5 Hard Truths About Being a Virtual Assistant

I still remember that day I made my business “official”: I took a lunch break and rushed to our Town Hall (I thankfully worked 20 minutes away) to fill out the paperwork. Once inside, I found out that the Clerk had gone out on HER lunch break and there was no knowing when she would be back. I waited 10 minutes feeling pretty good, but then 10 minutes turned into 20 and turned into 30…and I was fuming. I was at the point where I thought that maybe the universe was giving me a sign that I shouldn’t be a Virtual Assistant and that I wasn’t cut out to be a business owner. She finally returned after 45 minutes and I could barely hide my extreme frustration over this situation. But I’m glad I stuck it out and defied whatever signs I thought the universe was giving me.

DependableVA has been in business officially 5.5 years. I have been waiting to say I have owned my business for 5 years since I went to our local Town Hall and signed up as a sole proprietor. I had heard that many businesses fail within the first five years, so this milestone has been engraved into my psyche.

However, I’ve learned some lessons along the way that I never would have dreamed of when I first started. After doing this for the past five years, I wanted to share some hard truths about owning your own virtual assistant business (but these could also apply to any home-based business).


  1. Isolation

My job feels EXACTLY like this at times 😉

When you go from being a full-time Executive Assistant to an assistant who works from home, the amount of work you get done at home is astronomical. As an executive assistant in an office, you are usually the first point of contact for whomever you are supporting. The interruptions are endless. Going from constant interruption to none whatsoever is liberating. But after five years, I’m finally hitting the point where I crave other human interaction. Not like I had at the office, but something more than nothing. It feels very isolating and at times it’s frustrating to have no one to bounce ideas off of, help you take mental break, and keep you sane. Client woes get magnified and crazy days seems worse than they are.

It took me a while to realize that what I was feeling was isolation, but once I was able to pinpoint it, I became proactive and started a monthly lunch on Meetup with my local community for others who freelance, own their own business, or work from home. It’s only once a month, but it’s enormously gratifying and scratches an itch that I only recently realized was there.

  1. Getting Caught In Your Own Head

This slightly touches on the point above, but I’ve realized that when you work alone and your only interactions are with clients over phone/video calls about work, it’s easy to work things up in your head. Not just business related, but also personal and health issues.

This past year, I struggled with terrible insomnia that took a long time to get to the root of. I also had throat problems that got so bad that I every day I would spend hours down the internet rabbit hole trying to find different solutions. It was all I could think about. If I had worked in an office or even a co-working space, could I have more easily deflected this within my mind? Would I have obsessed as much?

Every person who works from home is different, but realizing I had this hypochondriac side that had never manifested itself until I worked by myself was a shocking discovery for me.

  1. Mo’ Money, Mo’ Problems

One of the blessings of having a successful business is that you are constantly looking for new ways to up your game, to become more successful, and potentially earn more money. But it’s a double-edged sword. I learned the hard way that more money sometimes causes more problems.

This past year and a half has been one of my highest earning years ever. It’s also been one of the hardest years in my business for one reason: I took on clients who were high paying but sucked energy, time, and emotion away from me.


I came to the realization that success, for me, does not always equal more money, especially if making that money comes with constant work, never feeling like I can catch a break and a feeling of stress that never goes away. I had ignored my gut feeling with these clients I ended up burned out – something I swore I would never let happen to me. I thought I understood my boundaries, but clearly, I didn’t.

  1. Evolving and Changing is Hard

We are constantly reminded by the media and other sources that change is good. Evolving your company is good. And while I agree with this, whole-heartedly, it doesn’t mean that change is any less hard.

When I left my full-time job to run my VA business, I worked anywhere 4-8 hours a day and still had plenty of time to have a good work-life balance. After I had my daughter, everything changed. I may still work 4-8 hours in a day but it’s split different ways. I’m usually up between 5:30-6:00am and working in the evening anywhere 7:30-10:00pm, plus hours between 9-5:00pm depending on the day.

I love the ability to have my toddler home with me some days and I wouldn’t trade that for the world. But I do miss the freedom I had before with my schedule and working within standard business hours.

I’ve had to evolve my business to change with my lifestyle. Do I regret it? No. Do I miss the copious amounts of freedom I used to have? Absolutely.

  1. Growing Too Fast is a Recipe for Combustion

I’ve grown my business in two ways over the past five years. The first way was when I had too many clients reaching out to me and not enough time. I decided to scale – and quickly. I created a Virtual Assistant team/agency that was similar to an account placement. Each client was an account and I would place them with the VAs on my team. I would stay in the loop for the most part and monitor activity, but generally let the client and VA work together.

It did not go well. The VAs that were on my team were not up to my caliber and most clients left after only a few months. When I tried to source quality, professional Virtual Assistants, most already owned their own business like myself and had no desire to subcontract with another VA. It reached a climax when I awoke to a 5:30am email from an angry client and I realized I had to rethink this process.

I stayed solo again for a bit, but within the past year, have taken on a team again. This time, they help me with projects in the background and I make sure to double check all work before passing it on to the client. This method has worked much better for my business and I take more time vetting VAs who would work well with DependableVA.

But it was a hard lesson to learn. I wanted to make more money, and I wanted to make it fast. Are we seeing a pattern here? 😉 I’ve learned that slow and steady sometimes wins the race. I can make all the money in the world, but if my reputation is getting damaged, then that money means nothing to me.


What will be interesting is to see is where the NEXT five years take me, the successes and lows. I’m also curious to see where the Association of Virtual Assistants will go, as that is my latest passion. What are the lessons I’ll learn – good and bad – by the time I reach my 10-year anniversary?

If anyone has been running their own business for 10+ years, comment and tell me what I should look out for!