The questions we ask ourselves can serve as helpful compasses.
The question I ask myself the most is,
What are you optimizing for?
It’s versatile, applicable at every altitude of life, all the way down to the base level.
At this base level, I aim to optimize for fulfillment and centeredness.
It’s simple in concept but infinitely complex to actualize.
Optimizing for fulfillment poses a unique challenge in money-worshiping societies like the United States, where money is often presented as inseparable from fulfillment.
This partial truth masks a more nuanced reality:
Money has a rapidly diminishing impact on fulfillment.
Meaning, money matters up to a point — then it doesn’t.
That point is “enough.”
Pre-“enough,” money holds importance.
Post-“enough,” money loses its significance.
In the pre-“enough” phase, optimize for two variables:
First, identify a vocation that doesn’t induce dread. Pursuing passion can be overwhelming. It’s simpler to uncover it through elimination. Remove the hay to find the needle.
Helpful guiding questions:
What do I like and dislike most about my current job?
What feels like play to me but work to others?
Take note of what aspects are a good fit and seek to replace the aspects that are not in the next role. Rapid iteration is key in this phase. If a role isn’t right, don’t wait. Try another one.
Second, increase income within that chosen field. Often, income is proportional to the value of problems one can solve.
A helpful guiding question:
Are there more valuable problems I could be solving?
As “enough” approaches, it is necessary to switch guiding questions. This transition can be challenging but is essential, as continued money optimization won’t unlock greater fulfillment.
In the post-”enough” phase, optimize for fulfillment and centeredness.
Helpful guiding questions:
What if money didn’t exist?
If money didn’t exist, would I ___?
If money didn’t exist, I would ___.
What will my future self wish I’d done more or less of?
What activities, people, environments make me feel most like myself?
These questions amplify the diminished role of money in post- “enough” life. They help filter decisions and surface one’s true self.
Ultimately, the journey towards and beyond “enough” is uniquely personal, guided by one’s own inquiries and experiences. “Enough” isn’t static — it’s a dynamic equilibrium that evolves as one does. Persist in asking and exploring, and let the guiding questions illuminate the path.
 Many cultures and societies throughout history consciously avoided a monetary system, recognizing its adverse impacts on human fulfillment. In such societies, everyone shares in a collective state of “enough”, with no personal pre- or post- “enough” stages. For more on this, I recommend reading The Dawn of Everything by David Graeber.
 The sequence here matters. Increasing income in a vocation that doesn’t induce dread is less strenuous. Liking one’s job is advantageous, as most individuals don’t enjoy their work. It also can lower one’s personal “enough” threshold. A significant fulfillment cost exists in attempting to increase income in an unsuitable vocation.