How I Got Started as a Virtual Assistant in 1999
What Might Be Holding You Back?
What’s really stopping you from starting your VA business? I’ve heard every version over the years — and, truthfully, I’ve lived most of them myself. Some new VAs tell me they don’t feel confident. Others worry they’re not good enough, or that they’ll never get clients. (Stay tuned to the blog in coming months for more tips on getting and keeping clients!)
Many hesitate because they don’t know how to market themselves or how to find time to build a business while still holding down a job and caring for kids. And then there’s that sneaky inner voice whispering fears about failure, success, and everything in between.
If any of that sounds familiar, you’re not alone. These fears were around in 1999 when I started my VA practice, and they’re still popping up for new VAs today. But let me share how I got started — because while the technology has changed dramatically, the mindset required hasn’t.
First Things First — What Are You Really Building?
Before we dive into my story, it’s worth asking yourself why you want to become a Virtual Assistant. It sounds like a simple question, but over the years I’ve found it’s actually the one that determines who goes the distance and who burns out quickly.
Are you starting a VA business because you want to be your own boss? Because you value autonomy, flexibility, time with your kids, or the freedom to run things your way? Or are you looking to earn a bit of extra income on top of your full-time role? There’s nothing wrong with wanting additional income — but that’s not the same as wanting to run a business.
The Virtual Assistant industry settled on a definition very early on:
A VA is a business owner — a highly skilled, independent professional who provides remote administrative, technical and/or creative support services to clients locally, nationally, or globally.
If you’re only dipping a toe in to make some side income, that’s not a business. It’s a hobby. And while hobbies are lovely, they come with an employee mindset that will keep you stuck. If your long-term goal is to work for yourself, then from the very beginning you must think and act like a business owner. You can absolutely keep a part-time or casual job while starting out — I recommend it. But don’t confuse casual work with a full-time commitment to business ownership.
Kathie Thomas wrote an excellent article on how not everyone can be a VA. Find it here and maybe give it a read before you take the leap.
My Story: How It All Began (With a Baby, a Mortgage, and Zero Guarantee)
Before I became a VA, I was an executive PA. I’d spent years working my way up through the legal sector — including criminal law — and later in hospitality as PA to the General Manager of a major convention centre. The hours were long, the pressure was big, but I genuinely loved my work and the people I worked with.
Then I became pregnant with my daughter.
We had planned everything down to the dollar: going down to one income, taking a full 12 months of maternity leave (back when paid leave didn’t exist), and making sure we could keep the mortgage afloat. I even did the classic new-mum thing: booked my unborn child into eight daycare centres with the hope of securing full-time care when I returned to work.
The universe laughed. When the time came, only two centres offered me places — and only for two days a week.
When our daughter hit six months, we realised our carefully-constructed financial plan wasn’t going to carry us through to the full year. So I went to my boss and asked to return early on a part-time basis, two days a week in the office and three days from home. I even handed him a document outlining exactly how I’d still meet every KPI.
He skimmed it, looked up, and said,
“See, this is why I need you back full-time.”
He simply couldn’t imagine a world where someone worked remotely.
I explained — repeatedly — that I did not have full-time childcare and could not return full-time. He suggested we “wait it out.” But we were running out of money. So, reluctantly, I resigned.
A Reality Check, and a Lightbulb Moment
Suddenly, I was home with a baby, no job, and the realisation that I was unlikely to be hired anywhere with a young child in tow. I’d always been the higher income earner, so the financial shock was real.
One night I said to my husband, “We’re trying to replace my income. But do we actually need to?” We sat down with our numbers and discovered I didn’t need a full-time salary to keep us afloat. I only needed to work the equivalent of two days a week.
That realisation flipped everything.
I found a job share role in a law firm for exactly two days a week, which gave us immediate breathing room. And then I remembered the plan I had pitched to my old boss — the fully thought-out working-from-home proposal he couldn’t understand. Just because he didn’t get it didn’t mean it wouldn’t work.
So I started researching ways to work from home as a secretary.
Keep in mind: this was 1999.
There was no flexible work culture.
No “remote workforce.”
No cloud apps.
No Zoom.
Only dial-up internet, and if the connection dropped, your all-night email download failed and you started again.
But I had a computer, a phone, a desk, and solid admin skills — so I started digging.
Finding the Industry Before the Industry Really Existed
During my research I discovered that, in the US, remote administrative support was popular among military spouses. Then I stumbled across the term “Virtual Assistant,” coined in 1992 by Thomas Leonard for his remote assistant Stacy Brice.
I tracked down A Clayton’s Secretary, founded by Kathie Thomas in 1996, and joined immediately. Then I joined the International Association of Virtual Office Assistants (IAVOA), founded in 1999, because I knew there was no reason I couldn’t support international clients.
Even before seeking clients, I invested in community — people who were already doing what I wanted to do. That made a huge difference.
Landing My First Clients — The Power of Relationships
Next, I considered who I actually wanted to work with. My background had always been supporting independent professionals, so I figured that was my sweet spot.
I contacted the chairman of the convention centre where I used to work and told him what I was doing. I knew he had no admin support, and he represented my ideal client. He signed up immediately. Then he referred two other directors to me. Within 18 months I had replaced my job-share income, resigned from the firm, and stepped fully into my VA business.
It grew from there.
Growing With the Technology (Even When People Told Me It Would “Never Take Off”)
As technology evolved, so did my practice. I still laugh thinking about the time I asked the Sony Centre about digital transcription and was told it would “never take off” and was “only for big firms.”
Thankfully I didn’t listen. I found an entrepreneur in Coffs Harbour building a digital transcription solution and became one of his beta testers.
No coach.
No specialist VA course.
No hand-holding.
Just transferable skills, determination, and the willingness to market myself and try new things.
Why Skills and Mindset Matter More Than Anything Else
Let me be blunt for a moment: you cannot leave school and start a VA practice. You need some foundational admin or office experience so you know what you’re offering. A webinar doesn’t turn someone into a webinar host, a Wix template doesn’t make someone a web designer, and two years in business doesn’t make someone a business coach.
I share this not to discourage but to set realistic expectations. Statistics vary depending on country and location, but generally various sources, including the Australian Bureau of Statistics, the Small Business Association, and the Commerce Institute in the US, cite on average:
- 30% of new businesses fail in the first two years
- 50% fail within five years
- 66% fail within ten
If you’ve been in business for two years and haven’t hit a sustainable profit yet, you’re still learning. That’s okay — but don’t jump into coaching others on how to do something you haven’t yet mastered yourself.
The number one thing new VAs need to cultivate is mindset. Think like a business owner. Keep your part-time job until your VA income is stable. Learn how business works so you don’t crash and burn early.
So What’s Really Holding New VAs Back?
Fear.
Fear of failure.
Fear of not being good enough.
Fear of not getting clients.
Fear of doing it wrong.
Fear of being seen.
Fear of stepping away from the safety of employment.
The good news? Today’s new VAs have an enormous advantage — resources. You have courses, webinars, online communities and conferences, mentors, podcasts, training, and a global network of VAs willing to help. I’ve included links to some on my resources page.
Just make sure the people you listen to have a track record. Longevity matters.
And remember: the VA industry is incredibly supportive. The VAs who try to undercut everyone else and treat fellow VAs as competitors never last long.
Your Turn
If you’re thinking about becoming a Virtual Assistant, know this: you don’t have to start perfectly. You just have to start intentionally. Work on your mindset. Build your skills. Join communities. Keep your job while growing your client base. And don’t let fear have the final say.
Good luck with your VA journey. I’d love to hear how you got started — or what’s holding you back.
Share in the comments!
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