Selling options at calculated risk Important to manage fear and greed

When do you sell options?
When the stock market is bearish, we can sell calls to earn premium by selling high now and buying low when the premium falls later.
When the stock market is bullish, we can sell puts to earn premium by selling high now and buying low when the premium falls later.
What are the risk of selling options?
It's VERY RISKY to sell options because your loss is unlimited.
For selling calls, you'll be forced to SELL 100 shares if the share price suddenly reverse and the strike price is in-the-money (ITM); your loss is unlimited when the share price keeps increasing. If sell naked or uncovered calls, you'll need to 'buy back' 100 shares at current price which by now is much higher than your strike price. Most will choose to 'roll over' your calls to avoid SELL 100 share but still incurred huge lossl.
For selling puts, you'll be forced to BUY 100 shares if the share price suddenly reverse and the strike price is ITM; your loss is unlimited when the share price keeps falling. You'll need cash to BUY 100 shares. If don't have enough cash, you will have no choice but to 'roll over' your puts to avoid BUY 100 share but still incurred huge loss. In extreme case your 100 shares become zero value when the company shut down and the stock delisted as in the case of Silicon Valley Bank not long ago.
Can I Sell options at calculated risk?
I sell puts for the purpose of buying 100 shares at dip (have already budget a sum of money). It's a calculated risk because I've done my research that the company is fundamentally sound (based on earnings report and other info) and the short term volatility is not a concern.
I sell calls for the purpose of selling 100 shares at soar price (have already acquired 100 share at low price). It's a calculated risk because I've done my research that selling the share at the strike price will earn profit at acceptable margin or (intrinsic) value calculated using fundamental analysis.
Have I make losses selling options?
The short answer is yes. It is usually due to panic sell (fear) and choosing a 'risky' strike price (greed). In the early days, I sell put without the intention to acquire 100 share. When the share price plunge, I buy back the put at a loss due to panic. Fortunately I set a 'buy back' stop loss and the loss is capped or limited but still a painful lesson.
Due to greed (try to earn higher premium), one may sell call at strike price lower that the share price you bought. If the option is ITM, you'll force to sell 100 share at a loss. When the share price unexpectedly surge, it is very stressful to see your  call losing money and eventually buy back at a loss. I have stopped doing this.
Bottom line
Buying options is relatively less risky than selling options. I'll not do 'roll over' because it is VERY RISKY; inexperience can end up selling another option at a worse strike price. I'll avoid at all cost to sell naked call or sell put without the intention to acquire the share. It is important to manage your fear and greed when selling options - only at calculated risk and mapping all possible situations. Dyodd if you want to sell options.