Full Width 
FOCUS MODE
Shortcuts 
Sign Up 
Log In 
Articles 
Reading List More from Irrational Exuberance
One of my side quests at work is to get a simple feedback loop going where we can create knowledge bases that comment on Notion documents. I was curious if I could hook this together following these requirements: No custom code hosting Prompt is editable within Notion rather than requiring understanding of Zapier Should be be fairly quickly Ultimately, I was able to get it working. So a quick summary of how it works, some comments on why I don’t particularly like this approach, then some more detailed comments on getting it working. General approach Create a Notion database of prompts. Create a specific prompt for providing feedback on RFCs. Create a Notion database for all RFCs. Add an automation into this database that calls a Zapier webhook. The Zapier webhook does a variety of things that culminate in using the RFC prompt to provide feedback on the specific RFC as a top-level comment in the RFC. Altogether this works fairly well. The challenges with this approach The best thing about this approach is that it actually works, and it works fairly well. However, as we dig into the implementation details, you’ll also see that a series of things are unnaturally difficult with Zapier: Managing rich text in Notion because it requires navigating the blocks datastructure Allowing looping API constructs such as making it straightforward to leave multiple comments on specific blocks rather than a single top-level comment Notion only allows up to 2,000 characters per block, but chunking into multiple blocks is moderately unnatural. In a true Python environment, it would be trivial to translate to and from Markdown using something like md2notion Ultimately, I could only recommend this approach as an initial validation. It’s definitely not the right long-term resting place for this kind of approach. Zapier implementation I already covered the Notion side of the integration, so let’s dig into the Zapier pieces a bit. Overall it had eight steps. I’ve skipped the first step, which was just a default webhook receiver. The second step was retrieving a statically defined Notion page containing the prompt. (In later steps I just use the Notion API directly, which I would do here if I was redoing this, but this worked too. The advantage of the API is that it returns a real JSON object, this doesn’t, probably because I didn’t specify the content-type header or some such.) This is the configuration page of step 2, where I specify the prompt’s page explicitly. ) Probably because I didn’t set content-type, I think I was getting post formatted data here, so I just regular expressed the data out. It’s a bit sloppy, but hey it worked, so there’s that. ) Here is using the Notion API request tool to retrieve the updated RFC (as opposed to the prompt which we already retrieved). ) The API request returns a JSON object that you can navigate without writing regular expressions, so that’s nice. ) Then we send both the prompt as system instructions and the RFC as the user message to Open AI. ) Then pass the response from OpenAI to json.dumps to encode it for being included in an API call. This is mostly solving for newlines being \n rather than literal newlines. ) Then format the response into an API request to add a comment to the document. Anyway, this wasn’t beautiful, and I think you could do a much better job by just doing all of this in Python, but it’s a workable proof of concept.
Last weekend, I wrote a bit about using Zapier to load Notion pages as prompts to comment on other Notion pages. That worked well enough, but not that well. This weekend I spent some time getting the next level of this working, creating an agent that runs as an AWS Lambda. This, among other things, allowed me to rely on agent tool usage to support both page and block-level comments, and altogether I think the idea works extremely well. This was mostly implemented by Claude Code, and I think the code is actually fairly bad as a result, but you can see the full working implementation at lethain:basic_notion-agent on Github. Installation and configuration options are there as well. Watch a quick walkthrough of the project I recorded on YouTube. Screenshots To give a sense of what the end experience is, here are some screenshots. You start by creating a prompt in a Notion document. Then it will provide inline comments on blocks within your document. It will also provide a summary comment on the document overall (although this is configurable if you only want in-line comments). A feature I particularly like is that the agent is aware of existing comments on the document, and who made them, and will reply to those comments. Altogether, it’s a fun little project and works surprisingly well, as almost all agents do with enough prompt tuning.
For managers who have spent a long time reporting to a specific leader or working in an organization with well‑understood goals, it’s easy to develop skill gaps without realizing it. Usually this happens because those skills were not particularly important in the environment you grew up in. You may become extremely confident in your existing skills, enter a new organization that requires a different mix of competencies, and promptly fall on your face. There are a few common varieties of this, but the one I want to discuss here is when managers grow up in an organization that operates from top‑down plans (“orchestration‑heavy roles”) and then find themselves in a sufficiently senior role, or in a bottom‑up organization, that expects them to lead rather than orchestrate (“leadership‑heavy roles”). Orchestration versus leadership You can break the components of solving a problem down in a number of ways, and I’m not saying this is the perfect way to do it, but here are six important components of directing a team’s work: Problem discovery: Identifying which problems to work on Problem selection: Aligning with your stakeholders on the problems you’ve identified Solution discovery: Identifying potential solutions to the selected problem Solution selection: Aligning with your stakeholders on the approach you’ve chosen Execution: Implementing the selected solution Ongoing revision: Keeping your team and stakeholders aligned as you evolve the plan In an orchestration‑heavy management role, you might focus only on the second half of these steps. In a leadership‑heavy management role, you work on all six steps. Folks who’ve only worked in orchestration-heavy roles often have no idea that they are expected to perform all of these. So, yes, there’s a skill gap in performing the work, but more importantly there’s an awareness gap that the work actually exists to be done. Here are a few ways you can identify an orchestration‑heavy manager that doesn’t quite understand their current, leadership‑heavy circumstances: Focuses on prioritization as “solution of first resort.” When you’re not allowed to change the problem or the approach, prioritization becomes one of the best tools you have. Accepts problems and solutions as presented. If a stakeholder asks for something, questions are around priority rather than whether the project makes sense to do at all, or suggestions of alternative approaches. There’s no habit of questioning whether the request makes sense—that’s left to the stakeholder or to more senior functional leadership. Focuses on sprint planning and process. With the problem and approach fixed, protecting your team from interruption and disruption is one of your most valuable tools. Operating strictly to a sprint cadence (changing plans only at the start of each sprint) is a powerful technique. All of these things are still valuable in a leadership‑heavy role, but they just aren’t necessarily the most valuable things you could be doing. Operating in a leadership-heavy role There is a steep learning curve for managers who find themselves in a leadership‑heavy role, because it’s a much more expansive role. However, it’s important to realize that there are no senior engineering leadership roles focused solely on orchestration. You either learn this leadership style or you get stuck in mid‑level roles (even in organizations that lean orchestration-heavy). Further, the technology industry generally believes it overinvested in orchestration‑heavy roles in the 2010s. Consequently, companies are eliminating many of those roles and preventing similar roles from being created in the next generation of firms. There’s a pervasive narrative attributing this shift to the increased productivity brought by LLMs, but I’m skeptical of that relationship—this change was already underway before LLMs became prominent. My advice for folks working through the leadership‑heavy role learning curve is: Think of your job’s core loop as four steps: Identify the problems your team should be working on Decide on a destination that solves those problems Explain to your team, stakeholders, and executives the path the team will follow to reach that destination Communicate both data and narratives that provide evidence you’re walking that path successfully If you are not doing these four things, you are not performing your full role, even if people say you do some parts well. Similarly, if you want to get promoted or secure more headcount, those four steps are the path to doing so (I previously discussed this in How to get more headcount). Ask your team for priorities and problems to solve. Mining for bottom‑up projects is a critical part of your role. If you wait only for top‑down and lateral priorities, you aren’t performing the first step of the core loop. It’s easy to miss this expectation—it’s invisible to you but obvious to everyone else, so they don’t realize it needs to be said. If you’re not sure, ask. If your leadership chain is running the core loop for your team, it’s because they lack evidence that you can run it yourself. That’s a bad sign. What’s “business as usual” in an orchestration‑heavy role actually signals a struggling manager in a leadership‑heavy role. Get your projects prioritized by following the core loop. If you have a major problem on your team and wonder why it isn’t getting solved, that’s on you. Leadership‑heavy roles won’t have someone else telling you how to frame your team’s work—unless they think you’re doing a bad job. Picking the right problems and solutions is your highest‑leverage work. No, this is not only your product manager’s job or your tech lead’s—it is your job. It’s also theirs, but leadership overlaps because getting it right is so valuable. Generalizing a bit, your focus now is effectiveness of your team’s work, not efficiency in implementing it. Moving quickly on the wrong problem has no value. Understand your domain and technology in detail. You don’t have to write all the software—but you should have written some simple pull requests to verify you can reason about the codebase. You don’t have to author every product requirement or architecture proposal, but you should write one occasionally to prove you understand the work. If you don’t feel capable of that, that’s okay. But you need to urgently write down steps you’ll take to close that gap and share that plan with your team and manager. They currently see you as not meeting expectations and want to know how you’ll start meeting them. If you think that gap cannot be closed or that it’s unreasonable to expect you to close it, you misunderstand your role. Some organizations will allow you to misunderstand your role for a long time, provided you perform parts of it well, but they rarely promote you under those circumstances—and most won’t tolerate it for senior leaders. Align with your team and cross‑functional stakeholders as much as you align with your executive. If your executive is wrong and you follow them, it is your fault that your team and stakeholders are upset: part of your job is changing your executive’s mind. Yes, it can feel unfair if you’re the type to blame everything on your executive. But it’s still true: expecting your executive to get everything right is a sure way to feel superior without accomplishing much. Now that I’ve shared my perspective, I admit I’m being a bit extreme on purpose—people who don’t pick up on this tend to dispute its validity strongly unless there is no room to debate. There is room for nuance, but if you think my entire point is invalid, I encourage you to have a direct conversation with your manager and team about their expectations and how they feel you’re meeting them.
I’m turning forty in a few weeks, and there’s a listicle archetype along the lines of “Things I’ve learned in the first half of my career as I turn forty and have now worked roughly twenty years in the technology industry.” How do you write that and make it good? Don’t ask me. I don’t know! As I considered what I would write to summarize my career learnings so far, I kept thinking about updating my post Advancing the industry from a few years ago, where I described using that concept as a north star for my major career decisions. So I wrote about that instead. Recapping the concept Adopting advancing the industry as my framework for career decisions came down to three things: The opportunity to be more intentional: After ~15 years in the industry, I entered a “third stage” of my career where neither financial considerations (1st stage) nor controlling pace to support an infant/toddler (2nd stage) were my highest priorities. Although I might not be working wholly by choice, I had enough flexibility that I could no longer hide behind “maximizing financial return” to guide, or excuse, my decision making. My decade goals kept going stale. Since 2020, I’ve tracked against my decade goals for the 2020s, and annual tracking has been extremely valuable. Part of that value was realizing that I’d made enough progress on several initial goals that they weren’t meaningful to continue measuring. For example, I had written and published three professional books. Publishing another book was not a goal for me. That’s not to say I wouldn’t write another—in fact, I have—but it would serve another goal, not be a goal in itself. As a second example, I set a goal to get twenty people I’ve managed or mentored into VPE/CTO roles running engineering organizations of 50+ people or $100M+ valuation. By the end of last year, ten people met that criteria after four years. Based on that, it seems quite likely I’ll reach twenty within the next six years, and I’d already increased that goal from ten to twenty a few years ago, so I’m not interested in raising it again. “Advancing the industry” offered a solution to both, giving me a broader goal to work toward and reframe my decade and annual goals. That mission still resonates with me: it’s large, broad, and ambiguous enough to support many avenues of progress while feeling achievable within two decades. Though the goal resonates, my thinking about the best mechanism to make progress toward it has shifted over the past few years. Writing from primary to secondary mechanism Roughly a decade ago, I discovered the most effective mechanism I’ve found to advance the industry: learn at work, write blog posts about those learnings, and then aggregate the posts into a book. An Elegant Puzzle was the literal output of that loop. Staff Engineer was a more intentional effort but still the figurative output. My last two books have been more designed than aggregated, but still generally followed this pattern. That said, as I finish up Crafting Engineering Strategy, I think the loop remains valid, but it’s run its course for me personally. There are several reasons: First, what was energizing four books ago feels like a slog today. Making a book is a lot of work, and much of it isn’t fun, so you need to be really excited about the fun parts to balance it out. I used to check my Amazon sales standing every day, thrilled to see it move up and down the charts. Each royalty payment felt magical: something I created that people paid real money for. It’s still cool, but the excitement has tempered over six years. Second, most of my original thinking is already captured in my books or fits shorter-form content like blog posts. I won’t get much incremental leverage from another book. I do continue to get leverage from shorter-form writing and will keep doing it. Finally, as I wrote in Writers who operate, professional writing quality often suffers when writing becomes the “first thing” rather than the “second thing.” Chasing distribution subtly damages quality. I’ve tried hard to keep writing as a second thing, but over the past few years my topic choices have been overly pulled toward filling book chapters instead of what’s most relevant to my day-to-day work. If writing is second, what is first? My current thinking on how to best advance the industry rests on four pillars: Industry leadership and management practices are generally poor. We can improve these by making better practices more accessible (my primary focus in years past but where I’ve seen diminishing returns). We can improve practices by growing the next generation of industry leaders (the rationale behind my decade goal to mentor/manage people into senior roles, but I can’t scale it much through executive roles alone) We can improve practices by modeling them authentically in a very successful company and engineering organization. The fourth pillar is my current focus and likely will remain so for the upcoming decade, though who knows—your focus can change a lot over ten years. Why now? Six years ago, I wouldn’t have believed I could influence my company enough to make this impact, but the head of engineering roles I’ve pursued are exactly those that can. With access to such roles at companies with significant upward trajectories, I have the best laboratory to validate and evolve ways to advance the industry: leading engineering in great companies. Cargo-culting often spreads the most influential ideas—20% time at Google, AI adoption patterns at Spotify, memo culture at Amazon, writing culture at Stripe, etc. Hopefully, developing and documenting ideas with integrity will hopefully be even more effective than publicity-driven cargo-culting. That said, I’d be glad to accept the “mere” success of ideas like 20% time. Returning to the details Most importantly for me personally, focusing on modeling ideas in my own organization aligns “advancing the industry” with something I’ve been craving for a long time now: spending more time in the details of the work. Writing for broad audiences is a process of generalizing, but day-to-day execution succeeds or fails on particulars. I’ve spent much of the past decade translating between the general and the particular, and I’m relieved to return fully to the particulars. Joining Imprint six weeks ago gave me a chance to practice this: I’ve written/merged/deployed six pull requests at work, tweaked our incident tooling to eliminate gaps in handoff with Zapier integrations, written an RFC, debugged a production incident, and generally been two or three layers deeper than at Carta. Part of that is that Imprint’s engineering team is currently much smaller— 40 rather than 350—and another part is that industry expectations in the post-ZIRP reentrenchment and LLM boom pull leaders towards the details. But mostly, it’s just where my energy is pulling me lately.
There’s a lot of excitement about what AI (specifically the latest wave of LLM-anchored AI) can do, and how AI-first companies are different from the prior generations of companies. There are a lot of important and real opportunities at hand, but I find that many of these conversations occur at such an abstract altitude that they’re a bit too abstract. Sort of like saying that your company could be much better if you merely adopted software. That’s certainly true, but it’s not a particularly helpful claim. This post is an attempt to concisely summarize how AI agents work, apply that summary to a handful of real-world use cases for AI, and make the case that the potential of AI agents is equivalent to the potential of this generation of AI. By the end of this writeup, my hope is that you’ll be well-armed to have a concrete discussion about how LLMs and agents could change the shape of your company. How do agents work? At its core, using an LLM is an API call that includes a prompt. For example, you might call Anthropic’s /v1/message with a prompt: How should I adopt LLMs in my company? That prompt is used to fill the LLM’s context window, which conditions the model to generate certain kinds of responses. This is the first important thing that agents can do: use an LLM to evaluate a context window and get a result. Prompt engineering, or context engineering as it’s being called now, is deciding what to put into the context window to best generate the responses you’re looking for. For example, In-Context Learning (ICL) is one form of context engineering, where you supply a bunch of similar examples before asking a question. If I want to determine if a transaction is fraudulent, then I might supply a bunch of prior transactions and whether they were, or were not, fraudulent as ICL examples. Those examples make generating the correct answer more likely. However, composing the perfect context window is very time intensive, benefiting from techniques like metaprompting to improve your context. Indeed, the human (or automation) creating the initial context might not know enough to do a good job of providing relevant context. For example, if you prompt, Who is going to become the next mayor of New York City?, then you are unsuited to include the answer to that question in your prompt. To do that, you would need to already know the answer, which is why you’re asking the question to begin with! This is where we see model chat experiences from OpenAI and Anthropic use web search to pull in context that you likely don’t have. If you ask a question about the new mayor of New York, they use a tool to retrieve web search results, then add the content of those searches to your context window. This is the second important thing that agents can do: use an LLM to suggest tools relevant to the context window, then enrich the context window with the tool’s response. However, it’s important to clarify how “tool usage” actually works. An LLM does not actually call a tool. (You can skim OpenAI’s function calling documentation if you want to see a specific real-world example of this.) Instead there is a five-step process to calling tools that can be a bit counter-intuitive: The program designer that calls the LLM API must also define a set of tools that the LLM is allowed to suggest using. Every API call to the LLM includes that defined set of tools as options that the LLM is allowed to recommend The response from the API call with defined functions is either: Generated text as any other call to an LLM might provide A recommendation to call a specific tool with a specific set of parameters, e.g. an LLM that knows about a get_weather tool, when prompted about the weather in Paris, might return this response: [{ "type": "function_call", "name": "get_weather", "arguments": "{\"location\":\"Paris, France\"}" }] The program that calls the LLM API then decides whether and how to honor that requested tool use. The program might decide to reject the requested tool because it’s been used too frequently recently (e.g. rate limiting), it might check if the associated user has permission to use the tool (e.g. maybe it’s a premium only tool), it might check if the parameters match the user’s role-based permissions as well (e.g. the user can check weather, but only admin users are allowed to check weather in France). If the program does decide to call the tool, it invokes the tool, then calls the LLM API with the output of the tool appended to the prior call’s context window. The important thing about this loop is that the LLM itself can still only do one interesting thing: taking a context window and returning generated text. It is the broader program, which we can start to call an agent at this point, that calls tools and sends the tools’ output to the LLM to generate more context. What’s magical is that LLMs plus tools start to really improve how you can generate context windows. Instead of having to have a very well-defined initial context window, you can use tools to inject relevant context to improve the initial context. This brings us to the third important thing that agents can do: they manage flow control for tool usage. Let’s think about three different scenarios: Flow control via rules has concrete rules about how tools can be used. Some examples: it might only allow a given tool to be used once in a given workflow (or a usage limit of a tool for each user, etc) it might require that a human-in-the-loop approves parameters over a certain value (e.g. refunds more than $100 require human approval) it might run a generated Python program and return the output to analyze a dataset (or provide error messages if it fails) apply a permission system to tool use, restricting who can use which tools and which parameters a given user is able to use (e.g. you can only retrieve your own personal data) a tool to escalate to a human representative can only be called after five back and forths with the LLM agent Flow control via statistics can use statistics to identify and act on abnormal behavior: if the size of a refund is higher than 99% of other refunds for the order size, you might want to escalate to a human if a user has used a tool more than 99% of other users, then you might want to reject usage for the rest of the day it might escalate to a human representative if tool parameters are more similar to prior parameters that required escalation to a human agent LLMs themselves absolutely cannot be trusted. Anytime you rely on an LLM to enforce something important, you will fail. Using agents to manage flow control is the mechanism that makes it possible to build safe, reliable systems with LLMs. Whenever you find yourself dealing with an unreliable LLM-based system, you can always find a way to shift the complexity to a tool to avoid that issue. As an example, if you want to do algebra with an LLM, the solution is not asking the LLM to directly perform algebra, but instead providing a tool capable of algebra to the LLM, and then relying on the LLM to call that tool with the proper parameters. At this point, there is one final important thing that agents do: they are software programs. This means they can do anything software can do to build better context windows to pass on to LLMs for generation. This is an infinite category of tasks, but generally these include: Building general context to add to context window, sometimes thought of as maintaining memory Initiating a workflow based on an incoming ticket in a ticket tracker, customer support system, etc Periodically initiating workflows at a certain time, such as hourly review of incoming tickets Alright, we’ve now summarized what AI agents can do down to four general capabilities. Recapping a bit, those capabilities are: Use an LLM to evaluate a context window and get a result Use an LLM to suggest tools relevant to the context window, then enrich the context window with the tool’s response Manage flow control for tool usage via rules or statistical analysis Agents are software programs, and can do anything other software programs do Armed with these four capabilities, we’ll be able to think about the ways we can, and cannot, apply AI agents to a number of opportunities. Use Case 1: Customer Support Agent One of the first scenarios that people often talk about deploying AI agents is customer support, so let’s start there. A typical customer support process will have multiple tiers of agents who handle increasingly complex customer problems. So let’s set a goal of taking over the easiest tier first, with the goal of moving up tiers over time as we show impact. Our approach might be: Allow tickets (or support chats) to flow into an AI agent Provide a variety of tools to the agent to support: Retrieving information about the user: recent customer support tickets, account history, account state, and so on Escalating to next tier of customer support Refund a purchase (almost certainly implemented as “refund purchase” referencing a specific purchase by the user, rather than “refund amount” to prevent scenarios where the agent can be fooled into refunding too much) Closing the user account on request Include customer support guidelines in the context window, describe customer problems, map those problems to specific tools that should be used to solve the problems Flow control rules that ensure all calls escalate to a human if not resolved within a certain time period, number of back-and-forth exchanges, if they run into an error in the agent, and so on. These rules should be both rules-based and statistics-based, ensuring that gaps in your rules are neither exploitable nor create a terrible customer experience Review agent-customer interactions for quality control, making improvements to the support guidelines provided to AI agents. Initially you would want to review every interaction, then move to interactions that lead to unusual outcomes (e.g. escalations to human) and some degree of random sampling Review hourly, then daily, and then weekly metrics of agent performance Based on your learnings from the metric reviews, you should set baselines for alerts which require more immediate response. For example, if a new topic comes up frequently, it probably means a serious regression in your product or process, and it requires immediate review rather than periodical review. Note that even when you’ve moved “Customer Support to AI agents”, you still have: a tier of human agents dealing with the most complex calls humans reviewing the periodic performance statistics humans performing quality control on AI agent-customer interactions You absolutely can replace each of those downstream steps (reviewing performance statistics, etc) with its own AI agent, but doing that requires going through the development of an AI product for each of those flows. There is a recursive process here, where over time you can eliminate many human components of your business, in exchange for increased fragility as you have more tiers of complexity. The most interesting part of complex systems isn’t how they work, it’s how they fail, and agent-driven systems will fail occasionally, as all systems do, very much including human-driven ones. Applied with care, the above series of actions will work successfully. However, it’s important to recognize that this is building an entire software pipeline, and then learning to operate that software pipeline in production. These are both very doable things, but they are meaningful work, turning customer support leadership into product managers and requiring an engineering team building and operating the customer support agent. Use Case 2: Triaging incoming bug reports When an incident is raised within your company, or when you receive a bug report, the first problem of the day is determining how severe the issue might be. If it’s potentially quite severe, then you want on-call engineers immediately investigating; if it’s certainly not severe, then you want to triage it in a less urgent process of some sort. It’s interesting to think about how an AI agent might support this triaging workflow. The process might work as follows: Pipe all created incidents and all created tickets to this agent for review. Expose these tools to the agent: Open an incident Retrieve current incidents Retrieve recently created tickets Retrieve production metrics Retrieve deployment logs Retrieve feature flag change logs Toggle known-safe feature flags Propose merging an incident with another for human approval Propose merging a ticket with another ticket for human approval Redundant LLM providers for critical workflows. If the LLM provider’s API is unavailable, retry three times over ten seconds, then resort to using a second model provider (e.g. Anthropic first, if unavailable try OpenAI), and then finally create an incident that the triaging mechanism is unavailable. For critical workflows, we can’t simply assume the APIs will be available, because in practice all major providers seem to have monthly availability issues. Merge duplicates. When a ticket comes in, first check ongoing incidents and recently created tickets for potential duplicates. If there is a probable duplicate, suggest merging the ticket or incident with the existing issue and exit the workflow. Assess impact. If production statistics are severely impacted, or if there is a new kind of error in production, then this is likely an issue that merits quick human review. If it’s high priority, open an incident. If it’s low priority, create a ticket. Propose cause. Now that the incident has been sized, switch to analyzing the potential causes of the incident. Look at the code commits in recent deploys and suggest potential issues that might have caused the current error. In some cases this will be obvious (e.g. spiking errors with a traceback of a line of code that changed recently), and in other cases it will only be proximity in time. Apply known-safe feature flags. Establish an allow list of known safe feature flags that the system is allowed to activate itself. For example, if there are expensive features that are safe to disable, it could be allowed to disable them, e.g. restricting paginating through deeper search results when under load might be a reasonable tradeoff between stability and user experience. Defer to humans. At this point, rely on humans to drive incident, or ticket, remediation to completion. Draft initial incident report. If an incident was opened, the agent should draft an initial incident report including the timeline, related changes, and the human activities taken over the course of the incident. This report should then be finalized by the human involved in the incident. Run incident review. Your existing incident review process should take the incident review and determine how to modify your systems, including the triaging agent, to increase reliability over time. Safeguard to reenable feature flags. Since we now have an agent disabling feature flags, we also need to add a periodic check (agent-driven or otherwise) to reenable the “known safe” feature flags if there isn’t an ongoing incident to avoid accidentally disabling them for long periods of time. This is another AI agent that will absolutely work as long as you treat it as a software product. In this case, engineering is likely the product owner, but it will still require thoughtful iteration to improve its behavior over time. Some of the ongoing validation to make this flow work includes: The role of humans in incident response and review will remain significant, merely aided by this agent. This is especially true in the review process, where an agent cannot solve the review process because it’s about actively learning what to change based on the incident. You can make a reasonable argument that an agent could decide what to change and then hand that specification off to another agent to implement it. Even today, you can easily imagine low risk changes (e.g. a copy change) being automatically added to a ticket for human approval. Doing this for more complex, or riskier changes, is possible but requires an extraordinary degree of care and nuance: it is the polar opposite of the idea of “just add agents and things get easy.” Instead, enabling that sort of automation will require immense care in constraining changes to systems that cannot expose unsafe behavior. For example, one startup I know has represented their domain logic in a domain-specific language (DSL) that can be safely generated by an LLM, and are able to represent many customer-specific features solely through that DSL. Expanding the list of known-safe feature flags to make incidents remediable. To do this widely will require enforcing very specific requirements for how software is developed. Even doing this narrowly will require changes to ensure the known-safe feature flags remain safe as software is developed. Periodically reviewing incident statistics over time to ensure mean-time-to-resolution (MTTR) is decreasing. If the agent is truly working, this should decrease. If the agent isn’t driving a reduction in MTTR, then something is rotten in the details of the implementation. Even a very effective agent doesn’t relieve the responsibility of careful system design. Rather, agents are a multiplier on the quality of your system design: done well, agents can make you significantly more effective. Done poorly, they’ll only amplify your problems even more widely. Do AI Agents Represent Entirety of this Generation of AI? If you accept my definition that AI agents are any combination of LLMs and software, then I think it’s true that there’s not much this generation of AI can express that doesn’t fit this definition. I’d readily accept the argument that LLM is too narrow a term, and that perhaps foundational model would be a better term. My sense is that this is a place where frontier definitions and colloquial usage have deviated a bit. Closing thoughts LLMs and agents are powerful mechanisms. I think they will truly change how products are designed and how products work. An entire generation of software makers, and company executives, are in the midst of learning how these tools work. Software isn’t magic, it’s very logical, but what it can accomplish is magical. The same goes for agents and LLMs. The more we can accelerate that learning curve, the better for our industry.
More in programming
What does it mean when someone writes that a programming language is “strongly typed”? I’ve known for many years that “strongly typed” is a poorly-defined term. Recently I was prompted on Lobsters to explain why it’s hard to understand what someone means when they use the phrase. I came up with more than five meanings! how strong? The various meanings of “strongly typed” are not clearly yes-or-no. Some developers like to argue that these kinds of integrity checks must be completely perfect or else they are entirely worthless. Charitably (it took me a while to think of a polite way to phrase this), that betrays a lack of engineering maturity. Software engineers, like any engineers, have to create working systems from imperfect materials. To do so, we must understand what guarantees we can rely on, where our mistakes can be caught early, where we need to establish processes to catch mistakes, how we can control the consequences of our mistakes, and how to remediate when somethng breaks because of a mistake that wasn’t caught. strong how? So, what are the ways that a programming language can be strongly or weakly typed? In what ways are real programming languages “mid”? Statically typed as opposed to dynamically typed? Many languages have a mixture of the two, such as run time polymorphism in OO languages (e.g. Java), or gradual type systems for dynamic languages (e.g. TypeScript). Sound static type system? It’s common for static type systems to be deliberately unsound, such as covariant subtyping in arrays or functions (Java, again). Gradual type systems migh have gaping holes for usability reasons (TypeScript, again). And some type systems might be unsound due to bugs. (There are a few of these in Rust.) Unsoundness isn’t a disaster, if a programmer won’t cause it without being aware of the risk. For example: in Lean you can write “sorry” as a kind of “to do” annotation that deliberately breaks soundness; and Idris 2 has type-in-type so it accepts Girard’s paradox. Type safe at run time? Most languages have facilities for deliberately bypassing type safety, with an “unsafe” library module or “unsafe” language features, or things that are harder to spot. It can be more or less difficult to break type safety in ways that the programmer or language designer did not intend. JavaScript and Lua are very safe, treating type safety failures as security vulnerabilities. Java and Rust have controlled unsafety. In C everything is unsafe. Fewer weird implicit coercions? There isn’t a total order here: for instance, C has implicit bool/int coercions, Rust does not; Rust has implicit deref, C does not. There’s a huge range in how much coercions are a convenience or a source of bugs. For example, the PHP and JavaScript == operators are made entirely of WAT, but at least you can use === instead. How fancy is the type system? To what degree can you model properties of your program as types? Is it convenient to parse, not validate? Is the Curry-Howard correspondance something you can put into practice? Or is it only capable of describing the physical layout of data? There are probably other meanings, e.g. I have seen “strongly typed” used to mean that runtime representations are abstract (you can’t see the underlying bytes); or in the past it sometimes meant a language with a heavy type annotation burden (as a mischaracterization of static type checking). how to type So, when you write (with your keyboard) the phrase “strongly typed”, delete it, and come up with a more precise description of what you really mean. The desiderata above are partly overlapping, sometimes partly orthogonal. Some of them you might care about, some of them not. But please try to communicate where you draw the line and how fuzzy your line is.
(Last week's newsletter took too long and I'm way behind on Logic for Programmers revisions so short one this time.1) In classical logic, two operators F/G are duals if F(x) = !G(!x). Three examples: x || y is the same as !(!x && !y). <>P ("P is possibly true") is the same as ![]!P ("not P isn't definitely true"). some x in set: P(x) is the same as !(all x in set: !P(x)). (1) is just a version of De Morgan's Law, which we regularly use to simplify boolean expressions. (2) is important in modal logic but has niche applications in software engineering, mostly in how it powers various formal methods.2 The real interesting one is (3), the "quantifier duals". We use lots of software tools to either find a value satisfying P or check that all values satisfy P. And by duality, any tool that does one can do the other, by seeing if it fails to find/check !P. Some examples in the wild: Z3 is used to solve mathematical constraints, like "find x, where f(x) >= 0. If I want to prove a property like "f is always positive", I ask z3 to solve "find x, where !(f(x) >= 0), and see if that is unsatisfiable. This use case powers a LOT of theorem provers and formal verification tooling. Property testing checks that all inputs to a code block satisfy a property. I've used it to generate complex inputs with certain properties by checking that all inputs don't satisfy the property and reading out the test failure. Model checkers check that all behaviors of a specification satisfy a property, so we can find a behavior that reaches a goal state G by checking that all states are !G. Here's TLA+ solving a puzzle this way.3 Planners find behaviors that reach a goal state, so we can check if all behaviors satisfy a property P by asking it to reach goal state !P. The problem "find the shortest traveling salesman route" can be broken into some route: distance(route) = n and all route: !(distance(route) < n). Then a route finder can find the first, and then convert the second into a some and fail to find it, proving n is optimal. Even cooler to me is when a tool does both finding and checking, but gives them different "meanings". In SQL, some x: P(x) is true if we can query for P(x) and get a nonempty response, while all x: P(x) is true if all records satisfy the P(x) constraint. Most SQL databases allow for complex queries but not complex constraints! You got UNIQUE, NOT NULL, REFERENCES, which are fixed predicates, and CHECK, which is one-record only.4 Oh, and you got database triggers, which can run arbitrary queries and throw exceptions. So if you really need to enforce a complex constraint P(x, y, z), you put in a database trigger that queries some x, y, z: !P(x, y, z) and throws an exception if it finds any results. That all works because of quantifier duality! See here for an example of this in practice. Duals more broadly "Dual" doesn't have a strict meaning in math, it's more of a vibe thing where all of the "duals" are kinda similar in meaning but don't strictly follow all of the same rules. Usually things X and Y are duals if there is some transform F where X = F(Y) and Y = F(X), but not always. Maybe the category theorists have a formal definition that covers all of the different uses. Usually duals switch properties of things, too: an example showing some x: P(x) becomes a counterexample of all x: !P(x). Under this definition, I think the dual of a list l could be reverse(l). The first element of l becomes the last element of reverse(l), the last becomes the first, etc. A more interesting case is the dual of a K -> set(V) map is the V -> set(K) map. IE the dual of lived_in_city = {alice: {paris}, bob: {detroit}, charlie: {detroit, paris}} is city_lived_in_by = {paris: {alice, charlie}, detroit: {bob, charlie}}. This preserves the property that x in map[y] <=> y in dual[x]. And after writing this I just realized this is partial retread of a newsletter I wrote a couple months ago. But only a partial retread! ↩ Specifically "linear temporal logics" are modal logics, so "eventually P ("P is true in at least one state of each behavior") is the same as saying !always !P ("not P isn't true in all states of all behaviors"). This is the basis of liveness checking. ↩ I don't know for sure, but my best guess is that Antithesis does something similar when their fuzzer beats videogames. They're doing fuzzing, not model checking, but they have the same purpose check that complex state spaces don't have bugs. Making the bug "we can't reach the end screen" can make a fuzzer output a complete end-to-end run of the game. Obvs a lot more complicated than that but that's the general idea at least. ↩ For CHECK to constraint multiple records you would need to use a subquery. Core SQL does not support subqueries in check. It is an optional database "feature outside of core SQL" (F671), which Postgres does not support. ↩
Omarchy 2.0 was released on Linux's 34th birthday as a gift to perhaps the greatest open-source project the world has ever known. Not only does Linux run 95% of all servers on the web, billions of devices as an embedded OS, but it also turns out to be an incredible desktop environment! It's crazy that it took me more than thirty years to realize this, but while I spent time in Apple's walled garden, the free software alternative simply grew better, stronger, and faster. The Linux of 2025 is not the Linux of the 90s or the 00s or even the 10s. It's shockingly more polished, capable, and beautiful. It's been an absolute honor to celebrate Linux with the making of Omarchy, the new Linux distribution that I've spent the last few months building on top of Arch and Hyprland. What began as a post-install script has turned into a full-blown ISO, dedicated package repository, and flourishing community of thousands of enthusiasts all collaborating on making it better. It's been improving rapidly with over twenty releases since the premiere in late June, but this Version 2.0 update is the biggest one yet. If you've been curious about giving Linux a try, you're not afraid of an operating system that asks you to level up and learn a little, and you want to see what a totally different computing experience can look and feel like, I invite you to give it a go. Here's a full tour of Omarchy 2.0.
In 2020, Apple released the M1 with a custom GPU. We got to work reverse-engineering the hardware and porting Linux. Today, you can run Linux on a range of M1 and M2 Macs, with almost all hardware working: wireless, audio, and full graphics acceleration. Our story begins in December 2020, when Hector Martin kicked off Asahi Linux. I was working for Collabora working on Panfrost, the open source Mesa3D driver for Arm Mali GPUs. Hector put out a public call for guidance from upstream open source maintainers, and I bit. I just intended to give some quick pointers. Instead, I bought myself a Christmas present and got to work. In between my university coursework and Collabora work, I poked at the shader instruction set. One thing led to another. Within a few weeks, I drew a triangle. In 3D graphics, once you can draw a triangle, you can do anything. Pretty soon, I started work on a shader compiler. After my final exams that semester, I took a few days off from Collabora to bring up an OpenGL driver capable of spinning gears with my new compiler. Over the next year, I kept reverse-engineering and improving the driver until it could run 3D games on macOS. Meanwhile, Asahi Lina wrote a kernel driver for the Apple GPU. My userspace OpenGL driver ran on macOS, leaving her kernel driver as the missing piece for an open source graphics stack. In December 2022, we shipped graphics acceleration in Asahi Linux. In January 2023, I started my final semester in my Computer Science program at the University of Toronto. For years I juggled my courses with my part-time job and my hobby driver. I faced the same question as my peers: what will I do after graduation? Maybe Panfrost? I started reverse-engineering of the Mali Midgard GPU back in 2017, when I was still in high school. That led to an internship at Collabora in 2019 once I graduated, turning into my job throughout four years of university. During that time, Panfrost grew from a kid’s pet project based on blackbox reverse-engineering, to a professional driver engineered by a team with Arm’s backing and hardware documentation. I did what I set out to do, and the project succeeded beyond my dreams. It was time to move on. What did I want to do next? Finish what I started with the M1. Ship a great driver. Bring full, conformant OpenGL drivers to the M1. Apple’s drivers are not conformant, but we should strive for the industry standard. Bring full, conformant Vulkan to Apple platforms, disproving the myth that Vulkan isn’t suitable for Apple hardware. Bring Proton gaming to Asahi Linux. Thanks to Valve’s work for the Steam Deck, Windows games can run better on Linux than even on Windows. Why not reap those benefits on the M1? Panfrost was my challenge until we “won”. My next challenge? Gaming on Linux on M1. Once I finished my coursework, I started full-time on gaming on Linux. Within a month, we shipped OpenGL 3.1 on Asahi Linux. A few weeks later, we passed official conformance for OpenGL ES 3.1. That put us at feature parity with Panfrost. I wanted to go further. OpenGL (ES) 3.2 requires geometry shaders, a legacy feature not supported by either Arm or Apple hardware. The proprietary OpenGL drivers emulate geometry shaders with compute, but there was no open source prior art to borrow. Even though multiple Mesa drivers need geometry/tessellation emulation, nobody did the work to get there. My early progress on OpenGL was fast thanks to the mature common code in Mesa. It was time to pay it forward. Over the rest of the year, I implemented geometry/tessellation shader emulation. And also the rest of the owl. In January 2024, I passed conformance for the full OpenGL 4.6 specification, finishing up OpenGL. Vulkan wasn’t too bad, either. I polished the OpenGL driver for a few months, but once I started typing a Vulkan driver, I passed 1.3 conformance in a few weeks. What remained was wiring up the geometry/tessellation emulation to my shiny new Vulkan driver, since those are required for Direct3D. Et voilà, Proton games. Along the way, Karol Herbst passed OpenCL 3.0 conformance on the M1, running my compiler atop his “rusticl” frontend. Meanwhile, when the Vulkan 1.4 specification was published, we were ready and shipped a conformant implementation on the same day. After that, I implemented sparse texture support, unlocking Direct3D 12 via Proton. …Now what? Ship a great driver? Check. Conformant OpenGL 4.6, OpenGL ES 3.2, and OpenCL 3.0? Check. Conformant Vulkan 1.4? Check. Proton gaming? Check. That’s a wrap. We’ve succeeded beyond my dreams. The challenges I chased, I have tackled. The drivers are fully upstream in Mesa. Performance isn’t too bad. With the Vulkan on Apple myth busted, conformant Vulkan is now coming to macOS via LunarG’s KosmicKrisp project building on my work. Satisfied, I am now stepping away from the Apple ecosystem. My friends in the Asahi Linux orbit will carry the torch from here. As for me? Onto the next challenge!
TokyoDev has published a number of different guides on coming to Japan to work as a software developer. But what if you’re already employed in another industry in Japan, and are considering changing your career to software development? I interviewed four people who became developers after they moved to Japan, for their advice and personal experiences on: Why they chose development How they switched careers How they successfully found their first jobs What mistakes they made in the job hunt The most important advice they give to others Why switch to software development? A lifelong goal For Yuta Asakura, a career in software was the dream all along. “I’ve always wanted to work with computers,” he said, “but due to financial difficulties, I couldn’t pursue a degree in computer science. I had to start working early to support my single mother. As the eldest child, I focused on helping my younger brother complete his education.” To support his family, Asakura worked in construction for eight years, eventually becoming a foreman in Yokohama. Meanwhile, his brother graduated, and became a software engineer after joining the Le Wagon Tokyo bootcamp. About a year before his brother graduated, Asakura began to delve back into development. “I had already begun self-studying in my free time by taking online courses and building small projects,” he explained. “ I quickly became hooked by how fun and empowering it was to learn, apply, and build. It wasn’t always easy. There were moments I wanted to give up, but the more I learned, the more interesting things I could create. That feeling kept me going.” What truly inspired me was the idea of creating something from nothing. Coming from a construction background, I was used to building things physically. But I wanted to create things that were digital, scalable, borderless, and meaningful to others. An unexpected passion As Andrew Wilson put it, “Wee little Andrew had a very digital childhood,” full of games and computer time. Rather than pursuing tech, however, he majored in Japanese and moved to Japan in 2012, where he initially worked as a language teacher and recruiter before settling into sales. Wilson soon discovered that sales wasn’t really his strong suit. “At the time I was selling three different enterprise software solutions.” So I had to have a fairly deep understanding of that software from a user perspective, and in the course of learning about these products and giving technical demonstrations, I realized that I liked doing that bit of my job way more than I liked actually trying to sell these things. Around that time, he also realized he didn’t want to manually digitize the many business cards he always collected during sales meetings: “That’s boring, and I’m lazy.” So instead, he found a business card-scanning app, made a spreadsheet to contain the data, automated the whole process, and shared it internally within his company. His manager approached him soon afterwards, saying, “You built this? We were looking to hire someone to do this!” Encouraged, Wilson continued to develop it. “As soon as I was done with work,” he explained with a laugh, “I was like, ‘Oh boy, I can work on my spreadsheet!’” As a result, Wilson came to the conclusion that he really should switch careers and pursue his passion for programming. Similarly to Wilson, Malcolm Hendricks initially focused on Japanese. He came to Japan as an exchange student in 2002, and traveled to Japan several more times before finally relocating in 2011. Though his original role was as a language teacher, he soon found a job at a Japanese publishing company, where he worked as an editor and writer for seven years. However, he felt burned out on the work, and also that he was in danger of stagnating; since he isn’t Japanese, the road to promotion was a difficult one. He started following some YouTube tutorials on web development, and eventually began creating websites for his friends. Along the way, he fell in love with development, on both a practical and a philosophical level. “There’s another saying I’ve heard here and there—I don’t know exactly who to attribute it to—but the essence of it goes that ‘Computer science is just teaching rocks how to think,’” Hendricks said. “My mentor Bob has been guiding me through the very fundamentals of computer science, down to binary calculations, Boolean logic, gate theory, and von Neumann architecture. He explains the fine minutia and often concludes with, ‘That’s how it works. There’s no magic to it.’ “Meanwhile, in the back of my mind, I can’t help but be mystified at the things we are all now able to do, such as having video calls from completely different parts of the world, or even me here typing on squares of plastic to make letters appear on a screen that has its own source of light inside it. . . . [It] sounds like the highest of high-fantasy wizardry to me.” I’ve always had a love for technomancy, but I never figured I might one day get the chance to be a technomancer myself. And I love it! We have the ability to create nigh unto anything in the digital world. A practical solution When Paulo D’Alberti moved to Japan in 2019, he only spoke a little Japanese, which limited his employment prospects. With his prior business experience, he landed an online marketing role for a blockchain startup, but eventually exited the company to pursue a more stable work environment. “But when I decided to leave the company,” D’Alberti said, “my Japanese was still not good enough to do business. So I was at a crossroads.” Do I decide to join a full-time Japanese language course, aiming to get JLPT N2 or the equivalent, and find a job on the business side? . . . Or do I say screw it and go for a complete career change and get skills in something more technical, that would allow me to carry those skills [with me] even if I were to move again to another country?” The portability of a career in development was a major plus for D’Alberti. “That was one of the big reasons. Another consideration was that, looking at the boot camps that were available, the promise was ‘Yeah, we’ll teach you to be a software developer in nine weeks or two months.’ That was a much shorter lead time than getting from JLPT N4 to N2. I definitely wouldn’t be able to do that in two months.” Since D’Alberti had family obligations, the timeline for his career switch was crucial. “We still had family costs and rent and groceries and all of that. I needed to find a job as soon as possible. I actually already at that point had been unsuccessfully job hunting for two months. So that was like, ‘Okay, the savings are winding up, and we are running out of options. I need to make a decision and make it fast.’” How to switch careers Method 1: Software Development Bootcamp Under pressure to find new employment quickly, D’Alberti decided to enter the Le Wagon Coding Bootcamp in Tokyo. Originally, he wavered between Le Wagon and Code Chrysalis, which has since ended its bootcamp programs. “I went with Le Wagon for two reasons,” he explained. “There were some scheduling reasons. . . . But the main reason was that Code Chrysalis required you to pass a coding exam before being admitted to their bootcamp.” Since D’Alberti was struggling to learn development by himself, he knew his chances of passing any coding exam were slim. “I tried Code Academy, I tried Solo Learn, I tried a whole bunch of apps online, I would follow the examples, the exercises . . . nothing clicked. I wouldn’t understand what I was doing or why I was doing it.” At the time, Le Wagon only offered full-time web development courses, although they now also have part-time courses and a data science curriculum. Since D’Alberti was unemployed, a full-time program wasn’t a problem for him, “But it did mean that the people who were present were very particular [kinds] of people: students who could take some time off to add this to their [coursework], or foreigners who took three months off and were traveling and decide to come here and do studying plus sightseeing, and I think there were one or two who actually asked for time off from the job in order to participate.” It was a very intense course, and the experience itself gave me exactly what I needed. I had been trying to learn by myself. It did not work. I did not understand. [After joining], the first day or second day, suddenly everything clicked. D’Alberti appreciated how Le Wagon organized the curriculum to build continuously off previous lessons. By the time he graduated in June of 2019, he’d built three applications from scratch, and felt far more confident in his coding abilities. “It was great. [The curriculum] was amazing, and I really felt super confident in my abilities after the three months. Which, looking back,” he joked, “I still had a lot to learn.” D’Alberti did have some specific advice for those considering a bootcamp: “Especially in the last couple of weeks, it can get very dramatic. You are divided into teams and as a team, you’re supposed to develop an application that you will be demonstrating in front of other people.” Some of the students, D’Alberti explained, felt that pressure intensely; one of his classmates broke down in tears. “Of course,” he added, “one of the big difficulties of joining a bootcamp is economical. The bootcamp itself is quite expensive.” While between 700,000 and 800,000 yen when D’Alberti went through the bootcamp, Le Wagon’s tuition has now risen to 890,000 yen for Web Development and 950,000 for Data Science. At the time D’Alberti joined there was no financial assistance. Now, Le Wagon has an agreement with Hello Work, so that students who are enrolled in the Hello Work system can be reimbursed for up to 70 percent of the bootcamp’s tuition. Though already studying development by himself, Asakura also enrolled in Le Wagon Tokyo in 2024, “to gain structure and accountability,” he said. One lesson that really stayed with me came from Sylvain Pierre, our bootcamp director. He said, ‘You stop being a developer the moment you stop learning or coding.’ That mindset helped me stay on track. Method 2: Online computer science degree Wilson considered going the bootcamp route, but decided against it. He knew, from his experience in recruiting, that a degree would give him an edge—especially in Japan, where having the right degree can make a difference in visa eligibility “The quality of bootcamps is perfectly fine,” he explained. “If you go through a bootcamp and study hard, you can get a job and become a developer no problem. I wanted to differentiate myself on paper as much as I could . . . [because] there are a lot of smart, motivated people who go through a bootcamp.” Whether it’s true or not, whether it’s valid or not, if you take two candidates who are very similar on paper, and one has a coding bootcamp and one has a degree, from a typical Japanese HR perspective, they’re going to lean toward the person with the degree. “Whether that’s good or not, that’s sort of a separate situation,” Wilson added. “But the reality [is] I’m older and I’m trying to make a career change, so I want to make sure that I’m giving myself every advantage that I can.” For these reasons, Wilson opted to get his computer science degree online. “There’s a program out of the University of Oregon, for people who already had a Bachelor’s degree in a different subject to get a Bachelor’s degree in Computer Science. “Because it’s limited to people who already have a Bachelor’s degree, that means you don’t need to take any non-computer science classes. You don’t need any electives or prerequisites or anything like that.” As it happened, Wilson was on paternity leave when he started studying for his degree. “That was one of my motivations to finish quickly!” he said. In the end, with his employer’s cooperation, he extended his paternity leave to two years, and finished the degree in five quarters. Method 3: Self-taught Hendricks took a different route, combining online learning materials with direct experience. He primarily used YouTube tutorials, like this project from one of his favorite channels, to teach himself. Once he had the basics down, he started creating websites for friends, as well as for the publishing company he worked for at the time. With every site, he’d put his name at the bottom of the page, as a form of marketing. This worked well enough that Hendricks was able to quit his work at the translation company and transition to full-time freelancing. However, eventually the freelancing work dried up, and he decided he wanted to experience working at a tech company—and not just for job security reasons. Hendricks saw finding a full-time development role as the perfect opportunity to push himself and see just how far he could get in his new career. There’s a common trope, probably belonging more to the sports world at large, about the importance of shedding ‘blood, sweat, and tears’ in the pursuit of one’s passion . . . and that’s also how I wanted to cut my teeth in the software engineering world. The job hunt While all four are now successfully employed as developers, Asakura, D’Alberti, Wilson, and Hendricks approached and experienced the job hunt differently. Following is their hard-earned advice on best practices and common mistakes. DO network When Hendricks started his job hunt, he faced the disadvantages of not having any formal experience, and also being both physically and socially isolated from other developers. Since he and his family were living in Nagano, he wasn’t able to participate in most of the tech events and meet-ups available in Tokyo or other big cities. His initial job hunt took around a year, and at one point he was sending so many applications that he received a hundred rejections in a week. It wasn’t until he started connecting with the community that he was able to turn it around, eventually getting three good job offers in a single week. Networking, for me, is what made all the difference. It was through networking that I found my mentors, found community, and joined and even started a few great Discord servers. These all undeniably contributed to me ultimately landing my current job, but they also made me feel welcome in the industry. Hendricks particularly credits his mentors, Ean More and Bob Cousins, for giving him great advice. “My initial mentor [Ean More] I actually met through a mutual IT networking Facebook group. I noticed that he was one of the more active members, and that he was always ready to lend a hand to help others with their questions and spread a deeper understanding of programming and computer science. He also often posted snippets of his own code to share with the community and receive feedback, and I was interested in a lot of what he was posting. “I reached out to him and told him I thought it was amazing how selfless he was in the group, and that, while I’m still a junior, if there was ever any grunt work I could do under his guidance, I would be happy to do so. Since he had a history of mentoring others, he offered to do so for me, and we’ve been mentor/mentee and friends ever since.” “My other mentor [Bob Cousins],” Hendricks continued, “was a friend of my late uncle’s. My uncle had originally begun mentoring me shortly before his passing. We were connected through a mutual friend whom I lamented to about not having any clue how to continue following the path my uncle had originally laid before me. He mentioned that he knew just the right person and gave me an email address to contact. I sent an email to the address and was greeted warmly by the man who would become another mentor, and like an uncle to me.” Although Hendricks found him via a personal connection, Cousins runs a mentorship program that caters to a wide variety of industries. Wilson also believes in the power of networking—and not just for the job hunt. “One of the things I like about programming,” he said, “is that it’s a very collaborative community. Everybody wants to help everybody.” We remember that everyone had to start somewhere, and we’ll take time to help those starting out. It’s a very welcoming community. Just do it! We’re all here for you, and if you need help I’ll refer you. Asakura, by contrast, thinks that networking can help, but that it works a little differently in Japan than in other countries. “Don’t rely on it too much,” he said. “Unlike in Western countries, personal referrals don’t always lead directly to job opportunities in Japan. Your skills, effort, and consistency will matter more in the long run.” DO treat the job hunt like a job Once he’d graduated from Le Wagon, D’Alberti said, “I considered job-hunting my full-time job.” I checked all the possible networking events and meetup events that were going on in the city, and tried to attend all of them, every single day. I had a list of 10 different job boards that I would go and just refresh on a daily basis to see, ‘Okay, Is there anything new now?’ And, of course, I talked with recruiters. D’Alberti suggests beginning the search earlier than you think you need to. “I had started actively job hunting even before graduating [from Le Wagon],” he said. “That’s advice I give to everyone who joins the bootcamp. “Two weeks before graduation, you have one simple web application that you can show. You have a second one you’re working on in a team, and you have a third one that you know what it’s going to be about. So, already, there are three applications that you can showcase or you can use to explain your skills. I started going to meetups and to different events, talking with people, showing my CV.” The process wasn’t easy, as most companies and recruiters weren’t interested in hiring for junior roles. But his intensive strategy paid off within a month, as D’Albert landed three invitations to interview: one from a Japanese job board, one from a recruiter, and one from LinkedIn. For Asakura, treating job hunting like a job was as much for his mental health as for his career. “The biggest challenge was dealing with impostor syndrome and feeling like I didn’t belong because I didn’t have a computer science degree,” he explained. “I also experienced burnout from pushing myself too hard.” To cope, I stuck to a structured routine. I went to the gym daily to decompress, kept a consistent study schedule as if I were working full-time, and continued applying for jobs even when it felt hopeless. At first, Asakura tried to apply to jobs strategically by tracking each application, tailoring his resume, and researching every role. “But after dozens of rejections,” he said, “I eventually switched to applying more broadly and sent out over one hundred applications. I also reached out to friends who were already software engineers and asked for direct referrals, but unfortunately, nothing worked out.” Still, Asakura didn’t give up. He practiced interviews in both English and Japanese with his friends, and stayed in touch with recruiters. Most importantly, he kept developing and adding to his portfolio. DO make use of online resources “What ultimately helped me was staying active and visible,” Asakura said. I consistently updated my GitHub, LInkedIn, and Wantedly profiles. Eventually, I received a message on Wantedly from the CTO of a company who was impressed with my portfolio, and that led to my first developer job.” “If you have the time, certifications can also help validate your knowledge,” Asakura added, “especially in fields like cloud and AI. Some people may not realize this, but the rise of artificial intelligence is closely tied to the growth of cloud computing. Earning certifications such as AWS, Kubernetes, and others can give you a strong foundation and open new opportunities, especially as these technologies continue to evolve.” Hendricks also heavily utilized LinkedIn and similar sites, though in a slightly different way. “I would also emphasize the importance of knowing how to use job-hunting sites like Indeed and LinkedIn,” he said. “I had the best luck when I used them primarily to do initial research into companies, then applied directly through the companies’ own websites, rather than through job postings that filter applicants before their resumés ever make it to the actual people looking to hire.” In addition, Hendricks recommends studying coding interview prep tutorials from freeCodeCamp. Along with advice from his mentors and the online communities he joined, he credits those tutorials with helping him successfully receive offers after a long job hunt. DO highlight experience with Japanese culture and language Asakura felt that his experience in Japan, and knowledge of Japanese, gave him an edge. “I understand Japanese work culture [and] can speak the language,” Asakura said, “and as a Japanese national I didn’t require visa sponsorship. That made me a lower-risk hire for companies here.” Hendricks also felt that his excellent Japanese made him a more attractive hire. While applying, he emphasized to companies that he could be a bridge to the global market and business overseas. However, he also admitted this strategy steered him towards applying with more domestic Japanese companies, which were also less likely to hire someone without a computer science degree. “So,” he said, “it sort of washed out.” Wilson is another who put a lot of emphasis on his Japanese language skills, from a slightly different angle. A lot of interviewees typically don’t speak Japanese well . . . and a lot of companies here say that they’re very international, but if they want very good programmers, [those people] spend their lives programming, not studying English. So having somebody who can bridge the language gap on the IT side can be helpful. DO lean into your other experience Several career switchers discovered that their past experiences and skills, while not immediately relevant to their new career, still proved quite helpful in landing that first role—sometimes in very unexpected ways. When Wilson was pitching his language skills to companies, he wasn’t talking about just Japanese–English translation. He also highlighted his prior experience in sales to suggest that he could help communicate with and educate non-technical audiences. “Actually to be a software engineer, there’s a lot of technical communication you have to do.” I have worked with some incredible coders who are so good at the technical side and just don’t want to do the personal side. But for those of us who are not super-geniuses and can’t rely purely on our tech skills . . . there’s a lot of non-technical discussion that goes around building a product.” This strategy, while eventually fruitful, didn’t earn Wilson a job right away. Initially, he applied to more than sixty companies over the course of three to four months. “I didn’t have any professional [coding] experience, so it was actually quite a rough time,” he said. “I interviewed all over the place. I was getting rejected all over town.” The good news was, Wilson said, “I’m from Chicago. I don’t know what it is, but there are a lot of Chicagoans who work in Tokyo for whatever reason.” When he finally landed an interview, one of the three founders of the company was also from Chicago, giving them something in common. “We hit it off really well in the interview. I think that kind of gave me the edge to get the role, to be honest.” Like Wilson, D’Alberti found that his previous work as a marketer helped him secure his first developer role—which was ironic, he felt, given that he’d partially chosen to switch careers because he hadn’t been able to find an English-language marketing job in Japan. “I had my first interview with the CEO,” he told me, “and this was for a Japanese startup that was building chatbots, and they wanted to expand into the English market. So I talked with the CEO, and he was very excited to get to know me and sent me to talk with the CTO.” The CTO, unfortunately, wasn’t interested in hiring a junior developer with no professional experience. “And I thought that was the end of it. But then I got called again by the CEO. I wanted to join for the engineering position, and he wanted to have me for my marketing experience.” In the end we agreed that I would join in a 50-50 arrangement. I would do 50 percent of my job in marketing and going to conferences and talking to people, and 50 percent on the engineering side. I was like, ‘Okay, I’ll take that.’ This ended up working better than D’Alberti had expected, partially due to external circumstances. “When COVID came, we couldn’t travel abroad, so most of the job I was doing in my marketing role I couldn’t perform anymore. “So they sat me down and [said], ‘What are we going to do with you, since we cannot use you for marketing anymore?’ And I was like, ‘Well, I’m still a software developer. I could continue working in that role.’ And that actually allowed me to fully transition.” DON’T make these mistakes It was D’Alberti’s willingness to compromise on that first development role that led to his later success, so he would explicitly encourage other career-changers to avoid, in his own words, “being too picky.” This advice is based, not just on his own experience, but also on his time working as a teaching assistant at Le Wagon. “There were a couple of people who would be like, ‘Yeah, I’d really like to find a job and I’m not getting any interviews,’” he explained. “And then we’d go and ask, ‘Okay, how many companies are you applying to? What are you doing?’ But [they’d say] ‘No, see, [this company] doesn’t offer enough’ or ‘I don’t really like this company’ or ‘I’d like to do something else.’ Those who would be really picky or wouldn’t put in the effort, they wouldn’t land a job. Those who were deadly serious about ‘I need to get a job as a software developer,’ they’d find one. It might not be a great job, it might not be at a good company, but it would be a good first start from which to move on afterwards. Asakura also knew some other bootcamp graduates who struggled to find work. “A major reason was a lack of Japanese language skills,” he said. Even for junior roles, many companies in Japan require at least conversational Japanese, especially domestic ones. On the other hand, if you prioritize learning Japanese, that can give you an edge on entering the industry: “Many local companies are open to training junior developers, as long as they see your motivation and you can communicate effectively. International companies, on the other hand, often have stricter technical requirements and may pass on candidates without degrees or prior experience.” Finally, Hendricks said that during his own job hunt, “Not living in Tokyo was a problem.” It was something that he was able to overcome via diligent digital networking, but he’d encourage career-changers to think seriously about their future job prospects before settling outside a major metropolis in Japan. Their top advice I asked each developer to share their number one piece of advice for career-changers. D’Alberti wasn’t quite sure what to suggest, given recent changes in the tech market overall. “I don’t have clear advice to someone who’s trying to break into tech right now,” he said. “It might be good to wait and see what happens with the AI path. Might be good to actually learn how to code using AI, if that’s going to be the way to distinguish yourself from other junior developers. It might be to just abandon the idea of [being] a linear software developer in the traditional sense, and maybe look more into data science, if there are more opportunities.” But assuming they still decide ‘Yes, I want to join, I love the idea of being a software developer and I want to go forward’ . . . my main suggestion is patience. “It’s going to be tough,” he added. By contrast, Hendricks and Wilson had the same suggestion: if you want to change careers, then go for it, full speed ahead. “Do it now, or as soon as you possibly can,” Hendricks stated adamantly. His life has been so positively altered by discovering and pursuing his passion, that his only regret is he didn’t do it sooner. Wilson said something strikingly similar. “Do it. Just do it. I went back and forth a lot,” he explained. “‘Oh, should I do this, it’s so much money, I already have a job’ . . . just rip the bandaid off. Just do it. You probably have a good reason.” He pointed out that while starting over and looking for work is scary, it’s also possible that you’ll lose your current job anyway, at which point you’ll still be job hunting but in an industry you no longer even enjoy. “If you keep at it,” he said, “you can probably do it.” “Not to talk down to developers,” he added, “but it’s not the hardest job in the world. You have to study and learn and be the kind of person who wants to sit at the computer and write code, but if you’re thinking about it, you’re probably the kind of person who can do it, and that also means you can probably weather the awful six months of job hunting.” You only need to pass one job interview. You only need to get your foot in the door. Asakura agreed with “just do it,” but with a twist. “Build in public,” he suggested. “Share your progress. Post on GitHub. Keep your LinkedIn active.” Let people see your journey, because even small wins build momentum and credibility. “To anyone learning to code right now,” Asakura added, “don’t get discouraged by setbacks or rejections. Focus on building, learning, and showing up every day. Your portfolio speaks louder than your past, and consistency will eventually open the door.” If you want to read more how-tos and success stories around networking, working with recruitment agencies, writing your resume, etc., check out TokyoDev’s other articles. If you’d like to hear more about being a developer in Japan, we invite you to join the TokyoDev Discord, which has over 6,000 members as well as dedicated channels for resume review, job posts, life in Japan, and more.
