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Deciding when to retire

The Island

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October 25, 2025

As more people approach the idea of stepping away from full-time work, it becomes ever more important to pause and ask key questions about the decision to retire.

Deciding when to retire

Retirement is often pictured as a reward after decades of labour—but it also marks a major transition, one that touches finances, identity, relationships, health and daily routine. Before handing in a notice or trading a career for leisure, it is wise to reflect on the things most easily overlooked.

First on the list is the question of finances and lifestyle. Do you truly have enough to live the way you hope once work ends? It is not just about whether savings and pension accounts add up. It is about whether income streams are reliable, whether your expenses have been adjusted for future inflation, healthcare surprises or economic downturns, and whether your desired lifestyle matches what the finances support. Without taking the time to estimate what you'll spend on an ongoing basis—including housing, travel, hobbies and daily living—you risk waking up to a different reality than the one you imagined. For example, many assume work ends and the paycheck vanishes, but fail to account for the shift from earning to spending. In other words, the question is not only “Can I afford to retire?” but “Can I afford the lifestyle I want after retirement?”

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