From Executive Assistant To Virtual Assistant

I’ll never forget my first administrative job. I was a receptionist and I didn’t even have a computer. Just a switchboard to answer the phones and a whole lot of file folders to send out the mail.  That was back in 1998 and I’ve come a long way since.

Once you’re a receptionist it’s an easy transition into the world of administrative assistance. I landed some great jobs and some less than stellar jobs, but one thing was for sure. With every new position, I learned more about more about what it meant to be the kind of administrative assistant that companies wanted to hire.

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Fast forward over a decade later and I was a highly sought-after administrative assistant.

I’ve worked with C-level executives of major corporations – getting the best hands-on education in business you could ever ask for. In an MBA, you learn theory, but there I was getting the best damn business education money can buy because I was learning on the job. I l learned how business really works.

In 2005 after moving halfway across the world to Israel, I landed an amazing job working at a fast-paced international venture capital fund supporting two insanely business venture capitalists. To say I loved my job would be an understatement.  I absolutely loved supporting busy executives with their day-to-day operations.

But just three months into my new job I found myself in a sticky situation, I was pregnant.

Don’t get me wrong, I was over the moon with excitement about my pregnancy, but I was scared that I’d lose my job. After all, I was only there for a few months so they could let me go as I didn’t have tenure.

Well, I didn’t lose my job. I ended up working for this company for several years. Along the way, I had two more children and with each child I was finding it harder and harder to make things work.

I can’t tell you how many times I had to call out sick because my kid had a fever.

Then there were holidays when there wasn’t any childcare BUT it was still a work day.  I’d fight with my husband because we both felt our jobs were more important than the other. Who would stay home with the children? Like most traditional men he felt it was my responsibility and I was getting sick and tired of the fights.

Thankfully my bosses were amazing and allowed me to work from home.  They knew I’d get the job done and I was just thankful that I had the technology to do everything I do in the office from home so I could take care of my children.

One day, I was surfing the internet and stumbled upon a job ad for a virtual assistant.

I had never heard of a virtual assistant before but suffice to say I had a good idea that it meant an assistant that did work virtually.

I immediately applied and had a face-to-face interview with the CEO of this awesome virtual assistant staffing firm based in Israel. They hired me and told me that it could take several weeks before they could match me up with a client.

Well, after just 6 weeks I had my first phone interview and I NAILED it. I started working with a financial services firm based in New York City.

It was AWESOME. I went to work a 9-5 job every day, came home, spent time with my children and husband and then as soon as the kids went to sleep I got online and started working.

Every night for 2-3 hours I worked as a virtual assistant creating travel itineraries for 6 different people. I would write out detail itineraries and upload all the details into their Outlook calendars. I did all of this virtually, from the comfort of my kitchen table (or my bed, where I liked to work sometimes from my laptop).

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0 thoughts on “From Executive Assistant To Virtual Assistant”

  1. Reese, I loved reading your story. I was asked by a business owner to work with her as a virtual assistant back in 2013. The exact words that crossed my mind (but I didn’t say out loud) where ‘what the f*ck is a virtual assistant?’. Haha. Once I found out I was like ‘oh wow, so basically it’s everything I’ve always been doing, but then online. Sweet, I can do that’. From then on things went really fast. I just loved it and decided to set up my own VA business. I’m thrilled to say that now, in 2015, I’m rocking it. I don’t live in one place, but travel the world and live wherever I am. Having my own VA biz was the last piece of the puzzle to live the life of my dreams.

    1. I’m sitting here nodding along in agreement with everything you wrote, Thamara. I love your moxie! It’s great to hear how you’re rocking your business. May 2015 be an even bigger year filled with more adventure!

      1. I find this an amazing concept –and though my reaction to this new title was the same as Thamara 🙂 I am very interested to know more and ways to get started as i think this concept is fairly new in the UAE where I am currently based and working but am more than willing to try it too —as this will provide me the flexibility to work as and when I want and set up my own VA business….await your feedback and advice.
        Best of luck in 2015 and thanks for sharing 🙂


        1. Hi Shirin! I’d encourage you to go through the posts on my website. Getting started can be as easy or as hard as you make it. Check out this interview I gave some time ago. It might help you!

  2. I love this article. I have heard of a virtual assistant; however,some of the postings do not sound legitimate.
    I have several children and need a way to earn extra money.

  3. I loved reading your story. I was asked by a lawfirm to work as an assistant back in Apr 2013. First I was unable to find where I’m? But later I just loved it and decided to set myself. I’m happy to say that now, in 2015, I’ve started enjoying it.

  4. I often wondered how to start with so many scams out there. I’ve been an Assistant for years and just recently started a new job, love the people but there are times I wish I could work from home.
    How does one find the right people to connect with and how secure are these jobs.

    I guess it all goes with building a clientele.

    Would love to get your feedback.

  5. Hi,

    i am also looking for these kind of options… do let me know if You come accross anything.

    I currently work as Executive Assistant to “C” Level Executives.

    Looking forwards to hear from you.

    With Best Regards

  6. hello Reese,Great article! It’s the first time I hear about this I think in Europe we need to update the work possibilities!
    How did you find out for this position it’s very interesting.
    Do you know if there are possibilities?

    In any case thanks a lot for the article its precious information

    Kindest regards,


  7. How does one find a legitimate VA job? There are so many scams out there on the internet.

  8. This is amazing that you can be a VA and create your own agenda. How do I find jobs like this?

  9. I just finished ready your story, when finished thought to myself how come I never thought about that.. CRAP… My kids are grown and have a granddaughter who I would love to spend my days with, but cant afford to quit my job.. I’ve been in a administrative position since 1990.. How and where do I seek help in this venture?? kudos to the both of you.. That would definitely be my dream job.

  10. wilma silbermann

    I did exactly the opposite. I worked as a VA for 5 years, I loved it – but I often felt lonely and isolated. I did however get lots of work done, and it crept into my personal life – I was working ’til 10 and 11 at night.
    One day I realized I had to have a more structured position – working with others. I came to realize I am a people person, and I need the energy of the people I work with, so I became an AA for an office of 120 people.

    Good luck with the VA position – hope you know when it’s time to close the office and be with your family.


  11. I’m an Administrative Assistant that would love to move over the VA world. I’m just not sure how to get started, any tips?

  12. Vittoria Laudari-Piroli

    I would love to become a virtual assistant. Do you know of any companies that are currently seeking this type of employer. I live in Toronto. I am not familiar with this work environment and any help to push me in the right direction would help me immensely.
    I am separated and have two boys to support on my own. I could definitely use the extra income.

    If anyone can help at all that would be great.

  13. Reese,
    How does one get their foot in the door as a VA? There’s so many scams out there that it makes me nervous. Can you recommend some legitimate websites that I can check out to learn more about VA opportunities?

  14. This article is amazing. We are currently looking to move to Colorado from California and this is just what I was looking for. How do you get in the loop or find a list of VA open opportunities? I am currently in a C-Level role but would love to work from home in a more remote setting. Any advice is welcome. TIA! Aimee

  15. As an Administrative Assistant for the past 17 years I loved reading your story. Been a Virtual Administrative Assistant sounds like an ideal job. Maybe I will consider it in the future. Congratulations and good luck in all of your future endeavors.

  16. I never heard of virtual assistant but this is awesome. How can someone like myself get started?


  17. That is a dream of mine! I went back to school after losing my husband in a fatal accident in 2011, graduated in 2013 and work for as an administrative assistant, exactly what I went to school for. I live in a rural area in Minnesota and would love to become a virtual assistant. The college I attended offered a program in VA after I graduated. I would so love to take the credits needed to do that. Right now, $$$ is the stumbling block, but will keep thinking of a way to be a virtual assistant. Kudos, ladies for your hard work!

  18. Hi Reese,I would love to hear more about how to become a VA. It’s been an up and down roller coaster for the past 3 years due to relocating. I would love to hear further information. I look forward to hearing back from you. Thank you for your time.

  19. Reese,I do this with my ex-boss. He is living now outside of the U.S.A and I assist him with personal and business administrative tasks.I love to do it because is an extra money and for me is very easy. I’d like to get more customers like my ex-boss and I’m working on it.It will be great to get my independent business doing this and say “goodbye” to my current boss!!

  20. Good evening,
    I would be very interested in learning more about VA opportunities and how one goes about finding such opportunities that are legitimate. Any suggestions would be welcome. I live in Maryland and I am currently a legal assistant with a law firm. Thank you, Kim

  21. Reese. I love your story. It is so very inspirational to me. This IS my goal. I have started my own business, however, I am still working the “day” job as well so I can be out of debt and preparing to move forward to running my business full-time. I hope to soon enjoy the pleasures of being a VA.

  22. I love your very interesting story, Reece! I am truly happy for you that you have found a way to balance family and work.
    Can you share some places where others can apply for jobs as VAs?

  23. Reese,
    Ive always wanted to be a virtual assistant but I could never find work. If you know where I could find clients please let me know.

  24. How do you find a customer? I have worked administrative 35 years and I am ready to be a VA, but where do I get my clients?

  25. That is awesome & a great transition!It would be wonderful to have an opportunity like that!

  26. Sounds pretty interesting. Was there a particular website that you were surfing at the time?

  27. I have heard of a virtual assistant but I would like more information on how you can become a virtual assistant. I live on a small island in the Atlantic ocean would it be possible to work as a VA for overseas Clientele

  28. Michelle Robinson

    Hello Ladies, I have never heard of a virtual assistant. I would love to learn more about it. Both of your stories sound great. I have a Diploma and Certificate in Office Automation. Good Luck to both of you. I hope you reply to my message.Thank you.

  29. Mari Medeiros

    Hi Reese! I’ve heard of a VA before but never really thought about more until I read your story. What a nice way to earn some extra cash on the side & still be able to have that flexibility with a family while doing something you’re clearly great at. I am currently working as a full time employee at a great software company with a boss who always understands the flexibility that I need when it comes to my children. That you can’t always find & sure don’t want to let go. I’m interested in trying it out and seeing where it can go. It would surely be nice to WFH one day so we can finally have our third child. Thanks for sharing your story.
    Warm Regards,
    Mari Medeiros

  30. I would like to know how to find a legitimate VA opportunity. Have been an AA for over 20 years.

    1. Rita, there are PLENTY of legit VA opportunities out there., hiremymom,, just to name a few. What I do is teach you the skills you need to start your own VA business so you can cut out the middle man.

  31. I would like to know more about how to become a VA as my current job is leaving me frazzled and I am not getting a lot of job satisfaction from where I am currently working? Actually I am really close to walking as I have been treated like s**t over the last couple of years. I hope someone can help point me in the right direction. Many thanks Iain

  32. I’m with most replies in that I have not heard of a VA until I read this article. I’ve held the position as a Senior AA to a Director for the last 5 years…in the Public Sector that is. Prior to that, I have held various jobs as an Assistant since 2003…none of which offer working from home. I would love to have that privilege especially since I commute 100 miles/day.

    1. Maryssa, 100 miles a day! Holy Moses that’s a lot. Goodness grief girl, we have GOT to get your VA business up and running so you can start doing what you do from HOME. xo

  33. I have wanted to be a virtual assistant for a couple of years now, but have yet to find legit company or anyone to provide step by step process. Most companies state you have to have a land line telephone. Like many, I only have a smart phone and the internet so I have not wanted to spend the roughly $200 it would cost for a land line (phone wires, phone and service)if I then could not actually get work as a VA. Can you provide useful information on how to actually become a virtual assistant? Thank you.

    1. Therea, welcome! You don’t need a landline to become a VA! Boy the misinformation out there is just mind boggling. I like you only have a smartphone and internet. I speak with all of my clients on Skype. I would be happy to help you figure everything out! Check out my work with me page.

  34. Reese,Love the article!! I have over 20yrs as a AA/EA for a healthcare company, now I am looking to start my own VA business.

    Thanks for sharing!!

  35. your stories are great but am sure this cant work in the part of country i live simply because technology has not so much advanced here. If i may ask what level of technology skill is required to do the job of VA?

  36. Good Afternoon Reese:
    Your article is very interesting. I would love the opportunity to pursue a position as a VA. Are there really legitimate companies out there? I agree with some of the other comments that have pointed out the fact that there are so many scams out there especially on the internet, one can hardly trust anything anymore. Can anyone provide a step by step process?
    Thank you so much for sharing your experiences.

  37. Great blog post! I was really inspired to read your story of becoming a Virtual Assistant. I’ve been a Virtual Assistant since April 2013, I started at the age of 16. When I first got started, I knew NOTHING ABOUT the different possibilities for being a VA. I’m learning ALOT from you and am realizing how to increase my hourly rate and build up my client list.
    For my first client in 2013, I was hired to write & schedule blog posts and import emails into the client’s email list. Since then, my skills and duties have increased to also managing social media, creating and editing videos and developing a complete membership site.

    My interests are in pretty much anything online. This is great since I have my head in the latest news but it also creates a slight conflict because I’m not really sure how to label myself and what niche to put myself into.

    How do you go about pairing down your skill level to the main things you love to do?

    1. Jonah, thanks! I was in your shoes. I found myself learning so much that my services grew and grew. I found it exausting to work on the things I wasn’t passionate about so I decided to focus on what I did love which was social media marketing and WordPress management. So my question to you is, what do you love doing as it relates to the services you’re offering? Start there. xo

  38. Thanks for the shout out Reese! I had a great time doing my interview with you! You were instrumental in my journey to become a VA. Your story is inspirational to many!

  39. Vanna Zimmerman

    Reese, I am interested in being a Virtual Assistant at night to make extra money. How do I get started? I have almost 30 years experience as an Executive Assistant. Any advice would be appreciated.
    Thank you!

    1. Hi Vanna! A great place to start is the VA Forums and here on my website of course! I am planning on creating some mini-courses to train VAs. Here is a blog I wrote ages ago that can help you as well.

  40. THIS IS AWESOME!!! I’ve never heard of the position but it TOTALLY makes sense in this day and age of technology!! I’m excited to look & find a position such as this. Hopefully it will allow me to balance kids, work and school evenly. Tell me, any advice…?

  41. Hi – any guidance on intro letters to local business owners. I work with a package plan and is there a course out there to spruce up what i”m all about?

  42. I am really encouraged by your piece. I am making plans towards my marriage and would really like to work as a virtual assistant as this will afford me the opportunity to still be with my family and have something to put on the table as well. I would really love it if you could connect me with those who are looking for virtual assistants.
    Have a lovely day ahead whilst waiting for your reply.

  43. I am encouraged by your article as well! I would love to work as a VA. It would be ideal and allow me to have time with my family as well as saving on commute time in a busy city where I live. I have been an AA off and on since 1991 and this would be a dream come true for me! Please advise how I can get connected with comanies seeking VA’s. Thanks so much and I look forward to hearing from you!
    Most Grateful,

    Lynn B Owens

  44. After the worst winter here in Boston, I’ve decided I need to find a new position that I could do from home. The commute alone has drained the life out of me. I’ve sat down and counted the hours I spend with my almost 1 yr old. I’m up and out the door long before he wakes up. My commute home only allows me an hour or 2 a night with him. Majority of it is him sleeping on my chest. I’m currently an Office Manager. I really enjoy what I do so I’ve been looking for Virtual Assistant positions. However I’m not finding much and I’m worried what I do find are scams. Any advice on how to find real positions? Thanks!

    1. Erin, your story resonates. I left my job because of long commutes and no time with my kids. I’m a hands on mom and I couldn’t stand not seeing them during the week. Erin you can check out or Zirtual. In addition you can start building up your own VA business. That’s the best route. It’s not easy building a business but it’s the only way for me.

  45. I have been working on setting up my VA Business. I have a website, business cards, forms. Pretty much everything I believe I will need to get started. Now I’m to the point of marketing myself. This may be a stupid question, but I’m just a little confused on how the sharing part works. In your story you mention setting up itineraries in someone else’s calendar/email. How do you get access to a calendar that is not your own. Is this something the company you are working for gives you access to or is there a program you need to use to obtain that access?

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