The “How Convenient”Syndrome- Why Success Changes the Conversation

I‘ve been listening to Sahil Bloom‘s The 5 Types of Wealth on Audible, and while I appreciate much of what he‘s saying, I found myself feeling a bit conflicted. Not because the ideas aren’t valuable but because they reminded me of a larger pattern I’ve noticed over the years.

The Pattern That Stood Out

It‘s a common trend among financially successful individuals where, only after reaching a certain level of security, they start talking about fulfillment, time freedom, and deeper types of wealth. It‘s as if, once financial success is no longer a question, the focus shifts toward what really matters beyond money.

And I get it. It’s a privilege to be able to step back and ask these questions. It’s natural that someone who’s built wealth would begin exploring fulfillment in other ways. But I couldn’t help but wonder would these same people have been saying this in their 20s? Or does financial stability itself create the conditions for this kind of reflection?

Context Matters

To be clear, I don’t think there‘ anything wrong with these realizations. In fact, they align with much of what Stoic philosophy, particularly Marcus Aurelius in Meditations, has taught for centuries:

You could leave life right now. Let that determine what you do and say and think.

The idea that time is finite, that relationships and purpose matter more than wealth - these are timeless truths. But when someone shares them only after becoming wealthy, it‘s fair to acknowledge the context in which those realizations took place.

I know many peers in my industry, highly successful entrepreneurs who have built careers that allow them autonomy, balance, and time freedom. But in the early years? That wasn‘t the focus. They were grinding, building, sacrificing. They weren‘t thinking about time wealth back then they were trading time for future financial security.

It doesn‘t make either perspective wrong, but it does raise an important question:

Are these insights only visible in hindsight?

Mitigating My Own Bias

Whenever I find myself reacting strongly to something, I try to step back and ask: Am I being fair?

Sahil’s message isn‘t about dismissing financial wealth it‘s about broadening the definition of wealth so that people don‘t spend their lives chasing money at the expense of everything else. That’s a message worth hearing.

At the same time, it‘s important to acknowledge that many people aren‘t at a stage where they can question what really matters. They’re still in the process of building financial security. For them, financial wealth is time wealth because without it, their options are limited.

Bringing Greater Understanding

This isn‘t about criticizing those who have reached success and want to reflect on deeper fulfillment. If anything, it’s about empowering the reader whether they’re still in the building phase or further along the journey to recognize that these perspectives shift over time.

If you‘re early in your career, and you’re still trading time for financial growth, that’s okay. That doesn’t mean you’re doing it wrong it means you’re in a different phase of the journey.

And if you‘ve reached a place where wealth is no longer your primary driver, and you‘re starting to explore fulfillment, that‘s okay too. The key is understanding that both perspectives are valid, and neither diminishes the other.

Final Thought

Sahil Bloom‘s book is valuable not because he’s the first to talk about these ideas, but because he‘s making them accessible in a new way. At the same time, it’s fair to ask whether these insights resonate differently depending on where you are on your financial journey.

Because if the only people questioning financial success are the ones who already have it, then the lesson isn‘t just about wealth it‘s about timing.