Beyond enough

Helpful questions for untangling fulfillment and money

Questions can be helpful compasses.

What are you optimizing for? is one of the questions I ask myself most.

I like it because it is applicable at any altitude of life, from the macro down to the micro.

My answers have evolved over the course of my life. Most recently “centeredness” has been my answer — i.e. to design initial conditions and live life in such a way that I feel as much like myself as possible. I find “centeredness” a helpful target as it represents a state of being where fulfillment, peace, and authenticity align.

The fulfillment > peace > authenticity order is intentional and personal to me, as gaining an increased sense of fulfillment has unlocked more peace and confidence to be my authentic self over time.

Though fulfillment as a concept worked for me, follow the path that resonates the most. There are many doorways in.

As I’ve sought to bring my life into better alignment, I’ve been noticing how challenging optimizing for centeredness can be in money-worshiping societies like the United States, where money is often presented as particularly inseparable from fulfillment.[1]

It’s difficult because the relationship between money and fulfillment is a partial-truth that 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.”

The precise threshold of “enough” is personal, but studies suggest it is less than most anticipate.

Pre-“enough,” money positively impacts fulfillment.
Post-“enough,” money stops impacting fulfillment.

Note: It’s important to highlight that “enough” isn’t a fixed/static value. It likely will be different in different seasons of life. What might be enough when one is single in their 20’s might be different than when one is married with kids in their 30’s etc. The amount is less important than attempting to be aware of where that point lies along the way. A lot of life and time can be misplaced by not doing the ongoing work of honing in on what is truly enough and overshooting enough via over-sacrificing, overworking, and over earning in misaligned ways.

Here are some field notes about navigating pre- and post-enough life in a money-worshiping society:


In the pre-“enough” phase, optimize for three 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?

Third, seek to maximize time spent with those who you aspire to emulate in both life and work. Beyond the what of one’s vocation, who one does life with meaningfully impacts one’s sense of fulfillment.

A few helpful guiding questions:

  • Who in your life leaves you feeling encouraged?
  • Who in your life leaves you feeling discouraged?
  • Who in your life lives a life you aspire to live?
  • Who in your life makes things you aspire to make?
  • Who in your life makes you feel more like yourself?

Jim Rohn’s quote, “You’re the average of the five people you spend the most time with,” is often truer than we realize.

Aligning with people who share similar aspirations and values can meaningfully increase fulfillment, and thus, meaningfully reduce one’s “enough” threshold.

Note: 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. Once in a sustainable vocation, a significant fulfillment cost exists in attempting to work with people who don’t share similar values or aspirations. Find your niche, then find your people.

Approaching “Enough”

As one approaches “enough”, signs begin to emerge. Here are a few I’ve noticed in my life:

  1. Reduced consumption (trips, restaurants, things, etc) as I felt less and less of a fulfillment “pop” from them.
  2. Increased honesty with myself about what aspects of my life were life-giving and life-draining. We can rationalize and talk ourselves into anything. The closer one is to enough, the harder it becomes to convince oneself to continue doing things that aren’t life-giving.
  3. Increased courage to make choices in the direction of more alignment, even if it meant having less money. We put up with a lot in life, simply because we can’t afford not too. As you approach enough, you begin to get the sense that you can afford to start saying no to net-negative things, and start saying yes to net-positive things without money being a primary variable in the decision.

Overall, I would describe the feeling as an increased sense of saturation, paired with less and less tolerance for aspects of my life that were energetically and emotionally draining, which then translated to increased courage to move towards a life that felt more internally aligned.


As one crosses the “enough” threshold, it is necessary to switch guiding questions.

This transition can be challenging but is essential, as continued money optimization doesn’t unlock greater fulfillment.

Arthur Brooks has a great line about this in his book, From Strength to Strength:

“As we grow older in the West, we generally think we should have a lot to show for our lives — a lot of trophies. According to more Eastern thinking, this is backward. As we age, we shouldn’t accumulate more to represent ourselves but rather strip things away to find our true selves.”

In the post-”enough” phase, shift from income optimization to centeredness optimization.

Helpful guiding questions to make the shift:

  • 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?

It can be difficult to move away from methods that got one to where they are. These questions amplify the diminished role of money in post- “enough” life. They help filter decisions and surface one’s true self. They help uncover where the next layer of “life” is.

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.


[1] 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.

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