By Jeff Nelson
The Internet has provided a wealth of career opportunities for those willing work hard. Carly Ottaway is one such person. Leaving a full time job in pursuit of internet self-employment, her experiences are an example of what to expect when journeying away from traditional employment. It had been her dream to pursue a writing-based career. Since acting upon her goals in 2010, she co-founded The Reply, a site dedicated to giving a voice to the often-criticized “millennial” generation.
She started her career at Zoomer, but her biggest lesson there was more existential than professional. It was due to this lesson that Ottaway eventually partnered with the other founder of The Reply, Christopher Rogers, and they launched their site—one which was clearly influenced by Zoomer. On it, you can see articles reassuring millennials that their personal and financial struggles are temporary.
I got the chance to ask Ottaway some questions. She spoke of her journey to self-employment, along with some of the struggles that she had to go through to get there.
IM: When did you first get the idea for your business?
CO: For as long as I can remember, I’ve always wanted to be a writer. I had other career aspirations along the way—I did some job shadowing at a vet clinic and with a human resources department. For a while, I was set on growing up to be the CEO of a company (I’m not sure where that stemmed from, to be honest). But one of my biggest dreams was to be an editor-in-chief of a magazine, one day. The funny thing is I’ve actually kind of achieved both of those last two goals. I’m the owner of Web of Words, where I help small business owners and solopreneurs build meaningful connections online through blogging and social media. And then, I’m also co-founder of The Reply, a magazine for millennials. In hindsight, the reality of these roles looks nothing like what I had imagined as a young girl. It’s every bit as exciting though.
I first started freelancing for some online sites when I graduated from the periodical writing program at York University in 2010. Eventually, I landed upon an opportunity to write for Zoomer, which was a pretty incredible way to launch my writing career. I was a 20-something recent graduate, writing for an audience of baby boomers on everything from planning your retirement to boosting your sex life. It was fascinating, and it showed me I could write for any audience, as long as I put in the legwork. I also had the chance to interview Jann Arden for the magazine when she was filming Canada Sings—that’s been a career highlight of mine, for sure. (Although it will be hard to beat the interview I had with Margaret Atwood when working as staff writer for an IT magazine).
But the biggest learning I took from writing for Zoomer was actually more of a lifestyle lesson. The magazine is built upon a mantra that it’s “never too late.” It’s never too late to try a new hobby, to change career paths, to transform old habits… This really influenced me early on in my career. I realized that not only is it never too late, but in a way, it’s never too early. I think I felt like I had to be a certain age—to have acquired the necessary wisdom—before I could write my first book or, say, launch my own magazine. But I realized there truly was nothing stopping me from reaching these goals.
I haven’t written the book yet (there have been a few drafts in the works). But a little over a year ago, I started thinking seriously about ideas for a magazine. I knew I wanted to reach out to the millennial demographic. There had been so much negativity about millennials in the media, and I wanted to give my generation a chance to share their voices and speak to the stereotypes, show the world that we’re far more than a group of spoiled, basement-dwelling hipsters.
I partnered up with a colleague of mine, whom I had worked with at an IT-business magazine, Christopher Rogers. He’s a great writer and also very well-versed in web design. We put our heads together and started visualizing what our magazine would look like. Deciding on the name was the hardest part. As soon as we came up with The Reply, everything just flowed from there.
IM: The grind of being a freelance writer is well-known. How did you approach pitching articles when you were unknown? Did you do free work to get your name out there?
CO: It’s kind of cliché to say, but I made sure I was writing every single day. I launched my own blog back in 2010, writing about “life as an aspiring writer”. Eventually, I started contributing to some online sites, where I got paid $25 per article. But I did a lot of writing for free. I think it’s almost a necessity in order to build a portfolio and make a bit of a name for yourself. People want to see what you’ve written before they hire you to write for their publication.
Once I had built up a bit of a portfolio, I started sending pitches everywhere I could think of. At first, I heard nothing back. But eventually, I started getting some bites. This was before I really understood the importance of building a personal brand online. I knew I needed a portfolio, but I had no idea what kind of value social media could bring in helping me build meaningful relationships with editors and publications. My approach to pitching is completely different now.
That said, I still do a lot of writing for free. I contribute to The Huffington Post Canada—which is unpaid, but provides great exposure. I blog for my own site and contribute guest posts for other bloggers. And technically, all of the writing I do for The Reply is unpaid, as our main focus in the initial stages has been on building up our audience. We’re currently working on launching our plan for monetizing the site.
Of course, there’s a controversial side to the writer pay debate. Yes, I do some free writing, but I put this in a completely separate category from writing for pennies. I cringe when I hear about writers who undervalue themselves enough to take $25 for a 500–700-word blog post. (Unless they are just starting out and trying to build a portfolio). But writers with years of experience need to charge what they’re worth. When you’re a self-employed creative, getting underpaid is worse than not getting paid at all. Free writing is like volunteering. You can prioritize it accordingly. But underpaid writing means you’re doing all the work for a lot fewer zeros. You’re also sucking time away from really wonderful, profitable gigs. Not to mention, you’re making it even harder for the rest of us writers to get by, because suddenly we get these new clients who expect to underpay.
CO: I’ve discovered some really valuable connections through local networking groups. I’m a member of The Writers’ Community of York Region, and I also meet regularly with other small business owners. Writing tends to be a very isolated endeavor, so it’s incredibly important to take the time to connect with other people—and not just online. I live online, since I manage social media accounts for small business clients, and I know firsthand that there is huge value in online networking. But it doesn’t ever replace in-person connections.
I also have an incredibly supportive husband. During those times when I really start to feel down on myself, he’s there to remind me what I’ve accomplished so far and how much more is possible. He always jokes to our family and friends that I’m going to write a bestseller one day and he’ll be able to retire early. The bestseller still feels like a bit of a stretch, but I know a number of freelance writers who have been able to retire their spouses, because of the businesses they have built. That seems like an achievable goal to me. So when I start to doubt myself, I also head on over to read some of their latest blog posts for a motivational boost.
IM: Was there a time when you were building your business that money was scarce?
CO: When making the leap to self-employment, I was leaving a well-paid job with benefits, so there was certainly a level of risk involved. My husband and I had worked hard to build up a solid financial cushion to lean on. It was important for us to hit that $10,000 number in our emergency savings account before I made any big moves. We definitely dipped into it in the early months, but Web of Words took off a lot quicker than I had actually anticipated. And I’ve had my husband’s regular paycheck to rely on as well, which has definitely been a huge relief. After six months of being self-employed, we were hitting our monthly savings goals again. And I’m on target to hit my financial goals for the end of the year. That said, when you’re working for yourself, anything can happen. So we still keep that cushion right where we need it.
IM: Was there a point where you wished you’d gone back into the steady world of 9–5 employment?
CO: When making the transition to self-employment, I fully expected to have regrets. I knew I was in for a roller-coaster of a ride. Maybe it’s because I set these expectations from the start, but I haven’t once wished I stayed in the 9–5 environment. There have certainly been scary moments, when I feared failing and having to start the job search all over again. But even in those early months when money was tight, I reminded myself to appreciate the newfound freedom I had acquired. After all, you don’t just launch your own business for the money. There are so many perks to being your own boss. And you really have to establish your own definition of success to make it work for you. Don’t waste your time comparing yourself to others. We all have our own set of priorities. And for me, the freedom alone has made it all worthwhile. I’m not just talking about being able to go for long walks with the dog or pick up groceries in the middle of the afternoon. But I’m also referring to the creative freedom to write what I want, work with people I respect and admire, and produce work I am proud of. This has made it a lot easier to welcome failure, instead of fearing it. Because I know failure is a necessary steppingstone to growth, and as long as I am growing, then I am doing something right.
IM: How big were social media and SEO when you were first getting started?
CO: I definitely had the advantage of building my career at a time when there was a lot of change happening. I guess some people might actually see that as a disadvantage, but to me, social media has produced a world of infinite possibility. It’s really incredible to think of how you can build a relationship with someone halfway across the world with just the click of a button.
Social media and SEO were still early concepts when I first launched my freelance career after graduating, but I was in the space right from the start. And I was excited about it and keen to learn more. I kind of fell into social media—my full-time job before I went out on my own was working for a social media startup in Toronto. And now, I’ve built my own business around it. The space is always changing and it certainly keeps you on your toes. That said, we’ve also come a long way from keyword-jammed blog posts that sound like they were written by robots. Google has worked hard to prioritize quality over quantity in the online world, and this has always been a key focus in my work. I think, as long as you write with your audience in mind, put the time and effort into engaging and building relationships with your readers, and make sure you’re being a little strategic about it all, you’ll see results.
Keep up with Carly and The Reply at http://the-reply.com/!
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Learn more about our interviewer at: Jeff Nelson