Three Reasons I Sucked at Freelancing

I spend much of my time writing for SitePoint about the success of others, and sharing great tips and tricks I have learnt myself.

One great quote I really live by is that you should learn from your mistakes. Mistakes happen to the best of us; as long as you walk away with a lesson under your belt, you’ve made the best of a possibly poor situation.

I want to share with you three reasons I failed when I first started freelancing back in 1997. In fact, let’s make that one failure from 1995, and then two more in 1997. That’s right; 1995. A long time ago now, so I’ll forgive you if you’re young enough to laugh when I say my first failure was trying to sell something most people hadn’t even heard of.

That’s right; I hit the pavement trying to sell websites to companies who hadn’t heard of the internet. This was 1995; back then, this internet thing really was the wild frontier, and many businesses hadn’t heard of it. I got a few customers on board, but not enough to pay for the fancy office space I had leased, so I quickly shut shop.

Lesson number one? You really can be too early. I should have waited another year, and by then, the web was all over the media. I either didn’t hit the right early adopters, didn’t know how to sell well (and that certainly was part of it) or I was just plain too early.

The next two failures were two years later. The web had exploded, people now knew of the web, and although not everyone was convinced it was vital to have a website, there were enough people out there to carve out a living.

Two of my mistakes this time around were very close to each other. Mistake number one was not estimating the time correctly. I didn’t keep timesheets, I just guessed how long things took, and given that when I got “in the groove”, time often flew past … I really sucked at judging time.

The issue here is I’d say that it took me two hours to design this element. In reality, it took me four hours, yet I kept saying two hours over and over, compounding the problem. The opportunity losses from working for free when your only commodity is time can quickly add up to be unsustainable.

Lesson number two: Keep timesheets and get good at accurately understanding how long it takes you to complete a task.

The third mistake, when coupled with the last one, made my second attempt at freelancing a failure too. I completely misjudged what I should be charging per hour.

I estimated working from home, using an old computer, with no insurance or other costs, meant I could get away with charging close to nothing. Heck, even twice my hourly rate was still close to nothing! Combine that with not even billing for the hours I was working on projects meant my clients were getting a fantastic bargain, but I was on my way to being worse off than unemployed.

No wonder everyone accepted my quotes! I really sucked at valuing my own worth.

Lesson three: Understand your real hourly costs, and don’t be afraid to ask for a realistic price. Selling yourself short means you’ll sell yourself out of business.

Luckily for me it really was third time lucky; I started my third attempt at freelancing 10 years ago this month, and now I’m pleased to report this time it was a success (well, it’s a company now, which happened within three months of my diving into freelancing, so technically I’m not a freelancer now).

Look back on your early business time – what were some of your failures? Let’s share and learn from our mistakes. Feel free to post a comment below!