Jul 8, 2026

ChatGPT Reveals the One Portfolio Move Most People Overlook Before Retirement

Written by Jordan Rosenfeld
|
Edited by Amen Oyiboke-Osifo
ChatGPT Reveals the One Portfolio Move Most People Overlook Before Retirement

By the time retirement is fully in your sights, it can feel like there's an overwhelming number of things to do, making it hard to stay focused. While some decisions can be made more lightly — like where you want to travel or what items to downsize — others, like how your portfolio is allocated, take more serious thought.

To drill down into what people most overlook before retirement, I asked ChatGPT to weigh in.

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ChatGPT said that many people are understandably focused on accumulation — watching that nest egg grow. But far fewer people prepare for the transition to decumulation, or how you’ll withdraw and spend those funds.

The artificial intelligence (AI) cited research and recent retirement-planning literature that, other than having too little money, the bigger concern retirees face is encountering a major market decline just as withdrawals begin. This is known as sequence-of-returns risk.

To illustrate sequence-of-returns risk, ChatGPT compared two scenarios of retirees who each start retirement with $1 million and withdraw $40,000 per year. Say that both earn an average annual return of 6% over retirement; what makes the difference is timing:

  • Retiree A experiences a 20% market decline in the first year, forcing withdrawals from a shrinking portfolio.

  • Retiree B enjoys several years of positive returns before encountering the same downturn later.

Even though their average returns are identical, Retiree A could end up with significantly less wealth because early withdrawals lock in losses and leave fewer shares available to benefit from the eventual recovery.

Rather than simply shifting from, say, 80% stocks to 60% stocks at retirement, an older piece of advice, ChatGPT said retirement planners now recommend creating a dedicated strategy for the "retirement red zone," approximately the five years before and after retirement.

That often includes:

  • Holding one to two years of spending needs in cash or very short-term fixed income.

  • Being deliberate about which accounts and assets are tapped first.

  • Using flexible withdrawals instead of rigidly withdrawing the same amount regardless of market conditions.

ChatGPT called out one of the more interesting findings from retirement research — that the traditional approach of steadily reducing stock exposure throughout retirement isn't always the best approach.

Some retirees may benefit from a “rising equity glide path” — that’s technical language for starting retirement with a somewhat lower stock allocation and gradually increasing it over time. The goal is to reduce vulnerability to a bad market immediately after retirement, when sequence risk is highest. However, certain rising glide-path strategies may produce better outcomes than traditional declining-stock approaches. It’s a good idea to consult with a retirement financial planner.

That doesn't mean everyone should increase stocks in retirement, either, the AI said. It just means that the conventional wisdom of "just get more conservative as you age" is often too simplistic.

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Without good advice, people may find themselves trying to do the impossible, such as beat the market, magically pick “the right” funds to invest in or achieve “the perfect” retirement number, ChatGPT said.

In doing so, they often neglect sequence-of-returns planning, creating a solid withdrawal strategy, having reliable cash reserves and preparing for tax efficiency. These are the factors likely to have a larger impact on retirement success versus just squeezing out another 0.5% of annual portfolio return.

Five years before retirement, ChatGPT recommended pre-retirees stop asking only, "How much do I have?" and start asking, "If the stock market falls 30% in my first year of retirement, where does my spending money come from?"

People who can answer that latter question usually have a much more retirement-ready portfolio than people who can merely quote their account balance.

This article was provided by MoneyLion.com for informational purposes only and should not be construed as financial, legal, or tax advice. It was created with the assistance of artificial intelligence and reviewed by our editorial team for accuracy; however, AI-generated content may be inaccurate, incomplete, or outdated. You should independently verify important information through reliable sources before making any decisions based on this content.

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Written by
Jordan Rosenfeld
Edited by
Amen Oyiboke-Osifo