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The CGT trap: CSL, property and super in retirement
Australian Retirement Podcast hosts James O'Reilly and Drew Meredith tackle a problem that quietly traps a lot of retirees and pre-retirees: when a great investment becomes too big to ignore, but selling feels impossible because of capital gains tax.
Using familiar names like CSL and Cochlear, they unpack why tax fear can keep people stuck in overexposed positions long after the risk has changed. The real question is not whether paying CGT hurts. It does. The better question is whether holding an undiversified portfolio is even more dangerous when one position starts to dominate your retirement plan and your future income.
From there, Drew and James widen the lens to the property market, why some investors underestimate downturn risk, and how high rates, weak clearance rates and stretched affordability could shape the next chapter for housing. They also explain why property often gets more emotional leeway than shares, simply because it is not repriced in front of us every day.
The episode also moves from theory to action, covering when debt reduction can beat extra investing, when additional super contributions deserve a closer look, and why understanding your cash flow matters more than most people think. If you want a clearer framework for balancing tax, diversification, super and cash in the years before retirement, this episode is a smart place to start.
Episode resources
– Ask a question (select the Retirement podcast)
Show partner resources
– Visit TermPlus to learn more
– Join Pearler using the code "RASKSWITCH" and get $32 of Pearler Credit
– Whatever comes next for your business, power it with Stripe
EOFY deals to know about - ending June/July 2026
– 1 free trade per month, for 12 months, for new Pearler customers
Rask resources
– All services
– Financial Planning
– Invest with us
– Access Show Notes
– Ask a question
– We love feedback!
Follow us on social media
– Instagram: @rask.invest
– TikTok: @rask.invest
DISCLAIMER: This podcast contains general financial information only. That means the information does not take into account your objectives, financial situation, or needs. Because of that, you should consider if the information is appropriate to you and your needs, before acting on it. If you’re confused about what that means or what your needs are, you should always consult a licensed and trusted financial planner. Unfortunately, we cannot guarantee the accuracy of the information in this podcast, including any financial, taxation, and/or legal information. Remember, past performance is not a reliable indicator of future performance. The Rask Group is NOT a qualified tax accountant, financial (tax) adviser, or financial adviser. Access The Rask Group's Financial Services Guide (FSG): https://www.rask.com.au/fsg
Learn more about your ad choices. Visit megaphone.fm/adchoices
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By RaskAustralian Retirement Podcast hosts James O'Reilly and Drew Meredith tackle a problem that quietly traps a lot of retirees and pre-retirees: when a great investment becomes too big to ignore, but selling feels impossible because of capital gains tax.
Using familiar names like CSL and Cochlear, they unpack why tax fear can keep people stuck in overexposed positions long after the risk has changed. The real question is not whether paying CGT hurts. It does. The better question is whether holding an undiversified portfolio is even more dangerous when one position starts to dominate your retirement plan and your future income.
From there, Drew and James widen the lens to the property market, why some investors underestimate downturn risk, and how high rates, weak clearance rates and stretched affordability could shape the next chapter for housing. They also explain why property often gets more emotional leeway than shares, simply because it is not repriced in front of us every day.
The episode also moves from theory to action, covering when debt reduction can beat extra investing, when additional super contributions deserve a closer look, and why understanding your cash flow matters more than most people think. If you want a clearer framework for balancing tax, diversification, super and cash in the years before retirement, this episode is a smart place to start.
Episode resources
– Ask a question (select the Retirement podcast)
Show partner resources
– Visit TermPlus to learn more
– Join Pearler using the code "RASKSWITCH" and get $32 of Pearler Credit
– Whatever comes next for your business, power it with Stripe
EOFY deals to know about - ending June/July 2026
– 1 free trade per month, for 12 months, for new Pearler customers
Rask resources
– All services
– Financial Planning
– Invest with us
– Access Show Notes
– Ask a question
– We love feedback!
Follow us on social media
– Instagram: @rask.invest
– TikTok: @rask.invest
DISCLAIMER: This podcast contains general financial information only. That means the information does not take into account your objectives, financial situation, or needs. Because of that, you should consider if the information is appropriate to you and your needs, before acting on it. If you’re confused about what that means or what your needs are, you should always consult a licensed and trusted financial planner. Unfortunately, we cannot guarantee the accuracy of the information in this podcast, including any financial, taxation, and/or legal information. Remember, past performance is not a reliable indicator of future performance. The Rask Group is NOT a qualified tax accountant, financial (tax) adviser, or financial adviser. Access The Rask Group's Financial Services Guide (FSG): https://www.rask.com.au/fsg
Learn more about your ad choices. Visit megaphone.fm/adchoices