"I Didn't Quit Teaching Overnight — And That Was the Best Decision I Ever Made"

There's a myth about leaving teaching that goes something like this: one day, you decide you're done. You hand in your notice, pack up your classroom, and start something completely new. Clean break. Fresh start. Off you go.

It sounds neat. It sounds decisive. But for most of the teachers I work with, it's not how it happens at all — and honestly, it doesn't need to be.

Some of the most successful VAs I know didn't leap out of teaching. They stepped. Quietly, deliberately, one foot at a time. And the result? They built businesses they actually felt confident in, without the financial panic that comes from cutting off your salary overnight.

Here's what that looked like for five real people.

Sarah: building something alongside teaching

Sarah had always admired entrepreneurs, but never imagined she'd actually become one. After years in the classroom, she reached a point where she knew full-time teaching wasn't sustainable anymore — but she didn't need to walk away from it entirely to find something better.

Now she runs her own VA business part-time, alongside teaching. She cherry-picks the creative work she loves, sets her own boundaries, and is building something that genuinely excites her. As she put it herself: "Everything I put in, I know I'm building something."

That's not someone who made a dramatic exit. That's someone who built a door and walked through it quietly, at her own pace.

Georgia: the portfolio career in action

Georgia's story is a brilliant example of what a portfolio career can actually look like. A Primary and Early Years teacher with a passion for R.E., she wasn't just tired of teaching — she was tired of missing out on the life she wanted. The family time. The energy. The ability to drink a cup of tea while it was still hot.

She found her way to a Regional Advisor role for an education group — working remotely, using her subject specialism, doing work she genuinely loves. But that wasn't the whole picture. Alongside that, Georgia built her VA business, Georgia Alice VA, through our Teacher to VA programme. Now she's balancing freelance work with her part-time role, and the two sit together naturally.

Georgia didn't have to choose one thing. She chose the right combination of things — and it works.

Rachel: starting slow and letting it grow

Rachel didn't put all her eggs in one basket either. She kept a part-time self-employed contract as an initial teacher training tutor while she started taking on her first VA clients. It meant there was no financial pressure to make the VA business work overnight — she could just let it breathe and develop.

It did develop. Quietly at first, then more and more. Eventually Rachel found herself in the opposite position — the VA work had grown so much that she needed to scale back the tutoring to keep up. She didn't plan it that way. She just gave herself permission to start small, and the rest followed.

Nicola: running her business during school hours

Nicola was in performing arts teaching for fourteen years. When she decided to make a change, she didn't disappear from education overnight. She ran her VA business alongside part-time teaching for a full year before stepping away completely. Now she focuses on tech operations and Google Workspace — and she does it all during school hours, fitting her working day around the rhythm she's used to.

The point is, Nicola knew her own pace. She didn't rush it, and she didn't need to.

Julie: proving it's never too late

Julie was sixty when she joined our programme. A former headteacher, she brought decades of experience and a sharp sense of what she wanted — and what she didn't. She wasn't looking to replace her income entirely. She was looking for something engaging, flexible, and genuinely hers to build, alongside her teachers' pension.

That's exactly what she's doing. Julie is building her VA business at a pace that suits her life, and she'd be the first to tell you: it's never too late to start something new.

Why this matters

The point isn't that there's one right way to do this. The point is that you don't have to choose between financial security and freedom. A portfolio career — a mix of teaching, VA work, tutoring, or other part-time roles — isn't a compromise. It's a strategy. And it's one that gives you time to build confidence, test what you enjoy, and work out what actually fits your life.

Teaching gave you an extraordinary set of skills. The way you organise, communicate, problem-solve, write, and manage — all of that travels with you. It doesn't have to go somewhere all at once. It can go somewhere a little bit at a time, and that's often where the magic happens.

Thinking about it?

If you're at the stage where leaving teaching feels appealing but the idea of just... doing it... feels too big, you're not alone. And you don't have to figure it out in one go.

We're hosting a free VA Q&A session on Monday 16th February — a relaxed, no-pressure live session where you can ask anything about what this kind of transition actually looks like. Our graduate VAs will be there to share their honest experience, including the messy, in-between bits.

SIGN UP HERE

Whatever stage you're at, it's worth a listen.

Jo 🧡