Why it is hard to do something that truly matters

I recently quit my job to focus on a very interesting idea. I saved some money and I now have a year to see if this idea can become a viable business or at least contribute to science. But the idea itself is not really the point of this essay. What I want to write about is an amplified feeling I now have. The feeling that I keep doing things that don't matter.

Dear reader, I can already feel your skepticism: How do you even define what matters? Argument taken. There is no clear definition. But when you have a specific goal, it is fairly easy to determine whether one thing matters more than another. If you want to become a great cook, cooking every night matters more than playing "Good Pizza, Great Pizza" on your Nintendo Switch. And this is where the conflict starts. Cooking every night is hard and progress is difficult to measure short-term. But "Good Pizza, Great Pizza" has a built-in reward system displaying progress to you AND a pause button. So, why not slightly redefine the goal as: becoming a great cook in "Good Pizza, Great Pizza". Deep down, we know that redefining success this way (although slightly) will not truly matter to our initial goal of becoming a better cook. This example might seem silly, but it is exactly what happens when you have layers of bureaucracy.

Welcome to team A led by a person called Chief in Organization SoftwareCorp. Chief is presenting progress to ChiefChief every month, which then will present results to ChiefChiefChief. Chief decides to look at some possible metrics for success:

1. Number of Completed Tickets
2. Removal of User Frustration
3. Probability of Company Survival

Number 1 gives Chief an easy chart to pass up the chain to ChiefChief and ChiefChiefChief, hiding a potential absence of actual value but significantly increases the chances of a good story. Number 2 is the product goal, however nearly impossible to capture in a PowerPoint if you want nice colors and an arrow going up up UP! Number 3 is the ultimate long-term metric, but everybody hates probability theory in school and you do not want to spoil the good mood. I think you get the point: the winner is number 1!

Before, when I worked in a larger company, I had the impression that this conflict of redefining success around the thing that gives us the clearest evidence of progress came from the very nature of large bureaucracy. But now I am on my own, the large bureaucracy is gone, and the conflict is bigger than ever. Weird, right?

We need to set up rules in order to define progress, without it we do not know what to do. Imagine being put on a football training field without knowing the rules, what do you do? It would probably paralyze you, and you would end up leaving the field when it got dark. That is why we have to invent rules of progress everywhere. To make us keep working. KPI's, likes, stock price, BMI, money, views. We basically want every environment to become a football match, so we can score and tell others about our amazing bicycle kick goal.

Doing what matters has to be measurable in order for us to feel progress. As systems become more complex so does coming up with simple definitions of progress. As true as it is, the more dangerous it becomes. Because we hate wasting time, the rules of progress we set up converge towards goals with very low friction, certain feedback and short term horizons.

Why is this even more on my mind now? Because all of the sudden I am both Chief, ChiefChief and ChiefChiefChief. My inner ChiefChiefChief wants to see results, now! Making the website pretty, posting an image from a tech conference, getting funding, getting employees and sending 100 sales emails a day. However, working 3 months on a very important hard problem that might be unsolvable but could justify the very existence of the company? Are you out of your mind? What a waste of time.

The things that actually matter, the things that can change the world or at least take the business to another level, are often right in the intersection of high friction and uncertain feedback. But for stupid human me, the feeling of progress beats everything. My point:

The things that matter most are often the hardest to measure, while the things that are easiest to measure increasingly determine what we do. And the things we do then matters less.

So what can I/we do about it? Maybe train our urge to not measure things, and make hard things more enjoyable to work on. But honestly, I do not know what to do about this issue. Plus, I have a funding application to finish, so I have no time to think about this more deeply.