Berg's Words

Convexity Rules Everything Around Me

Software and the people that make it


Today was a great day. Another engineering manager from a different group in our company, working on the same product, reached out to commiserate and ask for advice about how to effectively operate as a motivated builder trying to create value and do good within a political, corporate machine. Today was a great day because I found a fellow rebel and I apparently built a reputation as an independent, apolitical getter-done-er and thinker-for-myself-er.

This person wanted to know how to push back against the entrenched veto-holders keeping things as they are, slowing incremental progress, and outright halting step-function advances. The key ask though: how do you do that without pissing people off? Apparently there is some impression that I have accomplished some of that without upsetting anyone. Unfortunately, I have no idea how to push for real change and needed innovation in a corporate setting without sometimes coming off as too aggressive, too passionate, too idealistic, not “practical” enough, or not a “team player.” My advice: know what you’re willing to get fired over, maintain a perfectly consistent and simple narrative for how your actions are improving the company and/or humanity, always tell the truth, never make it personal, and get ok with upsetting some people because, for short-term personal gain-seeking corporate placeholders, collision with the truth and long-term optimality can be painful and such characters tend to default to blaming the messenger.

I remember being asked by a different new manager, a few years ago, how I, someone who seemed incapable of hiding my real thoughts about nearly anything, “owned the message.” At the time, this “own the message” line was all the rage in tech management and our new manager couldn’t see how he could maintain authenticity and trust while relaying a message he didn’t believe in. My answer: no one makes you a manager to be a parrot; if you add value it’s by exercising your judgement and acting authentically. I don’t “own” messages I don’t believe in. I also don’t badmouth the company unnecessarily. I develop an honest and authentic message, ideally aligned with the spirit of the official line if not its words, and speak to my team like adults.

There comes a point in every leader’s career where he or she realizes that their primary value is in their judgement. That is a true turning point, a permanent pulling back of the curtain when one sees for the first time that doing good means taking on personal risk, that no one knows exactly what they’re doing and we’re all just stumbling along making it up as we go, that big corporate shenanigans with billions of dollars at stake require those at the top to desire something other than what they say (the insanity embodied in some of what they say leaves us with the alternative that their actual goal is to devalue the companies they run, which seems implausible). Looking back on my experience, once I really got this, I saw a step change in my effectiveness and happiness. My job is to figure out what my job is and how to do it, it’s to have opinions, it’s to fight for those opinions, it’s to be a real leader—the type who can tell honest, hard truths to people while providing a glimpse of the better tomorrow we can reach with hard work towards our strategy; the type who is able to turn disaster into opportunity for those who are brave enough to seize it.

Perhaps the corporate bureaucracy is too afraid to commit to only hiring real leaders, to trusting its people with “the message,” but that fear bears a high price. Free people are breeding grounds of selection effects. A sanitized, plastic message of false optimism only excites the slow-witted or the unimaginative, it leaves the apathetic comfortable, and it drives away any with the slightest spark of genius, the faintest glimmer of desire to truly pursue meaning and mission with their work, or the first pangs of wanderlust calling them to follow their curiosity.

In investing I naturally veered towards value. The first time I read Soros talk about reflexivity I demurred. It seemed reasonable in specific pockets but surely too simple to rule in the large. After years of reading Taleb and starting my foray into Kaufman and Wolfram, I’m now fully bought in. Convexity, nonlinearity, and semi-permeable membranes reign high. These forces of accelerating momentum, these viscous (or virtuous) feedback loops and network dynamics are, I believe, behind much of the success or failure of companies and shape the interplay of industries. Self-selection, like other evolutionary selection mechanisms, may be among the stronger forces at work within companies. When a leader talks, first in mind must be the question of which type of employee would be energized and which type turned off by the message in the current context. It’s more than acceptable for some people at a company to be put off by your goals the vigor with which you pursue them. All that matters is that the right people take notice and redouble their own efforts at building value in the real world. Their efforts will be quietly recognized and builders and reality-believers will multiply.

Honesty is convex. The ability to authentically see opportunity in turmoil and to make others see and believe it is convex. Having a simple philosophy and a set of simple, constant principles and fighting for them openly is convex. Thinking independently, from first principles—the least creative thinking mechanism when presented as such but producing results so seemingly creative they are immediately rejected by the average bureaucrat—and doing so in public is convex. Being willing to stake out a position fiercely and still admit to the world when you’re wrong is convex.

I know because I’m starting to find a tribe of like-minded thinkers. We’re not numerous enough and not powerful enough and few of us have titles fancy enough to get done what we want, but we’re growing and we’re building. What yields convex payoffs and starts with few and weak, if sufficiently concentrated, explodes to many and powerful. Convexity rules everything around me.