A Conversation with WordPress Evangelist Maddy Osman

If you do a bit of reading about the subjects of WordPress, SEO or content writing, then you’ve very likely to come across some of Maddy Osman’s work. After all, her writing has appeared in a who’s who of online publications for companies such as Adobe, Automattic, GoDaddy, Search Engine Journal, WPMU DEV and a host of others.

She’s also spoken at various WordCamps (in addition to being an organizer of the Denver, CO event) and is personally involved in a number of tech and social-related organizations. In other words: Maddy keeps quite busy!

Thankfully, she still took some time to speak with me regarding her early start in web design, the process of finding her passion for writing, advice for freelancers and her thoughts on an eventful time for WordPress. Below is our conversation, edited for brevity.

Tell us a little bit about your background in web design. I hear that you started out at quite a young age!

Do you remember those AOL CDs we’d get in the mail to try the service? My love affair with the Internet started around the same time my parents installed a dial-up connection at our house.

It didn’t take long for me to be inspired by other people’s creations, intrigued enough to learn how to make my own websites. Lissa Explains it All was where I turned for simple instruction on HTML and CSS and Geocities is where I experimented and refined my skills. I was 11 years old when I started this new hobby.

I knew I was on to something in high school, when I entered a local business competition in a web design category and ended up winning some college scholarship money two years in a row.

At what point did you know that you wanted to pursue a career in the field?

It was all for fun until college, when I realized that my web design skills could be traded for a job that paid (slightly) more than minimum wage. Working for my school’s student life marketing and design department gave me the opportunity to experiment with several different content management systems: SilverStripe, Joomla, and eventually, WordPress.

My boss at the time encouraged me to take on a freelance project that he didn’t have time for and it was at that moment that I knew that my early dabbling in web design could support me, even in situations where I wasn’t working for a company full-time.

Although my business, The Blogsmith, isn’t primarily focused on web design at the moment, it was because of this early experience freelancing that made me eventually feel solid in my decision to quit my full-time job to freelance full-time.

Maddy Osman photo

You have become a prolific freelance writer as well. How did that come about?

While working at that same college job, I was given the opportunity to also contribute to the student life blog and social media channels. I had a lot of fun coming up with new topics to write about, then watching our social engagement grow.

These were my earliest experiences with creating content for an audience and a defining moment for where my freelance career would eventually lead me. Web design was my gateway to freelancing, but writing took over as my passion.

I took on a few freelance content creation assignments on the side of my full-time jobs after college. When I finally quit to start my own business, content creation (especially freelance writing) became the majority of the work I was billing clients for.

Today, I still design websites, but mostly for my own projects.

As far as becoming prolific, I’m not sure if I’m worthy of that word quite yet but I do think I’m well on my way to becoming a known voice within the niches I specialize in writing for. As far as how I got there, the TL:DR; is that I leveraged writing for high-authority publications, sometimes for free, to build more bylines.

I talked about it in more detail on a recent Clients from Hell podcast if you’re curious about the finer details.

You’ve written quite a bit about freelancing. In your opinion, what’s the biggest challenge in starting out on that path?

I think that fear of the unknown and the fear that you won’t be able to provide for yourself (or your family) are the biggest reasons that people who would be amazing freelancers hold themselves back.

One thing I learned early, perhaps because my first job post-college involved doing sales at Groupon, is that when it’s all on you to provide for yourself, you’ll keep pushing until you stumble on the right approach to land and keep clients.

There’s something both terrifying and empowering about being in charge of how much money you make.

My advice for the people who are nervous to bridge the gap between a full-time job and freelancing full-time?

Start a side hustle. Establish processes. Build out your marketing materials and start building up a list of clients before you quit your full-time gig. By the time you’re ready to dive fully into it, you’ll have done most of the heavy lifting — hedging your bets for success.

It sounds like you have an incredibly busy schedule. How do you manage it all?

Over the years, you refine your workflow and the processes that support a productive workday. For me, this has involved hiring help for a number of tasks in my business that include research and administration. I also outsource the things I know I’m not good at(/hate), like bookkeeping.

As soon as you can justify it (which I can almost guarantee is sooner than you think), I highly recommend doing the same.

It’s hard to leave money on the table by paying people to do things that you could probably do yourself but I think that you’ll realize that your quality of life as a freelancer gets a lot better when you don’t work 80 hours to avoid working 40.

On that note, constantly re-evaluate your existing workflow to determine where things can be automated/outsourced. I’m a big fan of creating process documentation for recurring tasks — partially to demonstrate to myself that with the right direction, these tasks can be easily handed off.

Screen capture from Maddy Osman's The Blogsmith

As someone who is actively involved in the WordPress community, what are your thoughts on the major changes it has undergone in the last year?

The hasty deployment of Gutenberg has been pretty polarizing between different camps in the WordPress community and I’m still not 100% sure where I stand in the debate.

On one hand, change is often a good thing when it comes to new technologies, even though it can initially be hard to accept. It’s hard to adapt an established workflow for something so radically new but Gutenberg definitely holds a lot of promise.

On the other hand, Gutenberg shipped out with some major compatibility issues that are still being worked out. So I’m hesitant to dive deep into how to best make use of it until the first movers fully vet it and all the kinks are worked out.

On a different note, I’ve recently been working with BigCommerce on a series of posts that highlight their new WordPress ecommerce plugin. As someone who operates a WordPress-powered ecommerce store, I’m excited by the potential this headless commerce solution introduces to the market.

Will WooCommerce remain supreme with this powerful new challenger? In the short term, absolutely. But as more people test out the new BigCommerce plugin, the game could totally change.

I’m excited to see what 2019 will bring for the WordPress community!

As you look at your career, where do you see yourself in the future?

This is an excellent question that I don’t know that I can answer.

In the immediate future, I’m working on growing as a paid speaker. I’m also hoping to leverage my blog to create more sponsored content for clients after having a lot of accidental success with this in the past year. In general, I’d like to spend this year being more intentional about growing my business with regards to these two items, as opposed to just letting opportunities fall into my lap.

One of my big goals for 2019 is to find more opportunities to give back — both monetarily and in terms of donating my time to worthy causes. I have something big planned to help new freelancers but you’ll have to stay tuned as I finalize the details. ;) Stay in the loop by subscribing to my email newsletter, which goes out once a week.

Our thanks to Maddy Osman for her time and insight! Be sure to check out The Blogsmith to keep up-to-date with her latest articles and speaking engagements.

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