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The Whys Behind My Life As A Freelance Virtual Assistant

There are no two ways about it, life as a freelance Virtual Assistant is hard work! I have lost count of the number of times over the past six years that I have thought about packing it all in. It is just you navigating all the marketing, finance systems, legal requirements, and then the actual paid client work. There’s no one sat with you in an office to bounce ideas off, to turn to for support, ideas, inspiration….

But do you know what, I actually really love it.

Yes, there is just you doing the marketing, the finance systems, the legal requirements, and the paid work. BUT, when those results and reviews start coming in, it’s still just you – that feedback is ALL yours – and that feeling is awesome!

However, whilst all these are major plusses for me, in this article I want to get down to my real whys behind my Virtual Assistant business.

Firstly, what is a Virtual Assistant?

It’s a common question I receive!

“A virtual assistant is a self-employed administrative or personal assistant who works remotely (usually at home) for various clients”

And my second most frequently asked question is – ‘How did you become a Virtual Assistant?’

My answer, quite honestly, is ‘by accident!’

If we take it right back to the beginning –

I studied International Hospitality Management for four years at university and after spending a year on placement as an Events Supervisor running events for high-ticket clients such as the England Rugby team, I decided upon graduating (with first-class honours!) to work in the organisation of events. It was still in hotels but in the sales office in a 9-5 role, rather than the erratic and long shifts in operations.

When the financial crash happened in 2008, I was only two years in, and the dream job I was aiming for (corporate events in a business such as a bank or law firm) just went up in smoke. No one had money to spend in hotels anymore and my job quite simply got boring!

We used to have trainers come into the hotel delivering apprenticeship qualifications for staff and I thought it seemed right up my street to drive around seeing different people and businesses all day. I loved the idea of freedom! Running my diary, planning my week. I found a job, applied for it, and got it. I loved it and was promoted 2 years later, actually whilst on maternity leave, to Curriculum Manager and I headed up the hospitality training team.

The WHYs incoming…

So yes, maternity leave – I had a baby! My eldest daughter was born in 2010 and I went back to work full time compressed into four days when she was 9 months old. She went to nursery and although childcare was expensive, it was doable for one child.

I started freelancing when I was on maternity leave with my second child four years later and was trying to earn some extra cash to top up my maternity pay. I signed up to a freelance job site, started bidding on jobs for Virtual Assistants, and won one!

One job turned into two and they kept on coming. I got my first regular client and as my reputation grew, I found myself thinking how I could just carry this on instead of going back to my full-time training job that had me driving around 500 miles a week visiting students in their workplaces, and working every evening to prepare lessons for the next day

My eldest was starting school and I was going to be working to pretty much just cover the cost of childcare fees for the two of them. That was even with my parents and husband doing a day of care each in the week. Plus, you know, I’d never see them!!

So – I found a part-time job, which I am still in five years later – two days per week in events and marketing for a prestigious university, and built up my Virtual Assistant business in my ‘free time’ i.e., evenings to begin with and then daytimes when my youngest started pre-school and then school.

I could choose my own hours, work around my family and not pay a penny for childcare.

Fast forward five years….

What began as a part-time admin side hustle has grown into a fully booked freelance Virtual Assistant business for the other half of the week and last year, I even started training others how to set up their own freelance Virtual Assistant business.

But still, and most crucially, all of my working hours are completed around my WHY – my family situation.

One thing I have been religious about since starting out as a Virtual Assistant is that I only work for clients for whom the work can be done at any time. Whether I chose to do it at 11 am or 11 pm, the hours have to be on my terms and so clients that require availability 9 am-5 pm are not a fit for me. I choose to work whilst my children are in school or during the evenings. I will snatch half hours here and there whilst they are engrossed in their favourite tv show after school or reply to emails/social media messages whilst I wait for them in their after-school activities. As long as I am meeting client deadlines, how I get there is 100% flexible.

Through working this way, I have:

  1. Found clients for my Virtual Assistant business who are just like me – i.e., mums and women in business who are operating their businesses around their families
  2. Been able to be there for my daughters for the past six years in a way I could have only dreamed of when I first had children

Freelancing, flexibility, and family life

Being able to be there for my daughters has driven me on through the darkest times as a Virtual Assistant – like last March when Covid struck, my clients’ businesses went into lockdown and I lost 90% of my freelance work over the course of a week.

I had huge wobbles, the uncertainty was too much at times and paid employment felt increasingly like the ‘sensible’ option over being a Virtual Assistant. I started looking at full-time jobs BUT always my girls, my why, brought me back in check.

My eldest is a gorgeous little dancer and trains for ten hours per week at her dance school. She was in a professional pantomime for the whole of December 2019 and has performed in competitions with her team all over Northwest England. None of it would have been possible if I was in a 9-5 job. I couldn’t have taken her to a theatre for 10 am, picked her up at 1 pm and been back again for 4 pm. I couldn’t get her to dance four nights a week. My youngest also dances three times a week and started football training just this last Monday – again, something that couldn’t have happened if I worked full time.

This is my why – yes, the saving on childcare fees is huge, but the opportunities that my flexible Virtual Assistant life affords these two girls I am responsible for raising is now key. When things get too much, I put myself mentally in the front row of a theatre or a packed arena watching my eldest perform on stage. I put myself in their school playground watching their happy little faces run out of school and into my arms. These are the things that matter to me and because of them, I make my business work.

In the past twelve months, I have made it back and my Virtual Assistant business feels stronger than ever before. I have had 44 students through my Udemy course I wrote whilst work was limited, and I have a renewed sense of direction – one that serves my family’s needs better than ever before.

What’s your freelance why?

Freelancing takes ambition (sometimes blind!), determination and drive – all helped along with a very clear vision of your why. Whether your why is freedom to travel, perhaps a passion or inner creativity that doesn’t fit within any employed role you’ve ever seen, or maybe you have simply vowed to never work to line someone else’s pocket ever again. Your why is so personal, but in my opinion so crucial, especially in helping you ride out the troughs that being self-employed brings, all so you can make the most of those beautiful peaks!

To learn more about getting started as a freelancer, check out these articles:

How To Get Started As A Freelancer

12 Books Every Freelancer Most Read Immediately

3 Top Strategies For Building An Audience For Your Freelancing Business

4 Critical SEO Strategies For Your Freelance Portfolio Website


Jen Taylor is a freelance Virtual Assistant in the U.K. who is living her freelance dreams. She began her career with a background in events and worked as a trainer in the hospitality industry for 7 years before deciding during her second maternity leave in 2015 to give freelancing a try. As she gradually increased her hours and client base, she found herself working with a variety of clients from a dental marketing consultant to a haberdashery and sewing school to a private scanning clinic to child sleep consultants as well as a COVID-19 scientist. She is currently living her maternity leave pipedream of being able to work around her family and is now teaching others how to do it too with her Udemy course, How to set up as a Virtual Assistant. You can learn more about Jen at www.jetvirtualassistant.com

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