Trying to Plan Away Doubt

Around high school I developed the desire to use my time well: COVID opened up a lot of free time and I wanted to instill structure that life away from school lacked. My belief was that this was a scheduling problem, so I implemented a calendar; however, I found I wasn’t getting much done. I wasn’t especially busy, but I felt the need to be—I ended up manufacturing a sense of productivity that wavered once I realized I was spending a disproportionate amount of mental effort micromanaging my calendar.

For a while I found greater success without a plan: online school permitted me to immerse myself for days at a time without a worry. One day I would spin up a website for my favorite manga, and the next I would cycle around taking photos from morning to night. Importantly, things were moving quickly and I was making progress on projects that excited me. But as I slowly returned to school, and my interests broadened, I felt myself spread thin, no longer able to dedicate myself to one thing without feeling like I was missing out on another.

Now that I was busier, I again approached this through scheduling, this time adopting Cal Newport’s method in How to Become a Straight A Student. Newport’s method was logical: each morning, you made a schedule for the day, carried it with you to capture new tasks and notes, and transferred them to your calendar the following morning.

Newport intended his method for university students with varying schedules and far more to juggle than I had in high school; expectedly, I didn’t find it very useful and used it only intermittently. I gave it another shot in university, but still struggled to stick with it: every few weeks the system would start falling apart. Work piled up, making the schedule repeatedly unrealistic, and the calendar became less and less focused. Newport himself acknowledges this as a shortcoming, but accepts periodic resets as necessary.

This was frustrating, but I noticed a pattern: I was performing well in school, but underperforming everywhere else. I wasn’t exercising consistently, building meaningful friendships, nor programming as often as before. Starting a project wasn’t an issue, but sticking with it was. New ideas would inevitably pile up as miscellaneous calendar items that increasingly overwhelmed me until I was unsure of what path to take, choosing to do nothing instead.

Newport’s method assumes you already know what is worth doing, and gives you the tools to decide when to do it. For externally defined or otherwise straightforward tasks, such as assignments, chores, and events, this is very effective. For everything else, deciding what is important emerged as the harder problem.

I attempted to solve this by writing a vision document. I reckoned thinking about who I wanted to be would guide what I needed to do. To an extent, this worked: the vision provided enough direction to narrow my curiosity towards a few identifiable goals. But even within this subset, the optionality was paralyzing. Every goal could be approached in infinitely many ways, and I had difficulty trusting that I had chosen the right one.

I tried to abstract away some of this choice by defining a few “base cases”: the minimum required to maintain or progress something. For example, a simple 20-minute workout, while probably not the most effective, is certainly better than nothing. I hoped by reducing the deliberation required and increasing the ease of certain more mundane duties, such as exercise, cleaning, and grooming, I would free up mental capacity to explore more interesting projects earnestly. However, this didn’t make me better at either: I had little interest in doing the bare minimum, and I didn’t suddenly gain an aptitude for choosing a project and sticking with it.

I then turned to projects: defining projects not only helped me group tasks, but also see clearly what my priorities were. Starting from my vision, I would derive a few of the projects that seemed the most important. Progress usually started strong, but inevitably wavered once the novelty faded, and forgone alternatives became louder as a result. The clarity provided was a double-edged sword, showing me what I had to do, while simultaneously intensifying my awareness of what I couldn’t do. The apparent opportunity cost of choosing incorrectly felt increasingly high, and I again found myself unwilling to commit myself to a path.

At this point, I asked myself why increasingly competent systems made me no more certain about what to do. I think the issue is that I have been asking too much of my systems: I wanted them to amount to proof, and I treated lingering doubt as evidence that I had not reasoned enough.

At fourteen, I had fewer visible options, and time felt abundant; under those circumstances, one choice did not seem to foreclose others. But as time becomes visibly finite, every choice begins to imply a rejection, and every alternative an accusation against whatever I am currently doing.

Indecision feels safe because nothing has been formally rejected; everything still feels within reach. But time passes anyway. By continually postponing commitment, I lose time without gaining experience that even the “wrong” path would have provided.

The tools I built up remain useful: they clarify values, compare possibilities, reveal tradeoffs. But they cannot make a guarantee, and I have stopped expecting one. A justified decision remains a wager—one that requires me to trust that I can survive imperfect choices, learn from them, and continue forward.