A Six-Figure Tax Bill and No Way to Pay It [Money Diaries w. Maddy and James]

Maddy and James are both senior, both earning well, and last year they opened a tax bill with six figures on it and no idea how they were going to pay it.

The problem was never income. It was employer equity. Every vest built the paper wealth and the tax liability at the same time, and they'd been covering it by selling shares and draining savings, three times over. Then they upgraded the house, sold more stock to fund the stamp duty, and the cycle got worse.

This is how they got out of what they call tax jail, and what changed once they did. Twelve months on they're comfortably up six figures, they've got pre-approval on an investment property, an ETF portfolio, and they're talking to architects about the renovation.

WHAT YOU'LL GET OUT OF IT

Why a bigger salary and an equity comp plan created a problem instead of solving one

The trap of selling shares to pay the tax on shares, over and over

Concentration risk when your income and your portfolio come from the same company

Why they held every vest for years, and the moment that changed

Getting burned by a previous adviser, and what they would look for now

How the budget capital gains changes made them pause an investment property

Ten years of lost super across four funds, and how it finally got fixed

Why top few percent earners still end up shuffling money at the end of the month