Side Hustle School Ep. 3324 - Failure Friday: “My virtual assistant was a fan of quiet quitting…”
Feb 6, 2026
Jack, who runs an advisory side business while working in finance, shares a Failure Friday story about hiring a virtual assistant who ultimately quit. He describes early success, a slow decline he missed, missed appointments and email errors. The conversation, quit, and recovery lead to lessons on onboarding, accountability, and the need for ongoing oversight when delegating.
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Delegation That Quietly Fell Apart
- Jack hired a virtual assistant from Upwork who seemed great for the first three weeks but then stopped doing work.
- He discovered missed tasks, typos, and missed appointments after digging in and the assistant eventually quit.
Keep Communication Visible To You
- Avoid routing important communications only to your assistant so you retain visibility into operations.
- Check work samples and systems regularly instead of assuming everything continues smoothly.
Schedule Ongoing Check-Ins
- Do maintain regular check-ins and ongoing accountability when you delegate tasks to contractors.
- Provide support and hand-holding longer than the first week or two to prevent lapses.
