7 Lessons from 10 Years Running a Virtual Assistant Business
When I started my Virtual Assistant business a little over 10 years ago, I was doing a ton of research, trying to get my business off the ground and bring in the kind of money and freedom I dreamed about.
But the first two years of my VA business were really hard. I launched my business the way everybody in the online space tells you to: Set your hourly rate at the industry average, create hourly packages of services you can offer, find clients in Facebook groups… I did all those things, and they weren’t working.
It was bad… to the point where I actually almost considered going back to my 9-to-5 job.
I often found myself thinking, “I wish I knew how to do X, Y, and Z.” And because I didn’t know how to do X, Y, and Z, I made a ton of rookie mistakes.
But that's not me now! I'm here to revolutionize the VA space because here’s the reality I’ve come to realize: The common advice out there sets everybody up to fail.
You read that right… I’m not here to name names, but *ahem* there are very few voices who are honest about what it takes to build, grow, and scale a sustainable Virtual Assistant business. I had to learn some hard lessons, but my goal is to help more women avoid the pitfalls of the industry.
7 Lessons from a Virtual Assistant Expert
I made a lot of mistakes when I started my Virtual Assistant business, and I want to give you the solutions I didn’t have so you don’t make the same mistakes I made.
If you’re in the early days of your Virtual Assistant business or have been a VA for a while and you’re starting to hit a wall, this is for you. Keep reading to discover the 7 things I wish I had known when I first started my VA business.
Lesson #1: Clients actually don’t care about your skills. (Really.)
Let’s talk about skills.
I feel like you're probably in this place right now. The very first lesson I learned and the thing I wish I had known when I first started my VA business is that clients do not care about your skills.
Yes, they care that you can figure things out. But at the end of the day, they don’t actually care whether you know how to use every platform under the sun.
For example, I found my first client on Upwork. The job post said you needed to have at least 3 years of experience with Kajabi, SignNow, experience posting graphics and creating content on Instagram… But I had none of that—literally nothing that was required in the job description.
So, I was very upfront with her in my application and said, “I know that you required all these things. I don't have any of that specific experience, but I know that I can figure it out, and I know that I'm going to be the best investment you've ever made in your business.”
It was a very bold statement and the only reason I actually said it was because I thought there was no way in hell she would even get back to me!
But she did, and she loved it.
She loved my confidence and then she literally said to me, “The fact that you came in telling me that you can figure it out – that’s everything I need to know.”
Just being able to be the kind of person who can go in and solve problems or Google something is such a desirable, marketable skill. You may be reading this and thinking to yourself, “Isn't that just common sense, Rebecca?”
Believe it or not, it isn’t.
Think about the people in your office… How many times have you caught yourself thinking, “Wow, how many times could they have just googled that thing?” (Or something along those lines.) ...It's probably a lot because that was my experience. 😆
New VAs are told (and I certainly was told and believed) that we need to focus on selling our skills: we need to learn new platforms and programs, and then put together a list of specialized skills and service packages.
But what we should really focus on is building trust and making that client feel truly seen—making them feel like you understand them. You can also tell them that you’re a problem-solver, you love troubleshooting, and that you can figure just about anything out (assuming that’s true!).
Sending a list of skills to potential clients does the opposite of what you want it to do: It immediately shows them you don't understand what they actually need. They don’t need a list of skills; they need a sidekick, a wing-woman, that right-hand person in their business and they’ve likely been looking for that person for a very long time.
That’s the person you need to be, and that’s what you need to sell: You need to sell that partnership—that idea and that feeling of being supported in their business. When you can do that, you’ll ultimately be able to charge more because you can integrate yourself more fully into their business.
Lesson #2: Your most valuable source of clients comes from the network you build yourself.
This is a huge question, and I get it all the time: Where do I find clients as a Virtual Assistant?
It took me almost two years to realize that the most valuable source of clients wasn’t Facebook groups or LinkedIn connections or even Upwork. (Even though, yes, I did find my first client on Upwork!)
I mean, sure, you could find clients there. But if you want a sustainable business, that's going to work long-term.
If you never want to worry about where your next client is coming from, you need to build a strong network of potential clients around you.
It's easier than you think. It all comes down to making intentional connections and focusing on reaching out to as many people as you can. Now, this doesn't necessarily always need to be business owners. You could cultivate and refresh your relationships with past colleagues or with people from professional groups you've joined. It can also include you reaching out to business owners you admire on Instagram.
Before we go any further, let me be clear: You do not need to have a VA business Instagram account to do this kind of outreach and relationship-building. I know this might sound counterintuitive, but hear me out.
Spending time to build a website or create a business Instagram profile and creating content for it is a complete waste of time at this stage of your VA business. Why? Because it’s not going to do anything to help you build this network around you.
Throughout my entire 10-year virtual assistant business career, my OBM career, and my business growth strategy career, I never had a website or business Instagram account. I didn’t do any of those things until I decided to start the mentoring side of my business. All of those things that other VA coaches and “experts” tell you to do just complicates everything and distracts you from what should be your #1 goal—finding your first client.
If you’re a Virtual Assistant who's looking for sustainability, freedom, and the ability to earn a consistent livable wage, you only need to work with a small handful of clients. You don't need to reach hundreds of thousands of people.
Building a network of people in a wide range of niches, running different kinds of businesses, who you like or admire, and who you think you might want to work with one day is the best way to keep your client roster full.
Lesson #3: Taxes are real, and you still have to pay them as a self-employed person.
I wish I’d taken taxes more seriously from the beginning.
This may sound obvious, and, I mean, sure, I knew I would have to pay taxes. But tax day seemed so far off…I figured I’d be able to scrape together whatever I would need to pay what I owed. But like many first-time entrepreneurs, I didn’t realize how dramatically things change when you go from having an employer cover some of your tax burden to suddenly being solely responsible for all of it.
I also made the mistake of thinking that my business expenses (many of which were things I didn’t necessarily need if I’m being honest…) would help offset my tax bill a lot more than they did. Basically, my understanding of how taxes worked wasn’t much better than David Rose’s.
When I started my VA business, I wasn’t making a ton of money—especially until I had more than 2 clients. I decided to invest in some things for my business, like a new laptop and a standing desk, which I knew I could write off as expenses.
All in all, I assumed I would need to pay about $6,000 in taxes that first year. I also figured that, given it wasn’t a huge sum, I could scrape that together in the last couple of months leading up to tax time, so there was no big reason to save any money for taxes after my clients paid their invoices.
In my mind, it was a “later Rebecca problem,” not a “right now Rebecca problem.” So I lived. It. Up (kind of). I wanted to live my life – after all, I worked hard to get where I was! – and I was finally making decent money thanks to my VA business.
I figured I deserved a treat, so I went on a little trip to Cuba because I could work from wherever I wanted. I enjoyed myself a lot, actually. I had the best time on trips; I bought a nice leather bag…
A few months later, I started getting more clients, my business started growing, and in the back of my mind, I kept telling myself I needed to start saving money for taxes… But it was never more than a thought, and I didn’t follow through.
As tax time rolled around, I owed about $20,000 😳and didn’t have anywhere close to $20,000. Because of that very first year in my business 10 years ago, I am still, to this day, behind in my taxes.
So, the moral of the story here: Make sure you’re saving money for taxes from day one—trust me.
I now keep my tax money in a totally separate bank account from my main account so I don’t see it or get tempted to use it for things I shouldn’t. I also have an accountant now which has been a big help. If you need someone to help you manage your finances so it takes some of the stress off your plate, try to find that solution as soon as you can afford it.
Taxes are no joke!
Lesson #4: Sometimes, you care more about your clients’ businesses and their success than they do.
I’ve tried to keep a good mix of things here—from practical business stuff to taxes and client stuff. But I also really want to acknowledge the emotional side of being an entrepreneur, and especially being a virtual assistant.
So, here’s the thing: Being someone’s right-hand woman takes a toll, especially if you’re working with a client who cares less (or appears to care less) about the success of their business than you do.
I never realized this was a “thing” until I was in it myself. And it might seem weird to hear or read that, but it happens. Sometimes, you’ll care more about your clients’ success than they do.
This first happened to me with one of my highest-paying clients. At the time, she was actually the highest-paying client I had, and I was super proud of myself for signing her. The money I was making from her was legitimately life-changing at the time. She ran a cool business, and I was interested in learning more about it, so I was excited when we started working together.
The first month seemed to go on as expected. But things started to change about halfway through our second month working together.
First, she stopped showing up to our weekly calls, even though we had weekly calls on the same day, at the same time, every week.
A few weeks later, she came to a few calls, but she would show up late, and I could tell she was trying to do things in the background.
I would also assign her tasks by certain deadlines, but she would constantly miss the deadlines. Projects were dragged out unnecessarily because she wouldn't take 5 minutes to do even simple things, like review something I sent for her approval.
I was really invested in her business. I loved her, I loved the business, and I wanted it to be successful. I really was doing every single thing I could to make that collaboration work and to make her business successful, but she wasn’t matching my drive and level of commitment.
People who don't care about other people don't tend to want to assist somebody, so knowing you’re here reading this tells me you’re not that kind of person. You want to be a Virtual Assistant who cares about other people. But it also tells me that you may be open and more vulnerable to these kinds of interactions with clients.
If you're like me, you may experience something like this: You'll care a lot about your client's business, but you might start realizing you care more about their business's success than they do.
You might be thinking to yourself, well, why is this such a big deal? And here’s my answer: Because it puts you in this weird place where you almost start resenting your client.
Think about it: you’re doing all this work for them, putting all the time in, but they're not reciprocating. You might start to feel like they expect you to make everything happen, almost like magic.
Anytime this starts happening with a client, try to have a conversation with them as soon as you start seeing or feeling this happen. It doesn't need to be a loaded, tough conversation where you say, “Hey you're like slacking on your business,” or anything! But you should be upfront about what you’re observing – that meetings are being missed or deadlines are being ignored. Ask what you can do to help or talk about revisiting the scope of the project.
At the end of the day, when this kind of mismatch happens, it takes a huge emotional toll on you. In my experience, these clients never get back on track. It’s incredibly taxing to care about somebody who doesn't really care about their business, but what it really feels like is that they don’t care about you.
Lesson #5: If you don't stick to your boundaries your clients won't, either.
This is an extremely important lesson!
If you’re a person who tells your clients, “I only work Tuesday, Wednesday, Thursday, and Friday,” and then you start sending emails on Monday, your client will not respect your boundaries. They’ll follow your lead and start sending you emails on Mondays… and suddenly, you’re working on Mondays.
Once a client starts seeing that you're working at a different time or you're working on a certain day, they may not say it verbally, but subconsciously, they're going to now expect you're working at that time.
I know how tempting it can be sometimes to respond to things outside your normal “hours.” Maybe a client sends a late-night email or a Slack message over the weekend, or maybe you suddenly think of something brilliant you want to share with them. Your first inclination might be to quickly bang out an email, reply to that message, or do a little work over the weekend. But don’t!
I know—I do the same thing. We have to resist the urge.
Even if you are working on a weekend or after your normal hours, your client doesn’t need to know that. And you don’t want to set any kind of precedent in their mind letting them think you’re available 24/7.
There’s an easy way to avoid this becoming a problem: Schedule that email or Slack message to go out on Monday or Tuesday, or whenever you're supposed to be working.
It’s extremely difficult to go back and reestablish your boundaries, so do your best to set and preserve them from the very beginning of your working relationships.
Lesson #6: If you present yourself as an employee, you’ll be treated like one.
This point is short but potent: You need to treat your clients as equals from day one.
Lead the conversation, stay firm on your rate, and come into their business as real and authentic as you possibly can. When you present yourself as an equal, you’re coming in with a level of confidence that they respect.
Here’s what this means in a nutshell: You’re a contract worker, you’re not employed by them. This means you set your hours of availability, you decide your rate (or negotiate if you’re open to that), and you have an equal right to decide whether the collaboration is working well or not.
You are not at a client’s beck and call.
You are not required to answer messages within a specific time frame they set.
You are not required to work within any specific hours they choose.
You are not required to play by the rules they set for their employees because you aren’t one. You make your own rules; you tell your clients how you work and what they can expect working with you.
Remember: Your client is a business owner and so are you. You’re not their employee, so you shouldn’t act like one.
Lesson #7: Transactional work will keep you stuck in a scarcity mindset.
Transactional work—and by that, I mean offering hourly packages or specific deliverables to clients—will always leave feeling like you’re struggling and like you're never sure where your next paycheck is coming from.
Unfortunately, this is how the industry teaches new VAs to start their businesses, and they promise you can be successful, but it literally doesn’t work for anyone.
I followed this advice and—SURPRISE!—it didn’t work for me, either. After two years of trying to run my VA business “their way,” I knew I needed to do something different because exchanging my time for money wasn’t getting me far and I was burning out fast.
Here’s what I discovered: Project-based clients or clients I worked with in a single or only a few areas of their business were not the best fits for long-term relationships. Instead, I needed to integrate myself into all areas of my clients’ businesses—even in areas that I had little or no experience in because I knew I could figure it out.
The best way to try to integrate yourself into all areas of your client's business is to have a weekly meeting with them and try to understand what's going on in their business overall, not just the tasks you're working on. Remind your clients that you're a partner and a collaborator in their business! It's okay to come to them with questions about what's going on in other areas of their business because they’re not your boss.
This is a big part of what I teach in my VA mentorship program, the Virtual Assistant Accelerator, because it’s a critical part of building a sustainable VA business.
At first, some clients may think it’s weird that you’re asking so many questions, but they’ll quickly realize that you can only help them on a deeper level if you partner together. You’re collaborating with them, and this is an open relationship. Everything should be out in the open, and there should be no secrets to hide.
Developing these kinds of right-hand, wing-woman, collaborative partnerships with your clients is how you can move out of transactional, hourly work into charging monthly retainers based on the value you bring to your clients and their businesses.
OMG, let’s wrap this up already!
So why should you listen to (or, in this case, read) anything I have to say?
Because like every new or inexperienced VA—maybe like you, right now—I’ve been where you are: in the trenches, trying to figure it all out while building the life all the “experts” promised me I could in every YouTube video, blog post, and free download I could get my hands on.
I was trying to figure out how I was going to get into the online space because I wanted the freedom to travel and work from wherever I wanted. I wanted to potentially live in a van (which I’ve been able to do across North America, and every trip is amazing!) and have the financial freedom I always wanted.
I also wanted mental freedom, and I think that's something not many people talk about. I wanted to feel more than just “okay”—I wanted to wake up and be excited about what I was doing and the people I was working with.
That’s when I realized I was going to have to stop listening to the “experts” and figure things out for myself. I ended up completely rejigging my entire business, which is exactly what led me to learn these 7 invaluable lessons.
I don’t want you to make the same mistakes I made. My hope for you is that you flourish from the earliest days of your budding VA business. Being aware of these pitfalls and lessons will help you avoid some major headaches and heartache on your journey to building a life of your own design.
