Pursuing the life of philosophy brings a greater knowledge of the truth, and of the different arguments for and against it, and of the main alternatives and the best arguments for and against them.
Oftentimes, one of the original motivations for starting down that path is the desire to stop losing debates, to stop being made to look like a fool, to stop finding every interesting discussion ending at an impasse. We can think of the young admirers of Socrates, if our own experiences do not furnish the demonstration of this.
It is good to pursue philosophy, and so it’s good that these motivations exist. But winning debates is often not something philosophy will allow us to do. Indeed, sometimes it has the opposite effect, because you’ll start playing by rules that others aren’t interested in imposing on themselves.
Once you learn some logic, you will be shocked at how often you’ll find seemingly intelligent people who are entirely comfortable having it pointed out that their entire argument is hanging from a fallacy. And I don’t mean one of the acceptable fallacies; sometimes, of course, something like an appeal to authority is unavoidable and completely acceptable if you don’t want, eg, to start cutting up cadavers to see for yourself how the internal organs fit together. Allowance often has to be made for those kinds of cases, which are common. But this doesn’t mean that all fallacies are no big deal! It can be shocking to find how many people will brazenly accept the presence of an unacceptable fallacy in their argument, if that’s the price of not admitting defeat.
There are a few different kinds of people who will not be any more easily convinced by an argument no matter how intelligent it becomes. There are the people who frown and dig their feet in and nitpick another’s argument, holding it to a standard they’d never hold their own arguments to. They want to believe what they believe, and intellectual argumentation will never budge them from where they’re standing. Then there are those for whom argument is sport. They might not care much who is right, but they have picked a side and they will find enjoyment fighting for it tooth and nail, come what may. You’ll never get anything like an admission of defeat from these. And then last, there are a very few people who use deliberately dishonest arguments, trying to trick the other side; I think these were more numerous in past ages, but I’m sure you can find them today as well if you know where to look, especially if you pay much attention to partisan politics.
But two things will have changed, nonetheless, in pursuing the life of philosophy: what you argue for, and what you look for in a conversation partner. I think what is argued for becomes generally more humble. Your side of the argument might often be reducible to either “I’m not convinced you’re right that x is true,” or, “I’m not convinced you’re right that x is false.” This isn’t an argumentative technique, but a reflection of a deeper change in the way you think.
And in terms of evaluating conversation partners, the focus will be much less on finding where the weaknesses are in their argument. Rather, the attempt will be to discern the motivation. People who have made up their mind and simply want to find arguments to confirm their conclusion, rather than being open to finding out whether they might be wrong, are not all that worthwhile to argue with, in most cases. However, there is a small minority of people who are aware of their ignorance, who are open to seeing something they haven’t discovered before, who seek not just the best arguments for their chosen conclusion but the best arguments simpliciter and who will shift allegiance, always provisionally, to whatever is best argued. Conversation partners like this are a great rarity, and a source of joy and of mutual instruction and encouragement when found.