If you manage a team, who are your teammates? If you're a staff software engineer embedded in a product team, who are your teammates? The answer to the question comes down to who your main responsibility lies with. That's not the folks you're managing and leading. Your responsibility lies with your fellow leaders, and they're your teammates. The first team mentality There's a concept in leadership called the first team mentality. If you're a leader, then you're a member of a couple of different teams at the same time. Using myself as an example, I'm a member of the company's leadership team (along with the heads of marketing, sales, product, etc.), and I'm also a member of the engineering department's leadership team (along with the engineering directors and managers and the CTO). I'm also sometimes embedded into a team for a project, and at one point I was running a 3-person platform team day-to-day. So I'm on at least two teams, but often three or more. Which of these is my "first" team, the one which I will prioritize over all the others? For my role, that's ultimately the company leadership. Each department is supposed to work toward the company goals, and so if there's an inter-department conflict you need to do what's best for the company—helping your fellow department heads—rather than what's best for your department. (Ultimately, your job is to get both of these into alignment; more on that later.) This applies across roles. If you're an engineering manager, your teammates are not the people who report to you. Your teammates are the other engineering managers and staff engineers at your level. You all are working together toward department goals, and sometimes the team has to sacrifice to make that happen. Focus on the bigger goals One of the best things about a first team mentality is that it comes with a shift in where your focus is. You have to focus on the broader goals your group is working in service of, instead of focusing on your group's individual work. I don't think you can achieve either without the other. When you zoom out from the team you lead or manage and collaborate with your fellow leaders, you gain context from them. You see what their teams are working on, and you can contextualize your work with theirs. And you also see how your work impacts theirs, both positively and negatively. That broader context gives you a reminder of the bigger, broader goals. It can also show you that those goals are unclear. And if that's the case, then the work you're doing in your individual teams doesn't matter, because no one is going in the same direction! What's more important there is to focus on figuring out what the bigger goals should be. And once those are done, then you can realign each of your groups around them. Conflicts are a lens Sometimes the first team mentality will result in a conflict. There's something your group wants or needs, which will result in a problem for another group. Ultimately, this is your work to resolve, and the conflict is a lens you can use to see misalignment and to improve the greater organization. You have to find a way to make sure that your group is healthy and able to thrive. And you also have to make sure that your group works toward collective success, which means helping all the groups achieve success. Any time you run into a conflict like this, it means that something went wrong in alignment. Either your group was doing something which worked against its own goal, or it was doing something which worked against another group's goal. If the latter, then that means that the goals themselves fundamentally conflicted! So you go and you take that conflict, and you work through it. You work with your first team—and you figure out what the mismatch is, where it came from, and most importantly, what we do to resolve it. Then you take those new goals back to your group. And you do it with humility, since you're going to have to tell them that you made a mistake. Because that alignment is ultimately your job, and you have to own your failures if you expect your team to be able to trust you and trust each other.

We didn’t used to need an explanation for having kids. That was just life. That’s just what you did. But now we do, because now we don’t. So allow me: Having kids means making the most interesting people in the world. Not because toddlers or even teenagers are intellectual oracles — although life through their eyes is often surprising and occasionally even profound — but because your children will become the most interesting people to you. That’s the important part. To you. There are no humans on earth I’m as interested in as my children. Their maturation and growth are the greatest show on the planet. And having a front-seat ticket to this performance is literally the privilege of a lifetime. But giving a review of this incredible show just doesn’t work. I could never convince a stranger that my children are the most interesting people in the world, because they wouldn’t be, to them. So words don’t work. It’s a leap of faith. All I can really say is this: Trust me, bro.

If you give some monkeys a slice of cucumber each, they are all pretty happy. Then you give one monkey a grape, and nobody is happy with their cucumber any more. They might even throw the slices back at the experimenter. He got a god damned grape this is bullshit I don’t want a cucumber anymore! Nobody was in absolute terms worse off, but that doesn’t prevent the monkeys from being upset. And this isn’t unique to monkeys, I see this same behavior on display when I hear about billionaires. It’s not about what I have, they got a grape. The tweet is here. What do you do about this? Of course, you can fire this women, but what percent of people in American society feel the same way? How much of this can you tolerate and still have a functioning society? What’s particularly absurd about the critique in the video is that it hasn’t been thought through very far. If that house and its friends stopped “ordering shit”, the company would stop making money and she wouldn’t have that job. There’s nothing preventing her from quitting today and getting the same outcome for herself. But of course, that isn’t what it’s about, because then somebody else would be delivering the packages. You see, that house got a grape. So how do we get through this? I’ll propose something, but it’s sort of horrible. Bring people to power based on this feeling. Let everyone indulge fully in their resentment. Kill the bourgeois. They got grapes, kill them all! Watch the situation not improve. Realize that this must be because there’s still counterrevolutionaries in the mix, still a few grapefuckers. Some billionaire is trying to hide his billions! Let the purge continue! And still, things are not improving. People are starving. The economy isn’t even tracked anymore. Things are bad. Millions are dead. The demoralization is complete. Starvation and real poverty are more powerful emotions than resentment. It was bad when people were getting grapes, but now there aren’t even cucumbers anymore. In the face of true poverty for all, the resentment fades. Society begins to heal. People are grateful to have food, they are grateful for what they have. Expectations are back in line with market value. You have another way to fix this? Cause this is what seems to happen in history, and it takes a generation. The demoralization is just beginning.

Yesterday, the tj-actions repository, a popular tool used with Github Actions was compromised (for more background read one of these two articles). Watching the infrastructure and security engineering teams at Carta respond, it highlighted to me just how much LLMs can’t meaningfully replace many essential roles of software professionals. However, I’m also reading Jennifer Palkha’s Recoding America, which makes an important point: decision-makers can remain irrational longer than you can remain solvent. (Or, in this context, remain employed.) I’ve been thinking about this a lot lately, as I’ve ended up having more “2025 is not much fun”-themed career discussions with prior colleagues navigating the current job market. I’ve tried to pull together my points from those conversations here: Many people who first entered senior roles in 2010-2020 are finding current roles a lot less fun. There are a number of reasons for this. First, managers were generally evaluated in that period based on their ability to hire, retain and motivate teams. The current market doesn’t value those skills particularly highly, but instead prioritizes a different set of skills: working in the details, pushing pace, and navigating the technology transition to foundational models / LLMs. This means many members of the current crop of senior leaders are either worse at the skills they currently need to succeed, or are less motivated by those activities. Either way, they’re having less fun. Similarly, the would-be senior leaders from 2010-2020 era who excelled at working in the details, pushing pace and so on, are viewed as stagnate in their careers so are still finding it difficult to move into senior roles. This means that many folks feel like the current market has left them behind. This is, of course, not universal. It is a general experience that many people are having. Many people are not having this experience. The technology transition to Foundational models / LLMs as a core product and development tool is causing many senior leaders’ hard-earned playbooks to be invalidated. Many companies that were stable, durable market leaders are now in tenuous positions because foundational models threaten to erode their advantage. Whether or not their advantage is truly eroded is uncertain, but it is clear that usefully adopting foundational models into a product requires more than simply shoving an OpenAI/Anthropic API call in somewhere. Instead, you have to figure out how to design with progressive validation, with critical data validated via human-in-the-loop techniques before it is used in a critical workflow. It also requires designing for a rapidly improving toolkit: many workflows that were laughably bad in 2023 work surprisingly well with the latest reasoning models. Effective product design requires architecting for both massive improvement, and no improvement at all, of models in 2026-2027. This is equally true of writing software itself. There’s so much noise about how to write software, and much of it’s clearly propaganda–this blog’s opening anecdote regarding the tj-actions repository prove that expertise remains essential–but parts of it aren’t. I spent a few weeks in the evenings working on a new side project via Cursor in January, and I was surprised at how much my workflow changed even through Cursor itself was far from perfect. Even since then, Claude has advanced from 3.5 to 3.7 with extended thinking. Again, initial application development might easily be radically different in 2027, or it might be largely unchanged after the scaffolding step in complex codebases. (I’m also curious to see if context window limitations drive another flight from monolithic architectures.) Sitting out this transition, when we are relearning how to develop software, feels like a high risk proposition. Your well-honed skills in team development are already devalued today relative to three years ago, and now your other skills are at risk of being devalued as well. Valuations and funding are relatively less accessible to non-AI companies than they were three years ago. Certainly elite companies are doing alright, whether or not they have a clear AI angle, but the cutoff for remaining elite has risen. Simultaneously, the public markets are challenged, which means less willingness for both individuals and companies to purchase products, which slows revenue growth, further challenging valuations and funding. The consequence of this if you’re at a private, non-AI company, is that you’re likely to hire less, promote less, see less movement in pay bands, and experience a less predictable path to liquidity. It also means fewer open roles at other companies, so there’s more competition when attempting to trade up into a larger, higher compensated role at another company. The major exception to this is joining an AI company, but generally those companies are in extremely competitive markets and are priced more appropriately for investors managing a basket of investments than for employees trying to deliver a predictable return. If you join one of these companies today, you’re probably joining a bit late to experience a big pop, your equity might go to zero, and you’ll be working extremely hard for the next five to seven years. This is the classic startup contract, but not necessarily the contract that folks have expected over the past decade as maximum compensation has generally come from joining a later-stage company or member of the Magnificent Seven. As companies respond to the reduced valuations and funding, they are pushing their teams harder to find growth with their existing team. In the right environment, this can be motivating, but people may have opted into to a more relaxed experience that has become markedly less relaxed without their consent. If you pull all those things together, you’re essentially in a market where profit and pace are fixed, and you have to figure out how you personally want to optimize between people, prestige and learning. Whereas a few years ago, I think these variables were much more decoupled, that is not what I hear from folks today, even if their jobs were quite cozy a few years ago. Going a bit further, I know folks who are good at their jobs, and have been struggling to find something meaningful for six-plus months. I know folks who are exceptionally strong candidates, who can find reasonably good jobs, but even they are finding that the sorts of jobs they want simply don’t exist right now. I know folks who are strong candidates but with some oddities in their profile, maybe too many short stints, who are now being filtered out because hiring managers need some way to filter through the higher volume of candidates. I can’t give advice on what you should do, but if you’re finding this job market difficult, it’s certainly not personal. My sense is that’s basically the experience that everyone is having when searching for new roles right now. If you are in a role today that’s frustrating you, my advice is to try harder than usual to find a way to make it a rewarding experience, even if it’s not perfect. I also wouldn’t personally try to sit this cycle out unless you’re comfortable with a small risk that reentry is quite difficult: I think it’s more likely that the ecosystem is meaningfully different in five years than that it’s largely unchanged. Altogether, this hasn’t really been the advice that anyone wanted when they chatted with me, but it seems to generally have resonated with them as a realistic appraisal of the current markets. Hopefully there’s something useful for you in here as well.