Ask HN: Obtaining a degree vs. learning by doing in IT in 2020

The title of your post is a bit misleading. You already have a bachelors and a masters in CS plus five years of experience. Doing another masters degree seems pointless. A second masters (in a field that's so closely related to your previous degree and your work) would almost look like a red flag on your CV.

Learning by doing is more of the hacker ethos than getting degrees.

There are various cultures where more advanced titles and more acronyms after your name are sought after. There are some fields like health care, social work and law where those things are required. Software development is not one of those fields. Another degree might hurt you in the resume review phase where you get skipped for various reasons.

What is your goal? Do you want to work for employers that prioritize people with lots of degrees and do research? Do you want to work for companies that prioritize building things?

If you are really into AI and want to make a life's work of it, go for something like a Phd focused on AI. Maybe its the same time commitment as another Masters since you already have a Masters?

If you want to learn, make connections, then find people also interested in AI, there is the internet. You could find some open source projects that are related that you could collaborate with others.

If you want to get another degree, get another degree. What you value is what you value. It doesn't matter what might be a better choice for other people.

Particularly in the current state of affairs, you are in the best position to understand your career ambitions and the options to achieving them. Good luck.

In general for someone trying to get in the field I typically say get a degree IF it makes sense in your lifestyle.

New grad from high school and wants to get into CS. Get a degree if you can afford it.

Took a few years off of college, really interested in CS, can afford to go back to school (even if afford means loans and it is a public university). Get a degree.

Mid 20's with family and children, main breadwinner, can't afford to stop working. Think hard about the decision to go back to school. Explore other options.

In general, it just has to fit with your lifestyle.

In your particular case I'd highly suggest not going. You already have a bachelors and a masters. Plus 5 years experience. The barrier to entry to get into the sub-field you're interested in isn't credentials at this point.

Reasons to get a degree:

Immigration - degrees help a lot, if you are trying to get a work visa.

Resume filtration in big companies - many companies have policies that they will consider someone for a software development position, only if they have a degree. You probably do not want to work for such companies, at least not for long.

Learning theory - personally I find it easier to learn theory in a classroom from a teacher, with peers.

A lot depends on the school and the curriculum too. If your goal is for immigration, get any approved degree from any school and be done with it. If you truly want to learn, then it would make sense to look for tough courses from reputed universities.

Everyone's situation is unique. It is kinda hard to give a generic answer.

In my opinion, the only reason you need a degree is to pass the resume screen. Yes, they are helpful for learning the fundamental concepts which are necessary to perform the job, but you could learn those in other ways too. When it comes to IT, almost every job will require on the job learning regardless of your degrees due to the plethora of technologies that are in use today and even the variance in how they are deployed at each company. You would be better off taking coursera courses and working on an AI project to show experience in that field.

Actually had that debate with a friend of mine who was tired of working as a full-stack web dev and found himself a new job in the field of machine learning after thinking of going back to uni for a phd. So everything is possible when you can code I guess!

Totally agree with @st1x7, you should be learning by doing at this point. There is enough material online to work with especially in the field of AI and machine learning and maybe you could also learn on the job like my friend.

All the best with your decision!

If you want a second masters, go for it but it will have a neutral to negative impact on your career.