Pros
Since your job is to help rich people relax, the environment itself is often relaxed. Caddymaster was often reasonable. Ample opportunities to network with the golfers (who frequently had established connections to individuals, companies, or industries). High rate of Evans Scholarships received. Rich people pay well, and Honor caddies often made upwards of $150 per loop.
Kontras
Caddymaster could be slow to promote. Reflects many social and institutional issues. As expected in service jobs, respect from the golfers could vary wildly, negatively. Typical to caddying, you were expected to work in any weather condition as long as the course was open, regardless of heat, rainfall, etc. Closing the course, temporarily or for the day, was a high bar. Working for rich people can be emotionally draining. Being a caddie from a marginalized community (women, African American, hispanic) led to different experiences, such as uncomfortable situations for women or hispanic caddies. There were hardly any African American caddies or golfers.