My Career as a Writer with Erika Cuccaro

An Interview with a Writer

Erika Cuccaro,
Owner/Writer/Editor,
James Street Writing Company

When Erika Cuccaro was considering her career options, she didn’t think her love of writing could make her a living. Instead, she pursued a degree in psychology and began her career in administration within the government. Of course, a passion for writing cannot fade away just because of your career choice so Erika joined NaNoWriMo and started working towards an English degree. As her government career progress, one of her bosses encouraged her writing by tasking her with writing newsletters, web content, letters, and more. Eventually, she realized writing really could make her a living so she gave her notice and struck out on her own!

The rest of her journey was anything but straightforward and shows just how much there is to learn as a freelance writer no matter what stage you are at. In this interview, we’ve worked with Erika to capture what her job is like and how she got to where she is today. If you are considering a career as a writer (freelance or otherwise), this is a great resource to get an inside look at how one person is living that life. We also invite you to watch Erika’s “Day in the Life” video for even more insight.

What is in a name (or job title)? As a writer, many job titles can apply to you depending on the work you do. In Erika’s case, some of the job titles she may go by are Freelance Writer, Content Creator, Copywriter, Copyeditor, and Proofreader.

My Career as a writer with Erika Cuccaro - An interview

The Essentials

What is your job description?

I research, write, and edit a variety of materials for clients including professional and business profiles, web content, online and in-class courses, and annual reports.

What are your main tasks?

Conducting interviews and online research, writing, revising, editing, book-keeping, marketing, as well as building and maintaining positive client relationships.

What is your salary or salary range?

$40,000 – $70,000 CAD

What education is required for this position, and what education do you have?

Writing and editing skills are essential but you don’t necessarily need to study English to succeed in this position. I have two BAs (Psychology, English Literature) and two certificates (Professional Writing  – specializing in marketing and public relations, and Writing for Publication).

A Day in the Life of a Writer with Erika Cuccaro

What skills are useful for the job?

  • Research skills including the ability to  recognize a credible online source
  • Curiosity
  • Soft skills like the ability to connect with people and maintain positive relationships with clients (and with the clients of your clients, if you are conducting interviews on behalf of a client)
  • The ability to translate dry subject matter or impenetrable jargon into an engaging story that will resonate with the target audience

What tools are used in your work?

  • Laptop
  • Monitor (two monitors are key for researching and writing at the same time)
  • MS Office Suite
  • Coffee maker!

What experience and other requirements are needed for this position? An understanding of how to operate a small business – whether through formal education or self-taught.

Life as a writer - An informational interview about being a writer

What is it like?

What is your workplace like?

I have two workplaces – my home office and a rented office at a professional creative collective called Media Mall. Both offices are set up the same way, though my home office is better decorated! I like working at Media Mall because I can get lonely working from home as I am an extraverted freelance writer (which is rare from my experience!). At Media Mall, I get to contribute to group marketing efforts, bounce ideas off of other creative people, and soak up the amazing vibe generated by 15 exciting businesses working to grow.

What are your work hours like?

Officially, I work Monday to Friday with office hours from 8:00 a.m. to 3:30 p.m.  But when there’s a big deadline looming, that can all fly out the window!  I’ve been known to work until 4:00 a.m. but I’m definitely trying to cut back on those late nights.

I have two young children that are off in the summers.  My husband and I are still trying to figure out what summers should look like.  In 2017, I spent the mornings with my kids and worked from 2:00 to 6:00 p.m. and then from 9:00 p.m. to midnight.  I don’t recommend that schedule!  It takes a lot of time to transition from “mom mode” to “ace writer-editor” mode and I burned out pretty quickly.

What is the workload like?

It depends!  For those looking to get into freelancing, it’s important to know that there will be dry spells. At least there were in my experience! Typically, I’m really busy from late August to December. Business continues at a good pace January through March and then slows down in April. May and June are slow and steady. Then July is very, very slow (emphasis on the slow).

Meet Erika Cuccaro - A freelance write who is here to tell her career story

Describe a typical workday if one exists.

That’s tricky because I don’t really have a typical workday.  So how about I describe today!  

Today, I don’t have any pressing project deadlines.  If I did, the project would take precedence over everything! First, I checked my email. This included connecting with two interview subjects for an ongoing client project, and we booking our meeting dates/times.  I also sent my PowerPoint presentation to an event organizer whose Business Success Summit I’m speaking at. Then I sent out four introduction emails, connecting a local business owner with local graphic designers. And registered for a professional conference in November. Oh, and I spent some time on this interview!

Next, I spent time working on my presentation for the Success Summit with a fellow freelancer. She gave me valuable advice on how to improve my presentation and hopefully generate more sales. She then practiced an important speech she will be giving soon and I gave her feedback that helped her whittle down her content to meet a strict time limit. I also spent some time tweaking the presentation from a 20-minute talk to a 60-minute workshop to be given as part of the Media Mall M3 Summit in November.

Finally, I spent about an hour book-keeping, sending invoices and tracking payments.

What are useful traits for people considering your career? Curiosity, Perseverance, and Creativity.

How is your job different from others working in this space?

My office in Media Mall makes things pretty different, I think.  As I said before, the opportunity to connect with ambitious, friendly and talented businesspeople has really upped my game.  I feel like I’m getting unofficial business training! Media Mall also gives me the opportunity to expand my reach, like taking part in a group radio campaign, putting on a charity golf tournament, and launching a new marketing summit in Ottawa in November 2017.  I love being able to grow my business while growing within the Media Mall creative environment.

I think a lot of freelancers strive for flexibility, and that is where my job is similar from others working in this space.  When I’m working from home, I can take a break to walk my dog.  I can also schedule my work so I can attend school events with my kids, which is important to me.

A Day in the Life of a Freelance Writer with Erika Cuccaro

Career Story

What is your story? How did you get here?

This is a bit of a long story!  

I’ve always loved reading and writing and when I was 10, I wrote my first novel! That book, “Pets of Spook Corner,” was bound in navy blue construction paper and pink yarn.

I wanted to be an author but I didn’t think I could earn a living as a writer so I pursued a degree in psychology at Carleton University. After I graduated, I got an administrative job working with the Government.  It was a good job with great people but it was not a good fit for me.

One November, I devoted my evenings to “National Novel Writing Month” (also known as Nanowrimo) and wrote a 50,000-word novel. With that under my belt, I pursued an English degree from the University of Ottawa. I graduated and moved to a new government department within the same organization. My new boss was great and encouraged my writing.  He asked me to write the newsletter, web content, letters and more.  With this encouragement, I realized that I really could write for a living!

I worked there for a year and saved as much as I could. Against a lot of well-meaning advice, I gave six-months’ notice and planned to set up shop as a freelance writer as of March 2009. On my first day of freelance life, I had business cards and a website but no clients and only a few work samples. Thank goodness for my savings because I got my first client in May 2009. I was walking my dog and started talking to a man walking his dog. He mentioned a friend needing a writer and I gave him my card!

What it is like to be a writer - Career Interview

By September, my business was limping along and my savings were running out so I got a job at a local boutique. The boutique sold clothing by independent Canadian designers. That job was a lot of fun but it wasn’t paying the bills. In January 2010, I was back in an office working as a Marketing & Communications officer for a government-funded organization.

I learned so much at my new job!  As I learned more about marketing and communications on the job, I continued to read business books, blogs, and websites. Around this time I had my son and we all moved back to my hometown to be closer to our families. In my hometown, I connected with the owner of the local marketing firm and he sent some work my way. Being in a smaller pond than Ottawa helped me build up a portfolio and a solid network of clients that my business needed to succeed.

In 2013, I was pregnant with my daughter and, along with a group of about 10 colleagues, was laid off due to a lack of funding.  That was both scary and exhilarating! I took the opportunity to rebrand my business to the James Street Writing Company and worked hard to build my business. Since then, my business has continued to grow. I work most often with two international NGOs, two tourism organizations, an instructional design firm and I’m always looking for great new clients to build fulfilling working relationships with.

What are useful abilities for people considering your career? People skills, Organizational skills, and Communication skills.

What did you want to be when you were younger?

  • Novelist (I still believe I have a novel in me!)
  • Veterinarian
  • Psychologist
  • Illustrator
  • Freelance writer

What has been the biggest obstacle in your career?

Imposter Syndrome. Writing is so intuitive that sometimes it feels like everybody can do it. It’s been a real process to gain confidence and assign a value to the services I provide. Fortunately, I have great relationships with my clients and I know they wouldn’t come back if I wasn’t providing value.

What is next for you?

I recently launched a new business called Haven Mavens. This is exciting for a variety of reasons! First, I’m working with a business partner, the amazing Jen Hood. Secondly, my role is Chief Operating Officer so I’ll be learning a whole new set of skills as we grow. Finally, as Haven Mavens is directed at the tourism industry, travelling is going to be part of my job description!

The challenge will be to balance both James Street and Haven Mavens. I’ve been playing with different time management models to figure out how to make this work!

Life as a writer - What you need to know

The Big Questions

What is your passion?

  • Family
  • Reading
  • Cooking, baking, and knitting
  • Getting outside (walking my dog, biking, and kayaking)
  • Entertaining

What is your favourite task or type of work?

I love finding great analogies for difficult concepts, writing believable scenarios for instructional materials, and more creative work. For example, this spring I wrote several tourism articles from the point-of-view of four animated characters. At first, I restrained myself from getting too creative but my client told me to let loose. I really got into the characters and the resulting articles are some of my best work to date! I also love book-keeping. It is motivational to send out invoices for completed projects.

What do you love most about your career?

  • Working with creative people
  • Flexibility with respect to scheduling
  • Landing an exciting new project (and the thrill of the chase!)
  • Opportunity to write about a variety of topics

What would you change about your career?

A more consistent workload would have to be number one. I also think it would be cool if there were an international certification for writers that holds them to a specific professional standard.

Job hunting tip: Be yourself.  Maybe it’s trite but if you present yourself as you truly are, it’ll be easier to identify a good match (or flag a bad match).

Writing as a career - what you need to know

Advice to Future Writers

Advice for someone interested in this career?

If you can, build your writing business as a side gig and save up 3 to 6 months worth of expenses before quitting your day job.

Also, when networking, genuinely offer to help people rather than just promoting your services. Find out where people are struggling and connect them with people in your network who can help.

How will this career evolve in the next 5 (or more) years?

I wonder how advancing technology will impact how writers work.  On one hand, technology makes it easier (and cheaper) to collaborate with clients around the world. But I wonder how video and photography, especially in social media, will impact the need for written content. That is part of the reason why I think it is important to stay nimble, keep learning, and take calculated risks. Doing so is providing a buffer for the future.

Provide your top career tip.

Specific to freelancing, I learned to divide every dollar earned into the following categories:

  • Savings for taxes
  • Debt repayment
  • Rent
  • Memberships
  • RRSP
  • Paying myself


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Tell us what career you are interested in learning about and join our email list for more career inspiration and advice.

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