I’ve built something my parents never could have imagined. My business reaches millions of people monthly, and financially, I’ve surpassed what they earned in their entire working lives combined.
But here’s the confession that keeps me up at night: despite all this success, certain comments from them still make me feel like I haven’t really made it.
You’d think that crossing certain financial milestones would silence those inner doubts. That building a company from scratch would finally prove you’ve “arrived.” But if you’re like me, raised in a working-class family where traditional success meant something very different, you know it’s not that simple.
My parents worked incredibly hard their whole lives. They navigated financial challenges with a resourcefulness that still amazes me. They valued education, stability, and putting food on the table. And they did all of this without ever complaining.
So when they make certain comments about my work, my lifestyle, or my choices, it hits differently. It cuts through all the external validation and goes straight to that part of me that’s still seeking their approval.
Maybe you know this feeling too. That disconnect between your bank account and your self-worth. Between what the world sees as success and what your family considers “real” achievement.
Here are the seven comments that still get under my skin, and what I’ve learned about dealing with each one.
1. “But is it a real job?”
This one stings every single time.
When I tell them about reaching 10 million readers monthly or closing a major partnership deal, there’s this pause. Then comes the question about whether what I do is actually… work.
They don’t mean it maliciously. In their world, real jobs meant showing up to a physical location, clocking in, having a boss. I spent time in a warehouse shifting TVs in Melbourne, and honestly? That felt more legitimate to them than anything I do now behind a computer screen.
What I’ve realized is that this comment isn’t really about me. It’s about a generational gap in understanding what work looks like today. My parents’ definition of “real work” was shaped by decades of industrial and service jobs. Digital entrepreneurship might as well be magic to them.
The lesson? Stop trying to justify your work in their terms. Instead, I focus on sharing the impact of what I do, the people it helps, the problems it solves. Sometimes they get it, sometimes they don’t. And that’s okay.
2. “When will you settle down?”
By “settle down,” they mean get a mortgage, stay in one place, follow the path they followed.
Travel and flexibility are core to my lifestyle. Working from different countries, exploring new cultures, diving deeper into Buddhist philosophy abroad – these aren’t vacation activities for me. They’re integral to my work and growth.
But to parents who built their entire lives in one community, this looks like instability. Like I’m still “finding myself” at thirty-seven.
In my book “Hidden Secrets of Buddhism: How To Live With Maximum Impact and Minimum Ego,” I write about the concept of impermanence and how embracing change is actually a form of wisdom. But try explaining that at a family dinner.
The book explores how different paths can lead to fulfillment, but this is a hard sell to parents who found their security in predictability.
3. “Your brother has a pension”
Ah, the comparison game.
Doesn’t matter that I co-founded Brown Brothers Media with my siblings. Doesn’t matter that we’re headquartered in Singapore and doing things they never dreamed of. What matters is that traditional marker of adult responsibility: the pension plan.
This comment reveals something deeper about generational financial trauma. My parents watched friends lose everything in economic downturns. They saw what happened to people without safety nets. To them, a pension isn’t just retirement planning; it’s proof you’re not being reckless.
I’ve learned to hear the fear behind this comment rather than the judgment. They’re not really saying I’m irresponsible. They’re saying they’re worried about my future because they love me.
4. “Why can’t you just be happy with what you have?”
This hits different when you’re constantly pushing for growth, launching new projects, expanding the business.
The irony? They taught me to never settle. They pushed education because they wanted me to have more opportunities than they did. But now that I’m constantly reaching for more, it looks like dissatisfaction to them.
There’s a Buddhist teaching about the middle way – finding balance between extremes. But in the entrepreneurial world, that restless energy is often what drives innovation and impact.
What helps me is remembering that their version of “enough” was shaped by scarcity. When you’ve struggled financially, reaching stability feels like winning the lottery. Anything beyond that seems greedy or unnecessary.
5. “Must be nice to make money doing what you love”
Said with just enough edge to make it clear: this is a luxury they never had.
They’re right, of course. It is nice. It’s also something I worked incredibly hard to achieve, precisely because I saw them sacrifice their passions for paychecks.
But there’s resentment in this comment that’s hard to shake. It suggests that somehow my success diminishes their sacrifices. That by finding a different path, I’m implying their path was wrong.
The truth? Both paths required sacrifice. Mine just looked different. While they were clocking overtime, I was building something from nothing, working seven days a week without any guarantee it would pay off.
6. “Are you saving enough?”
No matter how much I earn, this question persists.
Growing up watching them stretch every dollar, make impossible budgets work, and stress about unexpected expenses – that shaped them in ways I’m only beginning to understand.
When I reinvest profits back into the business or take calculated risks, they see recklessness. When I talk about abundance mindset (something I explore extensively in “Hidden Secrets of Buddhism”), they hear naivety.
They can’t help but see the world through the lens of scarcity because that lens kept them safe. It kept food on our table. It kept us housed and educated.
Now I see their financial anxiety as love expressed through worry. They’re not doubting my judgment; they’re trying to protect me from hardships they faced.
7. “We just want you to be secure”
This is the one that encompasses all the others.
Security to them means something very specific: predictability, stability, traditional markers of success. Security to me means something entirely different: freedom, impact, the ability to pivot and grow.
We’re using the same word but speaking different languages.
What I’ve learned is that I can’t make them see my version of security as valid. I can’t convince them that building something scalable is more secure than a salary. That having multiple revenue streams is safer than one employer.
But I also don’t need to.
Final words
Here’s what I’ve finally understood: these comments will probably never stop. And maybe that’s okay.
My parents’ concerns come from love, from their own experiences, from a worldview shaped by different circumstances. They’re not trying to diminish my achievements; they’re trying to protect me using the only framework they know.
The real work isn’t in getting them to understand or approve. It’s in finding peace with the disconnect. It’s in honoring their journey while walking your own. It’s in recognizing that their definition of success doesn’t have to be yours.
Some days, those comments still sting. Some days, I still feel like that kid trying to prove himself. But most days, I remember that success isn’t about escaping where you came from. It’s about taking the lessons, the values, the drive they gave you, and building something they couldn’t have imagined.
Even if they never quite understand it.
