere to the conflicting opinions, feels flummoxed and even occasionally paralyzed.

The problem with advice is that it’s uniquely contextual, which means it can be deceptively misleading. The opinions you maintain, and therefore the advice you dispense, are based on dozens of personal variables that may not be transferrable to someone else. What has worked for me in my journey traversing the minefield of life may not work for you, and vice-versa. In fact, my advice may lead you to step on a mine you wouldn’t have otherwise.

I’m not suggesting that all advice or opinions are misguided or unhelpful. Quite the opposite: I personally get immense value out of the knowledge and ideas shared by other people. In fact, one of my favorite things to do in life is question someone whom I respect for hours, on everything in their brain. I love looking into every mountain, valley, and crevasse of someone else’s mind.


What I am suggesting, however, is that the utility of advice can be realized only once it’s been unpacked. Here’s a story to illustrate (based on a popular fable).

Five monkeys are sitting in a room. One after another, they try to climb a ladder to reach a basket of bananas. But each time a monkey attempts to scale the ladder to get the bananas, they all get sprayed with cold water. After a few attempts, the monkeys get the picture and give up.

Then, one of the monkeys is removed and a new monkey enters the room and goes straight for the bananas. But the others pull it back, knowing that they’ll all get sprayed with cold water as a result of the attempt. And so it goes until there are five new monkeys, none of which has ever been sprayed with cold water. The monkeys behave this way not because they’ve had an experience being sprayed but because that’s the learned behavior based upon their life experiences.

Now imagine a new monkey entering the group and seeking advice from the sage monkeys who have years of experience in this given habitat, which they happily offer, waxing poetic and with great confidence.

Without questioning the underlying assumptions, the new monkey remains one degree away from ground-level truth, the information that we all actually want and need to make good decisions in life.

Through a single simple question of “why,” the entrenched behavior and beliefs of this monkey community could be turned on their head. It’s possible that circumstances have changed and they won’t be sprayed with cold water when attempting to get the bananas, for instance.

I personally went through this process when starting Braintree. There’s a lot of competing advice in general on how to best to start a company. For example, some say revenue must be the primary focus while others suggest that it’s user growth. In thinking through these different frames, something felt missing to me.

Aside from the strategic considerations specific to the payments industry, I wanted principles to build upon that were colored by my life experience. I settled on three: 1) we’d be the preferred payments platform by engineers; 2) team members would say that Braintree was the best company they’d ever worked for; and 3) our customers would write us love letters. I made these three objectives the heart and soul of the company and we built everything else on top of them.

My team and I pursued these objectives with great vigor – setting aside frequent advice in many cases – and it powered us to create something special and enduring.

The secret to advice is that the greatest value usually lies far beneath the surface – in the assumptions, beliefs, and life experiences that invisibly power it. Find these gems, and take the time to understand their implications, and it’s possible that you’ll get what you really need to successfully navigate your own path.


I commissioned an artist to draw the images above, which came to my mind as I contemplated this topic.