Tell us a little about yourself and your writing— what do you typically create?

I’m a freelance content marketing writer with a background in magazine journalism and digital content creation for editorial websites. You could say I started writing content marketing articles during my first staff editorial job at WeightWatchers.com in 2006. Clients often come to me for health and lifestyle articles rooted in service journalism. I also thoroughly enjoy writing about sleep, pets, and beauty topics for a number of clients. I love learning new things based on breaking research and expert interviews and sharing those findings with the masses in a conversational tone.

When and how did you decide to become a full-time freelancer? What was that process like for you?

I was always freelance writing on the side since 2006 (copywriting, article writing, press release writing) while holding down a full-time job. I continued to write as a side hustle until 2013, when I was laid off from my full-time Senior Online Editor role at a magazine. I was probably making about $15,000 or so on the side writing, but I don’t know if I ever would have had the confidence to freelance full time if I wasn’t pushed into it. I had about three months of emergency savings to float my expenses and see if I could make this work. I decided this was the perfect time to see if I liked freelancing full time and reached out to many previous colleagues and contacts to offer my services. I tell the beginner freelance writers I coach and those who are thinking about making the leap that I sent out over 300 personal emails around that time to let people know I was available for work. I received assignments -- and even went on a few interviews for full-time jobs -- and ultimately, I was able to earn a living freelance writing. Becoming a full-time freelancer takes work, diligence, and initiative. You have to let people know that you’re available for work and remind them of your skills and strengths. I still do this today as part of my weekly marketing efforts!

When/how did you realize that you could, or wanted to, help other freelancers take control of their careers?

For the past two decades, friends and associates of friends have frequently contacted me when they were interested in learning about freelance writing. The idea of writing for a living and working from home sounded glamorous to some. I would jump on calls to mentor people, send them links to books and websites I recommended, and follow up with them. I decided to start my freelance writing blog around 2017 (I think), to capture the guidance I was dishing out and reach a larger audience. If someone wanted to learn how to earn extra money on the side while holding down a full-time job, I wanted to show them how to do that. If someone always wanted to explore writing and see their name published in a magazine or website accompanying an article, I explained how to write an article pitch and walked them through the process. I created my self-paced Get Paid to Write Course on Teachable in 2018 to formalize the freelance writing process, help people learn how to get freelance writing assignments, and learn how to run a freelance business. I also do one-on-one coaching with clients and self-published a book, 100+ Tips for Beginner Freelance Writers, to share my 15-plus years of freelance writing learnings in different formats.

What did you find to be the most difficult part of becoming self-employed?

I think the most challenging part of being self-employed is all of the work it takes to run your business that isn’t freelance writing. I find it challenging to always be pitching and marketing my services to make sure more work is coming in when my projects end. It’s time-consuming to work on your own social media and promote yourself when you’re facing a lot of client deadlines. And while I consider myself pretty organized, it can feel tedious and annoying at times to stay on top of invoicing and payment processes, particularly if you’re working with 10 or more clients at a time like I frequently am.

Do you have a standard schedule or routine that helps you manage all the tasks that come with freelancing?

I love using the time-tracking software Togg.l. When I finally got diligent about tracking my hours (and minutes) working on articles and projects for clients, I was able to see where I was earning a higher rate for some pieces that might have appeared to be lower-paying -- and where some better-paying projects actually sucked up more time than I expected. I rely on time tracking to run a six-figure freelance business. I also use Google Sheets for tracking article assignments, moving them to a different tab after invoicing, and moving them to a final tab once the assignment is paid. I’ve been using the same document for about six years and it’s a good place to refer to when I’m looking for more work. I reach out to editors I’ve worked with a few years ago as a warm lead to see if they could use my help! Lastly, I make sure I write down the most important tasks I need to complete the next day in my paper notepad. I need to see a list of what needs to get done the next morning so I start my day focused and avoid procrastinating.

Have you ever found yourself struggling to balance the creative aspects of your role with the business responsibilities? How do you balance them out?

Yes! See above. I learned to delegate some aspects of my business to a virtual assistant within the past two years. She helps with social media scheduling, newsletter production, and research into new potential clients that we keep in a spreadsheet. I know many freelancers use software to manage their invoicing and keep track of payments, but I haven’t made the leap yet! I tend to work on admin tasks and accounting responsibilities on Fridays when my creativity is low.

Do you use any tools or technologies to help you manage some of these administrative tasks?

I rely a lot on the G Suite products where my VA and I share docs and can add comments and notes. We use Hootsuite for scheduling social media posts and I can log in and make edits or changes easily. I’ve also used Basecamp, Slack, Asana, and, of course, Zoom for client projects, and appreciate the organization those platforms provide, but I haven’t found myself needing them for my day-to-day business.

What’s a tool or piece of technology popular in the freelance world that you think is overrated or not as necessary? What's your alternative?

I think it’s helpful to try a tool or premium service for a month or two at a time to see if you’re going to use it and assess how much it serves your business. I pay for LinkedIn Premium one month at a time, maybe twice a year when I’m ramping up my marketing to connect with new potential clients. But I don’t think it’s necessary for me to use all of those tools every month. I am active on the free version quite a bit throughout the year and that helps me appear in their search algorithms. I signed up for one month of Ahrefs to brush up on my SEO skills and learn more about the search terms that were driving people to my website. I continue to apply what I learned from that month to my blog and website updates, but I don’t want to shell out the $100 or so a month it costs just for my business right now. While I wouldn’t say that these technology services are overrated, I do think they can be costly for a solo freelancer to shell out each month if they’re not using them to their full capabilities.

Do you do anything differently now that you wish you had known when you started out?

I wish I did a better job of tracking pitches in those early years. (Where did all of those great ideas go?) If I sent an idea to an editor and they didn’t respond or weren’t interested, I tended to forget about it and wouldn’t send it to another potential client. That means the time I spent on the initial pitch was wasted in a way. Now, I keep track of pitches in a Google doc. If it’s not a fit for one client, I try to rework it for a different client. This makes the ideation process more efficient and increases the chances of turning many ideas into assignments. I also try to think of an idea a few different ways and listen keenly in my interviews to see if the expert is sharing information that could be turned into a different article. This helps automate the pitching process and helps me earn more money throughout the year.

If you could give freelancers only one golden piece of advice to keep in mind, what would it be?

Just get started. Send that pitch or email to a potential client or editor! I know, it’s so simple, but I find that many beginner freelancers get caught up in self-doubt or perfectionism and are afraid of putting themselves out there. I’m here to say that yes, there are times as a freelancer that you will be ignored, you will be rejected, and you will wonder why you never heard back about that idea or email you sent. But, if you never try (and keep putting yourself out there over and over again), those amazing articles you were meant to write and the projects you should be lending your creativity to will never happen. Don’t let fear get in the way of sharing your talents with the world.

Check out Diana's Skyword profile and website to see more of her work!