The Path Isn’t Linear: Redefining Success When You Step Away from the 9–5

By Shannon Kate Murray, Editor of High Flying Design

“Wait… you’re not working?”

My friend - a PA in the finance industry by day and a makeup artist on the side - was winding down her contract. She wasn’t scrambling for the next role. She planned to take a month off. Her plan? Space. Rest. A reset.

But the reactions caught her off guard:

“You’re not applying for anything?”
“So what’s the plan?”
“Wait… you’re just not working?”

Freedom, it turns out, makes some people uncomfortable - especially when it disrupts the script.

The Script We’re Given

Get the good job. Marry the partner. Buy the house. Work hard. Be sensible. Stay safe.

Many of us follow the path. We do what we’re told will lead to fulfilment - and yet so many feel stuck. You hear it everywhere now, especially in quiet corners of the internet: women whispering that the job they worked so hard for is draining them. That the dream they chased is feeling more like a deadline. That they're building lives they no longer want to live in.

It’s not just burnout. It’s a kind of emotional claustrophobia - the slow realisation that ticking the boxes hasn’t led to the freedom we were promised.

Why It Feels Riskier for Women

When a man leaves a corporate job to freelance or launch something new, he’s often called bold. Visionary. Entrepreneurial.

When a woman does the same? People ask if she’s sure. They wonder when she’ll go back. They assume something went wrong.

That’s not just perception - it’s systemic. The Alison Rose Review of Female Entrepreneurship (2023) found women are 55% more likely than men to cite fear of failure as a barrier to starting a business. We’re encouraged to be reliable. Modest. Risk-averse. To trade freedom for security - even when the security is suffocating.

And when you step away from the script, people notice - not always kindly.

If you’re experiencing this, remember that people tend to react to change through the lens of their own fears. When you choose pause, freedom, or uncertainty, it can unearth something in them - a quiet wondering, maybe, of what they’ve denied themselves.

The Quiet Unlearning

To give High Flying Design my full-time attention, I left a stable, well-paying role in marketing and operations. It was a job people work years to land. On paper, it made sense to stay.

But something in me was ready for a new chapter. I just didn’t realise how much I’d need to unlearn.

Like many women I know, I felt I needed a “bridge job” - some kind of freelance work to make it look like I hadn’t really left. Something to prove I was still productive. Still responsible.

Because deep down, I believed this:

If it doesn’t look like a job, it doesn’t count.

But the truth? I’d already built something that mattered. A magazine. A platform. A space for women growing bold, beautiful businesses in their own way.

What I hadn’t built yet - was the trust in myself to let that be enough.

Therapists call this transition identity detachment - a grief process, of sorts. You’re letting go of the version of you who was rewarded for being endlessly reliable, endlessly available. It’s not a breakdown. It’s a recalibration.

What if Success Looks Different?

Success doesn’t always look like a title or a paycheck. Sometimes, it looks like peace.

It looks like:

  • Purpose instead of pressure

  • Rest instead of reactivity

  • A slow build instead of a sprint

You hear it in quiet stories: from women who say they don’t hate work - they just hate how worn down it makes them feel, and from women who feel so stuck they worry they'll never leave. These aren’t rare stories. They’re everywhere once you start listening. They’re what happens when smart, capable women realise they want something more - and decide not to wait for something to change on its own.

If You’re in the In-Between

You don’t need a new title to be doing something real. You don’t need full-time income to deserve space. You don’t need to explain your pause.

That pause? It’s not an accident. It’s not a gap. It’s a gateway.

If your dreams look quieter, softer, or freer than what you were taught to want - you’re not behind. You’re just beginning something different.

Most people won’t understand your vision until it’s working. So don’t wait for their permission to start.

A Quiet Permission Slip

So go ahead:

  • Take the pause.

  • Launch the project.

  • Publish the piece.

  • Build the thing.

The path less linear isn’t less valid. It just belongs to someone brave enough to design it.

And maybe - that’s exactly what you’re here to do.

And if you are, I’m so excited for you!

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