My Playbook for Success As an Introvert


I have long argued that the term “introvert” sucks – and it should be replaced with “power thinker“, which is both more accurate and more positive.

My follow-up point is that if you are more of a thinker in life (and less of an “over-talker”, my term for extroverts) then you will need a way to get your thinking out of your head and into the world. How do you have an impact as a “power thinker”?

My own playbook for this is just three points.

Point 1: Focus on one question that will make all the difference.

If your strength is thinking, then you want to focus that ability on 1-2 really important questions. You don’t want to move around. You don’t want to answer questions that others can answer. You want to pick 1-2 really important questions and then go deeper into them than everyone else. And you keep at it until you’re the best person on that valuable question.

This could be called the Albert Einstein rule. When asked to explain his success in life, Einstein said “If I had an hour to solve a problem and my life depended on the solution, I would spend the first 55 minutes determining the proper question to ask, for once I know the proper question, I could solve the problem in less than five minutes.”

I personally prefer the advice of Carlyle co-founder David Rubenstein. He basically said you should never study anything that doesn’t make you money.

Either way, the point is the same. Focus on 1-2 questions and make sure they are the right questions. Make sure they are the ones that will make all the difference in your business and life.

Personally I only focus on questions that will make me money – and are things I think I can do better than others. For example, I don’t do real estate. It’s interesting but everyone seems pretty good at it. I also want it to be a question I am fascinated by.

For my business / life, I eventually settled on the question: How does digital technology create and destroy competitive advantage? And I spend most of my time trying to answer it in quirky markets and complicated situations. I want to know which company is going to do well before it is clear to others. Plus a competitive advantage also often makes it easier to do a solid valuation.

Point 2: Track the 2-3 outcomes that matter most.

If I spend 80% of my time thinking about the above one question, how do I translate that into a valuable outcome? For me, the two outcomes I track are:

  • Investment returns (i.e., turning analysis / thinking into wealth). If you can identify which company is going to do well before others in various situations, you know what to buy. And avoid. Note: I also find this particular expertise can lead to lots of advisory work.
  • Talks and keynote speeches. If I am making progress against an important question, I find that speaking invitations tend to follow. This is also a good way to meet people who are interested in the same question.

Point 3: Have tools that convert your thinking into your desired outcomes.

I am looking for the shortest distance between my thinking (Point 1) and the outcomes I want (Point 2). And as a professional thinker, I want minimal execution. Not too many meetings. No operations. No building of anything. I want to spend 80% of my time thinking – and then the two outcomes to follow almost immediately from this.

For me the biggest tool for this is an investment network and/or platform. Lots of systematic thinking, levered up by partners and then a purchase. Warren Buffett is the model and he is arguably the world’s most effective and efficient introvert. His 23 person company in Omaha is worth over +$400B.

But you can really point to lots of companies in finance, Hollywood and technology that are effective at this sort of direct translation between thinking and outcome. Software, in particular, seems to directly translate thinking into profitable companies and widely-used technology.

A second tool I use are daily habits. I follow a routine that keeps most of my day focused on thinking (i.e., no phones, no internet, no meetings, etc.). Every day, I make sure I do my 4-5 key habits. These are cumulative habits that add up over time and move me forward.

In general, I’m a big believer in doing the same activities day after day. It’s a good way to get cumulative results over time. And you get more efficient and effective when you do the same things over and over.

Finally, I consider writing and teaching as tools in my playbook. I do one podcast and two articles per week. I like the phrase “if you didn’t write it you don’t know it.” I also use the writing process to figure out business questions I don’t understand (I keep a list of these questions on my iPad).


Anyways, that is my introvert playbook. Focus on 1-2 questions that will make a difference. Track the outcomes. And build tools to achieve them that are cumulative over time if you just stick at it. The below photo is pretty much my typical day (that one in Thailand).

照片 2017-8-18 上午10 45 44

Thanks for reading. Jeff


I write, speak and consult about digital strategy and transformation.

My book Moats and Marathons details how to measure competitive advantage in digital businesses.

I also host Tech Strategy, a podcast and subscription newsletter on the strategies of the best digital companies in the US, China and Asia.

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Photo by Ümit Bulut on Unsplash


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