Ask HN: Generalists, when do you say "I know enough" about any particular topic?

I stop when I find a solution to the problem. Most of the time the learning happens along the way, not necessarily in the solution itself but all the things you try and iterate on your journey to the solution.

Everything changes in tech by the minute ... but also nothing changes. For web applications it has been HTML, CSS and JS for nearly 30 years. XMLHttpRequest/AJAX came out 25+ years ago. There have been many improvements along the way, like applying design patterns instead of cgi-bin directories with scripts that had a +x modifier on them in the file system. But the base technologies have not changed all that much. We still submit HTML form's with input fields to a back-end server that handles that data. We're still rendering HTML and using CSS to style it. Gone are custom UI toolkits like Flash or Java Applets. Maybe WASM is something to look into but it feels like its not mainstream to me.

If you don't want to get left behind, learn the basic building blocks at a deep level, they don't change much.

I've found that LLMs help me find the boundary.

First I ask a bunch of questions in a chaotic manner. I explore the topic, check references, etc.

At some point the dots start to naturally connect. Then I start paraphrasing what I learned and the LLM either confirms it or clarifies where my understanding falls short.

At some point I feel naturally satisfied with the level of understanding that I have—it's likely because there's no „one more page of Google search results” trap there.

One thing to watch out is the „GOAT trap”—for instance, the default ChatGPT tends to reply with sth like: „You are the GOAT and your understanding and insight are unmatched. Let’s just clarify a few minor points”, followed by a destruction of my line of thinking, but worded in such a way that you're happy for the upcoming trip :). So you need a system prompt like „be very blunt”.

I follow the motto: "Don't spread yourself thin."

What I try to do is get into the core of whatever product I work on, as close to the beginning of the product's creation.

Then, I implement "good enough" solutions that work as a bridge until the team can grow to hire experts.

For example: At a startup I worked with another engineer on a desktop client. I focused on working mostly on the business logic, and muddled through the UI. We brought in a UI expert to polish the UI. Later, when we added a driver, we brought in a driver expert to implement the driver, and I worked on how it integrated into the product.

On that product I also became "good enough" at Mac programming because it was a cross-platform product, and I focused on our cross-platform logic abstracted Mac and Windows. We later brought in Mac experts who filled in the pieces that required more extensive Mac experience.

You learn just enough to get your problems solved appropriately. What's approriate is the thing you have to judge specifically within your problem space.

If you're working on life-sustaining / life-saving problem space, appropriate better be very robust. If you're hacking on a hobby project, appropriate is whatever you feel like.

Personally I learn something new (almost) every day. Some of it is related to my work, some of it I learn just because I find it interesting. That's how I've grown to be a generalist. I didn't strive to be one, it just happened due to life long learning.

I don't understand the question. One does not simply decide to stop falling down the rabbit hole, you keep going until it stops or you get taken down a different path. Never in my life have I made an active decision to stop learning about any one thing. You learn whatever skill is required to deal with the problem at hand and go on keep learning until you need a new skill or just get distracted.

But also you're making an extremely bad mistake in your thinking here. Being a generalist does not preclude being a master. In fact, I've found that in today's market you must have specializations. Right now I'm selling myself as an electronics engineer and embedded C programmer. But my deepest expertice is C#, where I consider myself to be a fairly high level expert. My current job is writing react native with some EE on the side.

You're trying to actively spread yourself even thinner which is a huge error. Knowing almost nothing about everything is not useful today, we just use AI for that. You need some real, solid skills to work from. You also need to be able to be a specialist and do specialist work because you are not likely to find a good generalist role. There aren't many such roles and they're getting harder to find.

But all in all my answer is no. There is no point where you should stop learning any one thing. Follow your passions and what's interesting. Finding a subject you're interested in and spending a ton of time learning about it isn't a bad thing. That's how you figure out what you like and how you build real skills. You should follow particular subjects into mastery because a generalist without any specialization is not actually very useful unless you're a world class engineer.

It's clichéd, but genuinely follow whatever subjects make you happy and find a way to make that work for you.

> when do you say "I know enough" about any particular topic?

Never. That's the trick. There is no good answer to this question. Only the one which works for you.

You need some to come up with some other mechanisms to trigger your move-onto next stuff (or stay-on subject depending on natural tendencies).

Overall my strategy is keeping my core competencies sharp. Don't be early adopter, but keep an eye on them to pick up when things more or less prooved their workability.

The things outside of my core I dig as much as I'm interested or as much as task requires. This gives freedom to pursue whatever seems to be interesting.

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> In 2025, with everything in tech changing by the minute,

Based on what do you build that? Based on news?

It's a FOMO. Are there objective reasons for feeding that feeling?

I never aspired to be a generalist, but I have come to realize my process has made me into one.

If I had to generalize how I work, I'd say it comes down to:

1. Identify the highest value thing I can work on that is feasible

2. Learn what I need to finish the work. Invest as little time/effort as possible into topics that have not proven to be timeless. Lindy's Law is your guide here.

3. when the solution is good enough, go back to 1.

Being a generalist doesn't mean you aren't an expert in anything. There are topics that I've identified as being so timeless and high value that I've more time and effort into them than others (making me a relative expert, I guess).

For me, it is more about targeting the goals at hand and learning just what I need than setting out to master the tools I like. Over time you will become an expert in the tools you trust.

In my experience you become a good generalist by learning deeply about many things. My real skill is learning the essence of a compoex topic quickly. It also becomes easier over time to learn deeply about a new subject.

I don’t think I consciously became a generalist, it just happened based on necessity. I’ve worked on a lot of things that have required me to jump around a lot. I learned enough to get the job done. I always think it would be nice to know more, but there is only so much time on the day, so I don’t sweat it.

Going out of my way to dive deep on something I will never use seems like a waste of time to me. My company sent me to Citrix training years ago. I was going to get certified, but didn’t end up doing it. The class and certification seem designed for someone setting up the entire Citrix infra for their company. In my role, I just made a publish app here and there, which I already knew how to do. After the training, our use of Citrix went down, and I haven’t touched it at all in 10 years. I’m glad I didn’t waste my time deep diving on technology I’d never actually use. If we use it again in the future, I’ll have to re-learn it either way, since it’s been so long.

I go beyond on topics I actually find interesting, or seem like they will be relevant to my job for a longer period of time, where I will see some pay off.

It depends on what purpose I have for learning something. If it's to accomplish a specific task, then "I know enough" when I have learned enough to accomplish that task.

If I'm diving into a topic because I'm interested in it, then "I know enough" when my interest in it wanes or is eclipsed by something else.

But the majority of my generalist knowledge didn't come from either of those things, but from a lifeline habit of recreationally reading about things that are not "my usual kind of thing".

You never know 'enough'. You just have broad interests and see how all things are more interlinked than any one specific branch of knowledge captures. So you naturally wander through a host of subjects rather than exclusively deepdive into a single specialization.

You don't become a generalist intentionally, you become one by wanting to do something that requires learning a bunch of things. So, I've never consciously thought "I know enough", I've just learned enough to do what I needed to.