So, You Want to Be a Freelancer? (Part One)

Brandon Osborne
5 min readSep 19, 2022

Real experience from a twenty-year veteran in the industry instead of contrived figures about how they “got rich in a couple of months” or whining about how it is impossible, usually from some college kid living in his parents’ house.

I was spurred into writing this article by the people posting ridiculous information on the subject around the internet. There seem to be two schools of thought prevalent in the writing that I’ve seen. They are both usually published by recent college graduates with no meaningful experience. The first school of thought seems to be the “get rich quick” crowd claiming they can use a WYSIWYG editor or learned PHP last week, and now they are millionaires. The other is the complete opposite; it is the whiney “It’s too hard” folks. These geniuses post things that defy reality. Simply because they are failures or are experiencing a failure to launch, obviously, web development or freelancing, in general, must be dying. 😳

“Nothing worth having comes easily. — Theodore Roosevelt

I started my freelancing career in the late nineties when I was still in high school — before the huge freelancing networks (or slave trade, as I could more accurately describe them). However, when they started to emerge a few years later, I found success in all of them. To succeed in freelancing, you need three main qualities: Skill, diligence, and reputation.

  • The first thing that you need is a kick-ass profile! While writing your profile, try to imagine it from the client’s perspective. He is getting dozens or hundreds of other bids. What makes you unique? Don’t just upload a low-quality and unprofessional (or boring) photo and list the skills you supposedly possess (many of which your clients won’t even understand anyway). The very first thing that a potential client is going to notice is your profile photo. Make it pop! For instance, I immediately increased my sales by 200 percent by simply uploading a picture of me wearing a smart jacket and a bright orange vest. Combine that with my big bald head, and their eyes are naturally drawn to my proposal.
  • Confidence is my secret sauce! I will never forget my first freelancing project. It was supposed to be a quick $300 WinForms project, but this toxic client recognized I was a good programmer and new to freelancing, so it dragged on for nearly a month before he finally paid me. That was a harrowing experience; twenty years later, it’s even more common! I remember that before one of my good friends died many years ago, he wrote the song “We Suffer What We Choose.” I never forgot that, and those words are still something I contemplate. Do not compete with people that sell their services for nothing! Do you want to be associated with that cadre or the professional folks that command a higher rate? I’m not telling you to increase your rates without the ability required to back up your claims. You will be found out quickly, and your reputation will suffer irreparable harm. Bad feedback early in your career can be a showstopper. Know your worth and charge accordingly.
  • Don’t submit copy and paste your bids! Nothing is more annoying to a client than seeing that you copied and pasted your proposal because you were too lazy to read their job specification. It is OK to use a template, but write something relevant to the customer’s project!
  • This one is gold: The customer is not always right! If they submit a ridiculous one or two-sentence request for a proposal, don’t waste your time! If they couldn’t be bothered to write a detailed RFP, then getting actual requirements and, ultimately, being paid will be like pulling teeth! Lastly, don’t be afraid to fire a client! You’re under no obligation to continue working for an employer that mistreats you, underpays you, or that you simply don’t like. You can never go wrong by following the 80/20 rule! If you don’t know what that is, I wrote an article about it here.
  • The freelancing marketplaces are the beginning; they are by no means the end of your journey! You have to compete with many unskilled workers and frequently equally unqualified or dishonest employers on those sites. Many new freelancers also operate under the misconception that the networks will protect them or fight for them in the case of a dispute. That is not the case! I remember several years back on, a friend and I decided to test the theory that the dispute “team” doesn’t even attempt to confirm the freelancer’s side of events. So, we created a fake project, chatted about it a bit, created a little mock-up that fulfilled the requirements, and installed Google Analytics on the testing site. It was no surprise when my friend won the dispute, and the only traffic to the demo website came from my friend and me. also kept its commission on the project. A “well deserved” fee for a job left undone entirely by them. Why do they do this? One word: money. Suppose they side with the freelancer, and the customer calls their credit card company to request a chargeback. In that case, loses the money, is assessed a chargeback fee, and actually has to get off their butts to eventually get the money back by fighting the dispute. All of their talks about guarantees and a fair marketplace is malarkey! So, don’t put all of your eggs in one basket! Find more places to acquire clients, or even better: learn to earn passive income. I’ll write more about that in a future article.

Thanks for reading! As this is a subject near and dear to me, I will be writing a lot on this topic, so sign up for my newsletter to hear more great tips about freelancing and always… follow your dreams!



Brandon Osborne

I’m the Chief Software Architect of I’ve been developing software on the Microsoft stack for 20 years & have been traveling the world for over 10!