TL;DR
- You cannot organize the startup. You can organize your thoughts, and that is the only order available to you.
- A thought you never write down does not disappear. It runs in the background, and whatever you leave unexamined, you end up believing.
- Unfinished work convinces you that you are not good enough. Slowness convinces you that you are stupid. Unacknowledged, these become facts about you that you never actually chose.
- Thoughts drive actions, actions drive emotions, and the loop runs both ways. That loop is the one lever you hold when everything around you is chaos.
Context
Yesterday I asked for a pen and no one had one.
A whole room of people building the future, and not one pen between us. Nobody writes anything down, and I do not think it is an accident. In an era where AI has made doing so fast and so lucrative, stopping to think can feel like a loss. Thinking slows you down. It is all motion and action. So organizing your own thoughts starts to feel like a waste of time, when you could just be doing instead.
But the thoughts do not leave because you ignored them. They stay in your head, more of them each day than you could ever catch. You feel things without naming them. You reach conclusions without noticing you reached them. They move through you unexamined, and you assume that because you never stopped to question them, there was nothing there to question.
Problem
You cannot always believe your thoughts. A thought that feels true today can be gone tomorrow.
I learned this the hard way. For a long time I believed every thought that came to me. I trusted all of them and checked none of them, and I could never understand why I woke up heavy one day and light the next. I assumed something was wrong with me. Really, I was just believing whatever happened to show up.
A thought you do not examine does not leave. It settles in, and slowly it becomes something you take as true about yourself. Unfinished work starts telling you that you are not good enough. Work that took too long tells you that you are slow, and then that you are stupid. You never decide to believe these things. You just never stop to check them, and an unchecked thought quietly becomes fact.
The startup makes this so much harder. It is chaotic by nature, and while that chaos does not change what is actually true about you, it scrambles your sense of why you feel the way you feel. You feel sad, or tired, and you cannot trace it to anything, so you reach for the easiest explanation and decide the problem is you.
Solution
I once had a therapist tell me that your thoughts shape your actions, your actions shape your emotions, and it all runs the other way just as easily. Change how you think and you change how you act, and then how you feel. Change how you feel and you change how you act, and then how you think. Your thoughts sit right at the center of it.
So I try to organize them, precisely because the startup never will. I write them down. A thought on paper stops being fact and becomes a claim I can actually look at. I name what I am feeling and trace it back to the thought underneath it, and once I can see the thought, I get to decide whether it deserves to be believed.
This is the one system I fully control. I cannot make the startup orderly, but I can refuse to carry its disorder into my own head. Because when I let the chaos in, no amount of good work feels like enough. I end up overwhelmed and quietly disappointed in myself in the middle of doing my best work.
The Categories
Here are the categories I sort my thoughts into. This is not filing for its own sake. Once a thought has a place, you can work through it, and working through it changes how you act, how you feel, and what you believe. The point is to walk into work with these questions already answered, instead of relitigating them every time a thought surfaces.
The answers you will find under each question are my own. I am not offering them as the right answers, only as proof that these questions can be sat with and worked through. Yours will look nothing like mine, and that is exactly the point. Do the reflection for yourself.
Existential
These are the questions sitting underneath all the others. Answer them once, deliberately, and they stop ambushing you in the middle of a workday.
Why are you doing this job?
I have a set of skills this company genuinely needs, and that it will not easily find elsewhere. I bring empathy to how we solve problems, with customers and with each other. I think visually, so I can make things clear, and clarity is what brings people together. And I try to be a light in the room, to encourage people and spread some joy while the work is hard. The fit runs both ways. This place needs what I have, and I become more by giving it.
I believe in what we are building. It is software that has to be reliable, the kind that banks, governments, and critical systems depend on. When it holds, it helps people, and sometimes it keeps them safe.
And I am here to grow. Technology is moving faster than anyone can fully hold, and it is deciding what our future looks like. Standing at the front of it lets me see the real problems firsthand and feel their human and ethical weight in the first person, so that when I speak to them I speak from experience and not from the outside. I want to make a difference in the world through technology, and I want to understand from the inside what is actually happening here.
This job is also teaching me myself, faster than anything else could. A startup pressure-tests you in tight, stressful moments, and what surfaces under that pressure is the truth about your priorities and your limits. When time is short, I learn what I actually value. When I am stressed and short with people, I catch a real sense of what it costs those who carry hard jobs every day. I never notice it in the moment. Only in hindsight do I see that this place has been teaching me empathy all along, turning it from an idea I hold into something I have lived. That is what I most want to carry out of here.
It shows me my strengths. I love making things visual. I love technology that moves, hardware I can take apart, the way an electric bike is just a set of parts to understand and play with and explain to someone else. I love teaching what I learn. It also shows me my failure modes. I ship things I do not fully understand because that is the pace, and I am still working out how much of that gap is me and how much is the environment. I learn that seven days a week breaks me, and that I have to build my week so that something each night brings me back. And underneath all of it, I am learning to forgive myself when I fall short, a grace I will carry into every job after this, and maybe into being a parent one day.
And beneath even that, there is a reason I do not always say out loud. I am a believer in the Lord Jesus Christ. I believe this is the place He has called me to, and that part of that calling is to endure a certain suffering here, so that His light and His glory move through me into this work, and into everyone I come in contact with.
Why are you doing this job now?
Because the timing is simple to me. AI is not going away. It is only going to become more woven into everything, and the questions that come with it are the ones I care about most: what it is doing to us, what it makes us now, how we relate to it, how we let it reorder our lives. I believe there is a future in helping lead through that, in discerning it and shaping the right approach to it, and I want a seat at that table while it is still being built. I love thinking and philosophizing about these questions, and this is where they are actually live.
Because of the people. I want to be around people who are ambitious, who love what they do, and who love other things too. Something stirs in me near people who are passionate about anything at all, whether it is the one who ships all day and disappears into the wilderness on weekends, or the founder of a company, or the one who just loves bikes and knows everything there is to know about them. Being close to that stirring helps me find where my own lives, whether it points at the same things or something else entirely. I am young, and I am still working that out for myself.
And because I think I may want to build something of my own one day. This is teaching me what that actually takes, especially the emotional regulation of it: how to hold the fleeting highs and the hard lows without being run by either. Living it myself is teaching me how to stay kind, and how to be someone who encourages the people around him. As a technology person, being grounded in your own emotions matters far more than it looks like it should.
What is the point of all this for you?
If I have to sum it up in one word, it is growth. This is a crushing experience, and it is teaching me a lot at once: how AI actually works, what I am good at, where I get set back, and how to serve the people around me in the middle of all of it. It is shaping my character. It is building my empathy and my resilience. It is teaching me not to be a workaholic, and it is teaching me my priorities.
Whatever a given night or week looks like, even a crushing one, even one where I have to take a day off, the big picture is the same. An enormous amount of growth comes out of this, and with it a kind of preparedness for whatever comes next. It is a formative season, forming me into whoever the next one will need me to be, whenever that season arrives.
When you have real answers, a hard day stops becoming a referendum on your whole life. The doubt still comes, but it has somewhere to land, and you already know what you decided.
Day to Day
The existential questions you answer once. These you ask every day, while the day is still in motion. They are how I keep the chaos from choosing my hours for me, and they come in a few kinds.
Pre-plan. When I wake up, what does my day look like? And what does my week look like? A month is too far out to plan.
I keep a simple tracker. Every task for the day and the week goes in it, even the long-term ones, and each morning I mark the few I am actually going to work on. Now I can see what is on my plate today and what is coming next, so when someone hands me one more thing, I can tell whether it actually matters.
The whole point of planning ahead is to stop being reactive to everything and start being proactive. I can see what is coming and where I stand, so I am not drowning in the moment. I have perspective. And waking up with perspective, knowing what the day is for instead of guessing at it, is how I start on a good foot.
The action. Keep a running tracker of the tasks you have prioritized for the day and the week, so that before you walk into work you already know what you are working on.
Ad hoc. As the day moves, what is coming up that I did not plan for?
As the day moves, people will bring you a hundred things. Some are hair on fire. Someone says, Rupa, this just broke, and it is urgent. Then I pause what I am on, add the fire to my tracker, work it, and when it is out I go back. My original list has not disappeared. It just got deprioritized for a moment, and I can see exactly where I left it.
Other things are not on fire. They are just new asks. Those go into the tracker too, but with a priority attached, weighed against everything I am already doing. Only then can I answer the real question: do I stop what I am on for this, or is this something I get to later, and when.
Sometimes the expectation is that the new thing and my existing work both get done at once. But I had planned three days for the task I was already on, and now there are two tasks in those three days. There are only a few honest ways through that.
I can manage expectations with the person, and say plainly what will actually be done by when. Or I can do a lighter pass on both, finishing each at a different level than I first wanted. Instead of a full end-to-end build with every feature, I ask what I can cut and still hit the same goal at a smaller scope, so both things get done.
Or I step back and look at how I am working at all. Where are the inefficiencies I can squeeze out? Maybe for one task I was going to write a detailed document, circulate it with the team, and record a Loom so others could pick it up. Some of that is real work, and some of it is ceremony I can cut. The trick is knowing which is which.
Underneath all of this is a harder thing. These asks come fast, and they force you to be snappy. You are on something, a fire appears, you jump, another appears, you jump again. That is the firefighter mentality: wherever the fire is, you go put it out.
I have watched two kinds of people do this. One is the firefighter, who puts out whatever is burning, even the long-term things, and seems to multitask without end. The other is more of an artist, who works in long strokes, slower but so detailed and so laser-focused that nothing slips. Both work. Both have a cost. The firefighter moves fast and sometimes breaks things, and his long-term projects get scorched, or he burns his nights finishing them because the days went to fires. The artist barely responds to the ad hoc at all, struggles with the short-term, and slowly gets handed only the long, quiet work.
It is like tennis. Some play short court and some play long court, and you pick a side, because the two ask different things of your body at once. Long and short, ad hoc and day-to-day, they stretch you in opposite directions, and our capacity to hold both is smaller than we pretend. I will come back to that in the limitations.
The action. Put every ad hoc ask into the tracker, mark whether it is hair on fire or not, and price it against what you already planned. When too much lands at once, reach for one of three levers: manage expectations, cut scope, or cut the inefficiency out of how you work.
The bottom line. When something comes at you, notice if your instinct is to react, and then take a moment to think anyway. We are not agents. We are not superhuman. No one feeds us an input and gets an instant output. We take time to process and to understand, and that is not a weakness. It is the very thing that lets us decide what actually matters.
Priorities. What is the most important thing for me to do right now, for tomorrow, and for the company? And what are the people around me talking about?
Priorities start with paying attention to what people keep calling important. In one conversation it became clear the dashboard was going to die and the CLI was where everything was headed, so my priority became getting closer to the CLI work. Reading the room that way tells me which bets to place now, so I am standing where the opportunity is and not where it is drying up.
Then there is the nearer question: what is most important right now, tomorrow, and for the company. If we are driving toward a launch, the launch is the priority, and everything else gets weighed against it. We have limited capacity, and judging what matters most is the best thing we can do with it. Sometimes that means asking my boss to clarify what the real priority is and what is actually expected of me.
What stops most people from setting priorities is not the work. It is the fear. The fear that acknowledging a limit means you are less. The fear that people will think badly of you for missing an expectation. The fear that deprioritizing marks you as underperforming, that everyone will see it, and that you will be let go.
All of that is true. People can think those things, I can think them about myself, and the limit can hurt. But I am limited, and so is the next person, and that equalizes us more than it separates us. Why I am here may have little to do with sheer output anyway. It can be the quality of the work, the urgency, the trust I have earned, things I do not fully control that keep me here because I am strong somewhere else.
And the boss I fear judging me might see it the other way entirely: someone who cares enough to do the research and understand what the priority really costs in time. That is what real decisions get made on, and it shows care and respect and a wish to do good work. Burning myself out only produces worse work. Naming the elephant and choosing the priority is how things actually get done, and protecting my own health turns out to be better for the company and everyone in it over the long run.
There is one last reason. Setting priorities lets other people see that I am human, and gives them permission to be human too. When you perform as if you can do anything, you set a bar no one can reach, and it only ratchets higher until people buckle under it. Admitting a limit and living inside it quietly lets everyone else breathe.
The action. Track what the people around you keep calling most important, and aim your priorities at it. When you cannot do it all, name the tradeoff out loud and bring your boss in to confirm it.
The bottom line. Setting priorities is not a confession of weakness. It is how you make honest decisions, protect the quality of your work, and let the people around you be human too.
Strengths and strategies. What are my strengths, and what strategy does a given problem call for? This is what tells me when in the day to do something, and which way into a problem actually fits me.
The first move is to choose work that fits your strengths. Mine is taking something vague, a loose set of requirements, and turning it into something shipped in a short window. So the things that need to get done, and the things important enough that one person has to own them end to end, tend to land on my plate. People can trust that I will chase down the clarity I need and ship it reliably, even when the ask starts out blurry. That is a muscle I am still growing, and naming it as a strength is what lets me lean into it.
Knowing your strengths also tells you when to do which kind of work. I plan best right after lunch, when nothing is pulling at me. I would rather plan the day before, so the next morning I am only executing what I already decided. A lot of my weeks run on that rhythm: one day to plan, one to build, one to test. When my brain is dead by evening, I move planning to the morning. When something needs days of testing, I plan on Thursday, execute on Friday, and let it test over the weekend. I have actually run my weeks this way.
Then there is strategy for the work itself. When a task looks daunting, the job is to find a way in, and it is rarely linear. You pick a strategy, it fails, you pivot. You go deep, hit a wall, pull back out, and reach for something you have never tried before.
I was building a recommendation engine once, and it did not work as well as I wanted. I felt ashamed, and I was sure the whole feature would get ripped out. So I tried something I had never done. The engine runs fast and light during onboarding, then does a slow, detailed sweep in the evening, so by morning the recommendations are genuinely good. It balances quick against accurate instead of choosing one. To get there I had to break a mental barrier, to let two things run quietly and treat it as an experiment rather than a verdict on me.
That taught me a bigger strategy: run small experiments inside the team and the system instead of trying to settle everything upfront. See by doing. Break something on purpose to learn the worst that can actually happen. My own version of move fast and break things is move fast, break things, fix them fast, and move again. As long as you can fix quickly and it is not hitting customers in real time, you have room to play.
The action. Name the work that fits your strengths and steer toward it, then build a weekly rhythm around when you actually do your best planning, building, and testing. When a task looks daunting, pick a strategy, and let yourself pivot the moment it stops working.
The bottom line. Your strengths decide what work to reach for, and your strategies decide how to get through it. Both only become usable once you write them down.
Limitations, or human caps. What are my limits as a human? Where are the natural caps on my attention and my energy, and how do I work with them instead of against them?
This one might be the most important: knowing my limits as a human. Some caps are just real. My attention is good for maybe four to six hours of true focus a day, so the real question is what I spend those hours on. Past about ten hours of work, tomorrow pays for it. I need seven or eight hours of sleep, and when it goes irregular, so does everything else. I need to actually eat, real meals with greens and fiber and protein, not whatever is fast.
Other limits come from priorities. Rest over work, well-being over work, family over work. Each one draws a line about when I have to clock out, and drawing that line is a hard sacrifice. But once I know why I am protecting a priority, the limit stops feeling like a failure. It becomes a signal, a radar for when to step away from the job, or from a priority, or to reset what people expect of me.
That is the myth worth breaking. Limits are not a weakness. They are revealing, and they are real, and they are not really about me. They are about being human. Naming them is how people get a better life and fewer burnouts. We are not superhuman. Maybe one day something like Neuralink changes that, but for now, knowing my limits is how I stay content with who I actually am and how I was made to be.
The action. Write down your real caps, the hours of focus, sleep, food, and rest you actually need, and the priorities that draw your lines. Then build your work to fit inside them instead of pretending they are not there.
The bottom line. Limits are not something to defeat. They are the shape of being human, and working with them is what keeps you and everyone around you whole.
Let the startup be disorganized. Do not let yourself be.