Let's say when gambling, you follow a specific pattern. Let us use lottery for example. You bet on the same specific set of numbers. What would be more regrettable? Betting on the same set of numbers for the rest of your life and not winning or... changing up the set you bet on only for your old set to win?
Basically, would you rather bet on the same thing again and again then regret not exploring more or explore different kinds of bets then miss out on a win?
Betting on the same set of numbers for years is just stupid. Doing the same thing over and over again and expecting a different result is the definition of insanity. If I was consistently playing the lottery, I would always change the set of numbers. The chance of hitting the jackpot is ridiculously small(one in a 14 million if a remember this correctly). Being limited to only one set of numbers reduces your chance of winning the jackpot even further. This isn't even a "strategy". I would call it an "anti-strategy", because it's way too stupid.
Regrets shouldn't be felt, when we are talking about gambling. If you feel regrets for all your lost bets(or for the events you are betting on), then gambling simply isn't for you.