Ask HN: Do you regret being a generalist?

Fair enough, nowadays you're probably better off writing a non-rhyming poem as opposed to a sonnet (at least if you're trying to be trendy). However I think a lot of the other skills are attainable and even worthwhile.

Generalists may always have a job in software, but specialists often have the interesting jobs. Everyone starts out as a generalist. Like you, I am always interested in vastly more things than I have time to properly grok.

Whether or not to be a generalist is a question of ambition and also where you are in your career. Life outcomes for generalists cluster around the median, outcomes for specialists have much higher variance. The idea of "t-shaped skills"[0] is valid and often excellent generic advice for optimizing career outcomes but it is not the right advice for everyone. I made a very intentional decision to ignore my polymath instincts and focus on just a few strategic areas when I was ~30 and it made a very noticeable difference in terms of the opportunities available to me.

It is difficult to know what you want to specialize in without generalizing first. True mastery of a domain typically requires considerable amounts of personal interest and focus, so it needs to be something you enjoy or you are unlikely to be competitive against those who do enjoy it.

An alternative, if a single specialization feels too limiting, is skill stacking i.e. specializing in two or three skills. This has more potential but requires more work. There may be only a few people in the world that can operate at the intersection of those specializations -- it can be very rewarding depending on what those specializations are. Complementary specializations can be synergistic.

Don't discount specialization happening accidentally by virtue of how your career evolves. I have a useful deep specialization that I never intended which is strictly an artifact of a truly random path dependency, not personal interest. Nonetheless, it is immensely valuable to me now because it complements other specializations I have so I maintain it.

Don't worry about it. If something is worth going deep in, you won't need anyone to tell you.

[0] https://en.wikipedia.org/wiki/T-shaped_skills

For me, becoming a generalist has been driven by broad curiosity across many schools of thought – not limited to just software nor even technology. I can't even imagine a world where I would have been content specializing.

One upside that hasn't been mentioned, is that not not specializing leaves more room for serendipity. I could not have followed many opportunities that have popped had I not been willing to start again as a novice.

The only, but big, downside has been that I had to quit my post-grad studies and the academia. Just the thought of pursuing a single avenue for a minimum of four years is unbearable.

Related to the above, I've also had to come to terms that I won't be one of the best in the world at anything (easily) measurable. It hasn't been easy to accept, but at the same time I've also begun to appreciate collaboration much more than competition. I believe it's also a healthier approach to life in general.

I can provide perspective from both sides of the table, to add to the wonderful comments already posted.

The first few years in my career were a will-do-anything attitude. So yes, like the OP, I did a bunch of different things. A few years in, I harbored similar thoughts of feeling inadequate. A jack-of-all-trades-but-master-of-none. Especially, since I was at Google and was surrounded by the best of the best and experts/specialists in anything you could name.

My next stint was at an early stage startup (Now, as a founder, my favorite hires are generalists. Engineers who have a wide breadth of experience, a do-whatever-it-takes mindset, and ideally, a sprinkling of product/business sense. They are the first-principles thinkers. They can handle ambiguity and change without batting an eye. They will figure when/where you need a specialist.

Be proud of being a generalist.

Every two or three years I find myself with the need of carefully planning my next steps, so that my generalist pattern does not disrupt the advancement of my career according to the criteria of my environment, this is very tough at particular moments because sometimes you have less time available to work on your broad base and on the development of specific skills that are needed for some of its corners, but I still don't regret it.