As your letter writing side hustle grows, you’ll need help to handle more orders without burning out. Hiring assistants allows you to scale your income while working fewer hours.
This guide covers:
✔ When to hire your first assistants for letter writing
✔ Where to find reliable writers
✔ How to train them to match your quality
✔ Pricing strategies when outsourcing
Signs You’re Ready to Hire Help
You should consider hiring when:
- You’re turning down orders because you’re overwhelmed
- You’re working more than 20 hours/week on letters
- Your monthly revenue exceeds $3,000+
- You want to focus on growing the business (not just writing)
Types of Assistants You Might Need
1. Handwriting Assistants
- Role: Writes letters in a style similar to yours
- Best For: Keeping the “handwritten” personal touch
- Where to Find:
- Calligraphy Facebook groups
- Local art schools
2. Virtual Assistants (VAs)
- Role: Handles emails, orders, and customer service
- Best For: Freeing up your time for high-value tasks
- Where to Find:
- Upwork
- OnlineJobs.ph
3. Shipping Assistants
- Role: Packages and mails letters
- Best For: If you sell 50+ physical letters/month
- Where to Find:
- Local part-time job boards
- Family/friends (trusted helpers)
Step-by-Step Hiring Process
1. Define the Job Clearly
Write a simple job description:
- Tasks (e.g., “Write 10 love letters/week in cursive”)
- Requirements (e.g., “Neat handwriting, responsive”)
- Pay Rate (e.g., “$3−5 per letter”)
2. Test Applicants Before Hiring
- Give a paid trial task (e.g., “Write one sample letter”)
- Check for:
- Handwriting consistency
- Attention to detail
3. Start with Part-Time Help
- 1-2 assistants at first
- Increase hours as your business grows
Training Your Team
1. Create a Style Guide
Include:
- Tone (romantic, professional, etc.)
- Formatting rules (margin size, ink color)
- Common phrases you use often
2. Record Video Tutorials
- Show exactly how you write letters
- Demonstrate packaging & shipping
3. Set Up Quality Control
- Review every 5th letter at first
- Use Google Forms for assistants to submit work
Pricing Adjustments When Outsourcing
| Your Old Price | Assistant’s Cost | New Price |
|---|---|---|
| $50/letter | $10 labor | $60−70 |
| $120/letter | $20 labor | $140−150 |
Key: Increase prices slightly to cover labor costs while keeping profits high.
Managing Assistants Long-Term
✔ Pay on time (use PayPal or Wise)
✔ Give feedback weekly (keep quality consistent)
✔ Offer bonuses for top performers