_{Exploring meta questions, the midnight oil, and selling the house}

Happy Thursday! Thanks for reading Intentional Dollar — where we look at old money ideas through a new perspective.

What’s inside?

• One idea to experiment with

• Two quotes from others

• Three questions to dig deeper

• Four lines of poetry for the point

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

_{One idea to experiment with:}

Meta Questions:

How often do you question your questions?

To ask yourself, am I asking the right questions, why am I asking these questions?

Scottie Scheffler, a decent golfer, recently caused a stir in an interview before going on to win the Open Championship—a championship that, prior to starting, was cause for some soul-searching by way of the meta question.

Throughout the interview, Scheffler, in a Socratic and rhetorical fashion, repeated derivatives of what’s the point?, highlighting his internal landscape and personal struggle with the unending circus of chasing wins. In a professional sport, you’re not supposed to question with why. Sport is about how questions. How can I be the best? How can I dominate the competition? How can I replicate my winning strategy? Scheffler said:

Scottie Scheffler is asking meta questions.

It’s a layer deeper. Instead of setting the filter at how can I be the best golfer, Scottie’s digging into the next layer—why do I want to be the best, and why does that matter?

However, one of the problems with this sort of Socratic self-dialogue is that it’s hard to grasp fully unless you’ve walked the bridge to the other side—it sounds tone-deaf. Most people without a modicum of success would trade places and gladly wear the woes of the powerful, wealthy, and externally adored. But that’s why Jim Carrey said:

So why is Scottie Scheffler, someone who seemingly has everything, asking what’s the point?  

At the heart of this Socratic process, we attempt to thin and strip away layers with carefully placed why’s, getting down to our root assumptions. When we get there, the foundation is often cracked—or missing—because our base beliefs aren’t strong, convincing, or even there.

How can you get what you want?
Why do you want that?
Where did this desire originate?
What other ways could you accomplish what you really want?
What other problems might arise after accomplishment?

I’ll conclude with 10 meta questions to reflect on this week:

1. What assumptions am I making without realizing it?

2. Am I solving the right problem—or just the visible problem?

3. How would an unemotional outsider look at this?

4. Will this matter in 10 years?

5. Am I selecting for urgent or important?

6. What question am I not asking that I should be?

7. Am I doing this to prove something, avoid something, or create something?

8. Who is the audience I’m doing this for?

9. What would a beginner ask here?

10. Has my current question brought me in circles?

_{Two quotes on the midnight oil:}

What standing problems could you solve with a few weeks of burning the midnight oil?

_{Three questions on selling the house:}

1. If I sold and moved to a new home today, what would I keep, what would I get rid of?

2. Why do I still have the things I’d get rid of? 

3. What if I sold them now, or gave them away?

Which question stuck with you? Questions like these are spotlights for the mind. Reply to this email and let me know which one shined light on a previously dark cave.

_{Four lines of poetry for the point:}

Contact Me:

Content ideas, questions? Reply to this email or reach out to me at [email protected]

Disclaimer: This is not investment advice. These weekly posts represent my simple thoughts, a few quotes, and some questions — for educational purposes only.

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