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From Secretary to CEO: One admin assistant turns entrepreneur and scores former boss as first client

January 2, 2009

Emily C. Morgan is a calm lady, not at all the  kind of loud-talking, forceful person who you might assume would go the intrepid route of writing off her company and boss and starting her own business.


Emily’s virtual assistant business, Delegate Solutions, started from her home when she was pregnant AND working full time as an executive assistant to the top management at her former employer, a local mid-sized company.  When the company unveiled plans to move to a new location several towns away, Emily faced an extended commute (as a big pregnant lady!), and her enthusiasm for being somebody else’ perpetual gopher, unsurprisingly, started to wane.

Emily decided that what she really wanted was to work from home, and have  more of a hand in her own employment. Working as a virtual assistant started as a side business for Emily, something she was doing to fill in those other 30 hours after she put in her regular 40 (yep, that’s right, this mama works about 70 hours a week).

Like Chad Hartvigson, Emily was shrewd, confident and probably a smart enough strategizer to beat last year’s Russian chess master. That’s why Emily’s first high-powered clients were her former bosses. Not only did this young mom-to-be, and sole breadwinner for her family,  negotiate a work-from-home deal, she actually convinced them that her QUITTING would be a good thing, and that they should continue to give her money as clients of her business.

So sly it’s damned foxy.

During our chat a few weeks ago, I discovered that you CAN be a nice young lady like Emily, ‘cheat’ on your company by starting your own, win them back, and, with a healthy dose of hard work, get just exactly what you want.

What I learned from Emily

1. Ask and receive. After starting her business, Emily had a dream to be on the Martha Stewart Living show. She wanted it, and decided she would get it. No matter that Martha’s all about cooking and crafting and Emily is an entrepreneur in the cutting-edge, but not very crafty, virtual assistant industry.

After much unsuccessful LinkedIn-mining (which requires its own form of constant asking), she finally got a hookup with a producer for the show, only to be told that Emily’s virtual assistant business was a cool story, but not quite ‘crafty’ enough for Martha. Instead of giving up (as I probably would), Emily kept asking. She eventually asked so many different people, so many times, that she found someone who worked for Martha’s radio show who was agreed to hear her out. A week later, Emily was up in NYC and talking up Delegate Solutions on MSL Radio.

2. All hail the day job! The more entrepreneur types I talk to, the more this one is becoming a major theme. Emily started out small by taking on just a few clients while she continued busting her butt at her regular job. As a pregnant lady, and later as a new mom who was a sole provider, she couldn’t afford the risk of free fall, and she needed the health insurance. Yes, she worked longer hours in the beginning, but to her, this was an investment not so different than putting money toward grad school, or working an unpaid internship.

3. Spin a loss (your company’s’) into a gain (yours AND your company’s’). When Emily first told the three executives at her company whom she assisted that she was going to quit, and to start her own business no less, they were skeptical. However, they were also needy, maybe even desperate, because Emily was a great assistant and had become an important enabler of their own success. Emily worked the ultimate magic when she actually convinced them that they should be happy to let her go, and that they should next enlist the services of her new company, Delegate Solutions, to fill the role.

Did she strong-arm them? Go in to the exec office with hardball negotiations lines written on the palm of her hand? No and no. She simply spoke their language, the much-loved language of money. Emily knew that cost was a concern to them, so she talked up the changeover in terms of cost – the company could save headcount money by purchasing her service instead of maintaining her as an employee. She didn’t bother them with too many details about her personal life as a mother and goals to own her own business. Honestly, nobody but your mom cares about these things, so it’s best to keep them out of important negotiations and explanations. When negotiating with employers – whether it’s for something complex like transitioning them from employer to client status, or for something simple like a raise – stick to the universal language of money and value.

4. Make it All-or-Nothing. In Dan Ariely’s book Predictably Irrational, he describes one study that illustrates how having more options (or even just perceiving that there are more options) can actually distract us from our primary goal and undermine our success. An All-or-Nothing situation actually increases our success – even after factoring in the risk of failure. Emily was her family’s primary breadwinner; her husband had been laid off a few months before and babies are still not allowed to perform wage labor in the state of New Jersey (why, I have no idea…).

Once Emily had enough clients and decided that Delegate Solutions was going to be her main work, she was basically putting her family’s survival on the line. Stupid move? Nope, it was an awesome move. After she saw that her business had a decent chance at succeeding, she set up the ultimate motivating mechanism for herself and made sure that she’d work her butt off. She eliminated failure as an option.

See the full interview notes below.

Why did you think you could start this business by yourself ? Why didn’t you think about joining an established virtual assistant firm?

I never really thought of that as an option. If you’re looking to do admin work and have no headaches, being a subcontractor through some virtual assistant firm is definitely the way to go. But, if you’re looking at this as a big picture, then this is the way to go. The only way to make serious profit is to start your own business. Anything else would only be capping your income potential.

In my case, there was no reason I couldn’t do it for myself, aside from a little fear of not making enough income to support my family. I had a good, realistic business model, and knew it was a way that would allow me to work remotely using the skills I’d perfected through my ten years in admin work.

The key is that you can’t just wake up one day and say “I’m going to do this.” Building a business is a slow process, and I built mine while I was working for somebody else’. It actually helped me because as I was working, I was building up my client portfolio until I could be independent.

How did you learn, or was this just like working for your company (without the commute)?

I didn’t have any business training, I didn’t know what LLC meant, and I didn’t know I had to go through as many hoops as I did, so starting this business took a long time.

I relied on my state’s small business association – a government program – that provided me with a ton of resources to get going with the basics of starting a business.

I also belong to two industry organizations, the IVAA and the DWAA. The virtual assistant industry is very supportive, and I used it extensively to network and find a group to support me.

What does your income look like now compared to being a regular full-time employee?

It’s not totally the same since I have to pay for health insurance, I no longer have a cushy 401k, and I have to pay for my own electronics and software. But, I’m really just starting out, and, with owning my own business, the opportunities ahead are so much bigger than anything I could achieve by working my way up the company ladder.

What does your husband think of all this?

He loves it. I work all the time, but he’s very into being Mr. Mom. When he lost his job, I went full force with the business. He helps me with business things, errands, cleaning, cooking.

I can have a baby, I can bring in some extra money – I didn’t really think anything other than this is a great arrangement.

Now that we’re in the situation that we’re in, this just sort of took off, and I’m just going with it!

It wasn’t what I had planned, but I’m not disappointed. We’re both in our element. I hope that one day I don’t have to work as much as I’m working now, but I’m working on setting up those boundaries. It can be hard when you have a home office because it’s always easy to get to work.

How did you get that fantastic mention in the New York Times?

Writer of nytimes article is a good friend of one of Emily’s clients. BC of the Times piece, she was able to get on Martha, and then NBC, etc.

I really wanted to be on Martha Stewart show. How are you gonna get on Martha Steward?? I worked the netowkr (linkedin) and connected with a producer on linked in.

Then, one day I came across a radio host who worked for Martha Stewart and she put me on her show!

To the producer on the show: found out she was a penn grad, kept emailing her, she finally wrote me back, and said, “I totally want to work for you and I have a  baby!” but this isn’t gonna fit on the show. But, after the Times piece, but I got a client from there and his coach posted to Martha’s blog, and E found out that she was the career coach on Martha Stewart radio. Contacted her…

Tpo be on nbc news – I emailed all the news channels with my story, and somebody called me back! My mba person pitched me to the magazines. “turning your former employer into your client”

Would you recommend this to my CEO’s executive assistant, Melissa?

Having your own company is the most fulfilling and draining things you could possibly do. A lot of people aren’t up for the whole working 70+ hrs per week thing. They don’t have the stomach for it and that’s fine – there are plenty of corporate jobs to be had.

BUT… anyone can do it if they really want it and can envision their own success. I’m not talking about new-agey visualizations, I mean being able to know that you can succeed at something.

My clients (and former employers) love it because they get treated like they’re a customer paying for a service rather than a company having to manage an employee. For me, I’m still an assistant helping them with the same admin tasks as when I was their employee, but it feels completely different to direct your work as part of your own business.

2 Comments leave one →
  1. January 3, 2009 4:56 pm

    I agree that being a VA is a wonderful business opportunity and allows you to basically make your own hours as long as the client work is getting done. IVAA is a wonderful organization. VAnetworking is another great resource for new or aspiring virtual assistants. They also have great resources and information for entrepreneurs who are thinking about partnering with a virtual assistant to move their business to the next level.

  2. Melissa T. permalink
    February 11, 2009 6:56 am

    Susan, this is a great article!!! And thanks for the special mention ;)

    Your article offers a fresh perspective for current administrative and executive assistants out there, especially for those who would like to find a way to spend more time at home. With internet access readily available everywhere, there really isn’t a reason why a Virtual Assistant couldn’t be as effective as an in-person Admin or Exec Assistant. (Except for the occasional running-around-the-office to look for the Boss when he is missing from an important meeting- which can be solved if he has his cellphone on him… LOL) I would say that 75% of what we do can be accomplished remotely- as long as we have Outlook, internet access, and a telephone at hand.

    This definitely opened my eyes to the perks of becoming a Virtual Assistant. Thanks!

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