Eight years ago, we launched The PA Diaries, a campaign that captured the hearts and minds of admin professionals around the globe. It was more than just a series of stories—it was a movement that showcased the unique, diverse, and powerful voices of our profession. Little did we know, it would lay the foundation for what we now know as The Assistant Room: the most collaborative, supportive, and diverse community of admin professionals in the world.
Today, we’re thrilled to bring The PA Diaries back. This revival is a testament to the growth of our industry, the strength of our community, and the stories that continue to define who we are. To mark this special return, we couldn’t think of a better way to begin than by featuring someone who embodies the spirit of our profession—Jane Squires, a virtual PA to Ultra High Net Worth Individuals and successful business professionals.
Jane is extraordinary. Her journey—from the stability of regular contracted work to the ambitious and often uncertain path of building her own client base—speaks volumes about the resilience, ingenuity, and courage it takes to thrive in our ever-evolving industry. We’ve long admired Jane for her passion for the PA profession and her commitment to excellence, values that align perfectly with everything we stand for at The Assistant Room.
In this exclusive interview with Assistant Room Founder Jessica Gardiner, Jane shares her insights into what it truly means to work with elite clients as a Virtual Assistant. Her story offers a glimpse into the day-to-day realities of navigating a world where precision, discretion, and professionalism are paramount. Whether you’re considering a career shift, seeking inspiration, or simply curious about the lives of those at the top of their game, this is an interview you won’t want to miss.
TAR: Jane, thank you so much for joining us today. Let’s start at the beginning—how did you make the transition from a traditional assistant role to becoming a Virtual Assistant, and what inspired that leap?
Jane: I’ve enjoyed all of my working experiences, every role has taught me something and led me to where I am now. I believe in challenging myself and had considered working for myself in the past, but it hadn’t felt the right time. A couple of years ago, I felt like I needed a new challenge and made a pivot to going freelance.
I liked the idea of working with a variety of clients and knew with my self belief and work ethic, I could do it. The way I saw it, the worst case scenario would be if it didn’t work out, I’d go back to working a 9-5 job.
TAR: An bold but brilliant move! Talking about the differences between past vs present, the journey into the world of VA work can look very different for everyone. What would you say was the biggest eye-opener for you when you first started working as a Virtual Assistant for private individuals?
Jane: That some clients will not be the right fit, and that’s ok. It’s not a reflection of you or your skills, I’ve learnt not to take things personally and focus on those clients that are the right fit. It can be discouraging, particularly when starting out, but know your worth and the value you bring and you will attract clients who align with you.
TAR: When discussing the reality of life as a VA we often see the conversation turn to the concept of you now being your own boss. What do you think is the real difference between being an assistant in a corporate environment vs running your own VA business?
Jane: I know that a VA (or any assistant role in fact) is often misunderstood. In the corporate sector, you’re working set hours, you get your allocated annual leave and things like sick pay and benefits. Generally you aren’t bothered out of hours, you don’t get that when you’re self employed. I set my hours, I don’t get paid time off, I’m working completely solo – not only am I doing the tasks required, I also have to manage all aspects of running a business. Invoicing, tax returns, expenses, training and development, seeking new clients and marketing myself. All of that is like a second job in itself! It can feel lonely at times so it’s important to seek out a support network. That’s why communities like The Assistant Room are so great, you have other people who understand the challenges you can face being an assistant.
TAR: So in your experience, what is the most common misconception people have about being a Virtual Assistant, especially in the high-net-worth space?
Jane: The biggest misconception is that you’re ‘just’ managing a diary and email inbox for someone else. I think a lot of people assume there’s not much skill to it and it’s an easy role. As you know, an assistant role of any type goes way beyond that! We have to pre-empt potential issues and solve problems before they arise. We take care of a number of tasks to allow those we are supporting to focus on their strategic decisions and actions. An assistant has to have such resilience and be able to think on their feet and have a calm nature amidst the chaos.
In terms of supporting high net worth clients, people assume it’s all very glamorous. The reality is, it’s a high stress environment, lots of moving parts and often very short timescales and deadlines. You have to be flexible and able to adapt quickly.
TAR: You touch upon the ability you need to have to manage different moving parts at once. How do you balance the day-to-day logistics of managing multiple clients with complex needs and the strategic goals of growing your own business?
Jane: I’ve learnt to lay out firm boundaries and stick to them. Working with a number of clients means I’m pulled in many directions and everyone has their own urgencies. I need to be able to allocate my time correctly to ensure no one feels undervalued or like I’m not fulfilling my priorities. I’ve always been conscientious, it’s not in my nature to ‘clock off’ because the hours say so but also it’s a very slippery slope trying to do just one more thing.
My to do list is always growing, I could keep working all night! Being realistic with timescales and communicating to your clients is key.
TAR: We often hear people say, “Anyone can be a VA,” but as we’ve previously discussed, “The question isn’t can everyone be a VA, but can everyone be a business owner?” What does that distinction mean to you, and how does it shape your approach?
Jane: It’s not for everyone. There’s no security or guaranteed clients. It can be hard to switch off and find a balance. The reality is, it takes time to build a sustainable business, to develop relationships with your clients and get to know their individual needs and ways of working. I try to take time to reflect on how my working week has gone, both the positives and negatives, to help myself plan ahead and adapt.
TAR: So what have been some of the unexpected challenges you’ve faced as a self-employed Virtual Assistant, and how have you navigated them?
Jane: The realities of balancing multiple clients. Even with the best planning and organisation, unexpected issues can arise; a sudden deadline, a task that takes longer than anticipated, or a last-minute change in priorities. I’ve learned to focus on what’s truly urgent versus what can wait. It’s not always easy, but setting boundaries and keeping clients updated goes a long way.
TAR: Risk is a big factor when it comes to running your own business. I’m a huge believer in not seeking advice when discussing the idea of starting your own business from those who are risk-averse i.e. the majority of the population. Can you share more about why you also feel this way and how it’s shaped your own journey?
Jane: Running your own business can be hard and isn’t always straightforward. As with anything that’s challenging, people can talk you out of it or put doubt in your mind. Many people are risk averse and that’s fine, we all have different qualities and personal priorities. A career that suits one of us would be a nightmare life for someone else. I think generally, it comes from a good place, people want to look out for you but I’ve never let other people’s worries or opinions limit me. I don’t rush into things, I work hard and I believe in myself. For me, if I never take a risk, I’m not going to be challenged. I don’t want to stop learning and developing myself and my career.
TAR: In the high-level VA space, growth and adaptability are key. How do you foster a growth mindset in your work, and how important has it been for your success?
Jane: I always look 3- 6 months ahead to plan for the future. For various reasons, clients may move on, or my services are no longer needed. This is why it’s key to build networks and relationships as you never know who may need your assistance in the future or recommend you to a potential client. I’ve had a number of my clients come via referrals, so to me that’s a success.
TAR: PR is such an important part of working with high-net-worth clients. What advice do you have for VAs when it comes to managing expectations, dealing with feedback, and not taking things personally?
Jane: HNW clients can be demanding and have high expectations of you so being resilient and able to adapt to last minute changes is key. You need to have a clear line of communication and be ready to tailor your ways of working where necessary.
You are going to get feedback, both good and bad. You can’t take it personally. Digest the feedback, be honest about what you did/could’ve done differently and use it to readjust. It’s all a learning curve.
TAR: One of the realities of working as a VA is the unpredictability that comes with each client and their needs. How do you plan ahead while staying agile enough to handle the unexpected challenges that always seem to pop up?
Jane: I think the key is finding the balance between planning and staying flexible. I make sure to check in with clients regularly – it’s important to ask for clarification if something isn’t clear, especially if it’s an industry I’m not familiar with. Most clients appreciate open communication, and it helps avoid surprises later on. That said, there will always be things you can’t plan for. The trick is staying adaptable and keeping a level head when the unexpected pops up. Stressful moments are part of the job, but they’re also opportunities to show your value by finding solutions. Ultimately, it’s about staying organised wherever possible and being ready to adapt when things don’t go to plan.
TAR: Looking to the future, where do you see the role of a Virtual Assistant evolving in the next 5-10 years, especially for those working with UHNWIs and top-level executives?
Jane: A lot admin tasks can be automated (thanks, AI!). There are great programs/tools to help with that and they will only improve in the coming years. It frees up time for the more strategic side of the role, such as research and planning, keeping on top of the latest openings or events.
A lot of execs’ mindsets have shifted, they understand their assistant isn’t just there for admin, we’re a much needed support in many areas and a vital part of their team. I think personal branding for assistants will keep growing – not just as a way for marketing ourselves externally, but also increasing visibility across a business, particularly demonstrating our value to other departments or colleagues.
TAR: Finally, what would be your number one piece of advice for any Personal or Executive Assistant looking to make the leap into VA work or even start their own VA business?
Jane: Honestly, I’d say go for it! If you’re currently employed, start building it up on the side so you’ve got a safety net and let everyone know what you’re doing. Networking is key, and you’d be surprised how many people will think of you when they need support once they know you’re offering it. Know your worth, be confident in your skills and the value you bring to your clients. There’ll be moments when it’s tough, but persistence and hard work pays off. Lastly, don’t forget the practicalities of running a business. Considering things such as insurance, tax returns, working out how many clients you’ll need, factoring in time off which you won’t be paid for is essential to make your business a success.
In short: plan smart, be bold, and remind yourself why you’re doing this—you’ve got this!
Looking for the support you need to excel in your career? Click here to gain exclusive access to The Assistant Room membership where you’ll find a dynamic suite of resources designed to elevate your PA/EA career including:
SPECIAL OFFER: RECEIVE ONE MONTH FREE WHEN YOU BECOME A RISING STAR MEMBER USING COUPON CODE ’30MEMBER’ WHEN YOU SIGN UP!
- Unparalleled On-Demand Learning: Unlock 50+ hours of expertly curated masterclasses, tailored to empower your growth as a top-tier Personal or Executive Assistant.
- Interactive Skill-Building Workshops: Participate in live, cutting-edge sessions designed to sharpen your expertise and expand your professional toolkit.
- Time-Saving Corporate Concierge: Leverage our dedicated concierge desk to streamline corporate requests, saving you valuable time and money.
- Global Community Support: Connect with a thriving members forum for daily insights, collaboration, and advice from a worldwide network of elite PAs and EAs.
- Comprehensive Resource Library: Access a wealth of templates and documents to simplify and optimise your day-to-day tasks.
- Vetted Supplier Network: Rely on a trusted list of suppliers for all your corporate and personal needs, ensuring quality and efficiency every time.
This is your gateway to mastering the art of assistance and unlocking limitless potential in your role. Become part of The Assistant Room today.