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My Self-Reflection on Success and Growth

In his essay "What's Going On Here, With This Human?", Graham Duncan discusses the importance of seeing people clearly, both in the context of hiring and in understanding oneself. He suggests asking the question "what's going on here with this person in front of me?" and provides a framework for expanding one's ability to see others more clearly. Inspired by this essay, I asked myself some probing questions to better understand my own strengths, weaknesses, and motivations. Here are my reflections:

Chasing Chase: Why I'll Never Trust Chase Bank Again, A Yuppie Nightmare

It always goes this way. Someone will try teaching you a parable or life story, but you never really understand it until you have to experience it yourself. Some call this ‘learning things the hard way.’ Some call this life. Now, folks always told me that consulting was either a feast or famine, which sounds straightforward, but it turns out I didn’t really know what this meant until I had to deal with Chase.

Earlier this year, for reasons that are still not fully known to me, and despite my existing relationship with Chase (dating back to my first job out of university over a decade ago!), Chase froze $180,000 of my money without warning. This left me scrambling to pay employees and nearly derailed my business—all without explanation. It was a major wake-up call not just for me but for any entrepreneur. The importance of diversifying your banking and choosing financial partners that actually support small businesses has never been more important.

Implementing Naturalistic Dialogue in AI Companions

Ever think, "This AI companion sounds odd"? You're onto something. Let's explore naturalistic dialogue and how it could change our digital interactions.

I've been focused on dialogue lately. Not the formal kind, but the type you'd hear between friends at a coffee shop. Conversations that flow, full of inside jokes and half-finished sentences that still make sense. Imagine if your AI companion could chat like that.

This post will define naturalistic dialogue, characterized by:

  1. Contextual efficiency: saying more with less
  2. Implicit references: alluding rather than stating
  3. Fragmentation: incomplete thoughts and imperfections
  4. Organic flow: spontaneity

We'll then examine AI-generated dialogue challenges and propose a solution using chain-of-thought reasoning and planning to craft more natural responses.

How I want you to write

I'm gonna write something technical.

It's often less about the nitty-gritty details of the tech stuff and more about learning something new or getting a solution handed to me on a silver platter.

Look, when I read, I want something out of it. So when I write, I gotta remember that my readers want something too. This whole piece? It's about cluing in anyone who writes for me, or wants me to write for them, on how I see this whole writing product thing.

I'm gonna lay out a checklist of stuff I'd like to have. It'll make the whole writing gig a bit smoother, you know?

Crafting Compelling Titles

I often come across titles like "How to do X with Y,Z technology." These don't excite me because X or Y are usually unfamiliar unless they're already well-known. Its rarely the dream to use X unless X is the dream.

My dream isn’t to use instructor, its to do something valueble with the data it extracts

An effective title should:

  • Evoke an emotional response
  • Highlight someone's goal
  • Offer a dream or aspiration
  • Challenge or comment on a belief
  • Address someone's problems

I believe it's more impactful to write about specific problems. If this approach works, you can replicate it across various scenarios rather than staying too general.

  • Time management for everyone can be a 15$ ebook
  • Time management for executives is a 2000$ workshop

Aim for titles that answer questions you think everyone is asking, or address thoughts people have but can't quite articulate.

Instead of "How I do something" or "How to do something," frame it from the reader's perspective with "How you can do something." This makes the title more engaging. Just make sure the difference is advisory if the content is subjective. “How I made a million dollars” might be more reasonable than “How to make a million dollars” since you are the subject and the goal might be to share your story in hopes of helping others.

This approach ultimately trains the reader to have a stronger emotional connection to your content.

  • "How I do X"
  • "How You Can do X"

Between these two titles, it's obvious which one resonates more emotionally.

You can take it further by adding specific conditions. For instance, you could target a particular audience or set a timeframe:

  • How to set up Braintrust
  • How to set up Braintrust in 5 minutes

NO adjectiives

I want you to almost always avoid adjectives and try to use evidence instead. Instead of saying "production ready," you can write something like "scaling this to 100 servers or 1 million documents per second." Numbers like that will tell you exactly what the specificity of your product is. If you have to use adjectives rather than evidence, you are probably making something up.

There's no reason to say something like "blazingly fast" unless those things are already known phrases.

Instead, say "200 times faster" or "30% faster." A 30% improvement in recommendation system speed is insane.

There's a 200 times performance improvement because we went from one programming language to another. It's just something that's a little bit more expected and understandable.

Another test that I really like using recently is tracking whether or not the statements you make can be:

  • Visualized
  • Proven false
  • Said only by you

If you can nail all three, the claim you make will be more likely to resonate with an audience because only you can say it.

Earlier this year, I had an example where I embedded all of Wikipedia in 17 minutes with 20 bucks, and it got half a million views. All we posted was a video of me kicking off the job, and then you can see all the log lines go through. You see the number of containers go from 1 out of 50 to 50 out of 50.

It was easy to visualize and could have been proven false by being unreproducible. Lastly, Modal is the only company that could do that in such an effortless way, which made it unique.

Strong Introduction

So, if you end up doing any kind of sales, you'll realize that.

What you actually need to understand is not what you have to offer as the product, but the size of the pain that the prospect is going through.

  • There are going to be readers that are just kind of curious and bored. They're not really going to be the ones that care about the product itself unless you can contextualize the pain for them.
  • It's really important to have an introduction that contextualizes the pain and foreshadows the solution.

If we can build that trust and I can correctly describe the pain that you are going through, then you will believe me when I am predicting the pain that you may also go through in the future. Ultimately, that is how you become a leader in the space—by demonstrating your ability to be right consistently.

The next time you publish or write something, they will believe it, and they will believe that they get value from it.

Strong Hooks

In the same sense that a title should often try to change the "how I" to a "how you" by eliciting an emotional response, the introduction can also help select the reader into a group that is feeling the pain.

This is the same reason why a plumber will have an introduction that says, "Do you have a leaky faucet? Call 1-800-PLUMBERS." That's a much more selective hook than just "I'm the best plumber in town." You can say that to everybody, whereas if someone answers the question of whether they have a leaky faucet, it automatically selects them to be a part of their readership.

I truly believe if you try to build a product too soon for everybody, you're gonna end up in a bad place.

Foreshadow Content

Once you hook them, you still have to first retain them. You can do that by foreshadowing the content you'll cover and even hinting at the reward.

For example, an introduction could look like the following:

  • If you're making $10,000 a month consulting right now, my goal at the end of this blog post is to help you increase your prices by:
    • Asking the right questions so you understand the value of the solution you're offering.
    • Providing tips on writing proposals and offering different options you can let your customer pay you more.
    • Lastly, sharing some anecdotes with you on how I became more comfortable with charging two or three times more than I did when I started

Here, I've pre-qualified the reader for a certain range and told them what their goal is by the end of the post.

Two things are just the tips and the questions I'm going to suggest, and then the final reward is something a little bit more personal. Ideally, they read the first two knowing that my personal stories are coming after. That intro itself outlines the entire post.

Use Lists

Once you've hooked your audience, you have to retain them and reward them.

You'll also see that as part of the foreshadowing content, I've listed three items that I want them to take away. I can also be specific with the number of questions and the number of tips I'm providing.

By using lists and counting things, I can give them a notion of progress towards the final conclusion. If I'm on the second part, I know where I am in the story. The list itself allows us to break down the body and give the reader a sense of position. Since they know where they are, they know where they're going to be.

Demonstrate being an Oracle

One thing that's also really valuable to call out is the fact that you want to be seen as a leader or an oracle to this audience.

For example, if we go back to this charging more case, it's one thing to demonstrate that you understand that the reader's dream is to be able to charge more. It's useful that you're giving them a couple of tips and stories. But what can be even more powerful is to simultaneously:

  • Demonstrate your knowledge of the current problem.
  • Predict future problems as they come.
  • Foreshadow or reference those future issues in later content.

For example, the things you do to go from $10,000 to $30,000 a month are very different from what you would need to do to get to $200,000 a month. They require things like hiring, prioritizing your services, and improving distribution. If you can foreshadow that and call that out, when your audience gets to those levels, there's a chance they will remember what you said.

They'll think, "Wow, Jason was not only right about where I was but also where I was going." This brings a tremendous sense of trust and value.

It's not just this idea of future work or future considerations of the current work, but actually being able to predict the problems they're going to have in the future and suggesting that you are also the solution to those problems. You can foreshadow that as part of a series or whatever, but the general idea remains.

Have a Strong CTA

You also have to think about what the reward for yourself is. Ultimately, you should be writing this because you think the message is important and that you believe your audience should and deserves to get this message. The content of this post delivers the reward to those who stay and finish the article.

But at the end, you also have to get something in return. You should ask your user to do something. If it's a tweet, a simple one could be a repost, a like, or a share. It could even be a follow. It could be entering some GitHub link and giving the repost a star, etc.

What I realized to be very important was to make sure you only ask for one thing and don't split the attention. If you do that, you can have solid metrics on how you phrase CTAs and how that converts to certain content. For example:

  • How many people from the tweet go to the blog post?
  • How many go from the blog post to a subscription to a newsletter?

The more I think about it, the more I believe that most people should be capturing information into a newsletter rather than just Twitter. A direct email is so much more powerful.

No matter what it is, make sure you only ask for one thing. Sometimes it's to sign up, sometimes it's to try a one-click deploy. But if there's no action that your users can take, you've definitely made a mistake.

It's also good to call out that taking the action should have some kind of outcome as well.

  • If you want to see more of this content, follow me because I post twice a week.
  • That would be an example that I can qualify as a user and set expectations on what the outcome is.
  • If you like it, then subscribe. You'll get two posts a week.

I also think in many situations we should have tiers of qualified CTUs.

If you want to split your traffic, you should have an obvious condition as to which one someone should take. For example, on Indexify:

  • If you're dealing with terabyte-scale datasets, contact us.
  • If you want to try the Open Source library

It sets a prequalifier.

The terabyte-scale dataset is an evidence-based pre-filter. It could have said "in production," but something so specific like a terabyte or a terabyte a day really qualifies who should contact indexify

Living My Best Life: A $20 Million Daydream

I've been playing a little thought experiment lately: If I had $20 million in the bank, how would I want to live my life? It's not about the money per se, but about imagining a life where financial constraints aren't the primary driver of my decisions. Here's what I've come up with.

Work: Finding the Sweet Spot

With financial freedom, I'd aim for a work schedule that balances productivity and passion:

  • 2-3 days a week of focused work
  • Flexibility to pursue projects I'm truly excited about
  • Time for creative exploration and learning

The goal isn't to stop working, but to work on things that truly matter to me, still enjoy learning and teaching.

Living Space: A Home That Inspires

My dream home would be a space that nurtures creativity and relaxation:

  • Spacious, with plenty of room for hosting friends
  • A dedicated home office for those work days
  • A killer outdoor setup for grilling and chilling
  • A pool for daily swims and relaxation
  • High-end audio system for immersive music experiences
  • Iconic furniture pieces like an Eames chair and Noguchi lamps

It's not just about luxury, but about creating an environment that fuels my passions and supports my lifestyle.

Activities: Pursuing Passions

With more time and resources, I'd dive deeper into the activities that bring me joy:

Pottery

  • Regular sessions to hone my craft
  • Potentially pursuing an apprenticeship or hosting a show
  • Exploring hand-building techniques
  • Creating functional art, like fish-serving plates

Brazilian Jiu-Jitsu

  • Low-intensity training 2-3 times a week
  • Focus on technique and enjoyment rather than competition
  • Staying injury-free and maintaining fitness

Swimming and Spearfishing

  • Daily swims in my home pool for fitness
  • Occasional spearfishing trips to connect with nature
  • Learning to prepare the fish I catch

Travel: Expanding Horizons

With financial freedom, I'd approach travel more intentionally:

  • Quarterly cross-country trips (2 weeks each)
  • Annual international trip to Europe or Japan
  • Two freediving trips per year, possibly swimming with whales or orcas

The key is balancing adventure with my home-based passions and work commitments.

Lifestyle: Quality Over Quantity

Money can't buy happiness, but it can certainly improve quality of life:

  • High-quality, varied meals (possibly with a personal chef)
  • Regular entertainment (monthly jazz or comedy shows)
  • Hosting friends for dinners and gatherings
  • House cleaner and personal assistant for support

The goal is to create a life rich in experiences and connections, not just possessions.

Personal Growth: Never Stop Learning

Even with financial security, I'd continue investing in myself:

  • Educating myself on investing and financial management
  • Being more selective with commitments and relationships
  • Focusing on "hell yes" experiences and friendships
  • Writing more, both for personal growth and to share insights

Reflections on This Exercise

This thought experiment isn't about daydreaming of wealth. It's about understanding what truly matters to me and how I can start incorporating elements of this ideal life into my current reality.

Some key takeaways:

  1. Balance is crucial - even with unlimited resources, I'd want a mix of work, play, and personal growth.
  2. Experiences and relationships matter more than possessions.
  3. Health and wellness are non-negotiable, regardless of wealth.
  4. Creativity and learning remain central to my ideal life.

While I may not have $20 million, this exercise has clarified my priorities and given me a roadmap for the life I want to create. It's a reminder that many aspects of our "ideal" life are within reach if we're intentional about our choices.

What would your $20 million life look like? More importantly, what elements of that life can you start incorporating today?

On Getting Recognized: The Unexpected Price of Online Success

I never thought I'd be writing about the challenges of being recognized in public. A year ago, I was just another data scientist trying to build connections and establish myself in the field. Now, I'm grappling with the unintended consequences of my growing online presence. Here's how it all unfolded, and what I've learned about the price of distribution in the digital age.

Advice to Young People, The Lies I Tell Myself

I'm really not qualified to give advice. But enough people DM'd me on Twitter, so here it is. I don't have to answer the same question over and over again. After some more editing I realised that I am actually writing this for my younger sister Katherine.

If you want to know who I am, check out blog/whoami or my Twitter. or consider subscribing to my newsletter below.

Don't read this if you're seeking a nuanced perspective

These are simply the lies I tell myself to keep on living my life in good faith. I'm not saying this is the right way to do things. I'm just saying this is how I did things. I will do my best to color my advice with my own experiences, but I'm not going to pretend that the suffering and the privilege I've experienced is universal.

Losing My Hands Pt. 2: The Two Jasons

This is part of an ongoing series that discusses my experience of suffering an RSI during the COVID-19 Pandemic and the ongoing struggles and disruptions it still causes. You can read part one here. My goal here is to interrogate how the injury affected my values and my approach to life. You'll probably be disappointed if you're looking for a detailed medical report.

This comment partly inspired this installation of the series. This article isn't meant to be preachy but rather introspective of the value systems that shape me and many other men.

Losing my Hands, Advice and Tips for RSI

This is the final entry (for now) of a series I wrote about my experience with tendonitis in both my wrists and thumbs during COVID-19. The injury occurred in 2020 due to overworking at my previous job, where I would put in excessive hours for weeks on end with minimal breaks. The debilitating pain prevented me from eating, dressing myself properly, and programming, leading to a significant disruption in my work and personal life. Ultimately, this experience led me to make three major changes:

  1. Consulting full-time: Sometimes, you need to take a leap of faith; other times, you need a swift, firm shove in the back to overcome your limitations. The RSI was the latter that lead me down the path of higher leverage.

  2. Revaluating my values: This doesn't necessarily mean discarding the traits that led to me getting an RSI, but it certainly made me rethink what is actually valuable and what I am trying to do with my life. Sorry to disappoint, but there has been no 'epiphany'. I am not discarding worldly possessions and pursuing a spirit quest to find 'my true self'. My hands are now a limited commodity, and I fear reinjuring myself. This means if I'm going to use my hands, it must be purposeful and deliberate.

  3. Writing: Thankfully, we live in an era where you no longer need hands to express yourself through text. Writing helped me realize that I have spent my first three decades learning and absorbing knowledge and information. Now, in my thirties, my goal will be to share the thoughts and stories I've collected.

You can read the previous two entries here: Losing My Hands, Losing My Hands Pt. 2: The Two Jasons.

Losing My Hands

The world was ending, and I couldn't even put my pants on. My hands had cramped up so badly that I couldn't grip a water bottle or type and could barely dress myself. A few weeks earlier, I had been riding the greatest decade-high anyone could have dreamed of. I was moving to New York, making 500k, working for an amazing company, and was engaged in what might be the most lucrative field on the planet. I was doing what I loved, getting paid well, and feeling like I was making a difference. Life was good. Well, as good as it could get during a once-in-a-lifetime pandemic. My name is Jason. I'm a machine learning engineer. And this is how I almost lost my hands.

When COVID-19 hit, I was a Machine Learning Engineer at Stitch Fix. Being remote meant avoiding the worst of the pandemic, which made life easier for me than most. However, as with many others, COVID-19 brought with it less-than-ideal coping mechanisms. While the world was falling apart outside, I was in a cocoon. I felt like I was just locked in and taking my job seriously because I enjoyed the work so much. What I didn’t realize was that I was seriously harming myself. The idea that value was a measurement of the function of hard work, length of work, and economic activity became a madonna that consumed me.

The Aleph and The Zahir

The Argentinian author Jorge Luis Borges wrote of two interlinked concepts, The Aleph and The Zahir. The Aleph allows the observer to see all things, while the Zahir gradually becomes the only thing the observer can see. Not to be too melodramatic, but in a similar motion, work was what allowed me to see the world differently and opened me up to an entirely different library of experience, but eventually became the only thing I was doing.

There would be ~6-week periods where I would wake up and start work around 7 am every morning, then code with few breaks until around 2 am, followed by long rest periods. Even to hardened engineers, keeping up this work rate and style of work is unsustainable, but what else are you going to do during a pandemic? When you’ve been conditioned to believe rightly or wrongly that your value as a human being is derived from the economic value you provide to those around you and all barriers to producing work have been removed by an unprecedented upheaval to social norms, it felt like there was only one path forward and that was working as hard as possible every day. This rat-brained mentality, combined with my binge work style is ultimately what I think led to the severity of my injury.

Another aspect that led to this insane cycle of overwork was that the team I was a part of was going through a lot of upheaval. Teammates were leaving, and I felt like I was left to pick up the slack. I’d like to think I was in control of my work, but consistently logging 12-15 hour days for weeks on end took its toll. At one point, my manager saw my commit history and took me aside, asking me what the fuck I was doing working this much. Imagine that. Your boss telling you that you’re working too hard. Ultimately, it came down to outside of pottery, BJJ and programming; there just wasn’t much else to do. My lifestyle had become a bubble, and when it burst, I came tumbling back to earth.

The loss of my hands came on suddenly and without much warning. One day, I woke up and realized I couldn’t hold my phone properly. I tried to get a glass of water but had the same issue. My hands were stiff and had a restricted range of motion; it was difficult to perform basic tasks. At first, it didn’t seem like a big deal; I just took a few hours off and rested. Maybe I had slept poorly or in an awkward position; maybe I had played too many video games that day. It’s not as if I was the first engineer ever to get pain in their hands, right? But things didn’t get better. Not that day or the next or even the next week. A sort of dread started to creep in as I realized most of the tasks I performed daily were becoming increasingly impossible for me to complete. This dread eventually transformed into an existential one.

The first fear was whether I could ever code again. If I can’t hold my phone, I can’t type. If I can’t type, I can’t work. Which quickly collapsed into If I can’t work hard, where do I derive my value from?

Patriarchal Values and Self-Worth

I've touched on how severely patriarchal value systems affect me and my worldview before, but even being aware of this facet of myself isn't enough to overcome it. It's something that I and imagine many others struggle with constantly. Where do I derive value from, not just as a person, but as a man, if not my ability to work and thus provide for my loved ones? What am I here for if I don't have value?

I slipped into a kind of depression because it was a listless kind of existence. I wasn’t sad per se, but I felt like my course had been rerouted, and I wasn’t sure where I’d end up. I would kind of just wander around New York, coping by going on dates or surrounding myself with non-tech-related people as I tried to get back into a normal routine. This was interspersed by periods of what is, in hindsight, less than optimal behaviours. I would do really stupid shit like go alone to Michelin-star restaurants for lunch or waste my day smoking a bunch of weed. It wasn’t quite a spiral as my life balanced itself out by diving into non-tech hobbies like spending 6-7 hours in Bryant Park playing ping pong, training BJJ, swimming a mile every morning and ultimately learning how to free dive, which helped me for a while to keep my mind off of not being able to work.

I went through acupuncture physiotherapy, tried anything that might work and threw as many resources at my hands as I tried to work through not being able to use them. I even considered peptides, PRP, and stem cells, telling myself even if it was a small fortune, it would be worth it if I could make a living again. All of these therapeutics and treatments helped to some degree, but I still deal with pain and stiffness even three years later. To this day, it affects my ability to cook, eat, get dressed, and say nothing about my hobbies. Even swimming would aggravate my wrists without treating them immediately afterwards. The whole experience of being this helpless is just insane to think about. Since being injured, I’ve hesitated to take on a lot of work despite enjoying it. Which has been the major push for me to shift roles slightly. I’ve turned down basically every offer to join a startup because I’m worried about reinjuring myself. And to be honest, I’m still trying to figure out what it all means. I don’t know if there is some moral or epiphany for me and how I approach work other than trying to be more purposeful with my work. Every time I code now, I have to weigh if what I’m doing is a valuable use of my time and resources. If coding adversely affects my health, it would be better for me not to do it.

I took roughly two years off of work. I wasn’t making much money or doing much programming. What helped was reminding myself that the skills that took me to ‘the dance’ are not the skills that will keep me happy for the rest of my life. You must keep moving and learning new things; otherwise, you will get left behind. In this current wave of AI optimism, I found myself enjoying things again and adapting. Again, I’m still trying to figure out what my injury means, but at any rate, I’m much more resilient now than where I was 3 years ago.

Focusing on Open Source and Consulting

Two things I've done specifically are: 1. Focus more on open source projects so the code I write has more leverage. 2. Pursue consulting as a way to scale myself as an individual while still being able to work with and help founders build exciting new solutions.

This idea that you have control over yourself and your actions and choices and can in some way shape your outcomes through nothing but your own decisions may sound haughty and full of myself, but I really do think it’s important to try and frame things in terms of what you’re able to do. Stop worrying about everyone else and things that are out of your control.

Existentialism and Personal Responsibility

Jean-Paul Sartre said, "The first effect of existentialism is that it puts every man in possession of himself as he is and places the entire responsibility for his existence squarely upon his' own shoulders. And, when we say that man is responsible for himself, we do not mean that he is responsible only for his own individuality but that he is responsible for all men."

I think the first time something really good happens to you—I mean really good—like when you can take a step back from life and breathe and look at it and go, ”Hey, I have it pretty good,” you tell yourself you got lucky. You met the right person, went to the right school, and landed an internship at the right startup; whatever it is, there's a feeling that it's out of your control. But, when you don’t understand nature or luck, you feel it’s impossible to reproduce it again. This was part of how I felt initially, but having gone through everything I’ve gone through over the last ten years or so, I don’t just mean a struggle, but all of my experiences have placed me in a position where I’m much more confident even though my hands still hurt and bother me to this day.

Byung-Chul Han's Insights on the Burnout Society

I've been reading a lot of Byung-Chul Han recently, specifically The Burnout Society; I'll spare you the lecture and just give you the Sparks Notes version graciously provided by Boris Smus.

Byung-Chul Han views contemporary society as no longer a disciplinary society but rather an achievement one. Within this, there are plenty of parallels to ideas like the panopticon and technology being an extension of man ala Marshall McLuhan mediating human behaviour and potentiality, however the ideas I found most relevant to my situation are:

  • Achievement society is a society of self-exploitation.
  • The achievement-subject exploits itself until it burns out.
  • The achievement-subject that understands itself as its own master, as homo liber, turns out to be homo sacer.
  • The achievement-subject is simultaneously perpetrator and victim, master and slave.

Emphasis is mine, and it's because I think this idea is the most impactful of the summaries Smus provided. Am I just my own subject exploiting myself till there is nothing left but a husk where Jason once stood? Again pardon the melodrama, but this injury forced me to re evaluate my entire value system.

Byung-Chul Han's Insights on the Burnout Society

Despite my injury, I still try to maintain a bulletproof growth mindset. I constantly ask myself why I shouldn't make more money every month. The worst part is I truly do not know whether this is a ‘good’ mindset to have. Should I abstract to something like ‘focusing on the process’ and results will come? Should I be working with new clients to solve new problems? Maybe this is part of what caused my injury in the first place and the poison I was leaning into. I truly believe all I need to succeed is my hands, brain, and laptop. As long as I have these three things, I’ll be fine.

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I write about a mix of consulting, open source, personal work, and applying llms. I won't email you more than twice a month, not every post I write is worth sharing but I'll do my best to share the most interesting stuff including my own writing, thoughts, and experiences.