Why You’ll Never Feel Rich Until Your Portfolio Pays You Every Month

The Hidden Psychological Trap

Lately, a lot of people have been asking me what I really mean when I talk about the flow part of the portfolio. And it makes sense, it’s probably the most misunderstood part of the entire asymmetric system.

Flow isn’t just about collecting dividends or receiving a paycheck. It’s a philosophy. It’s about building a system where you generate real, controlled cashflow without ever breaking your base, without selling your hard assets, without killing the compounding machine that’s quietly working for you.

I still believe the best portfolio is one where you never sell your core. You borrow against it when needed, using intelligent leverage or collateralized loans. That’s the most tax-efficient and strategically powerful structure there is. But even so, there’s a psychological truth we can’t ignore.

Humans need to see movement. To see money coming in. To feel that they can spend, that they’re moving forward, that something tangible is happening. There’s a cognitive bias (the so-called mental accounting bias) that explains why we prefer a visible dividend over an invisible capital gain. Shefrin and Statman described this decades ago: we mentally separate dividends and capital gains as if they were different things, even though mathematically they’re identical.

And that need for flow isn’t irrational. It’s deeply human. Taleb said it best: having a monthly paycheck is one of the psychological foundations of the 21st century. It gives rhythm, stability, a sense of control. That’s why in a financial system designed for freedom, flow plays that emotional and practical role. It’s what lets you live from your system without dismantling it.

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When I talk about flow, I mean three very specific things.

First, having assets that generate real cashflow: money that comes in without you having to sell anything. Dividends, interest, rent. Real estate works incredibly well here when structured properly, with controlled debt and positive net flow. Some constant-distribution ETFs, like JP Morgan’s JEPQ, also fit this box. It pays consistently, and over the long run it’s performed similarly to the MSCI World Total Return. It’s a simple, clean way to feel the movement of money without touching your base.

Second, being able to sell a small fraction whenever you need to. This doesn’t mean selling your core; it means setting up an automated system. Many brokers allow you to trigger small sales when your portfolio moves above or below certain thresholds. That way, you create a controlled flow without ever dismantling the foundation. And there’s a huge tax advantage: you only pay tax on the realized gain of the portion sold, unlike dividends, which are taxed at 100%.

Third, being able to borrow against your assets. From least to most efficient, this is the highest level of flow, but also the one that requires the most discipline. Borrowing liquidity against your holdings lets you live from your system while your compounding engine keeps working untouched. This is how wealthy families operate: they don’t sell, they borrow. But to reach that level, you need solid, antifragile assets and zero risk of forced liquidation.