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Why The First Five Years of Retirement Matter Most

When people picture retirement success, they often focus on a single question:

How are my investments performing?

That question matters. But there’s another phase that can quietly shape the next two decades even more — what we call the launch years of retirement.

The first few years after income begins often set the tone for everything that follows. Whether you’ve already started taking income or you’re a few years out, the decisions made early can meaningfully influence how long your money lasts and how much of it you keep. And most people don’t realize how much influence these early years have.

Why the Launch Years Matter

Two households with similar savings and similar average investment returns can experience very different outcomes in retirement. The difference often isn’t the market. It’s the structure.

In the launch years, questions like these become critical:

  • Which accounts should income come from first?
  • How much should be withdrawn each year?
  • Are withdrawals aligned with tax brackets?
  • How will this affect future Required Minimum Distributions?

And here’s a detail many retirees are surprised to learn:

Social Security can be Taxable

How much your social security is taxed often depends on how other income is structured. In some cases, withdrawing too much from the wrong account early in retirement can increase the portion of Social Security that becomes taxable. It can also influence Medicare premium brackets in later years. None of this is about avoiding income. It’s about understanding how the pieces work together.

Small Decisions, Long-Term Direction

Retirement doesn’t unravel because of one dramatic mistake. It drifts. A withdrawal taken out of habit. An income decision made without coordination. A tax consequence discovered after the fact. Over time, those small choices compound. Retirement doesn’t unravel all at once, it drifts off course quietly, one unexamined decision at a time. And the launch years are an opportunity to prevent that drift.

Coordination Creates Confidence

Successful retirement planning isn’t just about accumulation. It’s about alignment.

Investments remain important. But during the launch years, equal attention should be given to:

  • Income sequencing
  • Tax awareness
  • Social Security timing
  • Future RMD planning
  • Flexibility for changing circumstances

When these elements are coordinated early, retirees tend to experience greater peace — not because markets are predictable, but because their plan is intentional.

If you’re approaching retirement or have recently begun drawing income, this is one of the most important periods to step back and evaluate how everything fits together. The launch years of retirement don’t just determine how your income begins. They influence how your retirement unfolds.

Keith Leverentz, NSSA®, is the founder of The Life Group, guiding clients since 2003 with personalized financial planning, investment counsel, and retirement strategies. If you’d like to explore these ideas further or join them for an upcoming educational seminar visit Thelifegroupllc.com/events.

This article was originally published in CHOICES For Fifty Plus, a Dubuque area magazine for people that are 50 and older. Single copies are available at Dubuque area newsstands or click here to read the digital version of the latest issue.

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