Asset Rich, Cash Poor

I’ll call him Bobby. He’s a composite of several brilliant entrepreneurs I work with, but his story is very real and a conversation I have often.

On paper, Bobby’s net worth is stellar. His incorporated business is thriving. He lives in a beautiful home that he aggressively pays down each month from his personal draws. His corporate investment accounts are fully funded, and his personal equity sits well into the multimillion dollar range.

But sitting in my office last week? He was stressed.

His wife wanted to do a $100,000 kitchen reno to make their home even more beautiful. And for a moment, he hesitated. Not because he didn’t have the money, but because none of it was easily accessible.

It was tied up in the business. Locked in investments. Structured for growth… not for ease. On paper, he was wealthy. In practice, he paused.

Why? Because despite his ~$5 million net worth, his personal chequing account had less than $10,000 in it.

How does a multimillionaire end up here? By design. A game I call Financial Hide and Seek.

Look at your own accounts. Have you locked your wealth behind doors you can’t easily open? Mortgage prepayments. Long-term investments. A nearly empty chequing account.

You might call that discipline. I call it self-imposed scarcity.

For some, having a large, accessible pile of cash sitting in a regular bank account feels incredibly uncomfortable. It feels exposed. Your brain starts whispering: If I let myself feel financially secure, I might lose my edge. I might get lazy. I might stop grinding. And that money should be working, not idle.

So you recreate the conditions that feel familiar. You keep yourself cash-starved on purpose. The pressure of a low chequing balance keeps you vigilant. Sharp. Working. And it quietly reinforces the belief that you are always one step away from being broke.

But from a structural lens: Net worth does not buy groceries. Equity does not soothe your nervous system. Liquidity does.

Of course, I listened to Bobby, helped him breathe, and started talking with him about structural steps he could take to get through this kitchen renovation — crystallizing some of his corporate investments and accessing the capital dividend account and other strategies.

But the lesson here is that over-optimizing your balance sheet — tying up every dollar in investments or debt repayment — might make mathematical sense, but it can be psychological self-sabotage. You are trading daily peace of mind for a slightly better balance sheet.

Sometimes, the smartest financial move isn’t optimizing your balance sheet. It’s giving yourself enough liquidity, personally or corporately, to finally feel safe. So you can breathe.