Ask HN: Do you regret being a generalist?

But I'm also not stuck in this generic mindset. I'm good at C++ because I like it more, that's my freedom and my choice. And after one or two years in a company, I kind of become a specialist myself on what I'm working on.

The secret is to always learn new stuff. I have 20 years of experience and I'm still reading books to learn (C++20, Rust, etc.) I've seen way too many coworkers who were stuck for the past ten years in a boring job or a dead technology and could not get out of it, it's very sad. When we meet for lunch, I always have funny stories to tell about "my new company." Yes, my previous coworkers have stable jobs but the salary is not good, they have no raise, and if their company closes for good, they will have a very hard time adapting and finding a new job (because it's most likely they only worked for one company their whole life). They always come back to me for advice on what to learn, what to do, and how to find a new job. Last but not least, their knowledge is tied to their own company and is not transferable.

What seems to be fragile is actually a power: I can quickly learn AND adapt, and I can switch companies without being unemployed if the management becomes crazy or if a company is stalling and/or on the verge of closing due to lack of money.

For me, being a specialist is interesting because you know one subject deeply, but it can become soul crushing, you'll have a hard time switching jobs, and you seldom learn new stuff. The best example I've seen all these years is C++: when you work for a company, you use THE specific C++ of the company and most of the time the "tech leads" refuse to change and, again, you're stuck in that specific version which does not teach you anything.

Personally it's great, I can quickly build models to improve complex decisions, e.g., by defining things as an optimization problem, building small simulations etc. And I can dive into many topics because I've worked on the basic components of many things.

Also I can quickly prototype whole solutions end-to-end. This helps understand what's missing and how to build a roadmap.

Right now I work as a product manager, though it would be great to find something where I could actually use my problem solving skills more and create more value by modelling complex systems.

If I had a chance to start all over again, I would have definitely looked to be more of a generalist as I feel it gives you more flexibility, perspective/context, and (ofc) improves your skill set.

I definitely regret that now (in my early/mid 30s). But hey, never too late, I've started learning backend and microservices and while I know a lot more now than a few years ago, I'm craving for some experience of taking things to production.

If you value depth, specialize. In an industry (e.g security, healthcare, finance, etc.) or field (AI, distributed systems, scaling, etc.) You'll get intellectual satisfaction, emotional satisfaction if you intrinsically care about the space (e.g healthcare), and financial upside since people value specialization.

If you value breadth and wandering, generalize. You'll still get intellectual satisfaction from knowing a variety of things, emotional satisfaction from working on things you care w/o any industry constraints, and financial upside since generalists are valuable to startups and even though their failure rate is high, being in the right company at the right time could give you the same financial upside you'd get from say being at a large company in a specialized field.

I personally chose to speciailize because I value depth and find diving deep into a field more meaningful. I know many generalists with the same amount of experience who are doing equally well and I would hire them and value them in the same way if I built a company again.