What financial products other than options have expiration days.
I found I can trade the out of the money options near expiration day successfully. (standard contract length is one month). Then I remembered weekly options so I can trade once a week and not once a month. Something where the price will be zero at the end of a designated time maybe.
Futures also have expiration days, but they do not expire worthless, as they do not share with options the characteristics of an insurance policy.
What ever insurance you sell, it will expire worthless, if no event causing damage occurred. AIG made significant profits for years, until it had to pay for the damage once. This was enough to put it out of business.
You should only sell options near expiry, if you have a elaborated statistical model, which confirms that the options are overpriced, and thus selling them provides you an edge. Selling options means high win rates, but an awful average win to loss ratio. The regular wins are small, and the only huge loss that you may experience can easily wipe you out.
If I am playing with fat tails, I make sure that they will play out in my favor, giving me an exceptionally large profit once and then, but I am not betting against them. This would be similar to a Martingale strategy, when playing Roulette.