Maddy Osman Interview

Hello! This is the May edition of the Themeisle interview series. In this one, Maddy Osman – the founder of The Blogsmith – talks with us about productivity, WordPress, her current writing projects, and more.

If you missed last month’s interview, you can find it here. In it, Vova Feldman – the CEO of Freemius – shares insights about being an entrepreneur in the WordPress space. For your daily dose of inspiration, you can go through our full collection of interviews with WordPress professionals from around the web.

Maddy Osman interview at Themeisle

Now, about our today’s guest:

Maddy Osman is a freelance writer and owner of the SEO content marketing agency The Blogsmith.

We’ve actually had a chance to work with Maddy ourselves. She delivered several high-quality pieces of content for our CodeinWP blog.

Apart from providing content for B2B tech companies, Maddy is also a book author. She shares more about this special project of hers later in this post. If you’re curious already, you can have a sneak peek at her book, “Writing for Humans and Robots.”

When she’s not writing, she likes to help people master their content marketing skills by teaching one-hour classes on Skillshare (link). Her classes include topics like SEO, keyword research, writing, content promotion, copywriting, and many more.

Maddy Osman Interview – “If you’re going to labor for most of your waking hours, that labor should be something you believe in”

When and how did you start working with WordPress? Is there an interesting story here?

Maddy Osman:

The first time I used WordPress was in my college marketing agency job. We played around with many different CMSes—Silverstripe and Joomla come to mind.

The client we were working for, a video production student organization, I believe had requested WordPress, specifically. They wanted a blog that would be easy to update.

I fell in love and haven’t used any CMS besides WordPress for my own projects since creating that blog!

What’s your technique for staying productive throughout the day?

Maddy Osman:

Every day is a different story. I try to set my schedule the day before—or at least the most important tasks I want to complete. I use Evernote (currently migrating to Obsidian) to track progress towards these goals and any other important things that pop up during the day.

Also, I set time blocks and try to honor them, but that doesn’t always work out! I’ve had success with the Pomodoro method, especially when it’s a task I really don’t want to do. I do think it’s important to set goals and track progress towards them.

Mostly, I try not to force myself into a box. I’m not a morning person. I get my best, deepest work done in the evening when no one is expecting an answer from me.

How do you define “being successful”?

Maddy Osman:

At the most basic level, it’s being happy and content with where you are right now. But knowing that the future is bright if you keep pushing towards it. It’s about never being stagnant and complacent and realizing that life is a never-ending journey to keep learning new things.

Being successful is personal, so while you may benchmark progress against others realizing similar dreams, it means not letting other people’s success impact your perception of yourself.

What does “a good day at work” mean to you?

Maddy Osman:

A good workday involves completing all the important tasks I identified the night before or at the start of my day. It means feeling good about how I accomplished those tasks—essentially, not cutting corners.

A good workday makes me feel like I did more than put out fires and keep the ship running. It makes me feel like I moved the needle so that my business will run more smoothly tomorrow and onwards to the future.

As such, a good day usually involves building out or pressure testing processes that my team uses to get the job done.

Describe the WordPress community in one word.

Maddy Osman:


Even if you don’t know members personally, basically anyone who sees themselves as a member of this community would go out on a limb to help anyone who could benefit from their knowledge. After meeting many members of the WordPress community at WordCamps and otherwise, I do count them as personal friends.

What’s the no. 1 thing a new business entering the WordPress space should do?

Maddy Osman:

Get involved in the community. Go to a WordCamp! Better yet, volunteer at one or organize/sponsor one if you have the time and funds. It’s a fast track to insider status.

What’s your favorite/must-have WordPress plugin and why?

Maddy Osman:

There are so many, but one that immediately comes to mind is NitroPack. It’s a simple solution for improving WordPress performance. Any website could benefit from something like this or similar.

What do you think is the most efficient way to market a product/service at this moment?

Maddy Osman:

Focusing on building a network always is, and always will be, the best way to market anything. It’s not the end-all and be-all—you still need strategy and tactics. But it is the solid foundation from which to build everything else.

Investing in building my network by attending events, speaking at events, organizing events, and participating in online communities have resulted in my greatest client connections.

What is driving you to keep doing what you’re doing? What’s your personal mission?

Maddy Osman:

First things first, the work we do at The Blogsmith has to benefit the end reader we’re trying to reach. Helping a client reach their goals is also of high importance. It’s not worth our labor to create content that doesn’t serve the reader and client, adding value to what’s already out there.

I truly believe that making money shouldn’t be a means to an end. It should mean something. It should benefit more than just you. If you’re going to labor for most of your waking hours, that labor should be something you believe in.

For me, at The Blogsmith, this means pledging a portion of sales every month to a cause that’s doing some good in the world. Check out our donation tracker to see where the money is going—and consider increasing our impact with a donation to a worthy cause!

Running a remote-first organization also means being able to work with people from all over the world. Given the global pandemic, it means giving all of the individuals on my team a way to make money without the commute or fear of virus exposure. And empowering them to do the work they enjoy doing, on their terms and schedule.

I have no interest in micromanaging my team. I want to support them on their journeys to become better at what they do—even if that means they will eventually move on to start their own company!

What are you working on now?

Maddy Osman:

I’m putting the finishing touches on a project I started in November 2020 — a book tentatively titled Writing for Humans and Robots: The New Rules of Content Style. After going through a final round of edits, it will be available in early Q2 2022.

The book is an expanded version of The Blogsmith Style Guide, which my agency’s writers and editors use to consistently deliver on-brand content for the enterprise teams we work with.

In the book’s 22 chapters, we dive into subjects like how to intentionally choose words, how to thoughtfully incorporate formatting for readability, and how to optimize content to be found by your target audience in relevant search.

Each chapter shares helpful examples and context for creating your own brand style standards.

Learn more about Writing for Humans and Robots and sign up for launch updates and promotions.

That sums up our Maddy Osman interview. If you enjoyed it and want to learn more, please leave your comments in the section below. Also, if you have any ideas for who we should talk to next, feel free to share your suggestions with us!

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