do tiny projects expecting them to fail

do tiny projects expecting them to fail
Photo by Alan Rodriguez / Unsplash

My goal

I will do tiny projects expecting them to fail.

I will post updates (sometimes here, sometimes on my youtube) on what I did, how it failed, and what I learned.

Rinse and repeat.

If you find this framing helpful or have suggestions, feel free to comment or reach out to me at

Wish you all the best in your projects big and small.

Some rambling thoughts

I've been thinking a lot about what to write about here.

If I'm commited to writing a blog, what should it be about? My general thoughts in "very useful" stream-of-consciousness type posts? Coding tutorials, given that's my "professional background"? Book and TV show reviews where I share my "wise insights" into pop culture? Maybe I will touch on any or all of those later, but for now I just want to share where I'm at.

Essentially, I will do tiny projects expecting them to fail.

I hope this will be an antidote against my near-obsession with overthinking, overplanning, overanalyzing and ultimately not nearly enough doing. It's long been the case that the most comfortable place for me to exist is in my own head, where the difficult and unpleasant (if not terrifying and horrifying) aspects of reality can be ignored. But clearly something is missing when I'm just meandering from thought to thought. And doing tiny projects expecting them to fail is a step away from my thought-prison.

Obviously, "do tiny projects expecting them to fail" isn't a particularly new idea. Since the dawn of time, humans and generally pretty much all life has been based on trial and error. Try something new; fail; learn; try again a slightly better way. From early bacteria to modern man, all of it seems to be based on trial and error. Sure, humans are doing it in infinitely more complex and intricate ways than bacteria ever could, but to me there's surprising similarities at the root of it. Try something new; fail; learn; try again a slightly better way: from corporations to institutions to each person's journey through each day.

There is certainly much more to being human than just that cycle, something incredibly special about humans compared to the rest of life. I'm still figuring that part out myself, but language and especially storytelling seems to be a key part of it. But for the purposes of this post and my short term plan, I will focus on this cycle and my relation to it. I can "unravel the secrets of humanity and the universe" another time.

When I am lost in my thoughts, I am breaking the try; fail; learn; try again cycle. Instead it looks more like try; fail; think about how I failed; think even more, taking it even more personally; think about why I am thinking so much; think; think; ... realize what I'm doing; try; fail; think ....

Writing it out, it seems pretty clear to me where the problem originates. In the day to day, it is much more subtle and difficult to catch. A core part of the problem is associating a failure of a project with my personality or character, not as a natural part of the process. Taking failures personally and ruminating on them has cost me literal months of time, and if I'm not careful can cost me many more.

This distinction between "I failed" and "the project failed" was highlighted to me in an excellent conversation between Youtubers Dr. K and Pirate Software. Pretty much all of the insight and wisdom I am trying to channel in this post comes from this video. I highly recommend watching the entire video if you have the time, but a core part of their discussion is agreeing that framing failures as "the project failed" is infinitely more helpful than viewing it as "I failed". The former enables learning and moving on to the next project to try while the latter has enabled me to sink deeper and deeper into a thought-prison.

To come back to my goal, "do tiny projects expecting them to fail" highlights to me that projects failing is the natural way of things, and that learning what I can and moving on to the next project is a better reaction than overthinking endlessly. The projects being framed as "tiny" further helps speed up the learning cycle by making it easier to start each new project, knowing the end goal is not only in sight, but close at hand. Lastly, if a project actually does succeed, it would be a nice surprise (although I might learn less from it than if it didn't go according to plan).

A lot of this post has been pretty specific to my difficulties and what I need to do for me to grow, but I hope it inspires you to action as well. If you are feeling stuck (as I have been for a while now), I hope you also give "do tiny projects expecting them to fail" a try. I promise it will be worth it.

I'll update post updates here and on my youtube as I pursue this goal/framing over the next days/weeks/months(/years?). I can already feel some excitement and freedom and aliveness just thinking about what tiny projects I'll work on and which will very likely fail, but in a good way.

Again, feel free to reach out to me at with any comments or suggestions.

And again, I wish you all the best in your projects big and small.

Take care,

– Greg