How do I know if I should engage in passive investing?

To each his own. If you enjoy studying the markets and crunching numbers and statistics, active investing might be a more fufilling experience for you. If you aren't, then you are probably more suited to a passive investing style.

Here's a good read to explain the differences and what are some factors to look out for in investing :) https://advice.moneyowl.com.sg/the-right-way-to...

Passive investing could mean investing in an index. Upside is that you do not have to micro-manage your holdings, you have more time to do other stuff and your returns will not be too far off the market performance. However, this can be a limting factor when market performance is low and it'll drag down your portfolio performance.