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Self-expansion, not self-limitation

Making seemingly harrowing decisions comes down to one thing: how you preserve the artefact of your current self. Making big decisions undoubtedly changes who you are, but deciding what you want to preserve and what you want to test comes with every iteration of life. When you're in college, the first decision feels larger than anything. Over time, relative to every decision you've had to make, each one becomes less consequential, so the first decision feels bigger than any other one will.

My thoughts, aggregated from many conversations with people who have smarter thoughts than me:

  • Perfect information is an impossibility and so deciding the point where you are as well-informed as you will ever be is important. Finding out the information that would convince you to make the decision can only come after the decision and so finding the point of optimal balance between being informed and spending time always feels underwhelming. T.S. Eliot puts it best — paraphrased, it is that we only know what we want to say after we no longer want to say it.
    Because one has only learnt to get the better of words
    For the thing one no longer has to say, or the way in which
    One is no longer disposed to say it
    — T.S. Eliot, Four Quartets
  • Making a decision is the correct decision. There is no correct decision and even if there was, you would never find this out because we cannot relive our decisions. The most important thing is to settle on something and let yourself build conviction in it. The hard part about conviction is forgetting that you ever had to convince yourself.

    You can frame every decision to be the most exciting when you try hard enough, which is why it is hard to decide. The most important factor in being decisive is comfort in your certainty, not in the sense of knowing that your next move is cushy and comfortable, but that you are comfortable with how you came to this point. The things that seem to bog people down are fret over rejection and stress, the opposite of comfort. Once you accept these as part of the process, you allot attention to what energises you instead.

  • Let people into the process. The more you let people in, even those on the fringes of your life, the more opportunities you create to be prompted to think differently. Everyone loves giving advice because they want to feel helpful and believe their perspective on the world is right, and it's interesting to aggregate these.

    Generally, we do not listen to anyone, we listen to the feelings that resonate the most strongly. People will say things that make you think, but the only things worth thinking about are the ones you can't stop thinking about. I find that this is the beauty in sharing slivers of your life with anyone who is willing to listen — you come closer to dissecting the gaps between how they think and how you think, and this is how you better understand yourself.

  • You might not know what you want, but you should learn what you don't want. Putting things to paper or repeating them enough times to different people helps you better articulate what you value the most. An interesting framing of this is to think about the things you don't want to admit to yourself but expect to have in the future — things like a family, close friends, time to learn new skills, a well-designed home — it can be anything. It is so easy to put off these things for years, because we default to routine.

    Understanding these peripheral desires and aligning them with where every decision takes you will lead to fun daydreams about rogue paths you might take and how you can maintain focus on the subgoals needed to reach larger goals. The beauty of planning is that none of it will ever come true exactly as you imagine, you can only best prepare yourself for all eventualities.

  • Don't fulfil ideals, fulfil curiosity. There are many ideals out there that we buy into — I love the Slim Aarons description "attractive people in attractive place doing attractive things". Who wouldn't want to be that? The more you seek out these veneers, whatever they might be, you seek something in lieu of what you are actually seeking, often prestige.

    The classic grad jobs of investment banking, management consulting, and software engineering are all safe options on tried and tested paths that guarantee you a low risk of failure — something would really have to go wrong for that to be a bad decision. However, if you follow these paths for too long, you end up never having to break out of the system, you never make a real decision for yourself. You can make partner young, but still be scared to meaningfully uproot your life because you have only ever worked within closed confines. Navigating ambiguity is a skill you've avoided developing. That doesn't sound like a very fulfilling life.

  • Adjust for your risk aptitude but know that most decisions aren't risky enough, especially when you're young. Most of my peers pursue stability above all else. Stability on the surface is financial stability, but it really boils down to "peace of mind". The big differentiator I can see between those who seek this and those who don't is background. In reality, it is all a difference of mindset.

    There are so many people who would overcome this if they had met the right person willing to take a bet on them early enough in life. For many who have the profile but cannot dissociate stability from their mental frameworks of life, I seek to push them 1% closer to making riskier decisions every time, even if they never make the decision.

Choose something that expands your definition of yourself. Don't limit yourself to who you are right now and trying to upkeep this persona. Life isn't interesting if you're always trying to balance inputs and outputs to remain where you are, life becomes interesting when you try out every other set of coordinates and understand what you like and what you don't like. And when you're young, understanding what you don't like is more important than understanding what you do like. Make sure you're not climbing the wrong hill.

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