Career advice in 2025.
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.