The Progress Monster
The progress that can be measured is not the true progress
I have a lot of projects and active outlets (games, music, visual art, software, writing…) and by any reasonable standard things are moving forward. I built my gallery so I could prove to myself that I’m improving over time.
So... why do I always feel like I’m behind? That I could do more? If today’s list fills up, I start look for space on days later in the week where I can squeeze in 45 minutes validating (or invalidating) a crazy idea.
Why? I’m seemingly obsessed with moving forward. The only way I can convince my brain that I am doing the “right” thing is to keep up the creative momentum. I’ve learned many times that the only thing harder than stopping is starting again. So my adaptation is to use systems: lists, notes, project management tools, knowledge graphs etc. to keep me in the loop.
Honestly, it works a little too well, sometimes I end up turning myself into a robot. Unlike a robot however, if I don’t finish my list I feel guilty, and if I do finish it… Well, I just feel like I could have done more. The guilt and the insufficiency are the same thing, the part of me that is addicted to getting better and moving forward: the progress monster.
Try to keep up
I have dozens of projects sitting in various states of incompletion at all times. Some ideas stay in the tumbler for years, occasionally getting a prototype or mockup only to go back for longer. The painful truth is that I will never make the vast majority of the things that pop into my head. For a while, I thought the answer was to just get as many ideas out there as I can, but it’s never enough. The grief builds up, each abandoned idea was once the most exciting thing in the world.
I feel a sense of betrayal of my past self that I couldn’t see it all through. I feel disconnected from the version of me that cared enough to keep working on the idea, and it can start to feel like I’m just chasing fireflies. The progress monster rears its head: how are you going to make progress like this? Surely I can do better?
But progress is about more than output.
It grows in layers
When I give up on an idea, it’s not that I can’t relate to my past creative self. It’s that relation means more than agreement. It can mean tension, contradiction, guilt for a feeling that expired. That friction is the depth of creative work.
Doing the work is not just setting aside time for your projects, not just following through on reminders; it’s being present in the moment. Reflecting on evolving feelings about the work. The process of “making up one’s mind” is endless. When I grow as a person, I deepen my understanding of myself, the world and my place in it. There is no way of tracking this. No dashboard, no streak, no single convenient metric.
You know it when the work feels deep.
The progress that can be measured is not the true progress.
Entangled with the soul
What is this depth? I think it’s entanglement with your life. When a song is truly deep, it means it couldn’t have been produced without the creator’s person’s entire life leading up to that point. Each heartbreak, every boring afternoon, every half-forgotten conversation folded into the work. The meaning isn’t in the notes or the words. It’s in the density of everything that’s complected. You can feel it. We are all extraordinarily sensitive to whether something was produced by a flat, step-by-step process or by something that loops back on itself. Something recursive, self-aware, alive.
A shallow thing is one you can unwind. You can trace the steps, see the algorithm, feel the guess-and-check. And I don’t want to get good at making shallow things. It feels like progress but is it, really? Sure, you practice skills, you incrementally improve but that’s not where insight comes from.
A deep thing resists decomposition because the process that made it was reflexive: the creator was changed by the creating, which changed the creation, which changed the creator again. A cycle of insight. This is the nameless quality Christopher Alexander pointed at. It emerges not from planning but from an honest, recursive process of folding and unfolding: digesting who you once thought you were, and being reborn as whoever you are becoming.
This is what true progress is. Not just patience, not just “trusting the process” — but the literal deepening of how entangled your life is with your work. Every time you return to an idea and find it changed it’s because you changed, that’s the folding. When a sketch from three years ago suddenly connects to something you felt yesterday, that’s the reflexive loop tightening. Your work becomes dense with you, and that density is what people recognise as meaning, even if neither you nor they can explain why.
Uncertainty and hope
The mind craves certainty but our world provides none. I want to rest assured I am on the right track but, at any moment, I may be lead astray. This is the basis of suffering, but it also allows for hope. We genuinely cannot know what comes next. If you believe the future is doomed then you are certain about something you cannot prove. When I find myself gripped by existential angst, this is the way out: to notice that things are taking their own course, and while I have less control than I would like, the upside is that life will continue to surprise me endlessly… so long as I am open to it.
Life tends to defy my internal sense of progress and yet, when I step back, I am changing. As times goes on I grow less sure what lies ahead but I seem to be growing anyway. I no longer find myself drawn to prototyping every idea I have. I am scheming a little less. I don’t think I will ever slay the progress monster but… perhaps I can tame it.
✌️ Ben