Side Hustle Series #49: I’m a Virtual Assistant

[Guest article today by Melody, as part of our Side Hustle Series. Who not only lives on a freakin’ boat (!!!), but who’s also rockin’ a nice side hustle on TOP of her 9-5. A pretty interesting setup if you ask me – and hopefully you enjoy this as much as I did :)]

A few years ago, my significant other Chris and I had a quaint little house in a great neighborhood in Nashville, with comfortable jobs, yet we weren’t satisfied and we needed a big change. We talked about a move to another state, but still felt as though we might just be making a lateral move, and we figured if we were gonna upset the apple cart, we might as well tip the damn thing over.

So, being avid sailors, Chris suggested that we move onto a sailboat and do some traveling.

I told him he was crazy, to which he agreed, and then he said,

“We may end up in riches, we may end up in ruins, but I promise you one thing… it will never be boring.”

With that, I hopped on board, so to speak, and we sold the house and almost everything we owned. And, along with our dog Jet, moved onto a 35’ sailboat. Which means our actual living space is about 115 square feet, or the size of many of your master bathrooms. (Just think about that the next time you’re complaining that you don’t have enough space!)

We love the fact that we are traveling by five-thousand-year-old technology, and that under ideal conditions, we could essentially sail around the world without using a single drop of fuel, powered purely by the wind and sun. Every day, we have a million dollar view without the million dollar price tag, and if we don’t like our neighbors, we move!

Like anything, it has its challenges, and it’s certainly not for everyone, but for us it’s an amazing life.

How I Got Started With Side Hustling

I was fortunate enough that I was able to keep the promotional marketing job I’ve had for the past seven years, since all of my work is done via email and phone. I have a Verizon Jetpack which is basically a mobile modem that allows me to connect to the internet as long as I’m within range of a cell tower, which is great. But it also means we’ve been limited to traveling up and down the East Coast in order for me to stay connected.

As grateful as I am for my full-time gig, we still have dreams of traveling more extensively, and would love to do the Caribbean and make our way south to Panama or Mexico one day.

A year or so ago, I discovered J-Money’s blog and I learned the term “Side Hustle“, and I’ve been hustling ever since! My goal is to save enough money to allow me to cut the full-time employment umbilical cord so we can do some serious sailing.

Being a Virtual Assistant

My side hustle of choice is being a Virtual Assistant (or VA for short). This means that companies or individuals hire me for a range of things that don’t require me to report to an office – everything is done remotely, using just my computer or a phone. This is perfect for me because it allows me to find side work no matter where I am.

I also love that there’s a lot of diversity in the work I find. One minute I might be building a WordPress site for someone, the next minute I might be doing research or data entry. By far, my most interesting VA job was typing someone’s X-rated novel.  Yep. I totally went there.

Fifty Shades of Grey (Hair, That is)

dirty old man cartoonYou see, it all started with Craigslist. (I bet lots of interesting stories begin like that.)

I responded to an ad in the computer gigs section from a guy who needed someone to type his novel. His ad explained that he was not tech-savvy so he hand writes everything and needed someone to type it up in a word document. It sounded easy enough, so I took the gig after confirming via a writing sample that I could read his handwriting. At this point he mentioned that his book was an erotic novel.

Ok, I read 50 Shades – so what? I mean we’re all adults here. The funny thing is, he included a business card in the package with the manuscript, upon which was his photo. He looked like a friendly fella. He also looked like he was pushing 70. I giggled because I didn’t expect this man who looked like he could be my Grandpa to be writing erotic fiction. A dirty old man indeed, but hey – good for him!

Then I started typing… and let’s just say that the kink was in full effect. But that didn’t bother me. What bothered me was the fact that the book was poorly written. I mean, it was terrible! It had inconsistencies, and things that just weren’t right. Names didn’t match up, and for someone who is totally Type A, well, this was a major problem. (Keep in mind I was getting paid only to type – no editing)

However, once I began, the OCD in me wanted to correct things. But how do you call Gramps and say, “No way could she take off her underwear because earlier you said she wasn’t wearing any!”

After asking if he would be willing to pay extra for me to take the liberty of doing a little editing, he said, very emphatically, “No. That’s why I don’t let my wife type these for me, because she goes around and changes stuff.” Smart woman.

But I still gotta give it to the old guy. Bad writing or not, his mind was still young, that’s for sure!

The Downside of Being a VA

The drawback of virtual assistant work is that it can sometimes be hard to find something that is both enjoyable and pays well. In my experience, you might have to sacrifice one for the other, taking some jobs because you like them (social media type work is some of my favorite) even though you may not make as much, and other times taking jobs that pay pretty decent but are a total snooze-fest (transcribing or some research jobs may require lots of extra coffee for me to get the job done).

My highest paying job was building a series of one-page WordPress sites for a guy who sold domain names. He paid me $25 per site, and because each new site was based on the exact same template with only a few changes to the content, I got to the point where I could install WordPress and build each new page in about 15-20 minutes. That ended up being $100 an hour!

My least paying job was finding potential sales leads and contact info for a fashion-based company who offers paid advertising on Instagram to their hundreds of thousands of followers. I only made $8/hr but I did it for about 2 months for two reasons:

  1. It was fun to browse the websites of boutiques, jewelry designers and fashionistas to see if they would be a good fit for my client’s services. Being on a sailboat does not afford me the luxury of space to support my love for fashion (my closet is only 24 inches wide), so it was like window shopping for me!
  2. It helped me build my own database of thousands of boutiques and jewelry stockists, whom I soon plan to market my own line of nautical inspired jewelry to. [Editor’s Note: Mel’s bracelets are awesome!! Totally check them out when you get a sec.]

Where Can You Find Work as a Virtual Assistant?

old school computer

There are quite a few places you can find virtual assistant jobs. In my experience, I’ve had the most luck in the Gigs section of Craigslist. If you go onto any city’s Craigslist page, you’ll find the Gigs section underneath the Jobs section.

The downside to using Craigslist to find virtual assistant work is that you have to weed through a ton of MLM type gigs and other spammy stuff. But I usually peruse the Computers and Writing sub-sections once in the morning, once in the afternoon, and once late in the evening. The good jobs go quickly sometimes, so it’s good to check throughout the day for new listings.

One of my secret weapons is a website called It allows you to search all Craigslist cities at once which can often lead to a gig you might not have found otherwise, unless you manually go to each city’s Craigslist page to look for side hustles (in which case, you probably have too much time on your hands). Be sure if you search for something on here, to use the filters and sort ads by ‘most recent’, or you might find yourself applying for a gig from a year ago that was never deleted.

There are also several other places you can find work as a virtual assistant:

Fiverr ( This site is just AWESOME. Not only is it totally fun to browse to see how amazingly creative some people can be (wanna see someone’s hampster create a custom message from cabbage?), but if you have a special talent, interest or gimmick, you can promote yourself on here and let people come to you!

I have not used it to get work, but I have hired several people through Fiverr to help with things that I didn’t really want to do myself. Each gig is $5 but you can put “add-ons” to generate more income for yourself. Take some time to browse other gigs in your area of interest to get ideas and see what people are charging for what. While you may not get rich, it can be a fun way to market small tasks that you enjoy doing.

Elance ( This site has some great, quality side hustle gigs. While there is a lot of competition, it’s free to register, so it might be worth it to give it a glance. The way it works is you find a job that you’re interested in and you submit a proposal (a bid) and the client chooses the preferred candidate based on the bid and your skill set.

The good thing is that you can see how many other proposals have been made on a particular job, but unless you have the paid premium plan, you can’t see the actual bid amounts. Still, there are good virtual assistant jobs on there, and some of them have a long duration if you’re looking for an ongoing project. You can browse some of the available jobs here.

Hire My Mom ( I just learned about this site this week from a couple of fellow sailors who has found work through there. She said she was able to find a lot more legitimate work than on Craigslist, but the downside is that you have to pay for a membership ($29.95/quarter, or $99/year), and they only let you preview a few of the most recent jobs posted before becoming a member. However, I’m offering it up as an option because it came recommended by people that I trust. The website does say that while they are geared towards helping moms, they do not restrict anyone from joining.

ProBlogger ( While this isn’t a site that is specifically geared for virtual assistants, if you are a really good writer, you can find a plethora of good writing gigs on here. Like with Elance, there is a lot of competition, but it’s also free to join and who knows – you may stumble upon a really interesting writing job, like writing for a celebrity entertainment site!

Zirtual: ( I have not used this site yet, but it’s on my list this week to apply as a virtual assistant. What I like is that they have a pretty strict hiring process, which means if you do pass their tests, your competition isn’t as high as if, say, you were on Elance or something. They also only hire US-based college graduates, so it also eliminates the overseas competition that often scores the jobs due to their competitive pricing.

In Summary…

Hopefully this will give you a little more insight into what being a virtual assistant entails. If you like the idea of having diversity in your side hustles, you’re multi-talented and have good writing, speaking or administrative skills, you enjoy research, and perhaps even the occasional dirty novel – you might make a perfect virtual assistant!

dinghy dock

Melody is a 30-something year old who blogs at Saving To Sail, a tale of budgets, boats and dreams. She has her own jewelry line, Maggie and Milly, and manages the music career of her significant other, singer/songwriter Chris DiCroce, on top of a full-time job in the promotional marketing industry. Oh, and she never sleeps.

Like this series? Check out our other side hustle stories here.

**Have a side hustle (or interesting living situation?) yourself? Tell J. Money about it!**

[All photos by Melody, except for the computer one which is by humbert15]

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  1. Clarisse @ Savvy Scot March 27, 2014 at 6:30 AM

    Elance is a very good website but I must agree with you that there is a lot of competition in there. We have a website that exclusive for Filipinos online workers and I must say that they really make a good income, because the client needs to pay first for the membership in order to view the workers profile.

  2. Catina Mount March 27, 2014 at 7:46 AM

    I can’t stop singing “I’m On A Boat” by The Lonely Island….ha ha! What an awesome life! These are also great tips on getting started in the VA world.

    1. Catina Mount March 27, 2014 at 7:51 AM

      I would post the lyrics but it’s an “enter at your own risk without the kids in the room” type of song…but its SO PERFECT for this side hustle! Lol….

      1. J. Money March 27, 2014 at 10:31 AM

        Haha agreed! Just found the youtube and it was released 5 years ago already??? Crazy!

    2. Melody March 27, 2014 at 11:57 AM

      Hi Catina – Melody (the boat girl) here, and you wouldn’t believe how many times I’ve sung that song! haha

      1. Catina Mount March 27, 2014 at 9:24 PM

        Melody….that’s hilarious! Thanks for the great info…I think you have a pretty sweet life!

  3. a terrible husband... March 27, 2014 at 8:43 AM

    Love it! I’m interviewing VAs as we speak. No porn from me though…. Just good old fashioned administrative, content repurposing, and marketing work to free up more time for me to create awesome content! Way to hustle!

    1. J. Money March 27, 2014 at 10:32 AM

      Smart man. I have a hard time giving up responsibility.

  4. Liz March 27, 2014 at 9:14 AM

    I’ve been curious about the type of work people get as virtual assistants and thought it might be kinda interesting to try.Sounds like you’ve had a good experience with it. I think I might have to look more into this type of work. Thanks for sharing!

    1. Melody March 27, 2014 at 12:12 PM

      So far, it’s served me well, and obviously has provided some entertaining stories. ha. Good luck!!

  5. Richard Anthony March 27, 2014 at 9:42 AM

    Great article! Melody sounds the siren call to all who yearn to break free from a 9-to-5 cubicle. But as she notes, even such an idyllic life can impose limitations, as in her being shackled to the East Coast to “stay connected.” This sailing dilemma reminds me of Emily Dickinson’s poem:

    There is no Frigate like a Book
    To take us Lands away,
    Nor any Coursers like a Page
    Of prancing Poetry –
    This Traverse may the poorest take
    Without oppress of Toll –
    How frugal is the Chariot
    That bears a Human soul.

    Next time you’re feeling confined, Melody, say “frigate!”:)

    1. J. Money March 27, 2014 at 10:33 AM

      Getting all intelligent up in here! :)

      1. Richard Anthony March 27, 2014 at 1:05 PM

        Emily’s side hustle was poetry–and look where it got her! The poem fits, so I shared it;)

    2. Melody March 27, 2014 at 12:00 PM

      Love the poem – thanks, Richard! :)

      1. Richard Anthony March 27, 2014 at 12:43 PM

        My pleasure, Melody. Enjoyed your article:)

  6. John @ Sprout Wealth March 27, 2014 at 9:45 AM

    Very cool! I’ve been on both sides of the VA equation and while there can be a lot of competition, you can make some good side money with the right gigs. I think if we weren’t land locked ourselves, my wife would want to do the same thing you are. :)

    1. Melody March 27, 2014 at 12:05 PM

      Hey John! You’re totally right – I also like that it’s not always the same old thing, so it helps to have different things going on, to keep things fresh! And your wife sounds awesome! :)
      One thing we’ve discovered is that you don’t really have to sail off to far away lands to see some pretty spectacular stuff here. So many people don’t realize the beauty that is just a short road trip away, so even though you’re land-locked, you probably can see some cool places to keep the adventure-bug happy!

  7. Crystal March 27, 2014 at 11:25 AM

    Interesting life! :-D Sleeping is overrated, right? ;-)

    I saved this post in my “Ideas for the Future” folder. Thanks for listing specific sites to find gigs. I get sea sick, so I’ll pass on that one, but I hope you are having a ton of fun!

    1. Melody March 27, 2014 at 12:08 PM

      Thank you, Crystal! Yeah, sea-sickness kind of rules this life out for you pretty quick. ha. Luckily I’ve never gotten seasick (knock on wood)! I hope some of the ideas will help you out!

    2. J. Money March 28, 2014 at 12:06 PM

      Crystal – you can do your VA stuff w/ that parrot on your shoulders ;)

  8. AndrewsDad March 27, 2014 at 11:39 AM

    As I tweeted J$ last night, my sister does the virtual office thing, setting up peoples appointments and such. One of her clients is a psychic who does soul retrievals. That was not a typo. The customer sends “an offering”, usually a couple of hundred bucks and overnight, the psychic…. does something… that helps them somehow. Do I sound skeptical? I am told the psychic is booked solid months in advance.

    Now that would be a true side hustle… emphasis on hustle.

    1. Melody March 27, 2014 at 12:10 PM

      Haha – that is crazy!!! Wow. Maybe we’re all in the wrong business!

    2. J. Money March 28, 2014 at 12:07 PM

      I still can’t believe that… Different lives some of us lead!

  9. Marie @ My Personal Finance Journey March 27, 2014 at 8:33 PM

    I love what Chris said “We may end up in riches, we may end up in ruins, but I promise you one thing… it will never be boring.”, he really got a point in there! My father was a chief mate before, so he spent half of his life living on a ship.

    1. J. Money March 28, 2014 at 12:08 PM

      That was my favorite part too :)

  10. No Nonsense Landlord March 27, 2014 at 11:25 PM

    Now that you wrote the book, you can always get a webcam and be a virtual assistant that way…

    There are many ways to make side hustle income. I have done a lot, just not electronically. Mostly involves a bit of sweat and muscle. But that OK too, it keeps me in shape (maybe).

    Here in the USA there are unlimited ways to make money. All you have to do is find one, and exploit it.

  11. Sean Cooper, Financial Freelance Writer and Blogger March 28, 2014 at 6:34 PM

    Another great way to make money is through Focus Groups. Since 2010 I’ve made over $2,000 from attending focus groups. It’s great – you give your opinion and get paid. The last focus group I went to was about the infamous crack-smoking mayor of Toronto. Getting paid to talk about his misadventures was like a dream come true!

  12. payton April 6, 2015 at 3:45 AM

    Great article! What company did you work for that connected fashion influencers with that Instagram deal? That looks interesting!

    1. J. Money April 6, 2015 at 1:26 PM

      Great question indeed :)

      (Love your blog btw – just checked it out… I don’t know jack about fashion but it’s always fascinating to read/look at and learn about the other blogging worlds out there. Seems like a lot of fun!)

  13. William July 15, 2015 at 3:10 AM

    Making $100 an hour is huge! Basically, if you want to be a good VA, you must be skilled. Jack of all trades if possible. People out there will need lots and lots of tasks to be done but can’t do it due to certain reasons, this is where VAs come in. If you have a wide skill set and you are confident in what you do then there are more jobs and opportunities for you.

  14. SF July 23, 2016 at 10:34 PM

    “I giggled because I didn’t expect this man who looked like he could be my Grandpa to be writing erotic fiction.”

    I paused at this — wondering why you would have had that thought.

    I’m still baffled about the expectation even after reading it several times.


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