Stop climbing. Start building.

What freelancing taught me about strategy, identity, and showing up.

In this week’s Copy THIS, we’re getting personal. I’m pulling back the curtain on my own “wrong ladder” career detour, why writers make better strategists than they’re given credit for, and how to stop hiding behind perfect plans so you can actually ship the work that builds your reputation.

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Ten years ago, on a train rattling into Melbourne - at what I considered the real start of my career - I used to play a little movie in my head.

In it, I wasn’t in trackies drinking a Nescafé coffee sachet (the poor man’s latte).

I was her:

• Power suit

• Corner office energy

• The calm centre of a creative storm

In my mind, she was on the same train. On her phone, but not scrolling. She was solving. Putting out fires. Approving campaigns. Answering questions from her team, and from the CEO - whose trust she’d finally earned.

The dream was simple: climb the corporate ladder and one day see “CMO” on a business card. Maybe even see my name on a speakers list at a conference.

Nowhere in the dream was I:

• Working from a couch covered in my toddler’s ballpoint pen art

• Taking client calls between laundry cycles

Freelancing was never the fantasy. It was the plot twist.

When the ladder you’re climbing isn’t yours

I’ve never been good at playing the corporate game.

Sure, I’d do the work. Take on extra projects. Do the late nights. Be helpful and supportive to my team and peers.

But I was never good at the politics. And I wasn’t afraid to tell someone if I disagreed with them - whether it was the client or the CEO.

Looking back, I can see I probably should’ve reined my opinions in a little. It’s no wonder my career went the way it did: a string of redundancies and bad culture fits that left me doubting my instincts and questioning my capability.

By the time the final redundancy came, the strongest feeling I had wasn’t shock.

It was relief.

Because I’d known it wasn’t right. I’d been trying to ram a square peg into a round hole. I didn’t fit, and no matter how hard I tried, I was never going to.

On paper, I’d done everything you’re meant to do:

• Different sectors

• Different titles

• More responsibility

• More money

• More experience

But it didn’t feel like a career. It felt like a pattern. I wasn’t on a path that led to becoming the CMO from my dreams. I’d spent years trying to prove I was more than “just a writer” - and in the process, I’d lost sight of what actually made me good at my job.

Admittedly, when the relief faded I did have a brief panic. How was I going to face the job market again? Endless job applications. Rejection. Ghosting. Interviews where I had to be switched on and pretend I knew exactly what I wanted. Coming up with explanations for the inevitable question: “Why did you leave your last role?”

I couldn’t bear the thought of it.

Thankfully, a friend asked if I’d freelance for her. “Just temporarily, while you figure out your next move,” she suggested.

She’d asked me in the past, but I’d always said no. I wanted to focus on my career - not split my focus. This time, though, something made me say yes. I mean, why not? I’d just be writing, after all. That was easy. I could do that in my sleep.

But we quickly found a rhythm, and the questions I asked throughout the process always made her head explode.

“How have I been surviving without you?” she asked me one day.

That’s when something in me finally clicked.

That’s when I remembered I was good at this.

At our next meeting, I decided to make a thing of it. To stop climbing a ladder that didn’t belong to me, and take my first step towards a path that fit me far better than the last one ever had.

I got on the call and said to her, “I’m all in.”

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Freelancing is not a field. It’s a maze.

If you’ve been freelancing or running your own business for a while, you probably know what I’m going to say next:

You go solo and immediately drown in your own potential.

Suddenly, you are:

• The strategist

• The writer

• The social media manager

• The salesperson

• The project manager

• The operations manager

• The entire board of directors of “You, Inc.”

You’ll work with anyone who pays you. You’ll do anything they pay you for.

It gets overwhelming fast. So you seek advice, and they tell you to “niche down” and “pick a lane.”

But what lane? You have so many ideas.

You:

• Could write launch sequences for SaaS

• Love brand voice work

• Secretly want to write a novel

• Have this idea for a membership

• Also this idea for a course

• Also keep rewriting your newsletter idea in your head instead of sending it

You build beautiful, intricate strategies in your drafts folder.

You polish offers that never see the light of day.

You write entire business plans in Google Docs that no one will ever read.

You spend so much time architecting the perfect, towering funnel… that you forget to send a damn email.

Ask me how I know.

I’ve failed at building things more times than I can count

Before Wordcraft. Before brand strategy. Before anyone paid me to write a word, I built blogs.

So many blogs.

LiveJournal. BlogSpot. Tumblr. Wordpress.

I taught myself HTML and CSS so I could make my MySpace profile look fancy.

I once ran an Aragorn & Arwen fansite on FreeWebs using images from the Two Towers that I definitely didn’t have permission to use.

Every few months, I’d burn it all down and start again.

The problem wasn’t the ideas. It was the follow-through. Each new site came with a flurry of urgency:

• New name

• New brand colours

• New “About” page

• New content plan spreadsheet

And then… nothing.

I’d overthink every post.

Convince myself it wasn’t good enough yet.

Avoid telling anyone it existed.

Get seduced by the next “better” idea.

If you zoom out, it looks like a series of failures. And it was. But those failures did teach me two things that now sit at the core of how I work with clients:

1. Perfect strategy is a very pretty way to procrastinate

2. Writers are already strategists. Most of us just don’t give ourselves enough credit.

The secret every copywriter forgets

Let’s be blunt: strategy has branding.

In our industry, “strategist” often looks like:

• Someone with a trademarked framework

• A 90-slide deck with funnel diagrams

• A Notion database so complex it needs its own onboarding video

And if you’re a copywriter who has been told you’re “creative” and/or “emotional” your whole career, it’s easy to unconsciously file yourself under:

“Words person. Not strategy person.”

But the truth is, when you make decisions about:

• What story to open with

• Whose pain you’re centring

• Which belief you’re challenging

• Where you want the reader to end up

…that is strategic work.

You might not have a 3-letter acronym or a pretty diagram for it (yet). But if you can take a messy, complex idea and turn it into something a stranger actually wants to read?

You’re already doing the kind of thinking brands pay “strategists” for.

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The real enemy of your growth? Not a lack of strategy

I’m gonna tell you why so much of your best thinking never leaves the drafts. Let me know if I’m onto something:

• You care.

• You care about the craft.

• You care about nuance.

• You care about being right and helpful and not just adding to the noise.

And because you care, you raise the bar so high that nothing you write feels “ready” enough to publish.

So your marketing presence becomes an accidental museum of almost-finished masterpieces.

Kind of ironic for someone who writes for clients for a living, right?

It’s not that you’re bad at marketing yourself. You’re just using perfectionism as quality control.

Try to remember:

• The perfect strategy that never leaves your drafts might as well not exist.

• The most memorable brands aren’t necessarily the ones with the best ideas. They’re the ones who ship the ideas they already have, again and again, in ways people get to see.

Build the plane in the air. You’re a writer. You’re allowed.

This is where freelancing, for all its chaos, is a gift. No board to convince. No CMO to get sign-off from. No committee to water things down.

It’s just you, your brain, your keyboard, and the people you want to help.

You can:

• Test a new offer with four clients instead of building the “perfect” sales page first.

• Send an email to 100 people instead of designing a 16-email funnel for no one.

• Write one strong story post on LinkedIn instead of creating a 90-day “visibility campaign” you’ll never commit to.

You’re allowed to:

• Start before you feel fully qualified

• Learn publicly

• Refine as you go

• Change your mind

You’re not a junior trying to impress a senior strategist anymore. You are the strategist.

Your job is not to sit in the tower and design the perfect route.

Your job is to get on the road.

So what do you do with this?

If you’re reading this with a knot in your stomach thinking:

“Okay, yes, this is me. I have 47 partial strategies and nothing consistently going out.”

Here is your homework. No funnels. No fancy dashboards. Just three decisions:

1. Choose one lane… for 90 days, not forever.

• Pick one primary offer you want to grow

• Pick one primary platform to show up on

• For 90 days, everything you share ladders back to that

2. Use your writing brain as your strategy brain

Before you post or send anything ask yourself:

• Who am I talking to?

• What belief am I challenging or reinforcing?

• What do I want them to think/feel/do by the end?

That’s your strategy doc. It lives in the sentences, not a slide deck.

3. Ship the 80% version. On purpose.

• Open that draft you’ve been polishing to death

• Give yourself one pass to tighten

• Hit send or publish

• Make a note of what you’ll improve next time instead of trying to fix it all now

Is this messy? Yes.

Is it risk-free? No.

Is it how actual, strategic bodies of work get made?

Absolutely.

Being my own boss hasn’t made my life easier

I still overthink. I still start too many things. I still get tempted by shiny “new lane” ideas.

But it has given me this:

• Ownership over strategy

• Permission to test in public

• The reminder that my job is not to build a perfect system

My job is to keep showing up with words that move the right people.

And that’s your job, too.

For you, and your clients.

You’re not “just” a writer.

You’re the person who turns fragile, half-formed strategy into something a human being actually wants to read.

That is rare. That is valuable.

And it is more than enough reason to stop hiding in your drafts and start sharing what you already know.

P.S. Reading this and thinking, “I need someone to sit next to me while I figure this out”? DM me here or on LinkedIn. I’ve got a few experiments on the go, and I can point you to what might fit.