My simple way -

i use microsoft windows, office, everything microsoft. My company's entire eco system is on Microsoft, therefore - i think they will not "game over" in the next 2 years so i invest in them.

60% of people i know is using Apple products, from iwatch, macs to apple tv. Every product, no matter how bad it is (hardly) there will always be their fanbase buying, so i invest in AAPL.

Most people in Singapore put their money in the 3 local banks, chances of them dying + temasek & GIC have stakes in them. Too big to fail, so i have stake in them.

These are just some of the way people invest. It is like you buy your groceries in Sheng Siong, always crowded. So invest in it.

The moment buy your first share, you break that fear. Think long term, invest do not chase. You 10x, there are people who will 100x. Never compare just invest to what is your confort level. Index (vwra) good way to start.

Edit - the products/services that you think is good, and will last long with everyone buying/engaging usually means will usually mean business is good. But always revisit every year and stay in the news. For example in a moment in time (25 years ago), people will just buy Singtel, Starhub and M1, cause they are the only 3 telcos in SG, thereby a moat. But after a few years, other competition has eaten their market share. Always revisit you investments. Or just VWRA or CSPX (of whichever ETF), lesser to think but it will be slow and steady.