The Power of Carrying the Bag – Lessons from Caddying

In both construction and life, success often comes down to the details we overlook. One of the biggest lessons I’ve learned comes from an unlikely place—watching a friend caddy.

My buddy, a professional golfer, missed the cut in a tournament. Most would sulk, practice alone, or maybe unwind with a drink. But he did something different—he offered to caddy for another player who consistently ranked at the top. Why? To learn. To observe how this guy thought, played, and handled pressure.

That small decision changed everything.

While caddying, he noticed the guy’s putting routine. Instead of obsessing over long putts, he drilled two- to three-foot putts—the “free throws” of golf. He wasn’t chasing perfection in low-probability shots. He focused on what truly mattered—the high-percentage shots that could make or break a round. This wasn’t just about golf. It was about mastering the fundamentals.

In business or as a contractor, how often do we focus on the flashy projects, chasing the big wins, while neglecting the basics?

• Do we obsess over landing the next big client, but forget to follow up with existing ones?

• Do we pour hours into perfecting proposals but skip simple site inspections that could prevent costly mistakes?

It’s not glamorous, but it’s the small things that stack up.

The real question is: Who are you willing to caddy for?

Is there someone in your industry who’s outperforming you? Instead of viewing them as competition, what if you reached out, asked questions, or even observed their process? In construction, this could be shadowing another builder, exchanging insights over lunch, or just being open to learn from someone with a different approach.

The lesson? Master the fundamentals. Be willing to carry the bag, even if you think you’ve got the skills. Because sometimes, watching from the sidelines teaches you more than being in the game.