It’s rewarding to watch your investments grow over time. When the moment comes to sell, though, there’s more to consider than simply locking in profits. Whether you’ve reached a financial goal, want to rebalance your portfolio, or believe an asset has peaked, it’s important to approach the decision to cash in strategically.
Here are a few key factors to weigh up before making your move.
1. Is the timing right?
Timing plays a crucial role in determining whether selling is the right decision. If markets are down, it can be tempting to sell to avoid further losses. But doing so may mean you miss future recoveries.
When you sell, paper losses become real. Holding on might allow time for a rebound, depending on the investment and your broader goals. However, if you’re holding an asset whose fundamentals have changed, such as a company facing ongoing decline, selling could be the right call.
A financial adviser can help you assess whether market conditions or personal objectives should drive your decision, and whether other strategies, such as partial sales or diversification, make more sense.
2. Are you giving up future income?
Many investors rely on dividend payments or regular distributions as part of their income strategy. Selling dividend-producing investments can reduce your future cash flow and limit potential growth in those payouts.
Before you sell, consider what role those investments play in your overall income plan. For retirees in particular, dividend income can provide a valuable supplement to superannuation or pension payments.
If the sale is part of a longer-term transition, such as rebalancing towards lower-risk assets, ensure the replacement investments can meet your income needs.
3. Have you thought about the tax implications?
Capital gains tax (CGT) is a key consideration when selling investments. Any gain you make must be declared in your tax return, and the amount you owe will depend on how long you’ve held the asset.
If you’ve owned an investment for at least 12 months, you may be eligible for a 50% CGT discount. But calculating gains accurately requires detailed records of every parcel of shares or units you’ve purchased, their cost base, and the sale price.
“Understanding the tax impact of selling can make a significant difference to your overall outcome,” says Ben Sutherland, Financial Adviser & Partner at Halpin Wealth.
“A well-timed sale or a structured sell-down strategy can reduce unnecessary tax and preserve more of your gains.”
Your adviser can also help you plan the timing of sales to minimise CGT, especially if you’re expecting variable income across financial years.
4. Should you sell gradually or all at once?
If you hold a large investment, selling it all at once can feel risky. Market fluctuations, liquidity, and tax all come into play. Selling in stages, sometimes known as tranching, can provide balance. It spreads both your risk and your CGT liability while allowing you to stay partially invested if markets continue to rise.
Though this approach may involve slightly higher brokerage costs, the trade-off is often worth it for the flexibility and control it provides.
Sources: This article was originally published on Advisely with the title “Things to keep in mind when cashing in your investments” on 12 October 2025.
Planning your next move
Cashing in investments is about more than timing the market. A well-considered strategy can help you manage tax, preserve income, and keep your long-term goals on track.
If you’re thinking about selling or restructuring your portfolio, contact us to discuss how we can help you make informed decisions with confidence.
This information provided in this article is general advice only and has been prepared without taking into account your own objectives, financial situation or needs. Before making a financial decision based on this advice, you must consider whether it is appropriate in light of your own needs, objectives, and financial circumstances, and where relevant, obtain personal financial, taxation or legal advice. Where a financial product has been mentioned, you should obtain and read a copy of the Product Disclosure Statement (PDS) prior to making any decisions about whether to acquire a product.