Meet the Freelance Writer: Kaitlin Madden

Welcome to the forth installment our new series, Meet the Freelance Writer!

Here, you’ll meet a diverse range of individuals who have carved out a place in the world of full-time freelance writing. You’ll learn all manner of insights about the life of a freelance writer, such as how to start out, what a “typical day” day looks like, and all those other niggling questions we know you have. If you’re curious about freelance writing as a career, or are looking for some advice on how to improve your freelancing business, this is the series for you.

Today, we’ll meet freelance writer Kaitlin Madden.

1. Hi Kaitlin! Can you tell us a bit about yourself and your freelance writing work?

Sure! I originally wanted to be a magazine editor and went to Northeastern University for journalism, but I graduated college in 2008, aka the worst year in history to graduate college.

So I started freelancing out of necessity — I got laid off three times in 18 months. Once I got a secure full-time job, I did it on the side in case I got laid off again! After working both as a magazine editor and a brand editorial manager, I realized I wanted more flexibility and decided to pursue freelancing full-time. It took me two years after this epiphany to get to the point where I was comfortable leaving my day job, which I did in July of 2015.

It’s been crucial for me! For one, I feel like I’ve become an expert in the industry. I know who to call for quotes, what the trends are, and what showrooms carry which lines, and what makes something Bauhaus versus Baroque. I’ve also built relationships with the publicists in the industry, so I’m always getting fresh ideas from them.

All of these things make it much easier for me to write a story or blog post than if I were a jack-of-all-trades and had to educate myself from scratch. One of the biggest ways it helps is through my website — because I’ve tailored my site to my particular niche, I rank second in Google for the term “home decor writer.”

3. What made you want to become a freelance writer?

The biggest thing was the flexibility. I’m a creative person and the structure of a 9-to-5 job can feel stifling to me, even when it’s a creative role (I think lots of right-brained people can relate!). There is nothing better than being able to work when and where I want, with whom I want. It’s something I appreciate even more because I had a baby back in December. That was actually one of the catalysts for me leaving my full-time role. Freelancing is the ultimate mom job.

4. How did you make the transition to being a professional freelance writer?

I kept my day job while I built my freelance business. I think this is important for anyone without a trust fund since freelance income isn’t guaranteed. I made sure I had a steady stream of work (for me this comes from the brands who pay me to write their blog each month) before I quit. That way, I knew I could count on a certain amount of money coming in each month. Magazine stories ebb and flow, and now I look at them as a bonus.

5. Can you run us through what your “typical” work day looks like?

Of course! While the work I’m doing varies day-to-day (I have 6-7 ongoing clients I work for every month, plus whatever magazine stories I’m working on) I do try and keep some sort of regularity to my days, though. In the morning I wake up, drink coffee and check email, and play with my son. Our nanny comes at 10, and I go downstairs to my home office and work straight through until 1 or so, since I work better in the morning.

After that, I always need to get out of the house. I can’t sit in one place for too long, so I usually walk to a coffee shop. There are a ton in my neighborhood in Chicago, so I vary which one I go to. There are always other people working in them which inspires me to be productive and makes me feel like part of a little entrepreneurial tribe.

If it’s not a particularly busy day, I’ll use that time to run errands, or go to the gym, or clean my house. If it’s a crazy day, I’ll finish up work after my son goes to bed. My favorite days are the ones when I feel like I’m cheating and I get to work from a really cool place like the balcony of a hotel room or on a plane to somewhere fun.

Like many creative people I’m not a naturally organized person, so I have an overly thorough method to make sure I don’t forget things. I put everything I have to do in Google calendar. I create an “event” for anything I have to do on a given day and highlight it in green. Then once a task is done, I change the color of the event to red.

If I don’t finish a task that day, I move it to the next day. I’ve been doing it for years and it works like a charm. As a back up I also keep a to-do list in a notebook that I take with me everywhere, and cross things off as I finish them. If I don’t write something down in one of these places, I won’t do it.

7. Working with new clients is an integral part of keeping a freelance writing business thriving. How do you find new work?

I got lucky because I bought my domain name, kaitlinmadden.com, in 2009, so I’ve managed to build a solid search engine history. About half of my current clients find me this way. I’ve also worked at two different magazines so I keep in touch with the editors I’ve worked with. I also cold-email pitches, which has actually worked a few times! Lastly, I look on sites like Mediabistro, ProBlogger, and yes, FreelanceWriting.com, since all post freelance gigs.

To be completely honest, it really hasn’t made that much of a difference. Most of my writing jobs come from personal connections with editors I’ve worked with in the past, submitting pitches, or people finding my website. It always helps to be able to have clips from such amazing publications in your portfolio, though!

Magazine writing is more in-depth than writing for a blog or brand. For print story, you have a longer deadline, and you’re expected to call people and conduct interviews, and do original research. Then it’s fact checked and copy-edited, and occasionally kicked back to you if it isn’t just right. Once they layout is done, you usually have to write captions. With digital, speed is the priority. And brands don’t usually have a budget for the type of reporting or imagery a magazine can produce.

If you want to write in the digital space at all, I think it’s essential. Whether you’re writing for a publisher or a brand, they’re going to want you to write content that can be found, otherwise why write it? I don’t think you need to be an SEO expert, but understanding how to incorporate keywords, write meta-descriptions, and structure an article with the right H1 tags, for example, is definitely important.

I have! I have used the jobs portion to find clients before.

If you have no clips, you’ll probably have to be willing to work for free, or something like $15 a post in order to build up your portfolio. There are a ton of writers out there, and it’s just a reality of the industry, even these days. If you do have clips, work on building your network.

Don’t be afraid to cold email people and ask if they are looking for contributors or need help with their blog. Also, get good accounting software. I was terrible about invoicing and tracking my expenses until I got it. I’ve used Freshbooks and Freeagent, and like both.