Career & Money

Why Money Always Feels Like It’s Not Enough

All Insights

You earn more than you used to. Maybe significantly more.

The anxiety is still there. The tightness when a bill arrives. The guilt when you spend on yourself. Or the opposite: compulsive spending, money slipping through your fingers no matter what.

In twenty years, I’ve never found a money struggle rooted in a lack of financial literacy. It’s always a relationship — specifically, the one money had with your sense of self growing up.

What Money Meant in Your House

In some houses, money meant safety. Present: calm. Absent: danger. The child learned: money equals survival. The adult: you can never have enough.

In other houses, money meant conflict. The thing parents fought about. The child learned: money equals pain. The adult: you unconsciously push it away.

In others, money meant worthiness. The child given money was loved. The child who asked was a burden. The adult: spending on yourself feels like taking something you don’t deserve.

Your financial behaviour isn’t irrational. It’s perfectly rational — given the equation written in childhood.

Seeing the Equation

The first step isn’t a new budget. It’s seeing the equation. Once it makes sense, it can change.

Your money pattern has a root.

In a live session, I trace exactly where your relationship with money was written.

Join the Next Live Session Book a reading

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Every week, I send a short observation — about relationships, patterns, and the things we don’t see about ourselves. No fluff. Just one idea that might shift your perspective.