The dangers of the redesign

Redesigning your own website should come with a warning label, like a pack of cigarettes.

SURGEON GENERAL’S WARNING: Website Redesigns Cause Stress, High Blood Pressure, Depression, and May Complicate Your Sanity.

Around a year ago, I decided to redesign this website from scratch. Not only did I decide to update all the content, I simultaneously decided to learn Hugo, a static site generator. However, this post is not about Hugo, or even the challenges of learning a new technology. It's about understanding how creative people lay traps for themselves and how I might help you avoid doing the same thing.

Web designers who have outdated websites are a cliché in our industry, this is sometimes referred to as the cobbler's children trope. The basic idea is: “I'm so busy, I don't have time to work on my own stuff”. Redesigning your own website is difficult because it forces you to be your own client, and the truth is, you are your own worst client.

Why redesign in the first place?

Chances are the internal conversation goes like this:

"Crap, it's been years since I last updated this place. It totally doesn't reflect where I'm at creatively and professionally.”

Or maybe:

"My day job doesn't satisfy me creatively. I'm going to have fun and experiment here, no-one can tell me what to do. Ah hahahah!”

Without a plan or structure, the first trap you will encounter is moving towards the visual design or development too early. Maybe you open up Sketch or Photoshop and start creating mockups, maybe you start creating layouts in HTML and CSS. The irony here is you know this wrong, in fact, you tell your real clients or stakeholders this all the time. The problem is you are a terrible client with poor impulse control and so you start with the fun stuff first.

Really, don't do the fun stuff first

Writing and gathering your content before jumping into the visual design isn't fun for most designers. Fun for us means exploring layout, color, typography, or technology. Solving a unique design problem triggers an endorphin rush. Don't confuse this with productivity or progress, it's just your brain fooling you. The real work has been and will always be the content, which we all know is the king.

What I can guarantee is that your content is not in good shape. Mine wasn't. Not only did new copy need to be written and new images have to be added, but a lot of the the old copy didn't sound right anymore and had to be revised.

Putting visual design first often leads to making decisions simply out of convenience. Your content should dictate your design, not the other way around. Again, in your day job you know this, or you have team-members who are in charge of content. During a re-design,however, without some discipline and structure, you are probably a terrible content strategist.

Practical tip: To help structure this content and to make the eventual transition to HTML easier, consider using Markdown syntax: a simple formatting language that provides simple structure for elements such as paragraphs, lists, headings and more.

When's that due anyway?

Perfectionism or high standards is often an asset for designers, after all, we're paid to “sweat the details”. At the same time, we are intimately familiar with the crush of deadlines and being forced to ship, even though we want to do just a little more work on the leading in the copyright section of the footer.

Now is when you become not only a terrible client and a terrible content strategist, but also a terrible project manager. Here's how that might go: as you begin to revisit your old work, as you begin to write, as you run into technological roadblocks, as you try to define your visual identity to the world, you will simply get sick of yourself.

Actually, you're not sick of just yourself, you're sick of all of your selves. The content strategist is annoyed at the client for increasing the scope. The client is annoyed at the designer for insisting on that one typeface just because. The designer is annoyed at the content strategist for adding more text and forcing me to deal with overflow. Through all of this, we haven't even introduced yourself as the developer, who is responsible for making this all work and is sick of everyone's shit.

In a normal project, a good project manager would come up with a strategy to help people recharge but also stay on schedule. However, you're a terrible project manager and so you let things slide. One day turns into two, which turns into three, and suddenly you haven't done a single thing to your site in a month.

I do have one strategy that I find useful to avoid (some) of the burnout. When a creative person is in the flow or “the zone”, they want to extend that feeling as long as they can. The risk here is that at some point you will go cold, hit a roadblock, and create a fresh problem that you no longer have the energy to solve. The way to avoid this was articulated by Ernest Hemingway in 1935 who was asked by an interviewer, “How much should you write in a day?” Here is his response:

"The best way is always to stop when you are going good and when you know what will happen next.”

I try to follow this advice as much as I can. If I end my day's work knowing what I need to do next, I am far more likely to pick up where I left off. It's my gift to “Future Jeremy”. Rather than giving him (err, me) a mess to inherit, I try to leave him with an incentive to start.

Stop playing hero ball

Hero ball (basketball, derogatory): A style of play where a single player tries to be his team's hero by taking and missing many shots.

As a younger individual, I took a certain pride in “doing it all” and proving to myself and anyone who cared that I could lift all the things. I need to learn PHP just to make my contact form work? Sure, I'll take a month to do that and end up being a terrible PHP developer because that's not who I am. Over the years, I discovered that the final product is the only thing that matters and your audience could care less about how you got there.

If embarking on a redesign forces you to do things you are not good at, the obvious solution is to find people who are. While this is not bad advice, it's not always feasible. You might not have the budget to hire another designer, developer, content strategist or project manager to help you, or you might not know where to find one.

To that end, don't hesitate to ask for help. People in this industry tend to be generous with their time and effort. If it's not cold, hard cash you can offer, maybe it's a trade of services or a similar barter. For this redesign I received tremendous technical support from my friend and work colleague Mike Bifulco, he did most of the heavy lifting in getting Hugo set up and had the patience to help me navigate the foreign world of themes, partials, and front matter. Another friend and colleague Justin Gagne helped me tremendously when I did a redesign in 2013 and again this time when I got stuck on matters of design and execution. Lastly, my wife Kristin helped with accountability by keeping the pressure on, as well as providing feedback on all other matters from content to design (and copious amounts of patience and moral support).

Closing Advice

The biggest hurdle you will face is knowing when the site is done and it's time to ship. There will always be something else to fix, something else to work on. However I want to remind you that this is the Web, it's not print. It's OK to publish works-in-progress, you will have the time to fix them.

If you're still feeling self-conscious about it, maybe consider letting your audience know. That's what a colleague of mine Aaron Gustafson did, he put a note at the top of all his pages saying “This site is undergoing an open redesign, so if it looks strange, that’s why.” Whatever your strategy is, push yourself to publish before you're comfortable. You'll feel great when you do it and more importantly, you'll know exactly what needs to happen next.

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