What you’re about to read will make you uncomfortable.
And that’s the point - this is where any honest inquiry needs to begin.
I’ll go ahead and guess your life really isn’t so bad. In fact, there are quite a few people out there who would kill for a life half as good as yours. You wouldn’t call it a life void of worries, but it’s one with some structure in place, set upon a real foundation to build from.
That on its own is a luxury.
I imagine you live a life that’s largely settled. Not “30-year mortgage, 2.4 kids, and a dog,” kind of settled, although you might have that too. I’m speaking on a different version, where the biggest pieces of your life have been mostly figured out.
Any energy spent making life better is spent on the fringes. You search for the better version of your current job, moving to a nicer neighborhood of the same city, optimizing a routine without ever thinking to change what you’re truly optimizing for.
If this sounds like you, your questioning has a ceiling to it.
The height of that ceiling is the extent you’re actually willing to change your life without your entire identity breaking apart.
This ceiling is the subject in question this week. I’m here to help you raise this ceiling, one question at a time.
If you love your life and wouldn’t change a thing, disregard this essay entirely. But if you find yourself even mildly dissatisfied by your life situation, I believe these layers of inquiry will help you immensely.
A disclaimer before we continue: if you follow this advice, life may get worse before it gets better. In order to truly reassemble a better life, we need to blow the original one to pieces, find what to keep, and build everything else from scratch. You shouldn’t feel pressured to perform a complete overhaul, but don’t be surprised when nothing about your life changes because you changed nothing.
Socrates is still remembered for noting that “the unexamined life is not worth living.”
This quote still gets tossed around at high school graduations and motivational pep-talks; it doesn’t give us the space to stop and think about what it actually means. It’s a line that feels like encouragement, but it also posits a threat on the existential level.
Put another way, you must examine your life closely, because the cost of non-examination is, well, virtually everything. With that said, my thesis aligns every idea that follows:
You’re not undecided on the biggest parts of your life. You’ve already decided them - conscious or not. You forgot you ever decided, so they feel like facts instead of choices.
The process of questioning your own life, then, is a deliberate act of excavation. Raising the ceiling of our own thinking means you must first do the opposite: grab a shovel and start digging through the layers of your own psyche.
To build a better future, you must first look at the past you paved over and strike it with an army of jackhammers. From there, you’ll descend through seven layers - each one deeper and harder to stomach than the last.
It’s time to break ground and see what you uncover.
This is the topsoil. It’s the layer home to nearly every question you’ve ever asked yourself.
It’s the set of choices you actually remember choosing: the career path, the first city you moved to, your girlfriend or husband. These are the decisions you can feel the consequences of, day after day.
And this is where most self-examination begins and ends.
What distinguishes this first layer from the next is how every decision has a visible root. You can see where and when the decision was made, how it panned out, and what an alternate life might’ve looked like (if only you chose differently). I can ask how you picked out the home you live in or the restaurants you take your partner to dinners at, and you’d be able to reconstruct the reasoning - even if that reasoning has grown stale.
Layer One reveals a major flaw in our own thinking. Since these are the extent of the decisions we can see, we never think to dig deeper. We love to agonize over whether to switch jobs, apartments, or colleges, and we call it an examination. But this level only swaps out one option for another within the same frame: rearranging and replacing the furniture of our lives without questioning the room it’s all being placed in.
Before we move forward, you must answer one question honestly:
What did I consciously choose that I could still choose differently?
Jot your response down and you’ve earned the right to keep digging.
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