Welcome to Contractor Diaries
a blog series that dives deep into the unpredictable, often absurd world of contract technical authoring. If you’ve ever wondered what it’s like working freelance in the world of tech documentation, you’re in the right place.
What Is Contractor Diaries?
“Contractor Diaries” is a series of true stories from my experiences as a contract technical author. It describes the challenges of starting a new role, receiving vague briefs, and striving to bring organisation to documentation chaos—while navigating through confused stakeholders, missing templates, and unrealistic deadlines.
Each entry blends humour, hard-earned lessons, and the kind of honesty you only get from years on the freelance front line.
What you’ll read?
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“The Brief That Lied” – Where a “quick update” turns into a 115-page rewrite with no time and no context.
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“Death by Template” – The joy of receiving a ‘template’ that’s actually just a blank Word file.
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“Stakeholder Hide and Seek” – The timeless game of trying to find someone, anyone, who knows what you’re supposed to be writing.
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You’ll also find:
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A mock client rating system (★☆☆☆☆: “Didn’t pay. Haunted project.”)
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A healthy mix of laughter, disbelief, and mild therapy
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Real insights into the work behind the writing — because “just update the document” is never just that
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Who Should Read This?
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Contractors and freelancers who’ve lived the madness (and can laugh about it)
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Permanent staff curious about the chaos we walk into
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Hiring managers who might wonder why the last writer left so fast
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Anyone who’s ever stared at a 100-page document and thought, “Nope.”
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💡 Why I’m Writing This
Because too many technical authors work in silence. Because every weird, frustrating, borderline-ridiculous project comes with lessons. And because sometimes, you need to know you’re not alone in thinking, “What is going on here?”
🛠️ Coming Up in the Series:
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The EPOS Fiasco – Where I was hired to VISIO a failing network and fired before I got paid.
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The Vanishing Stakeholders – Everyone said talk to James. No one knew who James was.
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The Sprint That Wasn’t – The agile project with no backlog, no board, no plan.
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⭐ Client Rating System (Because why not?)
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★☆☆☆☆ – Didn’t pay. Hostile Wi-Fi. Haunted project.
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★★☆☆☆ – Team ghosted me. Someone offered tea.
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★★★☆☆ – Project chaos, but good biscuits.
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★★★★☆ – Knew what they wanted. I left with dignity.
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★★★★★ – Clear brief. Paid on time. Left with snacks.
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🔔 Follow Along
New posts every couple of weeks (or whenever something traumatic happens worth retelling). Subscribe, bookmark, or drop by when your current project makes you question your life choices.
Do you have a horror story? Let me know. We can compare notes or cry into a shared Google Doc.