Milestone map
Milestone map
3 milestones
Build a 3-piece portfolio and send first outreach
4 weeks
Publish three writing samples in a clearly defined niche (B2B SaaS, personal finance, health tech — pick one). Each piece should demonstrate the specific voice and depth the target clients need: word count matters less than showing you understand the audience. Publish on Medium, Substack, dev.to, or your own site with public URLs. Then define a per-word or per-piece rate and send the first 10 personalised cold emails to identified potential clients (editorial directors, content managers, or founders).
Proof required
Three published writing sample URLs with brief descriptions of their target audience and purpose, plus a log of 10 outreach messages sent with recipient, role, company, and date.
What gets checked
- Three samples published publicly with URLs, each targeting a specific audience
- Outreach log shows 10 personalised messages — different first paragraphs referencing the specific company
- Rate defined in writing before outreach begins
Common mistakes
- Writing about topics you find interesting rather than topics the client's audience needs — a portfolio that demos your interests rather than client-oriented writing rarely converts
- Targeting publications for bylines rather than clients who pay for content — getting published is different from getting paid
- Sending cold outreach with a vague 'I'm a writer' pitch rather than a specific 'here's how I can help you with [specific content gap]' message
Resources
Foundationstart here
Depthgo deeper
What a verifier looks for
- Open the three portfolio URLs and confirm they are publicly accessible writing samples
- Review the outreach log — confirm at least 10 messages with company-specific first paragraphs
Land a discovery call and submit a writing proposal
2 weeks
Convert a response from outreach into a discovery call to understand the client's content brief, target audience, voice guidelines, and deadline. After the call, submit a written proposal specifying the scope (article count, word count, topic, revisions), timeline, fee, and what is out of scope. For writing engagements, make explicit that research, interviews, or expert sources are in or out of scope — ambiguity here is the most common source of under-billing.
Proof required
Written proposal submitted to the client showing scope (piece count, word count per piece, topic), revision policy, timeline, fee, and a note confirming the discovery call occurred.
What gets checked
- Proposal specifies word count, piece count, topic, and revision rounds explicitly
- Research and source interviews are addressed as in or out of scope
- Fee and payment terms documented including whether a deposit is required
Common mistakes
- Agreeing to a broad 'help with content' engagement without defining the specific deliverables — this leads to ongoing unpaid scope expansion
- Not setting a revision cap — multiple revision rounds on a flat-fee engagement eliminate the engagement margin
- Quoting per-article rather than per-word for variable-length work, which creates incentive misalignment when clients add length
Resources
Foundationstart here
What a verifier looks for
- Review the proposal — confirm it specifies word count, piece count, topic, and revision cap
- Confirm research and interviews are addressed explicitly in the scope
Deliver a paid piece, receive payment, and confirm publication
3 weeks (engagement duration)
Complete the first paid writing engagement: deliver the agreed piece or pieces, receive payment, and issue an invoice. The ideal proof combines three elements: the invoice (service, fee, your details), the payment confirmation, and a published or client-approved URL of the delivered piece. If the client requires NDAs and the work cannot be shared publicly, a signed client delivery confirmation email substitutes for the URL.
Proof required
Invoice showing service description and fee, payment confirmation matching the invoice amount, and either a published URL of the delivered piece or a signed client delivery email confirming the work was accepted.
What gets checked
- Invoice shows service description, fee, and your name or trading name
- Payment confirmation matches the invoice amount
- Delivered piece is accessible via URL or confirmed as accepted in writing
Common mistakes
- Accepting payment via informal means (Venmo memo, cash) without an invoice — this is untracked income and a missed opportunity to build a professional paper trail
- Not following up when a client goes quiet after delivery — payment follows up, not just delivery; include a payment due date on the invoice
- Not asking for written confirmation that the work was accepted — this protects against disputes over scope compliance
Resources
Foundationstart here
What a verifier looks for
- Verify the invoice contains real professional fields (not a Venmo note)
- Confirm payment amount matches the proposal fee
- Verify the delivered piece URL is accessible or the client acceptance email is real and specific