Working on projects is never easy. A lot of it comes from the fact that before you begin, you’re required to provide an estimate of how long it should take you to complete. This is difficult particularly because no one ever has perfect information when starting a project. It is also impossible to account for everything that can go wrong. The entire project might go swimmingly right up to the actual demo which you confirmed was working the previous night. Unfortunately, somewhere between you turning off your laptop the previous night and making your way to the office early the next morning something changed and nothing works anymore.

This blog post is an update of my earlier post “Failing My Way to Success”. It’s loaded with additional insights that I gained from working on my final project.

“I learned that as long as you’re not seated in an exam room, a slow or small start isn’t necessarily a failure as long as you can constantly improve on the initial start.”

~An excerpt from my previous blog post

In the former, the main message was to split the task into bite-sized chunks that give you the confidence to start. My main challenge was the bite-sized chunk I originally envisioned turned out to be the tip of an iceberg that threatened to sink my project. It is hard to describe the feeling of utter helplessness that wells up as you realize you’ve vastly underestimated the amount of work that needs to be done. Think of it as signing up for a 100 metre sprint and in the middle of it learning that it’s a marathon.

The title of this post comes from a highly acclaimed book on writing by Anne Lamott. It provides insight into the essentials of writing and how to deal with writer’s block. 

While she was growing up, there was a requirement that you had to write a term paper on birds for primary school. The scope of the term paper was expansive enough to make it a task to be done all through the term. The paper was due on Monday, and on Saturday her brother admitted to their dad that he hadn’t started. He was in tears at this point because there was no way he would be able to finish before the Monday deadline two days away and panic had set in. Their dad put his arm around him and said, “Just take it bird by bird buddy. First, you read about chickadees and then you write a paragraph in your own words about chickadees and then you draw a picture. And then you take pelicans and you study up on pelicans, and then you write a paragraph or a passage on pelicans.”

I have not read the book itself, although I was fortunate to stumble across an interview she did. She was talking about giving yourself permission to do something badly. This enables you to start making immediate progress on a task. Once you’ve gained momentum, you can always come back and improve on your initial task. Making improvements is less mentally taxing than having to figure out how to start and where to start.

The thing I came to realize while doing my project was that sometimes, it is not enough to break down your task into bite-sized chunks. The more I worked on these chunks, the more work I realized each chunk required and the further away I realized I was from achieving my goal. This was particularly demoralizing to me and made me less willing to put in the work required to push my project forward. This led to a negative feedback loop where I know I need to put in work to finish my project but the more work I put in the more work I realize there is to be done and the less willing I am to put in more work.

The need to do a good job while faced with a daunting project scope crippled me and I had weeks where I was unable to do anything because my mind was stuck in a feedback loop. The key to breaking out of the loop for me was internalizing that the first try doesn’t need to be the finished product. I can always backtrack and improve on my initial work. This allowed me to lower my expectations of myself and be okay with an imperfect start. Coming back to polish up on already existing work was disproportionately easier since I had done it already. 

While it did not make the process of working on the project enjoyable, it did make it a lot more approachable and that is what enabled me to start and work my way slowly towards completion.

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