Amanda Aitken, entrepreneur and all round web goddess, reveals how she broke free from the 9-5 corporate job where she felt like a ‘square peg in a round hole’ and is now running two successful web based businesses in the glittering world of web design, working how and when she wants…

What did you want to be when you were a little girl?

I wanted to be an author. I was obsessed with Roald Dahl and all things magical, and I loved writing stories about fantastical things. I still love that stuff, and I still love to write – so in a way, I guess not much has changed!

Tell me a little more about your career path?

I taught myself HTML when I was 13 years old, and I had several web design- and communications-related jobs throughout high school. I graduated from the University of Western Ontario with an Honors degree in Media, Information and Technoculture (yep – that’s really what it was called!), and by that time, I was doing a fair amount of freelance web design work.

I wasn’t really considering entrepreneurship as a viable option for myself at that stage, so I promptly went out and got my first “real” job after graduation: I was one of a team of affiliate managers at an affiliate network based here in Montreal, Canada.

I did a lot of writing and marketing tasks in that position, which I really enjoyed – but looking back, I see I was kind of a square peg trying to fit itself into a round hole. I really wanted to please my superiors, and I would get pretty stressed about doing everything perfectly, which wasn’t exactly healthy.

Around the same time, I started to have the inkling that I was destined to do my own thing, and it was confusing. It was like I was in a constant state of identity tug-of-war: was I the conscientious employee, or was I a spirited entrepreneur?

While I was busy trying to figure that out, I decided I wanted to do something that would bring together my love for the web, writing and fashion – so I started a fashion and shopping website that I worked on in the evenings and on the weekends. It wasn’t long before I was hooked. I loved running the site, writing content for it, and building awareness of it online.

I went on to establish a boutique fashion copywriting firm, and I also began doing French to English translation for a major Canadian magazine called LOULOU. Eventually I graduated to writing for their beauty section as well, which was a blast.

Throughout all of this, I was still working full time in various roles, so my entrepreneurial exploits remained strictly on the side. I was getting more and more eager to make the jump to full-blown self-employment, but I was also terrified to take the leap. Then, just when I thought I couldn’t take another cay of “should I or shouldn’t I”, the Universe stepped in: my position as a copywriter at a well-known Canadian fashion retailer was abolished. I was free!

Fast-forward a few years later, and I’m running two unusual and fulfilling web-based businesses, providing sinfully gorgeous, satisfyingly fast web design to women entrepreneurs (, and teaching creative, driven women to design and code sites and blogs with my ultra-empowering online course, The Girl’s Guide to Web Design (

What was the inspiration behind your business?

I started The Girl’s Guide to Web Design for a kind of bizarre reason. I am all too aware that when it comes to being able to make money doing what I love, I’m in a pretty fortunate position. Because of the path I’ve taken through life and the interests I’ve chosen to pursue, I ended up with a really great skill set that allows me to conceive of an idea, brand it exactly the way I want it, and put it out into the world via the web so that I can help people and make a nice income from it. I don’t have to hire anybody to help me do this, unless I really want to. I can do it all on my own, and that’s immensely satisfying.

So where am I going with this? Well, in a nutshell, I hated seeing my web design clients suffer through not having those skills – especially when they would so obviously benefit from having them. As a web designer, I had worked with so many women who had these incredible ideas for businesses or products, and who had an equally amazing design sense, but they were forced to work with a designer (i.e. me) just because they didn’t have the web and coding skills to do it on their own. That meant they had to save up money to work with me, wait for me to be available, and then put in a lot of effort communicating their vision for their site or blog to another person (again, me) and hope that that person “gets it”. And even though my clients were always very happy with the sites I created for them, I could tell there was always that small, sad feeling of “it would have been even better if I could say I did it myself”. And at the end of the day, even though I give all my clients a guide to maintaining and updating their own sites, without knowing HTML and CSS, there’s a lot they can’t do or change on their own when it comes to how the site looks.

So, that’s why I created The Girl’s Guide to Web Design. I wanted to empower women to be able to be able to take ideas out of their heads, get them online and looking flawless, and turn them into viable businesses, projects, or movements and causes.

What does a typical day look like for you?

I work from home, so I pretty much roll out of bed at around 7 AM and get right to it! I recently treated myself to a beautiful bleached wood desk (it kind of looks like a huge piece of driftwood), which totally changed my life (I used to have the most non-ergonomic setup imaginable).

My day usually consists of a mixture of email, answering any questions that our students may have, doing design research for clients, writing articles and other content, and developing and executing marketing campaigns. I take a quick lunch break at around noon, and I might go to the gym or run some errands somewhere in there, too.

I’m planning my wedding right now, so there are also a lot of phone calls to make and appointments to go to sign off on things. I feel very lucky that I have the flexibility to sprinkle that stuff throughout my day instead of needing to cram it all in during the evenings and weekends!

I tend to log off of the computer around 6 PM, when my fiancé gets home from work. At that point, we catch up on our days, have dinner together, and then hit the couch for some iPad and TV time.

What’s the best thing about being a business owner?

I would say it’s the fun of constantly coming up with ideas for new tools, solutions, or types of content that you know your customers and fans are going to love. I get really fired up about inventing new teaching techniques or website features that will make our students’ lives easier. As the business owner, there’s no one to tell you “that won’t work” or “there are other priorities right now”. You get to be wildly creative and exuberant at all times. ☺

What’s your current biggest challenge?

Probably the fact that I’m still doing almost everything myself, which has kept me from moving forward with all my really big, awesome plans for The Girl’s Guide to Web Design and Better Than Chocolate. There comes a point when you absolutely must get help with customer service and admin tasks, and I reached that point a long time ago! My lovely and talented younger sister, Allie, played a crucial role in supporting The Girl’s Guide to Web Design back when we first launched, but she’s been working almost full time these days, so I’ve been handling everything on my own. Luckily, I’m about to start working with a truly awesome Online Business Manager, Jamie at Zenplicity ( I can’t even tell you how excited I am to get going with her!

How do you keep yourself motivated?

I’ve always been the overachiever type, and I’m 100% passionate and invested in what I’m doing with my businesses, so motivation isn’t usually a big problem for me, luckily. The only time I struggle with motivation is when I need to do something I hate…like bookkeeping stuff or really tedious website maintenance things. I try to force myself to do that stuff by blocking out time for it on my calendar. This is a trick I learned from Laura Roeder (if it’s not on your calendar, it’s not happening!).

What’s the most important thing you’ve learned on your career journey?

That everything works out the way it’s supposed to. Even when you have what feels like a massive setback, or that partnership you were so excited about falls through, there’s always a hidden good reason for it. In a few weeks or months, you’ll be able to look back with a fresh perspective and see how all the dots connected in a way that caused you to learn the lessons you needed to learn to set you up for amazing new opportunities.

What advice would you give to women who are fed up in their careers and want to make a change?

I would advise you not to make a half-hearted change. Go big or go home. Think of that secret thing that totally lights you up inside, and figure out how to make it into a viable career or business for yourself. It’s always possible, and the joy and energy you’ll get from doing that one thing that is YOUR thing is incomparable.


Check out Amanda’s web design business Better Than Chocolate here (don’t you just love the name?!) and her online web design training business, The Girls Guide to Web Design here



7 Responses to “From Corporate People-Pleaser to Web Design Empowerer”

  1. Dani on

    Amanda, I am really drawn to your business names! When I came across The Girls Guide to Web Design I felt like I had found a little place on the web that was made just for me. I love the visuals + practical tips.

    Keep up the good work and glad you’ve gotten some help!

    Take care,

  2. Wendy on

    I took the first GGWD class with Amanda and it was the best thing I could have done. I’d in the process of setting up my own little web biz and Amanda’s an inspiration for me and probably lots of other women webby entrepreneurs.

  3. Karen @ Moonflower Studio on

    Loved your Jetsetter course Amanda, really got me over the hump as a graphic designer as I have been doing WordPress sites for clients lately and having to struggle to find the way to make things work. You are awesome and thank goodness I found you!

  4. beth on

    Hi Dani- I absolutely agree. I think Amanda is hugely talented at really getting under the skin of her target market and marketing her businesses in a really innovative and savvy way. We all can learn loads from her…

    Wendy- I can see why Amanda’s GGWD course would have been perfect for you & thanks so much for sharing the feedback. I’m tempted to sign up myself to be honest for the reasons Amanda talks about above- there’s nothing like feeling empowered to know you can turn your unique vision into a reality yourself as opposed to relying on someone else you’re likely to be paying a ridiculous wad of cash for and is likely not to get it quite right! x

  5. Amanda Aitken on

    Thanks so much for the kind words, ladies! It’s wonderful to know that I’m able to do play a small part in spurring other women to make their dreams a reality online!

    The Girl’s Guide to Web Design family of students continues to grow with each passing day, and I’m so excited to see where we all end up! :)


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