So I'm twenty-nine now, and while that number doesn't mean much of anything, I feel more acutely that I can look back and forward with equal clarity. Too I can say with some certainty what has worked for me and what has not, so with humility and no philosophical pretensions I'd like to share the fruits of my reflections. Subject them to your own scrutiny and common sense and shun them sooner than do anything barbarous, but I hope you will consider them. These observations are not hierarchical, alas, so you'll need to be prudent about their application, that is, which is more important when.
Finally, I've not perfected doing or avoiding what I advocate here, and that seems like a good place to start.
1. You're a Work in Progress
Plato and Aristotle argued–so much for avoiding philosophical pretensions–that the gods must be unchangeable because they are perfect. You don't tinker with perfection, right? Well, unless you've joined the Olympian ranks, you should probably be changing. Not everything, mind you, but some things. Like a shrubbery, some parts need to be trimmed and some cultivated.
Unfortunately, I can't say much more. The art of curating your character is the art of knowing what you like about yourself and what you don't. It also requires–again shrubbery-like–patience. You can't change everything at once. You should probably look at some models to discover whom you admire. Speaking of which...
2. Get to Know People
It's hard to get your head around the fact that you need to know others to know yourself. Not only will you learn by knowing them whom to emulate and whom to avoid, but you'll develop relationships which will make demands of you. They'll want things from you and also for you, and you'll have to consider who you are when deciding how to react. What will what they want you to do make you? You'll also see yourself from their perspective and be able to ask whether you like the person that they see. Do you like how you act around them, or how you make them feel?
This doesn't mean that you use people to learn about yourself, but that your fulfillment is interwoven with the lives of others.
3. Reconcile Yourself to Tradition
This is a tough one, because no one is fully progressive, contemporary, or traditional. Everyone cherry picks what they like, and that's fine up to a point. There are good traditions and bad ones, but I would make two provisions.
First, decide what traditionalism is to you. Do you actually find beauty in doing things the way your ancestors did? Is there authority in precedent? If so, those imperatives have far-reaching implications, i.e. you can't choose which traditions to follow unless you think they're immoral. Maybe tradition is for you just a love of things which happen to be out of style at the moment. Perhaps you follow tradition to pay honor to the past or your parents. In any event, what you think traditionalism is has a lot to do with how you fulfill the name.
Second, understand the traditions. Study the history of everything and don't rely on caricatures or summaries. To put it another way: know your alternatives. It's alright to like rock and roll music–sort of–but not if you don't know what you're missing in Mozart and Bach. This study also applies to your family. Study its history–and that includes getting to know its living members–and decide what it means to you. Comprehend what your actions will do to the thing called your family.
4. Honor Your Parents
Yes, there is such a thing as a collective. Liberally-minded people–libertarians, liberals, progressives, and broadly independent people–have a hard time with this one. I'm not saying the culture, ethos, zeitgeist or whatever you call it has will or authority, but it exists. You contribute to it, and most immediately you contribute to your family, and most immediately that means your actions with your parents make a special little world among you. Honor them.
I don't mean that you should let them dominate you or that you should be obsequious to their whims, but you should consider their desires for you as legitimate ones. Those desires may be illogical or wrong-headed, but ponder them with care. If they're immoral, then you have a bona fide moral dilemma between piety and some other virtue: Good luck.
Short of that, try to please them. Let them help you in ways that they like. Keep them apprised of your whereabouts and comings-and-goings. If they're not traditionalists, you're off the hook. If they are, see #3. Do well for yourself, for them. They'll worry no matter what, but be successful enough at life that they don't
predominately worry. Above all, don't make them ashamed. Don't make them want to hide you, themselves, or the family. Look into the eyes of an ashamed parent and the pity you'll know will set you straight.
Their hopes for you extend ad infinitum. Of what they ask of you, you'll have to decide what's reasonable, moral, necessary, and desirable to accommodate. Not all requests are all of the above, and some will be contradictory.
5. Play Devil's Advocate
You'll need to weigh those choices, then, won't you? This means you'll need to look at all sides equally. Such requires the use of logic which, alas, requires a great deal of effort.
Unfortunately, thinking logically isn't the hardest part. What's harder than thinking clearly?
First, arguing with yourself. You need to be able to argue both sides equally, that is, be able to argue against what you think is correct. It's desirable always to argue against the best objection to your case, but you'll often need to argue your opponent's case better then they are able
Second, dealing with people who aren't logical is a distinct challenge. Disagreement usually gets somewhat heated, and it's hard for people to accept logical propositions when you've made them feel vulnerable.
Third, be humble. Remember that you can be completely logical and also completely wrong if you're missing the tiniest variable. Never lose sight of what you're trying to prove or accomplish and make sure what you're arguing both supports your premise and doesn't support anything unexpected.
Fourth, avoiding the use of reason as a weapon. Don't let the fact that you're right about something go to your head and cloud your judgment. In an abstract, academic debate that might be fine, but in life your main goal or at least a goal which you cannot ignore is
getting along with people. If there is a moral imperative at stake, proceed in argument, but with caution.
Also, people like to make up their own minds, so at least give them the illusion of choice. On that note...