January 2, 2026
The paradox of plenty

We tend to assume that the journey to financial success is linear. We imagine that as our net worth rises...

We tend to assume that the journey to financial success is linear. We imagine that as our net worth rises, our stress levels will fall. We believe that once we hit a certain number (let’s call it the "freedom number"), anxiety will simply evaporate.

Yet, in our conversations with successful individuals and families, we often find the opposite is true.

There is a strange gravity to success. As you accumulate more, the stakes feel higher. The focus shifts from "how do I grow this?" to "how do I not lose this?"

When you are starting out, risk is a necessity; it is the engine of growth. But when you have "arrived", risk transforms into a threat. This is where success itself can become a risk factor to your peace of mind and your decision-making.

This is known as loss aversion. The pain of losing money is psychologically about twice as powerful as the joy of gaining money.

As your wealth grows, you have more to lose. This can lead to a state of paralysis. We see investors hoarding cash in high-inflation environments because they are terrified of market volatility, guaranteeing a real-term loss in exchange for the illusion of safety.

Paradoxically, the fear of losing your wealth can become the very thing that erodes it.

This is what we call the complexity trap. You see, success rarely comes in a simple package. It usually brings complexity with it.

You might have business interests, cross-border tax liabilities, multiple properties, and trusts. With every layer of complexity, the mental load increases.

Suddenly, you aren't just managing money; you are managing a system. This complexity can obscure clarity. It becomes difficult to see if you are actually making progress or just spinning plates.

Perhaps the subtle risk of success is the "golden handcuffs" of lifestyle creep.

As income rises, expenses tend to rise to meet it. The bigger house, the private education, the club memberships. These are wonderful privileges, but they also raise your "burn rate".

When your lifestyle requires a high level of income to sustain it, you lose flexibility. You may find yourself staying in a high-pressure career you no longer enjoy, simply to service the lifestyle that success built. The tool (money) has become the master.

So, how do we inoculate ourselves against these risks?

It starts with defining "enough". This is not a ceiling on your ambition; it is a floor for your contentment.

It involves separating your net worth from your self-worth. It means building a plan that accounts for the emotional weight of money, not just the mathematical efficiency. If you feel the weight of your success more than the freedom of it, it might be time to pause.

We need to ensure your plan is robust enough to protect what you have built, but flexible enough to let you enjoy it. We don't just plan for markets, we plan for life.

Sometimes, the best financial move isn't another investment; it is the decision to stop worrying about the score and start looking at the game.

Peace of mind is a return worth investing in.

Liron Mazor

Greengrass Wealth Management is an authorised and licensed independent financial services provider with the Financial Services Board (FSP Number: 19308)
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