10 Years as a Virtual Assistant: What Freelancing Has Taught Me

I started freelancing in 2016 when the VA industry looked very different. Ten years later, I’m still here, still working, still learning, and, if I’m being honest, still struggling sometimes.

Back in 2016, when I decided to become a Freelancer / Virtual Assistant, I was completely sold on the dream. Working from home, choosing my own clients, having a schedule that actually bent around my life instead of the other way around. No more clocking in at a job that didn’t feel like mine. It sounded almost too good to be true.

And honestly, back then it was easier. The VA industry in the Philippines wasn’t nearly as crowded as it is now. Fewer people were doing this kind of work, which meant fewer people competing for the same clients. It wasn’t a walk in the park, but compared to today, there was a lot less noise to cut through.

Then 2020 happened.

The pandemic changed how people saw work almost overnight, and freelancing suddenly became everyone’s plan B, or plan A, for a lot of people. Suddenly everyone realized they could work from home and earn in dollars. And just like that, the VA space got a lot more crowded. 

The dream got louder online too. Buy a course, create an Upwork (formerly Odesk) or OnlineJobsPH account, polish your LinkedIn, learn a few tools, send some applications, and boom, welcome to the freelancing community. That’s the pitch, anyway.

What nobody really talks about is the quiet, messy middle. The part where you’re not new anymore, but you’re also not “there” yet.

I’m in that middle right now. After almost ten years of doing this, I’m still struggling to keep work consistent. I’ve lost clients along the way and had months where the income just wasn’t there. I’ve picked up new skills, tried different niches, and I still catch myself refreshing job boards and wondering when the next opportunity will show up.

And if I’m being really honest with you, it’s not all the industry’s fault.

Some of it is because I got too comfortable. Some of it is procrastination, plain and simple. And some of it is just life—it’s fuller now, messier, more complicated than it was when I started. But strangely enough, this hard season has been teaching me more about freelancing, and about myself, than any course ever could.

The Industry Changed. So Did I.

When I started in 2016, I didn’t have to think much about standing out; there just weren’t that many of us. Now? It’s a completely different world. There are so many VAs out there, and many of them are genuinely good, with specialized skills, polished portfolios, certifications, and confidence that sometimes makes me want to close my laptop and sell banana bread and crinkles instead. 😂

But that’s not really a bad thing. It just means the industry grew up.

Being Organized Isn’t Enough Anymore

When I was starting, I genuinely believed that being organized and good at admin work was the whole game. And look, those things still matter, a lot, honestly. But they stopped being the thing that sets you apart a long time ago.

Basic admin skills are the floor now, not the ceiling. Plenty of people can manage a calendar or answer emails well. If I want to stay competitive, I have to keep learning. And I’m still learning, kasi the moment you think “okay, I know enough now,” the industry moves the goalpost again.

Learned that one the hard way.

I Got Complacent, and I Have to Own That

I lost clients partly because I got comfortable. There were seasons where things were working, so I stopped pushing to improve. Looking back, I can see exactly how that happens. You mistake “this is working right now” for “this will always work.”

I’m not going to beat myself up over it, because that changes nothing. But I do want to learn from it. The market shifted, and I needed to shift with it. Staying intentional about learning, paying attention to where things are headed, and being okay with admitting there’s still stuff I don’t know.

The “Easy Money” Freelancing Isn’t Always So Easy

When freelancing blew up during the pandemic, I got why so many people were drawn to it. Earning in dollars from your living room? Sign me up, of course. But after years in this, I think the income side gets oversold.

I’m not saying you can’t earn well as a VA. There are really a lot who are earning very, very well, depending on their skills. The problem is people are led to believe that income is automatic once you “make it.” It’s not.

There are good months and painfully slow ones.

Clients who stay for years, and clients who disappear without warning. Weeks you’re buried in work, and weeks you’re just refreshing your inbox, hoping. Freedom and flexibility, yes, but uncertainty comes bundled with it, and I wish more people knew that before jumping in.

When You Need the Money, It’s Tempting to Say Yes to Everything

This is one I know too well. During slow seasons, it’s so easy to accept whatever comes your way just because something feels better than nothing. I’ve said yes to low rates and difficult clients simply to keep cash coming in, and I get why people do it. When bills are waiting, principles get a lot harder to hold onto.

But not every opportunity is a good one. A client who doesn’t respect your time can quietly turn a small project into something that eats way more of your energy than you signed up for, scope creep, constant revisions, unrealistic timelines. I’m learning that boundaries aren’t a reward you unlock once you’re “successful enough.” You need them while you’re struggling too, maybe even more so. I still have a long way to go here, but I’m getting more careful about what I say yes to.

Rejection Still Stings, But I See It Differently Now

There was a time when every “no” felt personal. You spend time crafting an application, explaining why you’re the right fit, and then, nothing. Or worse, a polite “we went with someone else.”

It’s so easy to spiral. Maybe I’m not good enough. Or my skills aren’t there. Maybe someone else is just better. I’ve thought all of that. I’m still learning not to let those thoughts overstay their welcome.

Sometimes a “no” just means the client found someone whose experience lined up better. Sometimes my rate didn’t fit their budget. And, sometimes my pitch just needed work. None of that automatically means I’m a bad VA. It usually just means something needs adjusting, and I’m trying to look at the whole process more objectively instead of taking every rejection as a verdict on my worth.

My Life Doesn’t Revolve Around Freelancing Anymore

Life looks different now than it did when I started. I’m raising my child alone, working part-time at a school as a registrar, running a household, staying active in church and ministry. I can’t dedicate every waking hour to my freelance career, no matter what the “hustle harder” advice says.

There are days I see tips telling VAs to spend hours networking, learning, applying, building a portfolio, creating content, and I think, that sounds great, pero kaya ko pa ba gawin ‘yan?  

The truth is, my time and energy are limited. After work and everything else that needs doing, sometimes I just need to rest. And I genuinely need that rest.

But I’ve also learned to be honest with myself, because sometimes “I’m tired” isn’t the whole story. Sometimes I’m just avoiding something.

The difficult part is that freelancing, being a VA, has always been my bread and butter. It has been our main source of income for years, so losing clients isn’t something I can simply brush off and move on from. As the clients slowly became fewer, the other sources of income I have weren’t enough to make up for the difference. I hate admitting this because I’ve always tried to make things work, but the truth is, I’m struggling financially right now.

And Yes, I Procrastinate.

This is the part I can’t blame on the market. I know what I need to do. I need to search for jobs, send applications, follow up with potential clients, sharpen my skills, and put myself out there. 

But there are days when I just don’t do it. With all that’s going on in my life, I find other things to work on first, telling myself I’ll get to the important stuff later. Then “later” becomes tomorrow, and tomorrow becomes “we’ll see.” 

Sometimes I think I’m being productive because I’m doing other things, but deep down, I know I’m also avoiding the thing I really need to face. And the longer I put it off, the harder it feels to finally sit down and get started.

I’m Learning to Stop Comparing My Journey to Everyone Else’s

Comparison hits different in this industry, because everyone’s highlight reel is right there in your feed. Someone started a few months ago and already has three clients. Someone’s income looks effortless. Someone’s home office looks like a Pinterest board, and their schedule looks perfectly balanced. Then you look at your own mess and wonder why you’re not “there” yet.

I’ve done this to myself more times than I’d like to admit. But I don’t know the full story behind anyone else’s success, just as they don’t know mine. And I have to remind myself I’m not starting from zero. Almost ten years of experience, different clients, different skills, good seasons and hard ones survived. I don’t need someone else’s career. I need to build mine, in the season I’m actually living in.

Turning to God for Guidance and Provision

There are days when I genuinely don’t know what my next move should be. Should I learn another skill? Focus more on SEO? Apply to more jobs? Reach out to old clients? Try a different niche altogether? I can overthink all of these things until I end up doing none of them, and that’s usually when I stop and pray.

Turning to God has always been part of how I deal with things, especially when I don’t know what to do next. I don’t just pray when everything is going well. I pray when I’m confused, when I’m worried about money, when I’m discouraged, and when I don’t have a clear answer in front of me. Asking God for guidance because I don’t always know which direction to take. I ask for wisdom when an opportunity looks promising but I’m not sure if it’s really the right one for me. And I pray for provision because the bills don’t pause just because I’m in a slow season. There are still responsibilities waiting, whether or not a client shows up that month.

And when I look back, I can point to so many times when God provided in ways I didn’t expect. There were things I worried about that eventually worked themselves out, opportunities that came at just the right time, and seasons when I wondered how we’d manage but somehow, we did.

That doesn’t mean I simply sit around and wait for a client to fall into my inbox. I still have to do my part. I need to learn, apply, improve my skills, follow up, and actually send the application I’ve been putting off. But I don’t have to carry the entire outcome by myself. I can work hard without believing that everything depends entirely on me. I can ask God for direction, do what I can with what’s in front of me, and trust Him with the things I cannot control.

And yes, that trust can still be difficult. I like knowing what’s next. I like having a plan, knowing where the money is coming from and what my week will look like. Freelancing doesn’t always give me that kind of certainty, so I keep bringing those worries back to God. I pray, I do what I can, and I leave the rest in His hands.

Because at the end of the day, my provision was never really coming from a client, a job title, or the number of projects on my plate. Those are means God can use, but He is the One I ultimately depend on.

Struggling Doesn’t Mean I’m Failing

This is probably the biggest shift happening in me right now. We’re surrounded by stories of people who seem to have it all figured out overnight, someone starts freelancing and is suddenly earning six figures; someone quits their job and builds a thriving business seemingly overnight. Those stories are inspiring, sure, but they also make an ordinary, slow season feel like failure by comparison.

I’ve had to remind myself: struggling doesn’t automatically mean I’m failing. Sometimes it’s just showing me where I still need to grow. Losing clients showed me where I’d gotten complacent. A tougher market reminded me I need to keep learning. Rejection is teaching me to adjust instead of taking it personally. Procrastination is forcing me to get honest about how I spend my time. And this whole season is teaching me to trust God differently than before.

I’m not where I want to be yet. But I’m also nowhere near where I was ten years ago.

After Ten Years, I’m Still Learning

When I started freelancing seriously in 2016, I never imagined that ten years later I’d still be figuring so much of this out. I thought experience would eventually make it easy. In some ways it has. I know more now; I’ve built skills I didn’t have before, I’ve worked with different kinds of clients, and learned from mistakes. But experience hasn’t made me immune to uncertainty. I’m still learning how to adapt, how to stay competitive, how to balance work with everything else life is asking of me. I’m still working on procrastination, and on not retreating the moment I’m tired. 

I wrote about something similar back in June, Starting Over as a Virtual Assistant? You’re Not the Only One, about rebuilding after losing clients and realizing some of my skills needed dusting off. That one was about starting over.

This one’s about something a little different, about being almost ten years in and realizing I might still have a long way to go. And maybe that’s not such a bad thing.

Maybe being a struggling VA doesn’t mean I’ve failed at this. Maybe it just means I’m being reminded, again, that I can never really stop learning, adapting, and showing up. I can own where I’ve fallen short without letting it define me. Grow without measuring myself against everyone else’s timeline. I can keep looking for opportunities while trusting God for the ones meant for me.

For now, that’s where I’m at.

Still learning. Working. And, still figuring it all out.

And trusting God to lead me through the messy middle, one cup of coffee at a time. ☕