Milestone 5: The Boomerang Milestone

Debtless by Design

Smart Money Milestone #10 is the finale — and reaching it places you far beyond the average financial overachiever.

We call this milestone Debtless by Design because it represents a thoughtful, intentional approach to debt — one guided by efficiency, flexibility, and personal values rather than rigid rules.

If you’ve followed the Smart Money Milestones in order, you may have noticed something intentional:

Debt payoff comes last.

Why Debt Comes Last in the Smart Money Milestones

Many financial frameworks prioritize becoming debt-free as early as possible. While that can feel emotionally rewarding, it isn’t always the most efficient use of capital.

Throughout the earlier milestones, the focus was on:

  1. Building liquidity
  2. Capturing tax advantages
  3. Investing consistently
  4. Maintaining flexibility
  5. Allowing compounding to work over time

In some cases, that meant intentionally carrying low-interest debt — such as a mortgage — while pursuing higher-impact financial priorities.

From a planning perspective, aggressively paying off low-interest or potentially tax-advantaged debt may not always align with broader financial efficiency, particularly when comparable or higher yields are available through conservative savings or investment options.

This is why Debtless by Design appears at the end of the framework.

What Debtless by Design Really Means

At Milestone 10, you’ve earned choice.

This milestone is not about following a rulebook or optimizing every decision purely by the numbers. It’s about having the financial strength to decide how debt fits into your life — or whether it fits at all.

At this stage, you may choose to:

  1. Pay off remaining debt for simplicity or peace of mind
  2. Maintain certain low-interest liabilities while keeping capital invested
  3. Eliminate all debt and simplify your financial picture
  4. Take a blended approach that balances efficiency and emotion

There is no single “right” answer — only what aligns best with your goals and preferences.

The Emotional Side of the Final Milestone

Up to this point, the milestones have largely been about structure, discipline, and optimization. Milestone 10 is different.

Here, the emotional component matters.

Even if a decision doesn’t make perfect mathematical sense, the ability to choose peace of mind, simplicity, or personal satisfaction is part of what makes this milestone meaningful.

You’ve earned that flexibility.

What It Means to Reach Milestone 10

By the time you reach Debtless by Design:

  1. Your major financial goals are funded
  2. Your savings and investments are working cohesively
  3. You’ve built resilience, flexibility, and optionality
  4. Your financial decisions are no longer driven by urgency

Congratulations — if you’re at this stage in life, in our opinion, you are financially free.

Not because every variable is eliminated, but because your money now supports choice, confidence, and control.

Let’s chat about how I can assist you in reaching Milestone 10!