Difference Between Never Did It and Did It

I spent my whole Saturday designing a new homepage for this blog. Pretty proud of the result, I showed it to my wife. She couldn't stop laughing at how bad it was. Not willing to admit defeat yet, I took it to /r/design_critiques/ seeking help from this post: I've been told this looks like shit already. What can I do to un-shit it? A particular comment there (quoted below) led me to write this article:

The design is very boring and it makes you look boring as a result. In a situation like this I'd recommend to just use a good looking template: https://www.tumblr.com/theme/36149 is a good one for your needs. It's not productive at all to try and do something you're 1. not great at, and 2. not looking for work in. Hope this helps.

Is gaining knowledge by trying new things not considered productive anymore?

Before diving into that though, you're probably wondering what my awful experimental homepage looks like. I wanted it to convey a clean and succinct message but it came out more like a careless job done in 2 minutes. Here's a screenshot.

new homepage prototype

An excerpt from another comment in the same Reddit thread:

Just remember that just as you might make engineering look easy, designers make design look easy. Having Excel doesn't make me a data analyst just as having server access doesn't make someone a web designer.

Emerging from my startup experience, I learned fast to be the Jack of all trades. User experience design, customer development, product management ... I am not so naive as to think that I can just jump in and take over anything. That's not the point. The point is that having some hands-on experience opened my eyes to how wrong I was in thinking I knew what other roles actually entailed.

Take user experience design, for example. I used to think that you just use common sense, right? No, you need to understand the user, understand the system, then somehow bridge that gap between the two. Or sales. You just talk to a lot of people, right? No, sales is about understanding user demand and discovering how their needs overlap with what you can offer.

Everything looks easy from 30,000 feet up because you don't see the details. When you've never done something, you really don't know what you don't know. We don’t realize how we automatically make assumptions and over-simplify things we don’t fully understand as a coping tactic to fill in the gaps. That's a useful tactic in everyday life, as I really can't be bothered with all the details around me. But it’s not so useful when bootstrapping a business as you can easily get blindsided. Once you've done a new job or solved a problem once, you don’t guess or handwave your way around the details anymore. You become aware of what you are unaware of. That is the difference.

Anyway, I answered my own question on whether gaining knowledge by trying new things can be productive. Yes, it can. After that, you just need a bit of practice.