Virtual Assistant: I Hired A VA And It Left A Bad Taste In My Mouth

So, I hired a VA or virtual assistant and it left a bad taste in my mouth.

…but not for the reasons you’d think.

My name is Cathy Banks* and I own an online travel agency.

This is my story – and Sara’s* (my VA from the Philippines).

Why I Thought Hiring a VA Would Change My Life

I’ve been running my online travel agency for a little over six years now. What started as a side hustle during my maternity leave somehow turned into a full-time business with more spreadsheets than I can juggle – along with raising my baby daughter.

Look, I love helping people discover hidden gems around the world, but between the client emails, itinerary adjustments, supplier follow-ups, and the never-ending admin tasks, I was running on caffeine and vibes. I needed a virtual travel assistant, stat.

I kept hearing fellow business owners rave about their virtual assistants, especially ones from the Philippines. “Total game-changer,” they’d say. “She runs my inbox better than I do.”

Intrigued, I went on some online platforms and started looking. It wasn’t long before I met Sara.

It sounds cliche, but the moment we hopped on Zoom for the interview, I felt like I found “the one.”

For starters, I could understand Sara perfectly. She had a neutral accent and expressed herself well, not in that overly polished, rehearsed way—but warm, intelligent, and precise.

She seemed to have a lot of relevant virtual assistant experience too. Sara had looked up my company online, referenced a few of our Instagram posts, and even had ideas for improving my booking workflow after testing it herself.

Unlike other candidates who gave very short answers, she also asked insightful questions.

I was so impressed that I hired her on the spot and even messaged my husband right after the call saying, “I think I just hired someone who might organize my life better than I ever could.”

I imagined sipping my morning coffee slowly for once, not frantically checking five tabs while replying to three emails (and overlooking at least five more).

Hiring Sara felt like the first step towards a more well-oiled version of my business, and yes, more time with my little one since she won’t stay so little forever.

Surprisingly, the biggest change wasn’t going to be in my calendar or inbox (although those were a VERY close second)—but in how I saw work, people, and myself.

How It Started: The Many Hats My VA Wore (And Wore Well)

From day one, Sara jumped in like she’d been with my agency for years.

She took over flight bookings with ease, juggling multi-leg itineraries, tricky layovers, and those pesky airline restrictions like a pro. Hotels? Handled. Transfers? Smooth as silk.

Sara managed the not-so-glamorous side of travel too—cancellations, rebookings, chasing down refunds like a polite bounty hunter. She even coordinated directly with clients and local tour operators, often in different time zones, without missing a beat. I’d be on a sales call while she was resolving a delayed airport pickup in Bangkok or sending a distressed honeymooner an updated itinerary. At midnight.

A good follower too—when I gave her a client onboarding checklist, she not only learned it by heart but suggested three improvements by the second week.

The bottomline? She got things done. Efficiently, quietly, and always with a polite “Done po” in Slack, which was a Filipino courtesy I grew to adore.

After years of running myself ragged doing everything, I began to wonder: how did I ever survive without her?

With Sara, I had a skilled, reliable, full-time virtual assistant for a fraction of the cost because my dollars went A LOT farther in the Philippines. I won’t divulge exactly how much I paid her, but sometimes, I felt a little guilty because I’d probably have to live on instant noodles on that same paycheck where I’m from.

But just when I thought I had found my unicorn of a virtual travel assistant, something changed.

The Honeymoon’s Over: When the Glitches Became Hard to Ignore

It started small—innocent, really. A missed Zoom call here, a few late task updates there.

Sara would apologize, always gracious, always professional. “Sorry po, internet was down in our area.” I waved it off. I mean, who hasn’t had Wi-Fi issues? I once held a client consultation from my car because my own signal went rogue. These things happen, no big deal.

But then it started happening a lot. One rescheduled meeting turned into three in a week. Sara rarely missed a deadline in the first few months—but she’d submit booking confirmations an hour late, send drafts of travel guides well past the agreed time, or respond to urgent client inquiries a tad slower than her usual speed.

A client would ask for an updated itinerary, and I’d find myself refreshing our shared board and wondering, Did she forget again? And a couple of times, I found myself double-checking Sara’s work more than I should have.

Initially, I shrugged it off. Yet, when three or four tasks piled up in a single week, I started to worry. My business relied on timeliness; those small lags might put off all the new customers we’d worked so hard to secure.

I wasn’t angry—just confused. This wasn’t the same rockstar VA I’d hired. Or was it? Had I missed something early on? Was I expecting too much?

So, I decided to sit Sara down for a proper one-on-one…

 

..and by the time we finished our little chat, I was left face to face with an ugly truth no one wants to talk about.

What No One Prepared Me For: The Truth Behind the “Bad Connection”

Our one-on-one started a little awkwardly.

Sara kept smiling politely, her eyes darting nervously to the side like she was bracing for bad news or a really bad scolding.

I had to reassure her—over and over—that she wasn’t in trouble. Just a conversation, I said. I wanted to understand where she was coming from.

That’s when I realized that many Filipinos, especially in remote roles, hesitate to speak up. With so many of them supporting entire families, their first instinct is to grin and bear it, lest the wrong word could cost them their job.

Eventually, the floodgates opened.

Sara shared that she’s a single mom raising two kids—both in elementary school. While we were both moms, her days looked very different from mine.

I had hired a nanny to look after my daughter when I started my company – and my husband does most of the chores in our house.

Sara’s days were filled with breakfast prep, uniforms, school drop-offs, chasing down homework, and the never-ending cycle of dishes, laundry, tutoring, and tears (hers and theirs, I imagine).

And somewhere in between, she was squeezing in client calls, building travel guides, troubleshooting hotel mix-ups, and dealing with me asking why a PDF was late.

The $X an hour I paid her? She budgeted every cent of it to pay rent, buy groceries, cover school supplies, and keep the lights on.

Sara also confessed that those “internet issues” weren’t always technical issues either. Sometimes, it was a sick kid. A power outage. Or just the sheer exhaustion of trying to be everything to everyone, all the time, while still showing up with a smile on a Zoom screen.

I sat there, blinking at my laptop, feeling like someone had quietly turned the mirror on me in the most unflattering light.

Everything I thought I understood about remote work challenges, outsourcing empathy, and professionalism suddenly felt… naive.

And I wasn’t sure what to do with that realization.

The Real Cost of Convenience: A Wake-Up Call As to Who REALLY Pays the Price

So, here’s the plot twist. Hiring a VA left a bad taste in my mouth not because of Sara, but because of what it exposed about my own expectations – and how out of touch they were with the actual realities of global outsourcing.

I wanted someone reliable, efficient, and low-maintenance. I got all that. What I hadn’t prepared for was the part where that someone was also a single mom, living halfway across the world, juggling more in a day than I’d want to handle in a week.

I had been unknowingly holding Sara to a standard I wouldn’t hold a local employee to—let alone myself. Would I expect a single mom in my own city to never reschedule a call or miss a task update if her child was sick? Would I think less of her if she asked for a little grace?

Then why did I feel so inconvenienced when Sara needed the same?

It’s not about Sara. It never was. It’s about the system. The ease with which we hire a VA online and forget there’s a real life behind every deliverable. The way convenience can quietly numb compassion, especially when you never have to share a workspace or a cup of coffee with the person on the other end.

I was so enamored by all the convenience that I forgot about who was really absorbing the costs: someone with fewer resources, less flexibility, and far more on their plate.

And I had to ask myself: Would I accept these conditions for someone I cared about? Especially now that I had a daughter who would one day join the workforce (possibly as a parent herself) and might also face a very uneven playing field?

What I Learned (So You Don’t Have To)

That conversation with Sara didn’t just change how I worked with her—it changed how I thought about remote work altogether.

I started showing up differently. I asked more questions, offered more flexibility, and stopped treating every minor delay like a red flag. I gave her room to be a person, not a tool.

And funnily enough, once I did that, her performance improved—not because she worked harder, but because she felt safer. Trusted. Seen.

We found a rhythm that worked for both of us. I adjusted deadlines where possible, built in buffers, and even encouraged her to block out time for her family during key hours. She, in turn, became even more communicative and proactive.

Now, we work as a team—no longer just as an employer and her virtual assistant, but as two humans trying to make each other’s lives a little easier.

If there’s one thing I hope you take away from my story, it’s this: The next time you’re frustrated with a VA, ask yourself—are you really upset with them, or with the uncomfortable truths they reveal about how we do business?

That question changed everything for me. It might for you too.

*Names have been changed to protect the privacy of the parties involved.