Risk is a matter of opinion. It is highly subjective and objective at the same time. Measuring risk involves unconventional contrarian thinking. What Howard Marks calls a ‘second-level’ thinking. Even then, it is almost impossible to definitively quantify.
How one perceives money or its importance thereof, determines how one makes an investment decision. The decision involves understanding risk, and to two people it will be two entirely different things. Taking a $10,000 loss may be the most risk-free strategy for a few. But for others, $10,000 could be life and death. Depends on what the investor’s approach is.
When you listen to the news or read an article about how much a stock has gone up or has the potential to go up, it tells you nothing. All it tells you is that there is an opportunity for you to analyze that stock. Utilize the knowledge available from wherever possible. Ask questions to yourself. One particular question I always ask is, with the information given or available, why would a particular stock fall/fail? Negatives are a good starting point for analysis. Remember that most stocks are bad! To find the gems, you have to carry pessimism towards the markets. It saves you money. It makes you money.