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Freelancer Spotlight: Carly Ottaway

I love learning from other successful freelancers and online business owners. It’s how I got so smart! ?

And from what you’ve told me, you do too! So each week, we’re going to try to interview someone new for us all to learn from. (Check out the last one we published with Nicole Dieker.)

Today we chat with Carly Ottaway, the super talented writer from Web of Words and one of the people behind The Reply – a digital magazine for and about Millennials. Carly is here to share with us the ups and downs of her freelancing journey.

What do you, Carly?

I run a copywriting and social media management company called Web of Words.

We’re all about helping small businesses share compelling brand stories and create meaningful relationships that matter. Often, your first impression with potential clients is made online; if they don’t feel an immediate connection with your brand, they won’t make enough effort to notice you.

We want them to see you. We want them to understand you’re different. We want them to believe you can change their lives. The only way to accomplish this is to give them an experience they can’t live without. This means connecting with your audience on an authentic level, showing them you’re real, showing them you’re human.

I’ve been in working (on the side) as a freelance writer since 2010, but in January of 2015, I made the leap to full-time entrepreneurship and officially launched Web of Words.

I always knew I wanted to build a career around words and storytelling, and I was fortunate to be graduating from university at a time when possibility was at my fingertips.

The online world brings so many opportunities for us to connect, and yet we fill it with noise rather than meaning.

I wanted to help cut through the clatter and make it about being social again.

What got you into freelancing? Was it what you expected?

I graduated from university with $25,000 in student debt. I started my own freelance writing business to bring in some income while searching for full-time work. I created my own blog, and started contributing to other online blogs and magazines.

I managed to land a great gig with a national magazine, and it became my main focus. Unfortunately, just under a year later, my client’s freelance budget shrunk. I remember it hit me pretty hard – I didn’t have a plan B.

I learned hard and fast to never rely on one client as a main stream of income.

Now, I have a number of core clients that I work with regularly and I also take on smaller, one-time projects every month.

I’m consistently marketing and working to keep my pipeline full; even on my busiest months. When you work for yourself, anything can happen, and you have to be prepared for the worst (while striving for the best, of course).

Carly shares the lessons she learned from being a freelance writer and business ownerWhat’s been most challenging part of solopreneurship so far?

There are so many challenges; it’s hard to narrow it down to one.

You have to learn how to manage the inconsistent income stream.

You need to be prepared to wear many hats; I may be the writer deep down, but I’m also the business owner, the salesperson, the bookkeeper, and the HR team. You have to find a system that works for you in terms of setting goals or milestones, and mapping out a plan to help you reach them. After all, you don’t have a boss to give you project deadlines or yearly reviews.

It’s hard, but if you’re truly meant to be an entrepreneur, you figure this stuff out along the way.

I’d say the biggest struggle so far for me has been learning to let go.

And I don’t just mean delegating tasks – although that’s certainly part of it. I mean knowing when to say no to a client when you know it’s not the right fit. I mean being able to turn off your inbox (or Twitter alerts) to enjoy some time with your family. I mean shutting down your brain at night so you can actually fall asleep.

When you work for yourself, your work becomes an extension of who you are.

It’s always on your mind. It’s a wonderful feeling, to be so infatuated with your job, but it’s also a dangerous slope if you don’t have anything else to hold onto, or someone in your life to scoop you up when you fall down. Because you will slide, you will slip, you will fall. And no one is there to catch you, but you.

If you’re truly in it for the long haul, you have to be able to get back up and try again – every single time.

Did you ever want to quit or give up?

I’ve been doing this for fourteen months now and I’ve lost track of how many sleepless nights I’ve faced. There has been a lot of doubt to overcome. And I don’t think I’ll ever reach a point where there isn’t. It’s just part of the job. And yet even on the hardest days – the days when I wonder if I am truly capable, if I am truly deserving – I never regret taking the leap and choosing to work for myself.

I never regret choosing the freedom to do the work I want to do, with the people whom I want to work with.

I never regret choosing the freedom to work when and where I want to work from, at a schedule I set for myself. I never regret challenging myself to grow and become a better writer, a better boss, a better spouse, and a better person than I was yesterday. There are no limits in the career field I have chosen. There is no one to snuff out my bursts of inspiration, no one to squash my potential.

This is my chance to truly realize what I am capable of.

What would you love to pay someone to take off of your plate?

Honestly? Grocery shopping. Cooking on busy weeknights (I enjoy cooking when I have the time, but otherwise it’s just a pain in the butt). Cleaning the house every once in a while (I could never give this up completely as I actually find it therapeutic at times).

Managing my inbox.

Some days I absolutely loathe email – it’s like a vampire that feeds on creativity – and yet it’s still so essential to the work I do.

What task in your own business would you like to do more of?

I always want to do more writing.

As our company grows, I find my to do list is shifting to focus more on business-related tasks rather than the writing projects I love so much. I still prioritize my writing projects, don’t get me wrong, but if there was more time in the day, I would spend it writing.

What are some big successes you’ve had recently?

Big successes are important, but sometimes it’s the smallest successes that are most meaningful.

Success to me is when a client gets retweeted by one of their heroes. It’s feedback from a business owner saying they feel like we’re in their head when we’re writing copy for them. It’s finding out the leads we drove on Facebook turned into top-paying clients or customers.

Success is being able to experience life within the walls of a local hospice for a magazine article I am working on. It’s learning about industries I’ve never worked in before. It’s about uncovering incredibly inspiring stories about entrepreneurs who turn their dreams into realities.

Of course, success is hitting income goals (and increasing them month after month).

But it’s also about working from my favorite coffee shop in the middle of the afternoon. It’s about taking my dog for a walk on the trail without worrying about my boss thinking I ducked out early. It’s about lying awake at night brainstorming ideas for a client campaign and feeling excited to wake up and dive in the next day.

It’s about working alongside my husband, building something with our own two four hands, and looking ahead at a future with unlimited potential.

What are some specific strategies, tactics or pieces of advice that helped you grow?

Make the effort to connect with other business owners or freelancers who are doing similar (and completely different) work than you are doing.

Don’t be afraid of failure; treat it as another stepping-stone to success.

Figure out what your personal definition of success is, and then chase that. (For most of us, it’s about a lot more than the money). Learn when to say no, and don’t be afraid of saying yes. Believe in yourself – it’s the only way you’ll convince others to believe in you, too.

Choose positivity.

Stay focused on the tasks and results you can control, and let go of the ones you can’t. Practice gratitude, every day. Delegate. Be flexible. Be vulnerable. Make time to play.

What are you most excited about for your business next?

I’m looking forward to taking advantage of the new flexibility my husband and I have built into our lives now that we are both self-employed. I enjoy watching him thrive as an entrepreneur. I love having a partner whom I can share this “wild affair” with.

Perhaps most of all, I am excited to continue on this path of growth – both in terms of the business and as an individual. I am constantly learning and evolving. I can’t wait to look back on this year and say: we did it. We created that art, we drove those results, we built this business. I can’t wait to see where we go from here.

Wow, I don’t know about you, but reading Carly’s interview makes me feel so inspired.

Thank you for sharing with us, Carly!

COttaway_headshot Carly has been blogging and managing social media for small businesses since 2012. She is also a freelance writer, and her work has been published in high traffic publications such as Canadian Business, Zoomer, The Globe and Mail and The Huffington Post Canada. To read more about her freelance writing, head on over to CharlotteOttaway.com.

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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