Richard Siminou on Why Most Pre-Retirees Wait Too Long to Get a Financial Plan

In my experience working with pre-retirees in New York, the single most common regret I hear is some version of the same thing: "I wish I had done this sooner."

Not because people were irresponsible. In most cases, they were diligent savers. They contributed to their 401(k), they paid down their mortgage, they built something real. The issue isn't the saving — it's the planning. Specifically, the gap between having money set aside and having a structured plan for how that money needs to work in retirement.

That gap tends to show up in a few predictable ways.

The sequence of returns problem. Most people understand that markets go up and down. What fewer people internalize is how much the timing of those moves matters in early retirement. A significant market decline in the first few years of drawing down a portfolio can permanently alter the trajectory of a retirement — even if the market recovers fully. Planning for this isn't about being pessimistic. It's about being deliberate with your withdrawal strategy.

Healthcare costs. For clients retiring before 65, the period before Medicare eligibility is often the most expensive and least planned-for stretch of retirement. The costs are real, they're often higher than expected, and they need to be built into the plan explicitly.

Social Security timing. This is one of the most impactful financial decisions a retiree will make, and most people make it without a full analysis. The break-even math, the impact on a surviving spouse, and the interaction with other income sources all matter — and the right answer is different for everyone.

Estate structure. Many pre-retirees have outdated beneficiary designations, assets held in the wrong names, or no coordination between their will and their financial accounts. These are fixable problems — but only if they're caught before they become irreversible.

If you're within five to ten years of retirement and you don't have a comprehensive written plan, I'd encourage you to get one — regardless of who you get it from. The difference between a thoughtful plan and no plan is enormous.

Richard Siminou, MBA, is the founder of Siminou Wealth Management in Kings Point, New York. This content is for educational purposes only and does not constitute investment advice.