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How I quit 9-to-5, built a graphic design business, and 2.5xed my income

morgan overholt headshot
  • Morgan Overholt

  • From Knoxville, TN, USA
  • Owner of Morgan Media LLC

  • Business Model: FreelanceAgency
  • $24,000monthly revenue
  • $16,000monthly profit
  • All info self-reported by interviewee
  • Published November 28, 2019
  • Reviewed and edited by Rita Epps

Who are you and how do you make money online?

My name is Morgan Overholt, I am 34 years old, and I quit my “regular job” in 2017 to become a full-time graphic design freelancer and owner of Morgan Media LLC – a small graphic design agency based out of Miami, Florida. 

We gross nearly $300,000 annually, and I personally take home about $16,000/month (which is equivalent to about a $200,000 salary). I employ one full-time contractor, my right hand (wo)man Alaina O’Neal, and three part-timers.

morgan overholt in the office

💻 Editor’s note: see our full list of ways to make money online.

What does a typical workday look like for you?

Owning my own successful business is truly one of the greatest honors of my life.

I make my own rules, set my own hours, and essentially, set my own pay – it’s changed my life in unimaginable ways. 

Three years ago, I was living in Knoxville, Tennessee (my hometown), making about $75,000/year and driving into work every day like a “normal person”. 

When I quit my job, I not only more than doubled my income but also opened up my life to endless possibilities. 

My husband (who is also independently employed) and I moved to Miami, rented an apartment in a gorgeous high-rise and sold our cars (don’t need a car if there is no daily commute and you live downtown).

morgan overholt with her husband

I roll out of bed most mornings around 8am, walk four blocks to my office (which I was able to purchase with money earned from the business), and start my work-day around 10am.

Most days I work until about 7 pm, but I do pull the occasional late night here and there. 

I work about 40 hours a week for Morgan Media LLC, but I am admittedly the consummate entrepreneur.

I spend most nights and weekends either blogging on my own site or working on my latest side-project, TheSmokies.com (a travel website).

I am driven by a need to constantly create and find new ways to grow my business and diversify my income. 

I’m currently on track to retire in my 40s…

…which is something that I would have never thought possible when working a “traditional” job.

What’s your backstory and how did you come up with the idea for your business?

I began my corporate career nearly 15 years ago, but constantly found myself working crazy hours (holidays, weekends, overnights… you name it), battling office politics, seeing little reward for my efforts and wondering whether or not there was more to life. 

I was having a particularly bad morning at work and nearing the end of a nine-day work ’week’ plus a double holiday shift when I sat down with my boss for what would turn out to be a meeting that would change my life.

It was a dark and dreary rainy morning – a detail that I remember well because there was a huge sky-light in her office and the rain was so heavy, that it gave off a foreboding ambiance that filled the room like some sort of physical manifestation of my state of mind.

As I expressed my frustrations, my boss looked at me and coolly replied, with a line I will never forget: “I’m sorry, but I just don’t have any sympathy.”

In that moment, something inside me snapped and I said: “My heart just isn’t in this anymore.”

I gathered my belongings and walked out the door, knowing that I’d never return to the corporate world again, at least not as an employee. 

How did you prepare to launch the business?

Graphic design has always been a part of my life – even before I knew it was something I could turn into a career. 

When I was a young teen, I often spent my summers hogging the family LAN line learning how to design and build a Harry Potter fan site. 

Keep in mind, this is WAY before computer professions were considered to be common, or lucrative for that matter – especially for women.

It’s not like my parents were encouraging my little hobby – in fact, I often found myself in trouble for spending too much time on the internet in those days. 

That’s really what sparked my interest in graphic design.

I was teaching myself an employable skill set without even knowing it, at a really early age.

And in case you’re wondering, I’m a Ravenclaw. 

morgan overholt ravenclaw

Fast forward to early adulthood and the skills I acquired goofing around on the internet as a teen were starting to pay my bills.

I freelanced my way through college and by the time I graduated, I was already one of the few in my class actively working in the field.

Even when I began working a full-time job in the corporate sector, I continued to freelance on nights and weekends just to supplement my income.

So, if I am being honest, I think I always knew in the back of my head that it was possible to support myself through freelancing – it just took getting really fed up to break free of the “normal job” to work up the courage to really pursue it as a full-time career.

How much money did you have to spend to get started?

The great thing about graphic design is that it doesn’t take a lot of money to get started.

The Adobe Creative Suite is about $50/month. It only costs about $100/year to run your own website (which I use as my portfolio). 

Unfortunately, I did pour some money down the drain in early days with failed marketing efforts to the tune of about $2,000 that I wish I could take back, but more on that later. 

Talk us through your first few months (or first year) in business.

The first few weeks were an emotional roller coaster.

I had moments when I felt like I was on top of the world and anything was possible – and I had moments when I thought I’d be eating ramen noodles for the rest of my life. 

Those closest to me were my support system at the time – my husband, my sister, my best friend and mother kept me sane and on track. My dad was also supportive but with a healthy side of worry and confusion. He frequently asked if I was looking for full-time work.

I find that people who are unfamiliar with the term freelance tend to think it’s code for “perpetually unemployed.” 

I had the distinct feeling that other friends and acquaintances suspected I was going through an early mid-life crisis. 

I spent every waking hour applying for gigs and updating my portfolio.

My biggest breakthrough was when my brother-in-law suggested I sign up for Upwork, a freelancer marketplace. 

Online trolls will tell you that it is “impossible” to make money on this platform. And I have to admit – it was hard to get started.

It took 2-3 weeks to get my first gig and even that was just a $10 logo tweak. 

Related article + video: What Ivan Did To Beat 50+ Freelancers On Upwork

But after I got that first review under my belt, work slowly started to trickle in on a fairly regular basis. 

I was DETERMINED not to fail.

I constantly reminded myself how miserable I had been in the corporate realm and refused to go back to that life. 

Within 3 months, I was bringing home about $5,000/month, which was equivalent to my old salary – THAT’s the moment I knew I was going to be okay.

morgan media lcc office

How did you make your first $100 online?

My first ever freelance gig was for a local realtor right after I graduated from high school.

It was a simple magazine ad and he paid me $25 – which sounds like nothing now but at the time, I was working at the local OfficeMax making $6.75/hour so by comparison – I thought I was rich!

How does the business make money today?

After almost a year of freelancing on my own, I decided to expand the business into a small design agency. 

Today, about 60% of our revenue comes from Upwork, the rest comes from design contracts we’ve procured through some good ol’ fashioned footwork.

morgan overholt upwork profile

Contrary to popular belief, I find procuring work through Upwork is MUCH easier than going it alone.

It’s like fishing in a pond where you KNOW the fish are biting.

Even at $95/hour – I am in the top 99% of hirees on the site (as in I am hired more often than 99% of my peers).

morgan overholt upwork statistics

There are four keys to finding success on Upwork, especially when you’re just starting out:

1. Being great at what you do and having an in-demand skill-set. 

In order to stand out in a crowded field of other freelancers, you have to be a rockstar in your industry.

And ideally, you’re a rockstar in a field that’s in high demand, like graphic design, where there’s never a shortage of potential gigs. 

2. Apply for jobs like your life depends on it. 

When I first started I applied for 5-10 jobs a day, every day. That’s the name of the game. It’s going to take a while to get your first nibble, be consistent and persistent. 

3. Know how to sell (yourself).

Learning how to write a stellar cover letter, that showcases your skills and convinces potential clients that you are the (wo)man for the job is absolutely crucial to finding success on the site. 

Related: 4 Proven Upwork Cover Letters To Save You Time And Win More Jobs

4. Treat your clients like GOLD and focus on LONG TERM relationships. 

One of the biggest secrets to my success is how I treat my clients.

I see my clients like I see myself – I see them as business owners in need of a professional to make their lives a little easier.

I also focus on long-term relationships, which not only reduces my need to apply for more work, but also reduces my Upwork fee (which dropped from an average of 20% my first month down to now 8% – that’s a 91% profit margin!).

My other contracts are mostly obtained through word of mouth.

What are some of the challenges particular to this kind of online business?

My biggest challenge is and always has been time management. 

As a freelancer, the name of the game is logging those billable hours.

If you’re spending too much time applying for jobs, fielding phone calls and performing administrative duties, it will start to cut into your bottom line.

And of course there are those two dreaded words that can throw a wrench in even the most perfectly planned week: “rush job.”

Cutting down on the need to apply for more work by focusing on ongoing client relationships, avoiding unnecessary conference calls, using tools that help you automate office duties (like creating contracts, logging time and sending invoices) and setting realistic expectations for both yourself and your clients is absolutely key to profitability. 

Side tangent: I remember a day when I was first starting out and had over 10 client-requested conference calls scheduled – most of which should not have required my attendance. I now strongly encourage my clients to reduce these types of calls, encourage one-on-one communications, emails and bill for my time accordingly. 

If you were starting the same business today, from scratch, how would you do it?

When I decided to start my own business, I was already so familiar with the world of freelance, I felt like I mostly knew what to do and what to expect.

But with that said, one of the biggest things I’d do differently if I started over again from scratch is signing up for Upwork on day one – instead of wasting my time on cold calls, Facebook ads and networking conferences (which ended up costing me a lot of time and money for virtually zero return). 

What books, podcasts, courses or other resources would you recommend to someone who wants to follow in your footsteps?

One of my favorite blogs – and one that helped me when I was just starting out – is Freelance to Win by freelance writer Danny Margulies. 

And of course I also highly recommend my own blog at MorganOverholt.com.

📚 Editor’s note: see our ultimate list of the best books for online entrepreneurs.

What are your top 5 business tools?

My team and I use the Adobe Creative Suite – if you’re going to be a designer, you have to know the big three – Photoshop, Illustrator and InDesign.

We use Upwork everyday for client acquisition, logging and invoicing.

We use Slack for most of our internal communications. It’s a great way to keep in touch and share files throughout the day, I couldn’t imagine trying to keep up with our workload without it and best of all – it’s free!

We use G-Suite for email and Google Drive, and Dropbox for collaborative file sharing. 

We use Rocket Lawyer for most of our contracts – and as a golden rule – we NEVER perform work without some kind of contract in place.

And we’ve recently been testing out a new platform for invoicing called And.Co by Fiverr.

Where can we go to learn more?

I am a big believer in “passing it on,” which is why I’ve created my own blog at MorganOverholt.com, where I frequently post tips/tricks about how to become a successful freelancer, especially on Upwork. 

Some of my most popular articles are:

You can also reach out directly to me on facebook at @MorganOMedia.

I’m also on Twitter and Instagram.

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  1. Thanks for sharing this encouraging interview!
    My heart sinks when I read what her boss said, “I’m sorry, but I just don’t have any sympathy.”
    One of my best friends got pregnant before. Hoping a better work arrangement can be done, she expressed her needs to her boss and that was what her boss said to her, “I’m sorry, but I don’t have sympathy for pregnant women.” And this line came from a corporate mother who has a daughter herself.
    When I think of how tough it is to run your own business, I sometimes get myself to think of how it’s equally tough, if not, tougher to live a corporate life.

    1. Thanks for the comment, Hazel!

      My heart sinks when I read what her boss said, “I’m sorry, but I just don’t have any sympathy.”

      Yeah, that bit hit me hard as well. So cold and heartless. And even worse in the case of your friend, wow!

      When I think of how tough it is to run your own business, I sometimes get myself to think of how it’s equally tough, if not, tougher to live a corporate life.

      I think corporate is often easier in the short-term, but in the long run it can really eat away at you.

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