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Your Strategy Is Only as Good as Its Downside

July 05, 20253 min read

Why most retirement strategies fail when it matters most—and how to build one that doesn’t.


Most Retirement Strategies Are Built on the Best-Case Scenario

If everything goes according to plan—
Markets grow.
Taxes stay low.
You stay healthy.
You live exactly as long as the averages say you will…

Then sure, your strategy might hold up.

But what if even one of those assumptions fails?

What happens if the market crashes the year you retire?
Or if tax laws change mid-stream?
Or if your retirement lasts longer than expected?

Most retirement strategies look great on a spreadsheet—until real life happens.
And if your entire future relies on the economy, tax policy, or perfect timing…
You’re not in control.
You’re at risk.


The Downside Is Where Your Strategy Gets Tested

A solid investment return might feel like the goal.
But the truth is,
your downside is what determines your lifestyle.

What happens when the market drops 30%?
When a medical event forces a withdrawal?
When RMDs push you into a higher tax bracket?

If your strategy doesn’t account for these possibilities, it’s not a strategy.
It’s a bet—on things you can’t control.

We believe your retirement should never feel like a gamble.


The Hidden Cost of a Fragile Strategy Isn’t Just Financial—It’s Emotional

When your strategy has holes, you feel it—long before the numbers show it.

You feel it when:

  • You second-guess that vacation.

  • You delay helping your kids.

  • You worry every time the market dips.

Even if you’ve done a great job saving, a fragile strategy forces you to live in fear of spending it.

That’s not peace.

That’s survival mode dressed up in financial language.


How the Wealthy Design Strategies That Withstand the Storm

What do the wealthiest families do differently?

They don’t build for the upside.
They build for resilience.

Here’s what that looks like:
Income that isn’t tied to the market—so lifestyle isn’t dictated by volatility
Tax efficiency—so rising rates don’t eat into what you’ve saved
Long-term care protection—so one event doesn’t wipe out your legacy
Growth that doesn’t jeopardize your lifestyle—because risk should be optional, not required

It’s not about how much you can make.
It’s about how much you get to
keep—and confidently spend—no matter what happens around you.


The Result: Confidence to Actually Enjoy Your Retirement

When you eliminate the biggest risks, something amazing happens:
You stop worrying about what could go wrong.

And that changes everything.

✅ You make decisions based on what you want, not what you fear.
✅ You enjoy what you’ve worked so hard to build.
✅ You focus on living—not limiting.

Because real financial freedom doesn’t come from chasing returns…
It comes from knowing your lifestyle is secure.


Final Thought

A retirement strategy that only works when the sun is shining isn’t a real strategy.
It’s a fragile hope.

If you want a retirement that lasts—through market crashes, tax changes, and health challenges—
you need a strategy built on
resilience, not just returns.


Want to Know How Secure Your Current Strategy Really Is?

We’ll show you—side by side—where the risks are, and how to create a strategy that secures your lifestyle no matter what comes next.

👉 [Schedule your no-cost Wealth Acceleration Strategy Session here.]

Your freedom depends on your foundation.
Let’s make sure it’s strong enough to last.

Book A Call


Chad Free | CEO Black Diamond Money Moves

Chad Free

Chad Free | CEO Black Diamond Money Moves

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The information provided is for educational and informational purposes only and does not constitute tax, legal or investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon. You should consult your attorney or tax advisor.