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The Freelancer as a One-Person Agency: Brand and Business as a System

25 prompts from this guide. Fill in whatever sits in [square brackets] — your own context, the document text or the name of your tool. That context is exactly what separates a generic answer from a usable one.

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What to gather, and where to look

I'm doing an inventory of my freelance business. I'm a [graphic
designer, 5 years of experience, visual identities and packaging for
small businesses]. I'm uploading: [an old CV, a project export from
Behance, 3 client presentations, text from my website] and here's
what I can't upload but can describe: [an Instagram portfolio — about
40 posts, a price list that only exists in my head, invoices spread
across three tools].

Build the inventory as four lists:
1. Finished projects — every one you can identify from the materials:
   name, client (if given), year, what it was about. For each one,
   note whether I also have an outcome or client reaction, or only
   images.
2. References and compliments — anything in the materials that reads
   like an assessment of my work.
3. What the materials say about me — the services I offer, the types
   of clients, what sets me apart. Write only what's actually
   supported by the materials.
4. Gaps — what you think I should have and don't have anywhere:
   missing outcomes, projects with no samples, outdated details in my
   CV.
Don't guess at anything; where you're not sure, write a question
mark.

Mining references from email

Go through the uploaded email threads with clients [or: search my
email, threads with clients X, Y, Z over the last 3 years]. I'm
looking for two kinds of sentences:
1. Outcome assessments — anything where the client says the work
   works, served its purpose, is liked, or delivered results.
2. Referrals — mentions that the client referred me to someone, or
   who a new inquiry came from.
Return a table: client, date, verbatim quote (don't shorten or
smooth it out), one-sentence context, which project it relates to.
Don't paraphrase anything — I need the exact wording, since I'll be
using it later with the clients' consent.

Getting the price list out of your head and onto paper

Help me get my price list out of my head and onto paper. I'm a
[freelance graphic designer]. Ask me one question at a time and
build a structured price list from my answers as we go. Find out
from me:
- what services I actually sell (not what I'd like to sell) and
  exactly what each one includes
- how I charge for them: a fixed package price, hourly, price by
  scope
- what I charged for each service on my last 3 jobs — a range is
  fine if I don't remember exactly
- what's not included in the price and gets billed separately (extra
  print-ready files, an additional round of revisions, font
  licenses, a rush fee)
- what I always hesitate over and why
At the end, give me back: a list of services with a description, a
price range, and a note on what's included and what isn't. List any
contradictions in my answers separately — don't resolve them for me.

Distilling from your own writing

I'm uploading 12 pieces of my writing: emails to clients, two
proposals, and project descriptions [insert]. Distill my personal
tone from them into a document, brand-voice.md, with this structure:
1. Who I am and who I'm talking to (2 sentences, no marketing
   adjectives)
2. Tone: 4-5 traits. For each one: what it means in practice, and a
   verbatim sentence from my writing that demonstrates it — quote it,
   don't invent it.
3. Vocabulary: words and phrases I use (including jargon), how I
   address people (formal/informal), how I write numbers, deadlines,
   and prices.
4. Banned phrases: what never shows up in my writing even though it's
   common in the field — and what I clearly wouldn't write, based on
   the sample.
5. Examples: 3 "not like this / like this" pairs for replying to an
   inquiry, handing off finished work, and following up on an unpaid
   invoice.
Work only from the uploaded texts. Where the sample isn't enough,
write an open question at the end — don't decide for me.

The “what I don't promise” section

Add a "What I don't promise" section to my brand voice document. Ask
me one question at a time and work the answers in. Find out:
- when I last promised something I regretted (a deadline, scope,
  availability) and exactly how that sentence went
- how fast I actually respond to messages, and when I'm unavailable
- what clients typically want me to "just quickly throw in" that I
  don't want to do (e.g. a logo in a day, managing social media,
  arranging cheap printing)
- how many rounds of revisions are in my prices, and how I say the
  next round costs extra
- what I do when a client wants a change that would make the work
  worse
For each boundary, also draft a polite sentence in my tone that I can
use to tell the client — I need it ready in advance, not improvised
under stress.

A stress test on uncomfortable situations

Here's my brand voice document [insert]. Write three texts based on
it:
1. Turning down a job that doesn't fit me (a small budget, a field I
   don't work in) — in a way that leaves the client comfortable
   recommending me further.
2. A price increase for a regular client starting next year.
3. A reply to a client who "doesn't like" the finished work but has
   no specific feedback.
For each text, add your reasoning: which rules in the document
pulled against each other and how you chose. Those are exactly the
spots we'll sharpen in the document.

Converting the inventory into data

From the inventory of my projects [insert the output from phase 1,
or upload the materials again], create a file portfolio.yaml. Schema
for each record: id, name, client, publish_consent (set to "no"
everywhere for now — I'll fill it in myself), year, service, tags,
problem, solution, outcome, quote, quote_source, images.

Rules:
- write problem and solution from the materials; where the materials
  are silent, leave the field empty with a TO FILL IN note — don't
  guess at anything
- fill in outcome only where it's actually supported by the
  materials; "the client was happy" is not an outcome
- quotes only verbatim from the materials, with the source noted
- suggest tags consistently across projects (15 distinct tags total,
  max), so I can filter by them
At the end, print a summary: how many records are complete, and how
many are missing a problem, an outcome, or a quote.

Filling the gaps: a project without an outcome is just a picture

From portfolio.yaml, pick projects missing an outcome or a quote
that are less than 3 years old. For each one, draft a short email to
the former client, in my tone per brand-voice.md:
- a one-sentence reminder of the collaboration
- 2 specific questions tailored to that project: what the work
  delivered (numbers, if they have them, but also just "does it
  still work?"), and whether I may show the project with their name
  in my portfolio
- no pressure, no deadline
Return the emails as drafts for me to review. Don't send anything.

The repository: where everything lives

Set up a private git repository, solo-system, with this structure:
portfolio.yaml, pricing.yaml, cv.yaml, brand-voice.md, folders
templates and images [attach the files from the previous steps].
Convert my CV [insert] into cv.yaml with this schema: experience
(from, to, role, client/company, what I did, outcomes), education,
skills, tools, languages, contacts. Add a README with the rule that
this repository is the single source of truth — the website, CV, and
proposals are all derived from it, and changes happen here, not in
the outputs. Add a .gitignore for .env files and working exports.
Before the first commit, print the complete list of files to be
committed so I can check that it doesn't contain contracts, invoices,
or anything with clients' personal data.

CV to PDF: one truth, several versions

Generate my CV as a PDF from cv.yaml and portfolio.yaml. Process:
1. Draft the content for one A4 page: a header with contact details,
   3 sentences about me in the tone of brand-voice.md (no "creative
   professional"), experience, a selection of 4 projects from the
   portfolio — take only ones with publish_consent: yes and a filled
   in outcome, ordered by relevance for [recipient: e.g. a tender for
   a city library's rebrand], skills and tools.
2. For each selected project, one sentence: what the problem was and
   what the solution delivered — numbers from the outcome field,
   don't round anything up.
3. Show me the text draft for approval. Only then typeset it as a
   PDF: clean typography, one page, no photos, no skill bar charts.
Save the typesetting source file alongside the PDF, so next time we
only change the data.

A personal website on Vercel that reads YAML

We're building my personal website (see the guide we used to set up
the project). Key requirement: the website has no text of its own
about projects. At build time it loads portfolio.yaml and
pricing.yaml from the solo-system repository and generates:
- a projects page: only records with publish_consent: yes; for each
  one, the problem, solution, outcome, and images
- a services page from pricing.yaml: descriptions and what's
  included, but no amounts — I'm not putting prices on the website,
  they belong in proposals
- an about page from cv.yaml and brand-voice.md
Propose the simplest way to get data from solo-system into the
website project and keep it updated, explain it to me like I'm not
technical, and wait for my approval. Write the website copy in the
tone of brand-voice.md.

Case study: the story that (almost) writes itself

Write a case study from this portfolio.yaml record [insert the
record] and the attached project materials [the brief, a few emails,
notes]. Structure: context — problem — process — solution — outcome.
Tone per brand-voice.md. Rules:
- keep it under 600 words; shorter is better
- every number and quote must come from the record or the materials;
  don't calculate anything I didn't give you, don't round up, don't
  add superlatives
- include one real dead end from the materials in the process
  section, if there is one — and explain why we backed out of it
- where information is missing, leave a TO FILL IN note in the text
  with a question for me, don't invent anything
Also return a list of 3 spots you think are weakest and could use an
extra number or quote from the client.

A consistency check: outputs against the source

Compare the derived outputs against the source of truth in
solo-system:
1. Website: does the project copy match the current portfolio.yaml?
   Is there a project on the website whose publish consent has since
   expired?
2. CV (the last PDF generated): does the experience and project
   selection match cv.yaml and portfolio.yaml?
3. Case studies: do any numbers in them mismatch figures that have
   since been refined in the records?
Return a table of differences: output, location, what the source
says, what the output says. Don't fix anything — I'll decide whether
the outdated one is the output or the source.
Don't report "all clear" until you've stated how many items you
compared.

Putting it together: the system assembles, the human decides

An inquiry has come in [insert the full inquiry email]. Draft a
proposal from my sources: portfolio.yaml, pricing.yaml,
brand-voice.md including the "what I don't promise" section, and the
case studies folder.

Structure: summary of the brief in my own words — proposed solution
and process — 2-3 relevant samples — scope and what's not included —
deadline — price and terms — next step.

Rules:
- pick samples by tags and similarity to the problem, only projects
  with publish_consent: yes; for each one, one sentence with the
  outcome and a quote if one exists — never invent references
- build the price exclusively from pricing.yaml and itemize what it's
  made of; where the price list doesn't cover the inquiry, write
  QUESTION and leave the decision to me
- don't propose a deadline — leave the field blank, I'll fill it in
  based on my calendar
- scope: explicitly list what's not included in the price, per the
  notes in the price list
- never promise anything from the "what I don't promise" section
- wherever the inquiry is unclear, write a list of clarifying
  questions for the client — I might send those instead of a proposal
Return the draft and a separate list of QUESTIONS for me.

A check before sending

Check this final proposal [insert] before I send it:
1. Promises: list every sentence that promises something (deadline,
   scope, outcome, availability), and compare it against the "what I
   don't promise" section and against what's in scope.
2. Numbers: does the price add up? Do the line items match the price
   list? Did an amount from a previous version get left in the text?
3. Names: is there a name of a different client left over from a
   past proposal?
4. Tone: sentences that don't sound like brand-voice.md.
Return the findings as a table. Don't rewrite anything.

Three tiers: a proposal that doesn't get rejected as a whole

Restructure this proposal [insert] into three tiers based on my price
list:
- BASE: the smallest option that genuinely solves the client's
  problem — not a stripped-down version I'd be embarrassed by
- RECOMMENDED: the scope I'd advise the client to pick if they asked
  — label it that way in the proposal too, and explain why
- EXTENDED: whatever makes sense on top, only if it genuinely makes
  sense for this type of client; if it doesn't, return just two
  tiers and say so
For each tier: what's included, what isn't, the price from the price
list, and leave the deadline blank. The differences between tiers
must be in scope, not quality — no "the base version will be worse."

The Notion MCP: what it can do at the time of writing

Set up a database called "Inquiries" in Notion (in the page I've
shared with the connector). Columns:
- Client (text), Contact (text), Referral source (text)
- Service (select — pull the values from my pricing.yaml [insert the
  list of services])
- Stage (select: inquiry / proposal / job / invoice / reference /
  lost)
- Estimated value (select: S / M / L — I'm not putting amounts into
  Notion)
- Last action (text + date), Next step (text), Next step — date
  (date)
- Notes (text), Proposal link (URL)
Also create views: "This week" (next step within 7 days, sorted by
date), "Waiting on me" (next-step date in the past), and a board by
stage. Add 2 sample rows so I can see how it works, and I'll delete
them myself afterward.

Logging an inquiry: the agent proposes, the human confirms

A new inquiry has come in [insert the email]. Prepare a draft record
for the Inquiries database: pull out the client, contact, source (if
they mention who referred me), suggest a service based on my price
list, stage "inquiry," estimated value S/M/L based on scope, and for
the next step, suggest what I should do and by when — usually
respond within 24 hours, or send clarifying questions.
Show me the whole record for approval. Only write it to Notion after
I confirm. If you find the same client in the database from before,
flag it for me and remind me what happened with them.

The weekly review: ten minutes that hold the system together

Go through the Inquiries database and prepare a weekly review:
1. WAITING ON ME: rows with a next-step date in the past or this
   week — sort by age, oldest overdue items first.
2. NO MOVEMENT: rows in the inquiry or proposal stage where the last
   action is older than 10 days.
3. UNFINISHED: jobs in the invoice or done stage that never moved
   into the reference stage.
4. THE PICTURE: how many items are in which stage, and what's
   changed since last week.
For each item in points 1-3, suggest a concrete next step in one
sentence. Don't write or send anything — this is material for my
Monday quarter-hour.

Follow-up discipline: the most expensive hole in a freelancer's budget

From the weekly review, take the items where the next step is a
follow-up, and draft an email for each one per brand-voice.md.
Rules:
- no "just following up" and no apologizing for writing; always bring
  a reason for the contact: an additional idea for the proposal, a
  question, news related to their project, or simply a clear offer
  of a next step
- the first follow-up short (3-4 sentences), the second even shorter,
  with a calm sign-off that I'm leaving the proposal open
- for reference requests, suggest 2 specific questions tailored to
  the job, so the client doesn't have to compose an essay
Return them as drafts. I send them myself, and after sending I'll log
the last action and next step in the CRM.

Customers and products: the price list, take two

Prepare setting up my services in Stripe (in the sandbox for now).
From my pricing.yaml [insert], propose a structure of products and
prices: which service becomes a product with a fixed price, where a
per-unit price makes sense, and what gets invoiced individually
(don't create a product for those — the invoice will have its own
line items). Show me the proposal as a table: product, price,
currency, note. Once I approve, create the products and list exactly
what you created. Don't create customers yet — they'll be created
one at a time, as I invoice each one for the first time.

Invoice: the agent prepares the draft, the human finalizes

The [client] job from the Inquiries database has reached the
milestone [50% deposit / completion]. Prepare an invoice in Stripe:
1. Find the customer by email [client's email]; if they don't exist,
   propose creating them with details from the CRM and wait for
   confirmation.
2. Build a draft invoice: line items based on the proposal
   [link/insert], prices from the products we already set up; break
   out individual line items separately.
3. Payment terms [14] days, and note the order/PO number in the memo
   if the client gave one.
4. Do NOT finalize or send the invoice. Show me a complete preview:
   line items, amounts, total, tax treatment, customer details.
I'll finalize and send it myself in the Stripe dashboard after
reviewing it.

Payment link: the fastest route to a paid deposit

Prepare a payment link for a deposit on the [description] job for
client [name]: amount [insert], payment description reading "Deposit
— [service], [client]." Set it up so they see a confirmation with my
name and contact info after paying. Return the link to me for review
along with a preview of what the client will see — I'll insert it
into the email myself. Then draft a CRM update: last action "payment
link sent," next step "verify payment" in 5 days.

The reading side: an overview that replaces scrolling through your bank

Give me a monthly financial overview from Stripe (read-only, don't
change anything):
1. Paid invoices and payments over the last 30 days — amounts,
   clients.
2. Overdue invoices: how many days, what amount, which client.
   Compare against the Inquiries database and flag anywhere the CRM
   says something different (stage "invoice" but actually paid — or
   the other way around).
3. Open invoice drafts older than a week — what did I forget?
4. Unpaid payment links older than 10 days.
For points 2 and 4, suggest a next step for the CRM and a reminder
text per brand-voice.md — a payment reminder is exactly the email I
hate writing. I'll send it myself.

Security: money, contracts, and other people's data

Run a security review of my system:
1. Go through the git history of the solo-system repository: look
   for anything that resembles a key, a password, a contract, or
   clients' personal data — including old commits.
2. List which connectors I have connected (Notion, Stripe, email...),
   with what permissions, and flag any I haven't used in the last
   quarter — candidates for disconnecting.
3. Check portfolio.yaml: are there projects with publish_consent: no
   showing up in any public-facing output? Is any consent missing a
   date?
4. Remind me to check active OAuth sessions in my Stripe settings and
   deployment protection in Vercel — list exactly what to click and
   where.
Sort the findings by severity, don't fix anything without my
approval.

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