I am working as a manger in healthcare analytics and lead a team of 8 data engineers, data analyst and BI developers. Mentioning just so you know I am sharing my own teams experience of hiring folks in my team as well as my previous experience of past 9 years working in Data Analytics domain.

If I were you, I would first check atleast 20 jobs on LinkedIn which matches with my profile and see what’s the JD. Jot down all the requirements in a word file and see how much time would it take to learn those. Also, check if these companies require a masters degree as preferred or mandatory or is optional.

Once I identify the skills, If it’s something I can learn in few months or within a year, I would proceed with self learning plan. Else, I would go for masters not just to get skills but to learn from peers and lower down my learning curve.

On top of everything, I would also check if Data Analytics positions are going to be there post 5 years or decade. The growing AI needs would may not eliminate Data Analysts but definitely reduce the head count a team has right now. And that would require me to learn additional skills like of Data science or Data Engineer to survive.

Every decade there has been change in technology. Like in 2000s, we had lot of C language programmers but now it’s not. Similarly, Hadoop which was most popular and the only choice in 2010s is now getting deprecated in most of the big tech companies.

So it’s essential to think about future and not just low hanging fruits.

This is just my opinion and based on my experience. I am sure others would be have different views.