The Sleep-at-Night Test: The Only Retirement Metric That Matters

Authored By: Nate Willardson, Managing Partner, Currents Wealth Strategies

In 2024, a client came to me with a decision that seemed straightforward on the surface: how should he pay for a new home?

He was in his early sixties, retirement was two years away, and he had the means to pay cash, take out a mortgage, or use a line of credit. He expected to sell an investment property within twenty-four months that would likely replenish whatever he spent. He wanted to know what the “correct” move was.

My training told me to start with the spreadsheet. I come from a long line of “number crunchers”. My grandfather was a CPA, my father worked in insurance, and several family members are financial advisors. My first instinct has always been to find the mathematically optimized outcome and present the result.

The case for keeping his capital invested was compelling. Mortgage rates were elevated and his portfolio was poised for growth. On paper, using leverage to purchase the home and leaving his assets in the market was the smarter financial move, especially with proceeds from the future investment property sale ready to retire that debt.

Then, I asked him a different question: “How would you feel carrying debt into retirement, knowing the market could drop 20% in the first year you stop working?”

He didn’t need to check a spreadsheet. He said it would keep him up at night. We both immediately knew what the right answer was.

He bought the home in cash.

The $500,000 Peace of Mind

About a year later, he called me. The market had performed exceptionally well. Because we had sold investments to fund the home, he had missed out on roughly $500,000 in gains.

That number is hard to ignore. But then he shared the best part: He hadn’t lost a single night of sleep.

That conversation reinforced a truth I’ve come to believe more firmly every year: the best financial advice is both an art and a science. A plan must be financially sound, but it also has to account for a category of risk that doesn’t appear in a Monte Carlo simulation. It’s the risk of not being able to stay the course.

Finance is deeply personal. If you are close to retirement, you’ve already done the hard part. You’ve saved, invested, and built something real. The question now shifts from “Do I have enough?” to “Does this strategy allow me to actually enjoy what I’ve built?” There is no virtue in optimizing every basis point of return if the anxiety required to do so costs you the retirement you spent thirty years working toward.

The “Sleep-at-Night” Test

If you are nearing retirement and wondering if your current strategy is right for you, run it through two distinct lenses:

1. The Spreadsheet Lens: What does the analysis actually say? You need the honest, mathematical answer, even if it’s uncomfortable. You must know the “cost” of your choices.
2. The Stress Lens: Can you live with this decision if things don’t go as expected? If the market turns, will you stay the course, or will the plan fall apart the moment you lose confidence?

If the answer to the second question is “no,” it doesn’t matter how good the spreadsheet looks.

My client couldn’t have told you exactly why carrying debt felt wrong. He just knew it did. That ‘feeling’ ended up being worth $500,000 to him, and he has no regrets.

The best financial outcomes don’t always come from the smartest strategies. They come from the right strategies, executed with confidence by people who are genuinely excited about what comes next – and who can sleep soundly getting there

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Author Bio: Nate Willardson, CFP® is the Managing Partner of Currents Wealth Strategies, a financial planning and investment firm that focuses on families preparing for retirement across the US.

With over a decade of experience managing portfolios for ultra-high-net-worth families at a world-renowned Private Bank, Nate now leverages that ‘insider’ expertise to help everyday investors navigate complex markets.

He is a specialist in comprehensive financial planning, investment strategy, and retirement readiness. Known for his commitment to transparency and a ‘people-first’ philosophy, Nate provides expert commentary on wealth management trends and personal finance.