Last summer I was barely scraping by working two part-time jobs and drowning in debt. One morning while scrolling golf forums I saw caddies in my area pulling $300+ per round. That got my attention real quick.
I started cold-calling every country club within driving distance. Most laughed me off the phone – turns out caddie jobs usually come through referrals. Finally got my foot in the door at Oakwood Golf Club when the head pro overheard me begging the assistant for any position available.
First week was brutal humiliation. Got assigned to some Wall Street dude who yelled “WHAT’S THE YARDAGE, ROOKIE?” when I blanked reading the pin sheet. He played Callaway Chrome Softs and I lost three balls in the fescue. Felt like burning my ugly bib overalls.
Started shadowing veteran caddies every weekend, studying their routines like a hawk:
- How they paced yardages walking diagonally across fairways
- That little clubhead wipe before handing over the putter
- The exact second to offer the towel without interrupting
Bought a cheap range finder and secretly mapped every sprinkler head at Oakwood. Memorized green slopes during twilight maintenance hours when nobody chased me off. Stuck Post-it notes all over my bathroom mirror with course knowledge until my roommate threatened to kick me out.
Big break came when I volunteered for senior championship week. Bag for a grumpy 70-year-old member who made me chart every shot in his yardage book. By the 18th green he slipped me two Benjamins and said “Kid, you read greens better than my bifocals”. Word got around.
Now I only take members who request me specifically. Key moves that built my client list:
- Always show up 45 minutes early with clean towels and tees
- Remember their drink orders from previous rounds
- Ask about their kids/spouse/dog by name
- Discreetly manage bets between players
Last month I cleared $600 on a rainy Tuesday carrying for two doctors who kept replaying the $50 Nassau. Still get nervous stepping onto the first tee sometimes, but walking away with seven crisp hundreds in my pocket? That panic attack feels real different now.
