I. Rigorous Thinking and Effectiveness 

The most effective people that I’ve worked with, or engaged with online, are extremely rigorous thinkers.

This, in some sense, is satisfying.

To the extent that the connection between effectiveness and rigorous thinking is causation rather than correlation, then increasing the rigor of one’s thinking can help lead to greater effectiveness.

II. Implicit and Explicit Instruction 

Of the extremely rigorous thinkers I’ve interacted with, only some of them are good at explaining why they think the way they do.

All of them, on the other hand, have been good at telling me when my thinking has not been rigorous enough.

Given the above, I’ve spent a lot of time trying to take their implicit and explicit instruction in order to improve myself.

One incredibly positive aspect of the internet is that it opens up thousands of avenues to learn how other people think.

III. Mentorship 

Another way to say all this: the value of a mentor (either in person or online) is that she should significantly increase the rigor of your thinking.

When you communicate with her, you should run as many cycles of feedback as you can –  pitching your ideas, getting her critiques, and learning.

But, at some point, this can lead to laziness: you might rely on your mentor to do the thinking for you rather than doing it yourself.

One way to test your potential laziness is to continually take stock of the delta between the rigor of your thinking and the rigor of your mentor’s thinking. If you are not closing the gap between the rigor of your thinking and your mentor’s thinking, then you are, in some sense, exploiting your mentor.

Ultimately, every mentor should become your peer. This should be the goal of all involved.

IV. My Journey in Unrigorous Thinking 

For whatever it’s worth, my biggest obstacles to rigorous thinking have come from the following:

1. Yearning for Silver Bullets: Very few quick fixes exist for hard problems. In part, I think I was drawn to law school because of the idea that passing the right law could fix things quickly. As it happens, this is very rarely true. Hard problems tend to have decade long answers.

2. Yearning to Have My Problems Solved: Related but slightly different: when confronted with thorny day-to-day problems, I’ll sometimes gravitate toward the easiest or first solution rather than taking the time to rigorously analyze the issue. This is nothing more than intellectual laziness but it is difficult to control, especially when you’re moving fast and making a lot of decisions each day.

3. Ignoring Politics: I’ve also succumbed to spending a lot of time on ideas or programs that never had a chance of being political viable.

4. Ignoring Executing at Scale: Even ideas that might be politically viable may not be possible to scale operationally. Especially earlier in my career, I deeply underestimated execution as a limiting variable.

5. Wanting to be Agreeable: The desire to please or get along with others sometimes trumps my effort to push to get to the right answer.

Those are the big ones: I could have avoided many of the biggest mistakes of my career had I been more rigorous at avoiding these pitfalls.

I suspect I’m not the only person in my line of work to make these types of mistakes.

V. Thinking More Rigorously Hurts Until It Becomes a Habit 

For all of the above issues, there has either been a professional failure or extremely direct piece of feedback that has provided a wakeup call that I need to be thinking more rigorously.

Even after knowing I have a problem with the way I think, many times the only way I’ve been able to make progress  has been by being exposed to leaders who are adept at avoiding these pitfalls.

This often all rather painful.

For me, it literally hurts to think more rigorously in an area where I have not previously been a rigorous thinker.

In some instances it feels like being a child who knows his parents are right but doesn’t want to admit it even though it is in his best interest to (1) admit it and (2) incorporate his parent’s way of thinking into his world view.

Eventually, it gets less painful – and then it becomes a habit.

And then it’s on to the next one.

VI. Accountability is an Accelerant 

One last point: putting yourself into situations with high accountability for outcomes is one of the best ways to increase the rigor of your thinking.

If you are not accountable for outcomes, then you will be tempted to avoid the pain that comes with thinking more rigorously.

If you are accountable for outcomes, then the pain of potential failure helps offset the pain of thinking more rigorously.