Four Things I Failed at in 2019

I’m going to be gracious and say that 2019 was one long lesson. While I landed some great clients and made some strides professionally, I also failed in many ways. While I would love to hop on here and write a masturbatory post about my successes, I think airing out my failures is more helpful. So! Gather ‘round and let’s pick through the hot garbage that is my 2019 failures.

Failure #1 – Producing a Film

During my last LLC journey post, I shared that I had secured a 5-figure contract for a project that I was super excited about. This project was a short documentary on a demonstration I was a part of while in graduate school. I signed onto the project in a consultant/project manager/producer role and hired two people (a videographer and another producer) to work on the project with me. Things were going swimmingly initially. The money came through and the team I had assembled was absolutely fantastic to work with. It seemed like everything was going right. Unfortunately, a day before we were set to fly out to the filming location, I received word from my client that we had to halt production due to some squabble with a high-profile interviewee and their issues with our standard release form. Long story short, the shoot got pushed back and pushed back again to the point where my team and I could no longer work on the film. The entire thing fell apart within a few weeks.


  • Make sure you write a contract that ensures you are compensated for the amount of work you do. Because I did this, I was still paid for my time despite not being able to complete the project.
  • Only work with people who trust your knowledge and expertise. The main reason this project failed is because I chose to work with a client who knew nothing about writing, editing, film production, or the like, but shared a lot of “insight” into how things should and would be done.
  • Know that you’re never too big to fail. I was so sure that because there was so much money involved in this project everything would, more or less, work out. I mean, when people invest a lot of money in a project, they’ll do everything in their power to ensure it’s successful, right? Well, the answer is: not always.

Failure #2 – Pivoting to Consulting Work

Once I realized how much money was involved in the consulting game, I tried to pivot my business to take on more consulting work. Unfortunately, this only led me down a pretty treacherous path, where I was chasing money rather than focusing on building on the skill set that had become my bread and butter (writing and editing). I also ended up working with a consulting firm that I am now in a legal battle with over unpaid wages (more on that at a later date).


  • Invest in what you’re good at, what you enjoy, and what makes you money.
  • Don’t chase after jobs just because they money is good. Really ask yourself whether taking on this job/client is the best move for you in the long run and if so, why.

Failure #3 – Launching a Website

Y’all. I still don’t have a website for my business. I’ve been putting it off for reasons that don’t make any sense (e.g., I’m not sure if my business will survive the year, I don’t have the money to build a nice website, I don’t have the time to construct a nice website, etc.). I definitely believe that not having a website has been a huge detriment to my business. Although I’m on social media platforms designed specifically to attract clients, people are more likely to request your services as a freelancer if you have your own webpage. They just are. This year I will be launching my website. No more excuses.


  • Understand that while social media is helpful, websites still provide a certain amount of legitimacy that social media alone cannot give you.
  • Sometimes you have to push past the bullsh*t excuses and just do what you gotta do.

Failure #4 – Booking More Long-Term Work

Although I had started the year with the idea of booking long-term work (6-month to 12-month long contracts), last year I mainly did one-off projects and very short contractual work. I thought the work I was receiving from one client was going to turn into a long-term contract let me go due to financial issues with their company. However, to be honest, I relied way too much on referrals and didn’t pitch myself to potential clients as much as I should have. By taking projects as they came, I also didn’t have as much of a say in the type of work I was doing.


  • Remember that nothing in the freelance world is a sure thing. While working on a consistent basis for one client is a great thing, know that you have to keep hustling to make sure that multiple revenue channels are flowing in your direction.
  • Prioritize outreach to bring in new business rather than relying solely on client referrals and recommendations.

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