How I Quit My 9-5, Started a Freelance Business, and Turned it into a Marketing Agency

13 min read
By: Maddy Osman

Please note: this article contains affiliate links for products and services I used for The Blogsmith’s rebranding process.

Transitioning The Blogsmith into a new business structure is the culmination of 5+ years as a freelancer and so many more as a lifelong student of business and entrepreneurship (thanks to the influence of my mom and dad). Thinking back on everything that led up to this point, it seems like a fateful move forward to undertake an agency model rebranding process.

In this guide, I’m going to cover a wide range of topics, so feel free to skip around to read about those that most interest you.

Allow me to start by sharing the journey for how I got here:

Why Rebrand Now?

The idea started brewing in 2019, when I went to my first WordCamp US event

If you’re not familiar with the WordPress ecosystem, WordCamps are conferences that volunteer organizers host in multiple cities around the world. 

I’ve co-organized WordCamp Denver for several years, which brings in about 300 attendees each year. WordCamp US is the biggest WordCamp in the Americas, attracting several thousand attendees each year.

It was an exciting trip for me because:

  • It’s rare I get to travel for business
  • St. Louis was a new city for me to explore
  • My talk idea was chosen

If you’re curious, here’s the recording of my talk:

Maddy Osman: How to Perform a Quality UX Audit on a Budget

While I was at WordCamp US, I got caught up in the excitement of meeting awesome people I’d only known through the Internet up until then, including many clients. 

Deciding to move to an agency model must’ve had something to do with being a part of this exciting, supportive environment. Something clicked in my brain about the direction I wanted to move forward with my business.

Also serendipitous was the fact that I was feeling extra introspective at that time due to a recent and difficult loss. I was thinking critically about what truly makes me happy and what I really want to get out of life.

I had the realization that I didn’t want content writing to be what I spent most of my time on. 

Let me be clear: I enjoy it, that’s why I quit my job to pursue it, but I didn’t want to be personally responsible for creating it anymore.

It dawned on me that my preferred role would be as someone who could scale the business while hiring other team members to take care of the day-to-day operations: doing keyword research, writing, editing, project management, and uploading a finished product to a client’s content management system.

In order to actually scale this thing, I’d need some clearly defined processes for each person to follow.

But first, if The Blogsmith was going into a new direction as a digital company as part of the rebranding process, I would need its public image to match. 

I needed to work on a new website design.

Rebranding Process for The Blogsmith’s Website

Truly, there was nothing particularly wrong with my old design. In fact, it served as inspiration for the new one.

Creating a New Website Design for The Blogsmith’s Agency Model

In terms of the major elements and sections that make up The Blogsmith’s new website, they’re not all that different from what appeared on the old website. 

That said, the first step I took to kickstart the rebranding process was to spend some time working on new copy for each page. I wasn’t going for perfect — just a general idea to understand how the length of each section would factor into the final design.

Working on the copy and considering how it would influence page structure also forced me to think about any elements that might currently be missing. Inspired by feedback from past prospects and customers, I put myself in their shoes and considered what else they may want to know prior to getting in touch/in order to make a decision about getting in touch.

Once the copy was heading in a good direction, I started thinking about information architecture and design elements that would persist as on-brand formatting across the website. I wrote notes about my desired look, feel, and functionality, adding visual examples to better illustrate what I was describing.

Using the Elementor Page Builder Plugin

My previous website design employed the use of an included page builder: WPBakery (previously known as Visual Composer). I had purchased a premium theme from Envato, which often includes access to premium plugins.

For my new website, I wanted to invest in a premium page builder or use Gutenberg. Since Gutenberg just isn’t completely where we all want it to be quite yet, Elementor eventually won out. I also considered Beaver Builder.

Ultimately, I grabbed an Elementor license during their yearly Black Friday sale and kicked off the rebranding process with the same website design agency that handles my WordPress maintenance needs, Zealth.

I think I took for granted the impact Elementor would have on website technical structure and that’s something I’m still troubleshooting. Since SEO is kind of my thing, I want my website to reflect my well-rounded knowledge of what works. And heck, I want my own content to rank, too.

Another caveat of using Elementor is that adding new blog posts to my website is now a much more involved task. That said, I suppose that using any page builder would add a similar layer of complexity to uploading new content (compared to just using the Classic Editor).

Creating On-Brand Web Design Elements

Take a close look and you’ll notice some Blogsmith brand details throughout the new design.

Here are some of my favorites:

Street art hero images:

All the street art on this website, including each blog image, are photos I’ve taken of street art around the world. I started my street art photography project many years ago and haven’t been able to track down every artist’s name but would love your help if something looks familiar to you! 

Street art hero images

Spray can bullet items:

As a nod to my love of street art and The Blogsmith’s edgy but creative content creation efforts, I wanted the nature of the brand to be present in even the most seemingly small details. 

Meet the Team section:

Now that The Blogsmith is operating with an agency model, I want clients to know more about team members they may be working with. I called in help from my Design Pickle designer to help me create simple, on-brand team photos.

How it Works section:

 I’ve been recommending this type of section to most clients I’ve written webpage copy for. Most, if not all clients, will have questions about how the process works, which is why you should also have a FAQs section.

Pricing table:

As part of my brand relaunch, I knew I’d be publicly upping my prices. I already had a decent template in place for my pricing table but Zealth helped me make it look beautifully on-brand — I love the ripped ends. It works perfectly to demonstrate the value of each package, including optional but included bonus value add-ons.

Pricing table

Speaking of which, I love the blog item hover state, which adds a ripped edge effect on hover.

blog item hover effect

Author bio:

I wanted the author bio to do a good job of highlighting each individual contributor to the blog as I sometimes feature guest writers and want to provide a platform that helps advance their goals.

Author Bio

That said, please don’t get in touch asking to guest post. I’ll let you know if I’m interested in pitches. I do offer sponsored posts.


It’s a simple design but I love the functionality. I get a useful frontend representation of each portfolio item by creating a custom post for each entry. Instead of offering unique portfolio pages for each piece of content, I wanted to avoid forcing people to click multiple times to get to the article. I also wanted visitors to have some infomation about the cotnent before making the decision to click.

Contact form:

I was testing out Gravity Forms but eventually decided to switch to Forminator since I have a WPMU DEV subscription. Forminator helps me execute some helpful automations via Zapier and Slack.

Forminator Contact Form

Link underline:

Part of the rebranding process included taking a critical look at past branding decisions and what I wanted them to be moving forward. I bought an AppSumo deal for a tool called Brandox and put together some basic brand style guidelines for The Blogsmith. One of my favorite updates is the new link underline style, which doesn’t quite fit within the lines (just like me).

link underline style

New Plugins with Agency Model

As part of updating my website, I also wanted to refresh my plugin stack.

Here are a few top picks from my current plugin stack:

  • Shortpixel: I had this plugin before but now I’m also using it to serve up next-generation .webp images. Cheers to the future and better image optimization!
  • Optinmonster: I use these as lead magnet forms across my website. They allow you to enable things like exit intent technology. You can set them to appear at the end of every blog post or just in certain situations.
  • WPMU DEV (Forminator Pro & Snapshot PRo): I snagged an awesome lifetime discount during Black Friday one year which included unlimited access to all premium WPMU DEV plugins and credit for hosting three websites. I use the hosting credits as test environments my writers can use to test out processes and grab screenshots.
  • Yoast SEO Premium: I had invested in Yoast SEO Premium before and transferred all my existing settings over to the live site.
    Pro Tip: Copy everything from your old site over before staging a new design because it’s a b*tch to transfer settings over in a more manual fashion.
  • This was an AppSumo deal I bought a while ago. It creates an audio version of your article, ideal for people who may not have time to read but could play audio in the background of what they’re doing.

After going through the initial stages of the rebranding process and thinking critically about what I needed in a new agency website, I decided to move forward by outsourcing the design process.


Hiring Website Development Help from Zealth Digital Marketing

I wanted a super fresh design for The Blogsmith, with all the bells and whistles. And I wanted to outsource development to a professional, partially to help keep the project moving. 

I somehow still managed to drag my feet on making decisions for much of 2020 (sorry Adam — Zealth’s owner/founder).

Zealth was the perfect partner for building a website for the business that would give me a new taste of the agency model entrepreneurship I hadn’t fully explored yet. And hiring them gave me time to focus on all the other details necessary to scale at the right pace (of which there were many).

That said, I’m no stranger to agency life and working on a team of marketers. 

My History Working at Agencies

From Freshman to Senior year in college, I worked at the Student Life Marketing + Design department. Working at this student agency remains one of my best jobs/experiences of my life, to date.

Our clients included various student organizations, special events on campus, and the university book store. I worked there officially as a web designer but occasional as an on-screen personality and other odd jobs.

Here’s one of the videos we made during my time:

One such odd job was helping with the student life department’s blog and social media accounts. It was during the process of creating a content strategy and watching it unfold that I discovered a love for digital marketing. 

It was this job that helped me to quickly determine that I wanted to pursue a degree in marketing, specifically.

I found myself thrust back into agency life to some extent when working at Groupon and officially back in it when moving on to a job at a boutique social media agency in Chicago. In both cases, I was working in sales, which I learned to be good at but it didn’t fulfill me. 

I knew I wanted to be a marketer, so I eventually quit my full-time job to make money on my own terms.

Developing Agency Processes

One of the most important “processes” I’ve put a lot of time and energy into creating and improving upon is my company’s style guide.

Early on during the rebranding process, I’d assume the role of editor, smoothing over the rough edges in other writer’s work so that it worked for my style. But I realized that if I ever wanted to stop being the editor, I needed to formalize the nature of the edits I was continuously making. 

Creating a style guide was also important for helping writers quickly get up to speed regarding what it means to write for The Blogsmith clients. 

As I added new people to the team, I kept learning more about how my guidelines could be misinterpreted, which helped me to clarify what I was really trying to say. Eventually, my style guide grew to 12+ pages of clear, actionable guidance regarding gold standard content.

Once I started the process of scaling up my business, I needed to think seriously about effectively documenting the rest of my processes and putting others in charge of executing them. I also needed to think critically about selecting project management tools and other tools we could use to communicate. 

I tried to deny it for so long but you really need some kind of asynchronous chat tool like Slack when building a remote digital agency. Heck, even a local business with an agency model could benefit from it. 

Running a team effectively involves keeping track of a lot of details. It’s hard to contain them within a project management tool and it’s burdensome to rely on email for every update. 

Slack is perfect for sharing updates and asking quick questions to get clarification. In either situation, the ability to have a back and forth on this medium is so useful in terms of how it helps improve the final result. 

In most use cases, with the exception of an enterprise agency model, you could probably get away with using the free plan. The secret is not to store knowledge in Slack — use some kind of organized intranet for that, instead.

Here’s a presentation I gave based on my experience in the first half of this agency model transition:

Maddy Osman: From Freelancer to Agency – How I’m Building Systems to Scale

Moving into the latter half of this rebranding process, I gave an updated version of this talk for The WP Buffs’ WPMRR Summit:

The main process I had to design was how the team would work together to create blog content. I created guidelines that also functioned as task management functionality, so that every member of the team would know what was expected of them, at what due dates, and in what order. 

I achieve process management functionality with a tool called Process Street.

Some tasks only show up conditionally based on input. For example, do we need to do keyword research? If yes, some tasks become unhidden. Furthermore, not everyone has permission to see everyone else’s tasks (so as not to overwhelm them with too much information). Instead certain roles have certain permissions and visibility into other relevant tasks.

While I’m still ironing out this team blog post creation process, it’s getting better every day thanks to real-time feedback from my team and working with clients. The more improvements I make, the less I unintentionally become an information gatekeeper or bottleneck in the process for the rest of the team.

Speaking of which, I’ve recently learned a lot about working on a team.

Developing Hiring, Onboarding, and Ongoing Management Processes

Learning how to work with people effectively is a skill. Learning how to manage people effectively is a completely different skill. The same could be said for creating a great process for hiring and onboarding new employees.

There’s just so much to figure out and most of it is situation-dependent, paired with lessons learned from trial and error.

Transitioning to an agency model has meant learning a lot about how to effectively communicate with and motivate the people who work for my company. 

The most important thing I keep in mind is to be respectful and not get mad at my team if something in the process goes wrong. Because more than likely, the reason it went wrong was because of me giving bad/incomplete direction.

It all starts with a great hiring process. And it’s so true that if you don’t do a great job with your hiring efforts, they will have a large negative impact on your outputs.

There are two major keys to a great hiring process:

  1. Consistently asking the same questions to all applicants (you can add more in for each individual) to create a baseline of comparison. Make sure that your questions give you an opportunity to learn about the candidate from multiple different perspectives: how they’d generally handle the role, dig into whether or not they understand any desired specialist functionalities you’re looking for, and determine how they’d handle working in your type of business, with teammates.
    Check out my writer job application >>
  2. Invite your top candidates to do a test project (hat tip to Jeff Hyman for this nugget) — ideally multiple test projects — before taking the time to onboard them into all your systems. It’s so worth it to invest the time in giving people a thorough test and seeking the opinion of others on your team. I have an editor look over every writer test I assign and ask for their detailed opinion regarding whether or not that person seems easy to work with and if they can follow our style guide. Just make sure that offering a test project doesn’t mean you expect free work because you really need to pay people whenever they’re doing work on behalf of your company, whether you can make use of it or not.

Once you’re feeling good about a candidate, confirm that you’re interested in working together long-term and start onboarding them into your systems.

For The Blogsmith, this entails sending an invite to a portal where they can fill out documents I need (including an NDA and working agreement) and complete certain training modules to get them used to our workflow. It also serves as a reminder for me to create user accounts and grant access to the various tools and documents we use on a regular basis.

Some of these shared tools include:

  • Asynchronous team communications and updates: Slack 
  • Document creation and management: Google Drive
  • Task/process management: Process Street
  • Generating SEO content briefs: Frase/Clearscope
  • Intranet: Notion

And from there, it’s just a matter of getting everyone more used to The Blogsmith’s processes. 

Creating an Account and Project Management Process

In order to truly get myself out of the day-to-day, I needed to put someone else in charge of project management. I also needed to train someone to take over account management and help execute processes related to it for when I eventually felt comfortable enough with my team’s operations to hand that over.

It’s definitely a challenge to articulate what your ideal situation for project management is. It’s also hard to envision it until you have to outsource it. But it helps to start by taking a step back and looking at your inbox and considering the business-related actions you take in response to these and other related communications.

It was using that line of thinking that helped me to create and improve a daily checklist that covers everything I can think of that I want my project manager to take care of, with room for explanations so I can make sure we’re on the same page and audit whether anything got missed.

As a second reminder, I’ve found that it’s ridiculous to be mad at someone if you have certain expectations but haven’t actually communicated them. Make sure that your project management process does as much as possible to clearly articulate the expectations you have for someone executing this role and what that looks like on an average day. You can continuously update it as you think of new and better ways to communicate your expectations.

Final Thoughts: The Blogsmith Rebranding Process: Freelancer to Agency Model

More than a year in the works, The Blogsmith’s rebranding process is off to a great start. But there’s still so much to learn and create to support my new agency model.


I’m excited to see where this goes.


Maddy Osman

The Blogsmith

Maddy Osman is the author of Writing for Humans and Robots: The New Rules of Content Style. She's a digital native with a decade-long devotion to creating engaging, accessible, and relevant content. Her efforts have earned her a spot in BuzzSumo’s Top 100 Content Marketers and The Write Life’s 100 Best Websites for Writers. She has spoken for audiences at WordCamp US, SearchCon, and Denver Startup Week.

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