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Retiring Early Shouldn't Be a Guessing Game

Retiring Early Shouldn't Be a Guessing Game

June 05, 2025

If you're dreaming of leaving the workforce before 65, you're not alone. Early retirement, typically defined as retiring before you're eligible for Medicare, can offer more time, freedom, and fulfillment. But without a solid plan in place, it can also feel like you’re stepping into a financial fog.

Let’s clear that up.

The Retirement Age is Trending Upward

Over the past few decades, Americans have been retiring later. In 1994, the average man retired at 61 and the average woman at 59. Fast-forward to 2024, and those numbers have crept up to 64 for men and 62 for women. While the trend might be slowing, the message is clear: many people are working longer, often out of necessity—not choice.

In fact, the average worker over 50 now expects to retire at 67, according to the Transamerica Center for Retirement Studies.

But what if you want to buck that trend?

The Catch: Retiring Early Requires More Than Just a Dream

If you're aiming to retire early, you’ll need more than good intentions. You need a detailed financial plan that answers some tough, but critical, questions:

How much money is enough?

Comfort looks different for everyone. Do you know your number?

What about healthcare?

Medicare doesn’t kick in until age 65, so if you retire at 60, you’ll need a plan for those gap years. COBRA may help temporarily, but it’s not a long-term solution, and premiums can spike into the four figures monthly after age 55.

When should you take Social Security?

Sure, you can start at 62, but doing so comes with a 30% reduction in monthly benefits compared to waiting until your full retirement age at 67. Wait until 70, and your monthly check will be roughly 24% larger than at 67. Timing matters, and so does your plan.

A Plan Makes the Difference

Retiring early without a plan is like hiking into the woods without a map or compass. You’re hoping it’ll all work out, but the risk of getting lost, or running out of resources, is high.

A solid financial plan doesn’t just project your retirement number. It also:

  • Maps out your income sources over time (including Social Security, investments, and withdrawals)
  • Addresses healthcare costs and inflation
  • Considers tax strategies for early withdrawals
  • Builds flexibility into your plan for life’s surprises

Where Advanced Time Segmentation Comes In

One of the biggest reasons people delay retirement is uncertainty. "Will my money last?" "Should I touch investments now or wait?" "What happens if the market dips right after I retire?"

That’s where our strategy called Advanced Time Segmentation can change the game.

We divide your assets into segments based on when you’ll need to use them. For example:

  • Segment 1 takes care of income immediately
  • Segment 2 covers a little bit later
  • Segment 3 is focused on long-term growth

This approach helps you feel more confident spending in the early years of retirement, especially before Medicare or full Social Security kick in, because you know your near-term income isn’t tied to the ups and downs of the market.

It’s a planning-first strategy that helps you stop guessing and start living.

Let’s Chart Your Course

If you want to retire early, it is possible, but it takes intentionality and planning. As a CFP®, I help people take the guesswork out of early retirement, align their investments with their values, and make sure their plan holds up to real life, not just spreadsheets.

Because retirement should feel like a new adventure, not a leap into the unknown.

Ready to get started?