I spent a lot of time in 2022 looking at the world and feeling down about how polarizing everything and everyone seem. I took a class that had interesting content around that. The content modules, called ‘perspectives’ talked about rational and irrational thoughts (The elephant and the rider metaphor), confirmation bias and moral foundation theory. It made reflect about how I too have some strong opinions and having them questioned makes my palms sweat and I feel a rush of blood.

In 2023, I’d plan to do precisely that. I’ll pick one thing I feel strongly about every month. And then I’ll spend the month openly considering being wrong about it. If possible, I’d like to pen my thoughts and conclusions and share it with others.

So for January, I spent some time questioning my belief around the need for planning and structure.

Pre-January 2023 beliefs on planning and structure:

Here are my strong opinions on planning that I put through the ringer. Each point is not a unique belief, rather this cluster of 10 opinions is a big, fuzzy, multi-legged opinion-creature.

1. I am an organizer. I love organizing things, thoughts, reading material, furniture, events. You name it.
2. Clear plans mean clear intentions.
3. I believe all information that comes into our life should be stored in a trusted system (a la David Allen’s GTD)
4. I am not a big fan of changing plans too frequently.
5. I do not like ‘winging it’. I like to know at all times what’s on my plate, what my role is and what the desired outcome is.
6. I like to ‘label’ and ‘tag’ stuff. From kitchen cabinets to academic paper reading, everything is labelled or tagged.

1. I think about all the different areas of life as systems that I have to manage and optimize.
2. I fully get behind “Measure what matters”.
3. Tasks/Projects/Meetings that are even slightly unstructured (eg. brainstorming) are not my cup of tea.
4. At any given time, I really want the ability to know if I am making progress or not.
5. If I do not understand fully why I am doing something, I struggle with getting started.

Open reflection: Why do I feel the need for so much clarity?

I’ve always enjoyed organization. I think it was reasonable and harmless till the first time a lack of clarity and planning had negative consequences. The first time that happened was way back in 2014.

I was a brand new international student in the US, and had barely finished my undergrad a month before my flight to Texas. During my undergrad, I was sailing through most of the things I was a part of, including academics. But the truth is, I had chanced upon how the education system works, and I was merely playing that system, not really learning the craft. So I graduate with pretty good grades and a fantastic American university accepted me.

So I thought to myself, “All right, I think I’ve got this career thing all figured out. Time to cruise”

And that was that. I started thinking of the upcoming graduate school journey as a vacation of sorts. Did not put much thought into why I was going to graduate school, what I wanted to focus on,…nothing.

And for someone as woefully unprepared as me, graduate school can be fairly unforgiving. And it was. I could not keep up with the intensity and the massive step-up. I did not know this new system, so I could not ‘play’ it. Only way out was through. And it was difficult. But its when I went looking for some certainty. That turned into a search for clarity. Which turned into a search for structure. And lastly, **planning.**

I started keeping track of things. Events, tasks, email, drafts, immigration documents….you name it. I sought clarity in classes and meetings. I went to see Professors after class. I got started on work early. All of a sudden, I saw improvements. I thought to myself,

‘**Whoa, I am not smarter than I was a few months ago, but just being organized makes things so much better”.**

And that, I think, was the turning point for how I’ve felt about the need to plan and organize. It went from being something I would enjoy doing from time to time, to a savior when nothing else was working. And I completely surrendered to it. I made planning and structure a cornerstone to all areas of life, personal and professional.

I seek clarity out of fear

The old adage is pretty relevant here, ‘Too much of anything is bad’. Because my belief is rooted in insecurity, I’ve realized that I lean on it a little too much. I am scared that if I am not always prepared with a plan, I will be lost like I was before. And so:

1. I spend too much time thinking about how busy my calendar is.
2. I try to give every hour a job
3. I constantly measure myself in different ways.
4. I feel so much weight to ‘keep an eye’ on myself, that I don’t give myself permission to try crazy, creative ideas.
5. I figure if I can catch my mistakes before anyone else does, it will be less embarrassing.
6. I get caught up in some serious bike shedding. (It’s a pretty cool term, right? → It means getting caught up in minor details)
7. I run away from obscure and subjective big ideas like ‘value generation’ and ‘negotiation’. I can’t measure negotiation skills as easily as my daily step count, so I focus on the latter.
8. I’ve grown to favor short or medium-term payoffs with reasonable timelines over uncertain pay-offs and long timelines.
9. I get frustrated in the absence of clarity, which pushes clarity further away.
10. I use my tracking and measuring and organizing to convince myself I am making progress. This often stands in the way of the difficult unclear things.

I came across this article by the excellent Khe Hy, and it really called me out on a lot of things, which led to the 10 points above:

Why optimizing everything is a creativity-killer

Post January 2023 updates: What next?

Honestly? I don’t know. I used to take a lot of pride in my ability to remain organized, and I do not want to stop doing that overnight. The challenge ahead is to build the habits of good planning on healthier foundations. So that I don’t feel scared when plans go off the rails, when outcomes are not clear, when I am not sure that the experiment I want to do will lead to something. But I do it anyway.

Some thoughts I’ve had to adjust my opinions:

• There is value in ambiguity. Sometimes you just connect with someone to chat. No plan or agenda necessary.
• One way to stop planning every outcome is to iterate really fast and just look at the errors.
• Ask yourself regularly, “Does this extra planning time really move the needle for me?”

• Recognize that ‘being organized’ itself is a subjective term.

  Not everyone needs a task manager and synced databases to stay organized. I know folks that are extremely productive with just a pen and a piece of paper.

Opinions I still stand by:

• I still believe in ‘Measuring what matters’
• I still believe in robust plans that should not change every other day
• I fully stand by the fact that organizing information, tasks, ideas, etc. is best when it happens outside my brain. But there are diminishing returns.
• Systems thinking. Thinking of parts of life as systems has served me well and I still believe in it.