Critical thinking is much-prized nowadays. We are encouraged to think carefully about things, rather than just to take them on faith.  When someone claims to know something, critical thinkers immediately ask for data. If a marketing executive claims that the new product packaging is superior, she should expect to be asked whether she sold more units, or reduced costs. Critical thinkers look for gaps in reasoning.  Perhaps improved sales were not the result of better packaging, but were caused by a news story that increased demand for the product. Was there a controlled experiment?

“Paris 2010 – Le Penseur” by Daniel Stockman – Flickr: Paris 2010 Day 3 – 9. Licensed under Creative Commons Attribution-Share Alike 2.0 via Wikimedia Commons

According to the The National Council for Excellence in Critical Thinking — really, there is such a thing! — critical thinking is the “intellectually disciplined process of actively and skillfully conceptualizing, applying, analyzing, synthesizing, and/or evaluating information gathered from, or generated by, observation, experience, reflection, reasoning, or communication, as a guide to belief and action.”  It takes a critical thinker to parse that definition, but, to simplify, critical thinkers are more like the logical Mr. Spock and less like the intuitive and emotional Dr. McCoy.

When making important decisions, or analyzing situations, critical thinking is generally a good thing. But what happens when critical thinking becomes nothing more than criticism?

I was struck recently by a story of a venture capitalist who had retired because he was no longer emotionally capable of making investments. Every deal he saw reminded him in some way of a previous deal — a company with a similar business model, a similar product, a similar management team, etc. — on which he had lost money. Despite a long record of picking more winners than losers, and delivering good returns to his investors, he had lost the ability to believe in start-ups. A VC must of course be critical; he must separate the good investments from the bad. But this VC was no longer a critical thinker; he had become just plain critical.

My friend Janet Geluardi recently explained to me that Buddhists are taught about three kinds of laziness. The first is sloth, i.e., what we commonly think of as laziness. Sloth is sleeping in, watching SportsCenter all day, or ignoring the dishes piling up in the sink. The second kind of laziness is busy-ness, i.e., filling time doing lots of unimportant things.  An interesting implication is that the person who works ten hours a day, always goes to the gym, and spends time volunteering may be, in some sense, lazy — if all that activity isn’t truly worthwhile. The final kind of laziness is “giving up heart,” i.e., ceasing to believe in oneself. Even a person working hard to pursue a laudable goal is lazy, if he or she doesn’t believe the goal is achievable. The VC mentioned earlier had become, in this sense, lazy.

I have rarely been challenged by sloth. I like getting out of bed and doing things. I make lists of things to do, and I check things off those lists. I have a sense of duty, and I try hard to keep my promises, to myself and others. And, besides, I find SportsCenter tedious.

However, at times, I certainly fall prey to being unnecessarily busy. It’s easy to come up with things to do that seem worthwhile. It is surely good to work out, to volunteer, to attend a seminar, to meet a friend for lunch, to read a thought-provoking book, or to play with your children. But, life, unfortunately, is an optimization problem; it’s not a question of finding good things to do, but, rather, the best things to do. Sometimes, I find that I’m doing good things because that is easier than doing the best thing.

Most importantly, there have been times when I have given up heart. For example, I’ve realized that although I greatly enjoyed playing baseball as a child, I never really quite believed I was a baseball player. I was just a kid who played baseball, not a baseball player. That mindset was inherently limiting; instead of approaching every at-bat with confidence, I had to face the pitcher feeling like an impostor.

In contrast, I never questioned my chess-player-ness. As a 16 year-old Class A player, I was certainly good — but there were plenty of far superior players in the adult tournaments where I competed. I knew I was no Bobby Fischer, but I could sit down at any chess table with complete confidence that I deserved to be there. I still think of myself as a chess-player, and I haven’t played in a tournament for nearly twenty years. It’s not that I over-estimate my ability; it’s just that I know that the beautiful game of 32 pieces on 64 squares belongs to me, and I to it.

In the same way, I never questioned my ability to lead CodeSourcery, or to perform as a General Manager at Mentor Graphics. I knew that I would make lots of mistakes, and that I would always have a lot to learn. But I also felt that the necessary skills were all within my grasp, that I could learn whatever I needed to learn, and that, somehow, whatever obstacles appeared could always be overcome. When I sit down with executives who have achieved much more than I, I am impressed, but not awed; eager to learn, but not afraid. I play the same game that they do, and I am prepared to play at any level.

However, I’ve found starting a start-up to be challenging in an unexpected way: I have not quite believed. Entrepreneurs and executives are somewhat different breeds; operating a business, however large, is different from conceiving it. CodeSourcery started so organically — literally, as an accident, thanks to an unexpected call from Scott Haney — that the deliberate creation of a new enterprise feels like something I have never done. I have wondered whether I have what it takes. I am not, after all, a 23 year-old wunderkind with an idea for a new instant local sharing-economy social messaging network. I a neither a brilliant biochemist with a cure for a chronic disease nor do I know how to sell ice to Eskimos.

However, I’ve had plenty of plausible start-up ideas. After nearly a year of angel investing, I can certainly say that I’ve seen significant money invested in worse ideas. And some of those investments have paid off handsomely! But, I think critically about my ideas, and like the retired VC, see only how they can go wrong. I’ve invested my own money in other start-ups, even after thinking critically about them. In retrospect, I don’t think those ideas were better than my own; rather, I think that I have had more faith in a stranger’s ability to execute than I have had in myself.  It doesn’t take much critical thinking to realize how silly that is.

So, I shall take heart — not give it up. I’ve always believed that a large part of success in business is noticing opportunity knocking, and being willing to open the door. I can hardly wait.