Life’s Curveballs

May 20, 2026by Jon Dockery

As a dad and part-time baseball coach, I’ve spent countless hours on the field watching kids learn one of life’s toughest lessons: you can practice your swing for weeks, but when that curveball comes looping in, everything changes in a split second.

One moment the batter looks confident, the next he’s ducking or swinging wildly because the ball did something he didn’t expect. I tell my players and my kids the same thing every season: the great hitters aren’t the ones who never face an off-speed pitch – they’re the ones who’ve practiced their timing, adjusted their stance, and stayed ready for whatever the pitcher throws next.

Parenting and coaching have taught me that life works the same way. You’re cruising along, the kids are thriving, the career is steady, retirement plans are coming along and then wham. Life throws a nasty curveball. A surprise medical diagnosis. A job loss. A house fire or flood. A market crash that wipes out months of gains right when you need the money most.

After almost 30 years as a CPA and financial adviser, I’ve sat across the table from too many families when those curveballs arrive. And here’s the raw truth I’ve learned: It’s rarely the curveball itself that breaks people financially. It’s the lack of preparation.

You don’t have to live in fear. You can build a plan so solid that when life throws that nasty pitch, you stay in the game – and even swing back stronger.

These surprises often fall into three gut-punching categories:

  • Health Sinkers — Sudden illness, chronic conditions, or the staggering cost of long-term care
  • Income Changeups— Job loss, disability, divorce, or losing a breadwinner
  • Asset Cutters— Market crashes, natural disasters, lawsuits, or unexpected expenses that just won’t stop

The scary part: According to the Federal Reserve data, nearly 40% of Americans couldn’t scrape together $400 for an emergency without borrowing or selling something. Many families are one bad medical bill or layoff away from chaos.

When unprepared folks get blindsided, they make painful moves – draining retirement accounts, racking up credit card debt, or selling stocks at the absolute worst moment. But here’s what separates the families who bounce back stronger from those who don’t: They saw the curveballs coming and built a plan that could handle them.

Three Pillars of Curveball-Proofing

Here are three non-negotiable pillars I hammer home with every client:

  1. Build an Emergency Fund That Actually Saves You – An emergency fund is your safety net to avoid bad decisions caused by desperation.
    • Start by saving at least one month of take-home pay
    • Build towards 3-6 months of essential living expenses. If your income fluctuates a lot, a 9-month emergency fund might be a good idea to create peace of mind.
  2. Design an Investment Portfolio that doesn’t surprise you – Your investments shouldn’t act like a surprise curveball. Your portfolio should be built to achieve your goals in a way that doesn’t provide undue anxiety from lack of understanding or inaccurate risk tolerance. If you haven’t already, you should discuss the following topics with your financial professional:
    • Risk Tolerance
    • Asset Allocation
    • Diversification
    • Rebalancing
    • Regular Investing/Dollar-Cost Averaging
  3. Lock Down Your Legal Documents and Beneficiaries – Wills, powers of attorney, and beneficiary designations aren’t just for retirees. If you have kids, a house, or any meaningful assets, get them done — and keep them updated. Nothing causes more unnecessary stress and expense than outdated beneficiary designations or missing documents when emotions are already running high.

The Peace That Comes From Being Ready

Preparing for life’s curveballs isn’t about living in fear or expecting doom around every corner. It’s about freedom. It’s the deep confidence that no matter what life throws at you, you and your loved ones will be okay.

That peace of mind is worth more than any investment return.

Life will throw you curveballs. It’s not a matter of if but when. The only question is whether you’ll be ready to knock them out of the park or strikeout.

If any of these topics resonate with you, let’s schedule a 30-minute lesson to get your swing in good shape. Because the best time to get prepared is always right now, while there is still time left in the game.

Jon Dockery

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