My Story: How I Got Started as a Freelance Writer and Virtual Assistant

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It was a dark and dreary day way back in 2014 – Tax Day (April 15th) to be exact. Sitting at my desk staring at my dual monitor computer screens, I realized this career was no longer for me… no matter how great of an opportunity it was.

(I don’t know if it was actually dark and dreary, but it sounds more dramatic, right?)

While I feel like I’ve told the story of how I got started as a freelance writer and virtual assistant a million times over, I still get questions about it almost every day.

And that’s cool, I’m happy to answer them. But then I thought maybe I should write “my story” out once and for all to make it easier on myself and anyone interested in learning more.

So here goes…

It really was Tax Day…

Why is this important?

Because tax season is a pain in the butt in the financial services industry and Tax Day marks the end of it (for the most part). During tax season, I would end up spending more time fielding calls and emails about tax statements, printing them out and mailing them (even though the home office had already done so), faxing them to accountants, etc. than almost anything else.

Suffice it to say, it’s a good day when tax season is over. You can actually focus and get work done again. 😉 Even if you’re a little (okay a lot) exhausted…

(Side note: If it was bad for us, I can’t imagine how it feels to be an accountant or CPA during this time!)

So what did I used to do for a living?

I was part financial advisor and part support person (at the end anyway). At age 21 (in 2005) I was hired on the employee side of a financial advisory firm and started as a full-fledged financial advisor… from scratch.

To say there was a learning curve in that field is a severe understatement.

Not only did I need to learn all about retirement, estate and education planning, I also had to learn the ins and outs of insurance, stocks, bonds, options and other investment strategies (and pass really hard tests like the Series 7 and 66). In addition to the foundational financial planning knowledge I had to acquire, I also had to get a handle on our firm’s product line-up, figure out how to market my new business (and actually land clients) and then find appropriate products to enhance their financial situation.

And I was paid on commission… 100%. Fun times! 😉

Throw in navigating compliance and it was literally the most stressful time of my life! In hindsight though, I learned some very valuable skills. Skills that I was able to take with me after leaving my career in finance that have helped me build a pretty lucrative business online.

Change is the only constant in life.

As the Great Recession was unfolding, the firm made some pretty big changes to our commission structure. This was in 2009, and Wade and I were talking about starting a family… Not great timing, but when exactly is?

So I investigated my options. I had a small, but thriving practice at the time and liked the company as a whole.

My search led me to a brief stint filling in for a support person of a franchise advisor that was going on maternity leave. I had to commute an hour each way (not accounting for traffic), but it eventually allowed me to take a position closer to home. I joined a family run practice about 10 minutes from my house. Ironically, I took over for my high school math teacher as he made his way back to teaching after trying out a more traditional 9-5.

I spent five and a half years working with the most wonderful family – a family that treated me like one of their own. Impressively, my former boss (and the senior advisor of the practice) is still at it with over 40 years in the business (with the same firm!), his son and business partner has to be going on 20+ years as a financial advisor and his lovely wife still happily greets clients at the door.

(They’re a great example of working because they want to work, not working because they have to work, and great role models in life overall.)

I ended up having both of my babies while working there.

(Not in the actual office, just while I was working there 😉 ).

In fact, they let me bring our firstborn to work on Wednesdays for the first couple of months (in hindsight not the best idea, but mainly because it made me so darn stressed out). And then my colleague’s wife watched him for the next several months. How awesome is that?!?

I also negotiated a four day workweek after giving birth. Suffice it to say, I had a good thing going…

So why would I want to leave?

  • I worked less than 10 minutes from home.
  • I only worked four days per week.
  • I had amazing co-workers.
  • And I had the opportunity to grow with the practice.

Who in their right mind would give that up?

Well, it wasn’t my first choice.

I had known for some time that I wasn’t in love with finance.

Sure, I’m “a numbers person” and loved meeting and working with the client base I had built. But another 30 years of the same thing (including the ridiculous compliance hoops that we had to jump through at an increasingly nauseating rate) – well, it made me want to throw up.

To be extra clear, it had nothing to do with my clients or the practice I worked as a part of. They treated me better than I probably deserved and I’ll forever be grateful to them all!

I just wasn’t passionate about it.

But I really tried to be. For example, before considering alternative career options, I tried doubling down on my career in finance by enrolling in the CFP (Certified Financial Planner) certification, which is the most sought after professional designation in the space.

I took and passed the first course, but instead of falling more in love with the subject matter, I felt more dislike for it. And the Type-A in me just couldn’t have that!

I.e. I’ve always wanted to be the best I can be in anything I fully commit myself to (not necessarily the best, but MY best), which is why I sought out the designation and pitched a long-term plan for buying into the practice.

But it didn’t work.

When I finally gave myself permission to be honest with myself, I realized being a financial advisor wasn’t really what I wanted to be when I grew up.  It was settling for something that could provide a comfortable life for me and my family.

But not something that made me spring out of bed in the morning, excited to go to work.

(Side note: Wade left work behind in July, 2013 to become a full-time SAHD to our kiddos after I returned to work from a six week maternity leave when our second was born – our children are 19 months apart.)

And working to provide for our family was kind of necessary.

Fear of failure is a fallacy.

Unfortunately, there was this fear of failing that held me back too.

Even though I was almost a decade into my career in personal finance, I felt that making a career change meant that I had failed. That it showed the world that I couldn’t hack it as a financial advisor.

I now hear how stupid that sounds.

Changing careers doesn’t equate to failure or not being able to “cut it.” It was just a pivot that brought me one step closer to my career destiny. I now know there’s no certain end game either – there’s just where I am presently and a million possibilities of where my business will take me over the next however many years I’m blessed with here on earth.

Instead of that scaring me these days, it excites me. At least most days that is… 😉

The transition came one step (and one action) at a time.

It’s easy to land on a website like Horkey HandBook and think that someone like myself made a big life change and started a new, successful business overnight.

But that’s not at all true. I suspected for YEARS that I wasn’t in love with finance. That I wanted to do something different.

And like I talked about earlier, my transition started with trying to fall “back in love” with finance first – not pursue a new career or business. I did this through studying, finding a mentor, reading a bunch of career books, etc.

Then came Tax Day, 2014.

  • The day I was finally fed up trying to pretend I loved doing something I didn’t.
  • The day I finally gave myself permission to consider other career opportunities.
  • The day I started doing some research online.

And found that freelance writing was “a thing.” That people got paid to write more than just novels or technical reports.

People just like you and I were getting paid sometimes hundreds of dollars to write blog posts. Simple 500-1,000 word articles for the web.

My mind was BLOWN!

It also started spinning with possibilities.

I liked to write. I was pretty good at it. Sure, I wasn’t a journalism major, but I knew how to piece cohesive sentences together and write in a way to evoke emotion or motivate people to take action.

I could do this. Right?

While I knew it was a possibility, I didn’t know for sure if it’d pan out. So I figured why not start it on the side quietly at first? Figure out if I could make a go at it without jeopardizing my current job.

And that’s exactly what I did.

At the time I had a 10 month old baby girl and a two and a half year old son. And I worked full-time (four, nine hour days). I did have a supportive husband that manned the home front going for me. But baby was still waking up once a night to nurse and I really wanted to be a present mom when I wasn’t at work.

So I started waking up at 4:30am each weekday to get a couple hours of work in before the rest of the house woke up. Then I’d say good morning, feed the baby, eat breakfast, take a shower and head into the office for a full day’s work.

On Fridays, Saturdays and Sundays I’d do what I could (Fridays being more reliable) to build my new freelance writing business. It was definitely a balancing act there for awhile!

On turning a profit.

I found freelance writing on April 15, 2014.

I launched this website, started learning about the business and sent my first pitch in May of that same year. I cashed my first paycheck in June, 2014.

Being a numbers person, I kept track of mine. Here’s what my first year as a freelancer looked like (that first $205 line item was what it took to launch my new writing biz):

I worked between 10-20 hours per week growing my freelance business and within eight months of even looking into it in the first place, I had put in my notice and left my 9-5 behind.

How’d I do it?

I already shared above how I got up really early to work on my business before heading into the office each day. So designating a specific time each day to work on growing my new freelance writing biz was one important factor.

Being consistent was another huge one.

Again, being a number’s person, I had metrics that I challenged myself to meet each and every week around how many pitches I needed to send (at least 10) for paying work, how many pitches for guest posts (to build my writing samples and get my name out there) and how many bloggers I aimed to interact with (to start networking/building relationships).

I also took a few shortcuts like enrolling in an online course on the subject to cut my learning curve and hiring a coach to give me advice and keep me on track. I’m a huge proponent of both to this day!

Probably because they were the difference between trying freelance writing as a hobby and building a successful business from scratch, which enabled me to quit my job – even though I was the breadwinner of our young family of four.

On adding VA services to the mix.

I started offering virtual assistant services to the mix a few months after getting my freelance writing business up and running.

The whole thing was rather serendipitous really. I had taken a course from an online peer about raising my rates and noticed in our correspondence that he was having a hard time getting back to me, but it seemed like he really wanted to.

Managing email was something I was pretty good at and I had experience doing it for the practice I worked in when everyone was out of town, leaving me in charge of the office every so often. I felt confident I could help him and I said as much in a reply, asking him to hire me.

And he said yes!

I started by charging him hourly and later we transitioned to a retainer model – the consistency of which allowed me to put in my notice and quit my 9-5.

I spotted a need, re-purposed skills I already had and asked to be hired.

Not as hard as one would think, right? (Probably those valuable skills I learned in my career in finance helped a bit! 😉 )

I’ve only ever had three VA clients – two of which I’m still working with currently and both of whom were referred by client number one. While I started with (and still do) email management, I’ve also helped my VA clients with writing (case studies and sales copy), editing, social media management and more.

While some of these were skills I already had, others I had to learn on the fly. One of my motto’s is “Always be learning!” and I continue to strive to learn new things and strengthen my existing skill set. Implementing similar strategies in my own business also helped me to learn my client’s businesses better as a result.

What happened after I quit my job?

My last day was just before Christmas in 2014, so I started a fresh year in 2015 as a full-time freelancer.

I also introduced my first online course, 30 Days or Less to Freelance Writing Success about the same time (early December, 2014). So in addition to freelance writing and offering virtual assistant services, I was also in the online products business.

In hindsight that was a lot to take on at once, but it worked out!

I pieced together income selling services (writing, VA and a small amount of coaching), offering my online course (via email at the time) and from the sale of my financial planning practice. I also consulted with my former office on a very part-time basis for the first five months of 2015.

You can probably see by now that doing just one thing isn’t in my DNA. 😉

And the rest is… history?

Between then and now I’ve worked probably harder than ever.

In fact, I just returned from my first week completely offline (unless you count Netflix) since I started (with the exception of a mission’s trip in late 2016). I’m not very good at taking vacation…

I continue to learn, have new ideas and execute – the latter of which I’m probably best at.

And while I stress myself out more than I probably need to (by setting public deadlines to ensure I get a project done, for example), I absolutely LOVE IT!

  • I love that I get to choose when I work, whom I work with and what I do.
  • I love the my schedule is flexible and my income potential is unlimited.
  • I love that the online business world is constantly changing and there are always new things to try and learn.
  • I love the level that the people I associate with play at.
  • I love meeting new people and helping them start a new business or change careers like I have.

There’s a lot to love.

There’s also a lot not to love. Or in other words, a whole slew of challenges.

  • Ever-changing and imperfect technology probably tops my list. 😉
  • Customer service (for both myself and my VA clients) can put me to the test.
  • Competing priorities and never having enough hours in the day runs a strong race.
  • And then there are self-limitations, like limiting beliefs, caring too much what others think and self-doubt.

The challenge’s side of things tries its own case in court.

But I continue to remain undeterred and optimistic about the future of my business. And why shouldn’t I?

The opportunity that exists in online business is nothing short of AMAZING.

… Provided you want to work for it, that is. 😉

25 thoughts on “My Story: How I Got Started as a Freelance Writer and Virtual Assistant”

  1. I love reading people’s how they got started stories, especially when they’re super successful like you are! Thanks so much for sharing – it really shows that with hard work (and getting up early!), you can persevere 🙂

  2. Hi Gina! I’ve read over time you talking about your story but not quite in this manner…which i guess is why you did it lol
    I love that i can pick up the humor too. I enjoy that you are so personable, even while having an income that is many people’s goals! I guess I also understand a bit, for example I am on a health journey and dropped 40 pounds so far! So I’ve had a few people say they were “jealous” of me…and it actually made me feel like a little offended or angry (i will explain) because there is real work and sacrifice that goes into meeting a goal! Just like what you sacrificed to reach your goals!
    So thank you for always being so transparent and supportive of me! I’m recommitting to my 30 Days Freelance course (by actually doing it, in spite of fear) and I can’t wait to guest post for you one day! (see? I’m posting a goal public like you have been doing all this time !!!)

    • Hey Danielle!

      Congrats on your weight loss goals – losing weight, building a business or any other audacious goal aren’t for the weary. Go you!

      Thanks so much for your kind comment – you’re welcome to pitch us ANY TIME!

      Best of luck with your re-commitment,


      • Thanks for sharing your story Gina! I’m currently still working a 9-5 in the financial services industry. However I’m not a rep. I’ve worked on the operations side for a while. Looking for a change because the industry is not what it used to be. Unlike your situation, I was severanced 2 years ago and have bounced a little with jobs. Your story was inspiring to read.

  3. Thanks for sharing your story. It really resonates with me as I am in a similar position. Finally landed the “perfect” job, close to home. 6 figures, 4.5 days but I am just not passionate about it.

    I have 15 years experience in marketing and copywriting but still have the hesitation of taking the leap myself as I am the sole income earner (hubby SAHD to our 1 and 3 year old).

    I see all these people offering such cheap rates on writing blogs or social media management and it just would not be worth my while to compete with that. I have to trust I will find the clients that are willing to pay for quality work.

    • Hey Cath – sounds like we have really similar stories! There are good clients out there, so no need to settle for the bottom feeder prices – maybe tap into your network and start building your biz on the side like I did? Sounds like you have a lot of great experience!!

  4. Thanks for sharing your story.

    I’ve been a homeschooling mom for the last 15 years and my youngest just graduated. I started a blog to help encourage and equip other homeschool moms and would love to eventually work full-time from home. Your story inspires me to do the work and make it happen!

    (And I hope to meet you at Activate:) )

    • Hey Kay – would <3 to meet you at Activate, so PLEASE seek me out! And go you - just remember, it's just one small step after another, after another, after another... and pretty soon you'll have "arrived!"

  5. Loved the honesty of your journey to freelancing, especially the struggle you had deciding to make the plunge into it to begin with.

    Just think, if you hadn’t faced the “fear of failure” by moving out of finance, you never would have written your course and inspired so many others!

    So THANK YOU so much for paving the way and believing in yourself! You’re pretty amazing, and I’m so thankful for all that you’ve taught me!

    • And thank you for being an amazing star pupil Lisa – your progress inspires me like you wouldn’t believe. So proud of you – I’m still in awe of all that you accomplish with a large family, hobby farm, etc. If there was ever a real-life Wonder Woman, it’d be YOU!

  6. Hi Gina,

    I’m interested in becoming a VA and in taking your 30 Days or Less to Virtual Assistant Success. However, I have a question about the course that I don’t believe I saw addressed in the promotional information. Does the course provide guidance on what one needs to set up with an attorney, an accountant, and insurances?

    • Hey Rene – we do touch on business topics like taxes, entities, etc, but you may need to get in touch with local professionals to confirm what’s need in your specific situation depending on where you live. Hope that helps!

  7. Wow, what a great and inspiring story! Thank you for sharing! I am learning so much from your 30DOL VA course, it is WELL WORTH every penny! There is no greater feeling than overcoming procrastination, and that’s truly a defining feature of your course: the action steps. You inspire action that we can pursue autonomously, without feeling like you gave us the answers. Oh, I’m dealing with many of the same challenges, believe me! Minus the kids … unless you count my husband, HA! But you make the effort needed to overcome the procrastination easy. Point is, now I understand the brilliance of your courses; you couldn’t have made them so effective and thorough had you not walked the path yourself.

    Again, thank you for letting us get to know you! Very well-written, I might add. 🙂

    • What a wonderful testimonial Sarah – thanks SO much for all of your kind words. 🙂 So glad to hear that the course is going well for you and you’re taking so much action – action is where it’s at!

  8. And I just keep finding more great articles by you! I was looking through some files that I had downloaded of yours off of emails and such and I realized that I hadn’t read all of them and missed out on some important things that I am now able to piece together now…If only I had of read them sooner! Oh well, you are one smart cookie and thanks for sharing all your hard work and hopefully us VA’s that learn from you will be just as successful in the future 🙂 Take care and have a great weekend Lady! You deserve it!

  9. Gina,

    I have the VA course, and I’m very happy with it.

    However, the web designer and 50 something in me is having fits with the font on this page. It’s not very readable for older eyes. 🙁

    • We’re sorry to hear that, Kelley.

      But thank you for letting us know.

      We’ll definitely keep that in mind when we do our next site redesign.

  10. I love this. It makes me feel not so alone about the whole sitting in my day job parking lot tapping away at the laptop. I’m not successful yet but I’m hoping to be. Like you said ,if we are willing to work for it. Wow is it a lot of work. Thanks so much for sharing these type of details.

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