My First Big Failure as a Web Designer - Self-Made Web Designer

My First Big Failure as a Web Designer

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Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.

The one objection I hear most often about starting a web design business is the fear of not being able to deliver what you promised to clients or majorly screwing up on something important.

Let me put your mind at ease with 6 simple words:

“You are going to screw up.”

It’s inevitable. It’s going to happen. Any time you start something you are going to be bad before you are good. Think about it. When you first started learning to tie your shoes did you watch a “How To” video, read a few blog posts, and get it right from that point on?

No. It took trial and error. Why would you expect something different from your journey as a web designer?

NOW, let me cut to the chase and tell you the really good news.

Screwing up doesn’t have to negatively affect the success of your web design business.

You could even screw up majorly on a project and still have a pleased client that comes back to you for repeat business.

To tell you how I know let me tell you a story about my first big flop as a web designer:

It was the biggest gig I had gotten so far. A fresh redesign for a membership site with over 8 years of blog posts and about 30 gigs of video that all had to be transferred over to Vimeo.

My asking price? $1250. It hurts me to write that figure now knowing how much I should have asked for BUT you gotta start somewhere.

This was the personal site for a well-known futures trader that had made a name for himself as a thought leader in the field. On this site was his course teaching people how to do what he had done as a futures trader and also daily updates of the futures market.

He also had a business with an application that thousands of traders used to evaluate the market. All of his websites and the app itself were running on the same host. 

2 months into getting hired the site was ready to go. He loved it. It looked awesome! At least I thought it did at the time 😉 All that was left was pushing this puppy live for all the internet to see.

The plan was somewhat simple. Point the old domain to the new server where the freshly designed site lived. The only problem was I had only done this 1 time before. Was I going to tell him this? Heck no! He was paying good money, at least for me at this stage. And, after all, I was a web design expert.

So, I did what every professional does. I googled. I found a process that looked pretty close to what I was trying to accomplish and followed the steps.

I had been working on this thing well into the early morning. So, right after I pointed the domain to the new server it was nap time! Another perk of being a freelancer…

When I awoke I found my phone had been lit up with phone calls, messages, and emails. What had happened?

Not only had I pointed the domain incorrectly BUT I had also changed the way every single one of his domains was pointing to their server.

EVEN the server where his app lived. The server that 1000’s of high strung anxious day traders needed access to at the very busiest time of day. 

The result was 1,000s of his clients without access to something they needed to run their business at a crucial part of their day resulting in them losing a lot of money. I don’t even want to guess how much it could have actually been. 

I didn’t know what I had done wrong and I couldn’t figure out how to fix it. But, thankfully, this guy was smarter than me. 

After a big “I’m so sorry,” session we both went to work and finally figured out what the problem was. I say “we” but truly it was him. This had stumped me. Within a few days, we had turned around the project, I was given good feedback on Upwork, and paid in full.

Fast forward 3 years later. This same client I royally failed calls with a slew of new projects he wants me to work on.

You read that right. The same client that I had failed 3 years before was happy enough with me that he wanted to give me more business. 

But guess what! I was now too expensive for him. My demand had become too high to charge what I had previously and I was out of his price range.

What’s the lesson? Screw-ups and failures don’t have to mean the end of your web design business. In fact, they are an essential part of learning and growing. So, please please PLEASE don’t let the fear of failure keep you from learning how to start your own web design business. 

Broken computer screen on floor


Hi, I'm Chris and I'm super glad you're here. 7 years ago I taught my self-web design and freelancing. Now, I do my best to teach others what I've learned so they don't have to struggle as much as I did.

Every week, I write an article and release a podcast episode. Sign up if you want to get notified when that happens.



  1. If you aren’t failing while learning, then you aren’t learning. Can you imagine learning _anything_ without failing? It’s not possible. Businesses often want $10K websites for $500 and it’s just not possible. They’re taking huge risk and they should know it. They’re paying for you to take the risk of failing and a slimmer possibility of success.

    • Chris Misterek says:

      Yeah, thankfully, I think he knew this when he hired me and was willing to put in the extra work with me for the price he was paying. I think the most important thing is not allowing your fear of failure to keep you from going for it. There are limits to this of course. But, at the end of the day, you kind of have to say, “yes” premptively and then figure out if you can do it.

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