About hiring freelancers

A routine content update became a deployment nightmare when GitHub deprecated a critical artifact on which I depended. Every push triggered failures, leaving my website stuck in limbo.

After hours of troubleshooting with no success, I decided to take a step back and do what I’ve done many times before: turn to Upwork, my go-to platform for hiring freelancers. Within a few hours, an expert diagnosed and fixed the issue, all without me lifting a finger.

This wasn’t my first time outsourcing a technical challenge, and after spending over $7K on freelance talent, I’ve learned a lot—sometimes the hard way—about hiring the right people. Here are my biggest takeaways:

1. Be open to discovering hidden talent. It is relatively easy to discover hidden talent. Every freelancer starts with zero reviews, which makes it tough to compete with experienced pros. This can be a great opportunity to find skilled newcomers who charge low rates to build their reputation, but it also comes with the risk of sour experiences.

2. Avoid hiring unknown freelancers on open-ended hourly contracts. Such agreements require a higher level of trust and commitment from both parties, which should be built over time through smaller fix price projects first.

3. Learn trust, with boundaries. Giving freelancers access to systems, access tokens, or prototypes is sometimes necessary, but it should be done carefully. Use temporary credentials, limit permissions, and revoke access when the job is done. Trust grows through time, good communication, and reliability. Over time, a freelancer on the other side of the world can become just as dependable as someone in the same office.