A $200K freelancer shares 3 big mistakes she made when starting out

  • Morgan Overholt is the founder and owner of Morgan Media LLC, a graphic design agency, and earns $200,000 in take-home pay a year.
  • Before her freelancing career took off, Overholt made her fair share of mistakes. She tells Business Insider the three avoidable mishaps she made as a young businesswoman and what she would’ve done differently. 
  • Looking back, she says she wishes she developed a game plan to actively pursue opportunities, and trusted her gut instinct with certain clients. 
  • While Overholt isn’t defined by her past, she hopes her lessons can help the next generation of freelancers and small business owners avoid the same costly mistakes she made. 
  • Visit Business Insider’s homepage for more stories.

When you begin to experience some level of career success, it’s easy to forget about the blood, sweat, and tears it took to get you there.

It’s even easier for those around you who might only be tuning in for your social media “highlight reel” to assume your success must simply be a matter of luck rather than trial and error. 

But as a now successful freelancer earning multiple six figures a year, I can tell you that luck has had little to do with it. 

My path to success was wrought with trial, tribulation, and failure. The difference maker, at least for me, was how I chose to overcome those failures.

I’ve never let mistakes define me. I simply learn how to adapt and move on. While it’s impossible to avoid every stumbling block, I enjoy sharing some of my most hard-fought lessons with other up-and-coming freelancers and small business owners in the hopes that it could make the next person’s journey a bit easier. 

With that in mind, here are the top three, completely avoidable mistakes I’ve made in business and as a freelancer over the course of the past decade.

1. I waited for opportunities to come to me

Truthfully, I was guilty of this for many years, even before I decided to become a full-time freelancer.

I blame it on watching too many Disney movies as a child. 

As a young woman, I often assumed one day my prince charming/fairy godmother/big career opportunity would just land in my lap. I just had to be patient.

That is, until I found myself completely broke at the age of 22 and living in my mother’s basement. 

That sobering experience made me realize if I wanted something, I was going to have to actively pursue it. I wasn’t going to be “recognized” or “discovered” for my innate talent. 

Don’t get me wrong, it’s a vulnerable way to live, constantly putting yourself out there and having doors slam in your face. It’s never a great feeling to hear the word “no.” But the pay off — eventually hearing the word “yes” — makes it all worth it. 

When I was in the corporate world, I asked for raises, I asked for promotions. I wasn’t afraid to switch jobs if I wasn’t receiving the respect or opportunities I deserved. 

Today, as a freelancer, I actively pursue large contracts and big clients. I ask for higher rates and am not afraid to remind prospective clients of my worth. 

For instance, people often complain that clients are too cheap or unwilling to pay a fair market rate, especially on online marketplaces like Upwork. 

I’ve never held this against the client, I always just assume the client might not understand what that market rate should be. That’s why I regularly submit bids on projects that are over double or even triple the client’s listed budget. And more often than not, I get the contract.

Think about all the freelancers who passed those opportunities right up because it didn’t occur to them to just ask for more!

I make my rockstar status known. I’m not afraid to sing my own praises. 

I’m shameless. I go after what I know I deserve. I’ve learned the hard way that no one will ever be as invested in my future as I am. 

You have to ask for what you want in this world if you want to achieve great things.

2. I didn’t have a game plan

I didn’t start out thinking that freelancing would be the key to unlocking the kind of success that would put me on track to early retirement. 

There were several other business attempts that failed miserably before I got to this point.

I once developed an iOS app with my then-boyfriend (now husband) and his college buddy. We made exactly $0 and wasted a year of our lives on graphics and development.

A few years ago, I got the bright idea (pun intended) to start a custom candle line with inspiring phrases and sell them on Etsy. I sold one candle and am still stuck with unmovable inventory to this day. 

I also did a short stint as a TV host at a home shopping network thinking it would bring me fortune and fame. To my disappointment, it brought neither.

What each of these forays was lacking was a solid game plan. 

When we developed the iOS app, we had no idea whether or not there was a demand for it, and had no clue how to market it. The same could be said for my failed candle line. 

By the time I decided to pursue full-time freelancing, I knew I had to approach it much differently than these other failed business attempts if I wanted to make it work.

I knew I needed a real game plan.

And so I honed my skills and learned how to sell and identify potential customers early on. I knew where my buyers were and how to get their attention. 

From the moment I decided to take freelancing seriously, I made a list of online freelance marketplaces to pursue. I reached out to all of my old contacts, created a budget for my business, identified milestones, and set goals for myself. I put in the groundwork. 

Far too often I see wanna-be freelancers far too focused on the transactional side of “gig work.” They think it’s just about doing work and getting paid. 

The truth is, freelancing is a business like any other. You have to develop a strategy. All freelancers must ask themselves the following questions:

  1. What unique skill sets do I bring to the table?
  2. Who’s my target audience and how do I find them?
  3. How can I effectively market myself?

If you aren’t able to answer these basic questions before you begin, your likelihood of success is low.

3. I didn’t trust my gut

Have you ever had that sinking feeling before taking on a new client or a new project? 

Sometimes the red flags are subtle, sometimes they couldn’t be more obvious.

I’ve talked to many different freelancers who’ve experienced the same classic situations: A client comes across as rude, or too needy, or perhaps they just haggled a bit too much on your price tag or convinced you to proceed sans-contract. 

Your gut told you it was a bad idea. But for whatever reason, you brushed it off and threw caution to the wind.

While disaster isn’t always inevitable in these situations, an excellent outcome is unlikely.

The worst experience I’ve ever had was a client who stiffed me to the tune of $2,000 on a project that went belly up before I received a dime. I even put some of my own money into the project, purchasing almost $600 worth of licensed stock video and images. 

I had no contract in place. Heck, I didn’t even have an address had I wanted to hire a lawyer and go after him. 

As they say, hindsight is 20/20, and bumps in the road are not always avoidable. 

But I would say that by learning to trust my gut and vetting my clients beforehand, I’ve experienced a sharp increase in quality projects. In fact, I would say I vet my clients as much or more than they vet me.

I look for clients who are excellent communicators. They need to be kind, professional, and treat me with the same respect that I show them. 

Today, I would estimate I turn down almost 50% of the contract offers I receive. If I have even the slightest bit of hesitation about taking on a new job or a new project, I have no issues with saying no. I lose way less sleep at night worrying about missed opportunities than I do fretting over a difficult contract or a cantankerous client. 

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