A colleague once told me a story about his great-grandfather. He called it The Day My Great-Grandfather Fell. It goes like this.
When my grandfather was 9 years old, his father, my great grandfather, climbed onto the roof to make repairs. He couldn’t afford to hire a professional. He fell. He died.
He left behind my great grandmother, my grandfather, seven other children, and a lifetime of “what ifs.”
That’s one of the earliest and most painful examples of something I call DIY-itis: the belief that “If I can’t afford it, I’ll figure it out myself.” For many families, especially those with limited means, DIY isn’t a choice. It’s survival. But sometimes the cost of doing it yourself is far greater than money.
Research backs this up. One study found that wealthier individuals are significantly less likely to rely on DIY. Not because they’re incapable, but because they understand the power of outsourcing, delegating tasks to protect their time, energy, and safety.
Today, YouTube makes everything look doable: investing, financial planning, home repairs, even teaching children. Anyone can learn it in an hour… right?
But think about your own career. If you’re a seasoned educator or administrator, are you better today than you were with your newly minted college degree or State teaching certificate? Expertise takes years. And we’ve all seen the consequences when someone overestimates their ability. Like the well-meaning homeschooling parent whose child ends up one to two years behind.
Even for upper-middle-class families, there are moments when hiring help isn’t a luxury. It’s a smart investment:
✅ Working with a tax professional
✅ Using licensed experts for home repairs
✅ Engaging a financial planner for guidance and a long-term investment strategy
✅ Seeking legal or business support when needed
✅ Outsourcing repetitive tasks to free up time and reduce stress
DIY can feel resourceful. But sometimes, it’s what keeps families from moving forward. Or exposes them to avoidable risks.
Knowing when to seek help is a sign of strength, not weakness. And in many cases, it’s one of the best financial decisions you can make.
Stay safe
David Brown was the Chief Financial Officer/Business Administrator at Blanchard Memorial School, Groton School, Alexander Dawson School, Rippowam Cisqua School, and Portsmouth Abbey & School over a 23-year school career. During that time, he advised and/or helped heads and administrators assemble and negotiate benefit packages that would ensure a comfortable life through “end of plan”. For over 10-years Dave has helped his clients effectively plan, save, and invest to and spend appropriately through retirement.
For personalized financial planning and/or investment guidance, contact Clear Skies Planning & Wealth Strategies at www.clearskieswealthplanning.com or directly at 720-833-8611.
Clear Skies Planning & Wealth Strategies, Inc provides advisory services through XY Investment Solutions, LLC, an SEC registered investment advisor. All views included in this communication are subject to change. Please contact Clear Skies Planning & Wealth Strategies to receive a copy of our Form ADV and other disclosure information.