Have you ever stepped into a room filled with high achievers and felt an unspoken sense of evaluation? I experienced this firsthand at a rooftop gathering in Singapore last year. Almost immediately, I noticed the subtle questions and quiet observations. On the surface, everything felt relaxed, but in reality, each interaction was carefully designed to understand whether I truly fit within that environment.
After years of moving between Saigon and Singapore, attending countless networking events, and building Brown Brothers Media alongside my brothers, these patterns became impossible to ignore. Successful individuals often rely on an instinctive set of signals to quickly identify people who share their mindset, values, and outlook on life.
These aren’t acts of arrogance or exclusion. They’re simply ways to find authentic connections with people who understand their world. Once you become aware of these cues, you start noticing them everywhere.
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They focus on how you spend your time, not your job title
“What’s been keeping you busy lately?”
This question is very different from the standard “What do you do?” Wealthy people rarely start with titles because they know meaningful success often exists outside conventional roles. What truly matters to them is how you manage your most valuable asset: your time.
They’re listening to whether you control your schedule or feel controlled by it. Do you talk about obligations or possibilities? Are you building toward something or merely maintaining what already exists?
I learned this lesson years ago while working in a Melbourne warehouse moving televisions. Despite holding a psychology degree, I defined myself by that job, completely overlooking the larger vision I was working toward.
They explore how you respond to challenges
One interesting pattern stands out: successful people enjoy discussing problems, but not in the way most expect.
They may casually mention an issue they’re dealing with and observe your reaction. Do you immediately complain and empathize through shared frustrations? Or do you naturally shift toward solutions, lessons, and possibilities?
This aligns with a concept I explored in Hidden Secrets of Buddhism: How To Live With Maximum Impact and Minimum Ego—seeing obstacles as teachers rather than enemies. Wealthy individuals have internalized this approach and use it to gauge whether you see problems as permanent barriers or temporary puzzles.
They talk about experiences instead of material items
“Have you checked out the latest exhibit at the National Gallery?”
When engaging in casual conversation, wealthy people rarely bring up possessions. Instead, they reference experiences, travel, or cultural moments. This helps them understand whether you prioritize growth and experiences over accumulation.
Responding by discussing things you own or plan to buy can miss the mark. Sharing your own experiences or genuine curiosity, however, shows alignment.
This shift became clear to me after leaving Australia for Southeast Asia. Choosing experiences over stability reshaped my understanding of what wealth truly represents.
They notice how you handle silence
This test is quiet but powerful. Successful people often allow pauses in conversation.
Many rush to fill silence, often oversharing or trying too hard to impress. Those comfortable with success understand that silence creates space for thought.
Being able to sit calmly, reflect, and respond intentionally signals confidence and self-awareness.
They assess your money mindset indirectly
“What’s your take on the remote work trend?”
Questions like this aren’t really about the topic itself. They’re designed to reveal your financial philosophy. Do you speak about freedom and opportunity, or focus on security and benefits? Do you view money as a tool or as the end goal?
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Rather than discussing figures, they listen for how you perceive money—as something that flows and creates value, or something to hold tightly.
They reveal a small flaw and observe your reaction
“I completely misjudged a situation last week…”
When a successful person shares a minor mistake early on, it’s intentional. They’re testing emotional intelligence and trustworthiness.
Do you use their vulnerability to elevate yourself? Do you sense gossip potential? Or do you respond with empathy and perhaps a relatable experience?
True confidence includes comfort with imperfection, and they know it.
They ask about your learning habits
“Come across anything interesting recently?”
This open-ended question reveals a lot. They’re not asking for a specific book or topic—they’re checking whether curiosity and self-growth are natural parts of your life.
Your response shows whether you’re actively learning through books, conversations, or experiences, or passively consuming information.
Since co-founding Brown Brothers Media in 2020, I’ve noticed that every successful individual I meet is consistently learning something new, often outside their main field.
They observe how you treat people who can’t benefit you
This is perhaps the most important test, and it often happens silently.
Successful people pay close attention to how you interact with service staff, assistants, drivers, or anyone in a supporting role. Do you show respect, gratitude, and equality?
They understand that character is revealed through how we treat those who have nothing to offer us in return—and character ultimately determines trust.
Final thoughts
These unspoken tests aren’t about exclusion or judgment. They’re about alignment. Successful people know life and business flow more smoothly when surrounded by others who share similar values and perspectives.
Recognizing these dynamics allows you to be more authentic rather than performative. There’s no need to impress—only to show up honestly while remaining aware of the subtle communication happening beneath the surface.
Passing these “tests” isn’t about entry into an exclusive group. The real benefit lies in developing the mindsets and behaviors that naturally align with success, no matter where you currently stand.
After all, wealth follows mindset—not the other way around.
