Want To Achieve Design Mastery?

Here’s 3 Killer Principles I’ve Learned From 15,000hrs On The Job.

Chadd Weston
Apr 18 · 16 min read
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So far, I’ve logged about 15,000 freelance design hours and racked up more than 200 (mostly) happy clients across 25 countries…

And somehow through all of it managed to survive and build what I think amounts to a pretty decent freelance design career.. so far.

As of this writing, I’m 32 years old. I’ve never been employed. I started freelancing while in University eleven years ago and have had the great fortune (and oftentimes misfortune — that for another day) of never looking back. For some reason I’ve always been drawn to the idea of partnering with people instead of working for people. Freelancing allows me that choice. I’m drawn to the wild ambiguity and freedom that freelancing (can) offer.

There are three common threads across all my projects over the years that I think have really served me well and I want to share them with you. I call them the 3 principles of design mastery. If you’re a designer of digital things (web, UX, presentations, etc.) then I think you may find these relevant.

And you should know I don’t throw around the word “mastery” very lightly. But I believe these 3 principals merit that level of recognition. They are very, very hard to do well. I have and will spend my career trying to get better at making use of these — I’m convinced they are the key to powerful storytelling through design.

First, some background context:

My very first contract was for $100 bucks from a church pastor my uncle referred to me in South Florida. It was a little postcard for an upcoming event he was promoting. It took me a couple hours but I managed to dust off an old Seagate hard drive and dig up the project files. This is what the pastor got for $100 bucks!

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At the time I thought it looked great. (Not so much anymore)… and 11 years later I still have the thank-you note from the pastor:

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Researchers have settled on what they believe is the magic number for true expertise: ten thousand hours. “The emerging picture from such studies is that ten thousand hours of practise is required to achieve the level of mastery associated with being a world-class expert, in anything. — writes the neurologist Daniel Levitin” (Outliers pg. 40)

11 years, 200 clients and probably about 15,000 paid design hours sit between that first little design gig and my latest contract. Does this make me an expert? Who knows and honestly who cares. One thing I know for sure is that I’ve learned a LOT. I’ve been on a constant learning curve since the start.

Complacency is the enemy — but it’s a tempting posture to occupy.

Especially when you find yourself several thousand hours into your craft and things start to go smoothy. All those hours are starting to pay off. People start to see you as a bit of an expert.. you can charge more… demand more.. set the tone.. etc. And don’t misunderstand me — all of those things are wonderful. They are the fruits of mastering a labour so enjoy them, but…

The world moves fast.

Design trends change.

Technology is constantly shifting shape and form.

The mechanisms by which people consume information and interact with digital experiences is a fluid, ever-evolving continuum (Think: the evolution of the smartphone from the PC, and the upcoming trends around immersive experience — VR/AR etc.). The mechanics of designing world-class experiences will always be on the move and keeping pace with these shifts I think is important.

Today though, I want to outline for you 3 design principles that I believe transcend these shifts.

They are:

  1. Intuition
  2. Immediacy
  3. Immersion

The reason I believe these principals in particular have staying power is because they have more do to with the way a human experiences design than the design mechanics (ie. whitespace, layouts, typography, color etc.). Critically, the way a human experiences design should inform the design mechanics. It’s one thing to make something look nice using trendy fonts and appealing gradients… its a whole other ballgame to accomplish the seamless and effective transmission of a complex narrative from your design to a human being.

It starts with the human, always.

This is why usability testing in UX design is so important. In UX, starting with the user is a little more doable because you can watch mouse movement history in apps like Hotjar (highly recommend them btw) and replay the human experiencing the design. With a pitch deck, or any kind of powerpoint presentation.. its a little more tricky. You can’t exactly replay where someone looks when they are flipping through a printed deck.. so leaning on conventional wisdom of how humans experience information has been very helpful.

When it comes to making someone’s vision palpable, or any kind of effective communication for that matter, I believe the 3 design principles of intuition, immediacy, and immersion are the foundations of a masterful digital experience.

Design Mastery Principle #1:

Intuition

Intuition is all about designing for what a user expects to experience, given the context of that experience. Miklos Philips captures this sentiment perfectly in his exploration of mental models in product design:

“People will transfer expectations they have built around one familiar product to another that appears similar.”

In the context of a product, people typically expect their profile photo and search to be in the top right, logo on the top left, menu in the middle, help/support chat bottom right and so on.

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In the context of a presentation, people expect to see a slide cover, an agenda in the first 2–3 slides, speakers bios early, and then the main content, followed by a Q&A slide and perhaps an appendix, depending on the complexity/density of the material. At the slide level, it would be unnatural to have slide numbers in the middle section of the screen, or prominent titles at the bottom, with supplementary information above.

Going up against conventional experiences in a given design context will confuse people and cause them to spend their precious mental faculties on the task of figuring out “what’s off about this” vs. freely absorbing the material without a worry in the world.

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For me, I really see the rule of intuition as clearing the way of any possible debris within a design context that could distract people from focusing on the story coming from that context (ie. presentation). At baseline, you want to make sure your design is sensible in the way it’s structured so people know their way around the instant they show up. The last thing you want is people feeling like they are in unfamiliar territory. They need to check off the “I know this place, I’ve been here before’” box when experiencing your design.

“Good design, when it’s done well, becomes invisible. It’s only when it’s done poorly that we notice it.”

— Jared Spool (famous UX designer)

Design Mastery Principle #2:

Immediacy

While intuition pertains to making information consumption as natural and fluid as possible, the rule of immediacy pertains to making the most important information instantly accessible on the design canvas. In product design, immediacy can also be affected by page load times, and the “quickness” of the interface.

Here’s the wikipedia definition of immediacy, I think its a decent one:

Immediacy is a philosophical concept related to time and temporal perspectives, both visual, and cognitive. Considerations of immediacy reflect on how we experience the world and what reality is. It implies a direct experience of an event or object bereft of any intervening medium.

In my view, an “intervening medium” in the design context could be serving up less important information before serving up the most important information. While intuition ensures people’s attention spans are “all clear” — immediacy is about making the most of that attention span by serving up the most potent, “get to the point” messaging as fast as possible. It’s all about information architecture and prioritizing what parts of the message to be picked up first, followed by supplementary statements and artifacts which layer on and reinforce the main point. (this can and often should be illustrative imagery, info graphics, etc — not just text).

Intuition helps people stay focused by not getting confused, immediacy respects the attention span of the viewer and gives them what they’re after right away. (think: “get to the point will ya? geeeze!!”)

On a practical level, immediate design can be manifested by stuff like font prominence (think: size, color & contrast, transparency, spacing) and of course, the text information delivered by that font in order of most important to least important.

Here’s an example:

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Note only the typography in the slide above. Notice where I am using bold, extra vertical line-height, and larger font sizing to make the most important parts of this slide immediately discoverable. There are 91 words on this slide. I only want you to initially see 9 before working your way through the rest. You don’t have to look very hard to to pick up the main title (“Sustaining Wealth Across Generations”) and the statement on the black bar ending with “as low as 30%”.

The placement of the largest text on the right side of the slide (the title) is on purpose. Look at the slide again quickly, where does your eye want to go after reading the title? I’ll bet its not below the title! Because its the largest text, your eye is drawn to the title first.. but notice the pull you feel to the left side.. this is because there is unfinished business on the left side of the slide (which is where I’ve placed the second most important piece of information “Research suggests that the odds..”).

In left-to-right reading countries, its a bit weird to skip over the left side text, especially at the top. If you’re like me, you feel obligated to go back and work through that stuff first before returning to the lighter text and bullet points under the title on the right.

That’s immediate design at work.

Design Mastery Principle #3:

Immersion

This is my personal favourite. Immersion is the reason plain bullet points in Times New Roman on default MS Powerpoint templates are the surefire way to bore your audience to death. In fact, “death by powerpoint” is a thing. You can read more about it and its origins involving NASA here. One excerpt from the article I think is amusing:

It is now estimated that more than thirty million PowerPoint presentations are made every day. Yet, PowerPoint is blamed by academics for killing critical thought. Amazon’s CEO Jeff Bezos has banned it from meetings. Typing text on a screen and reading it out loud does not count as teaching. An audience reading text off the screen does not count as learning.

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From a visual perspective, immersion is what makes the difference between a death by powerpoint presentation that people want run (or die) from and a visual masterpiece that people don’t want to look away from. I don’t think I’ll ever be able to convince Jeff Bazos to re-introduce presentations into his meetings, but I do think presentations have their place in storytelling — in fact, I’ve bet my career on it.

One thing Jeff and I agree on… it sure as hell can’t look like this:

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You know what’s worse than the sound of screeching nails down a chalkboard? The slide above. You know what’s worse than a migraine? The slide above. Oh and guess what worse than COVID? THE SLIDE ABOVE. (alright too far.. I take that last one back). I trust you get my point.

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Immersion is all about inviting the viewer to get lost in the narrative by way of design techniques (like white space, dark mode, focus pull) where they almost fall into a state of trance with your story because the visual design is so compelling. It’s taking them for a ride. The viewer is at ease with what they are seeing, things are clear and making sense.. they aren’t engaging active mental faculties to filter information overload (think crammed bullets on a single slide like above), so instead they are free to lose themselves in the flow of the narrative and connect on a deeper level with the story that’s coming their way. An immersive experience is captivating and instantaneously preferential to the lesser alternatives. I think this is why “dark mode” interfaces have become so popular in recent years. It is the digital version of a theatre experience. Why do we watch movies with the lights off? It all about immersive experience.

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Immersive Design Example 1:

Example of immersive design in a recent deck I did for a VC firm leveraging “dark mode” with vibrant colours where the most important information is housed (follower count and exposure value). Notice on the slide they handed me, its difficult to pick apart what information matters most.. and it also looks like crap. For the remaster, I was trying to accomplish much more than just highlighting follower count and exposure value — I wanted the investors to feel the energy and excitement around the influencer market and the explosive potential this channel wields.

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Immersive Design Example 2:

Another quick example is with the this e-learning design prototype I worked on for a global cosmetics company. They have an ultra-modern look. Precision & cleanliness were important to them. The first image is one of the course pages:

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And when you click on the menu button (top right) you are presented with an all black overlay:

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The menu is the only instance across the entire module that has a dark backdrop. The course screens are all clean white. I’m doing this so when you are in the menu system, you are completely free to focus on navigating to where you want to go next, and not thinking about anything else.

Immersive Design Example 3:

Alright last one and then onto final thoughts. So this is a focus pull technique I use to layer on additional info in the same slide. So the slide would start out like this:

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…which already has a lot of information. But there’s a few extra pieces that I want to add before leaving to the next slide… what to do? Well, I could cram more text on here which isn’t at all ideal.. or I could use a popup with some magic sauce.. ready for it? A lens blur effect:

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And boom! Notice the immersive qualities of what I’m up to here. By using a popup box and blurring out the current slide, I’m able to layer on additional narrative without losing context that the slide has already established. This popup spells out the paradigm shift underway (robo advisors) as a result of the market forces listed on the slide above.

Focus pull technique: You can’t do a lens blur in Powerpoint, you need to finish the original slide, export the slide as an image and add the lens blur in Photoshop. Come back to Powerpoint and use the blurred slide image as a background image on the next slide after the original slide. You can then draw a “pop-up box” with a large soft shadow to create some depth and add your content, like I have above.

Wow.. we made it — if you’re still reading this you’re an absolute gem. Ok final thoughts:

Design matters: the utility of intuition, immediacy, and immersion in design storytelling.

In recent years, I’ve honed in on a nice little niche in the startup space. 80% of my clients are funded early stage startups or venture capital/private equity groups who need pitch decks, annual reports, or other communication pieces for very high stakes interactions with current or prospective investors.

Their stories are complex, the audience is usually even more complex, and time is always extremely limited. Most of my VC clients for example, see 1,000 deals each year and invest in 8. That’s a 0.08% hit rate. Think about that for a minute. It’s a pretty staggering number. 0.08% of all deals a VC sees in a given year they will invest in.

This tells me a few things about how much credit and attention they give to any one of the 1,000 startup teams they see at the top of their deal pipeline. It’s apparent to me that if you’re a startup, unless you truly have some world-changing momentum and are crashing servers like Zucks in his Harvard days (product-market fit), you need to be pitch perfect.

This is where intuitive, immediate, and immersive design has strong utility.

Investment propositions in raw form are dense and generally incomprehensible (without a good amount of time invested). It takes me a great deal of effort to get my head around the gist of a founding team’s story in its entirety. It’s an even greater deal of effort to capture and translate that expressive passion into something visually stunning and narratively palpable that will delight VCs. So I can only imagine how many deals don’t happen because founders aren’t able to get to pitch perfect form and end up blowing something big… even if its a subtle technicality or misconception.

“Simplicity is the ultimate form of sophistication.”

— Leonardo da Vinci

This is a philosophy I subscribe to. I believe great design has an uncommon ability to move an expression from a maze of ideas on a whiteboard into the form of a captivating, well-understood story. I have come to understand more clearly now than ever that powering this transformation — from the complex & inarticulate to the simple & compelling … is my gift. And design is the engine of that transformation. The story doesn’t change. The characters don’t change. But how that story is comprehended in a 10 minute pitch meeting could be the difference between a million dollar raise and knocking on more doors. This is why intuition, immediacy, and immersion are so important to me.

I am in the business of making palpable the vision, energy, and conviction of a founding tech team to the most important early stakeholders they can communicate that vision, energy, and conviction to.

To date, $20 million have been raised in AI, healthtech, real estate, and other private equity ventures with my pitch decks. Now don’t get me wrong, the stories behind those pitch decks were amazing, these teams were all investment-ready.. obviously. But I do like to think the decks at least played a small part in helping those stories come to life.

Pitch deck design is no small task. Simplifying and making palpable a maze of ideas from brilliant tech geniuses keeps me at my creative limits year round. It is the design mastery principles of intuition, immediacy, immersion that keep me afloat. They guide me through these complex mental gymnastics and help me work out designs that really pack a storytelling punch.

Here’s an example to close:

Earlier this year I was approached by a 16 year old brilliant machine learning entrepreneur wiz kid working on a virtual reality project that seeks to address many human and environmental challenges around hunger, bullying, sustainability, mental health, and connectedness. This entrepreneur was seeking mentorship and wanted to tell his story properly in meetings with potential mentors (including Elon Musk). Some of the highlight features of his tech included VR Life: Last Dance With Lost Loved Ones — the ability to upload old videos of your lost dog or loved one so Jose’s machine learning algorithms could deep learn on your lost best friend’s sentiments, emotions, and gestures and re-create a virtual version that had near exact traits of the real thing…

How the heck was I supposed to capture that in a pitch deck??

Oh and by the way he needed the deck THE NEXT DAY for a meeting with the one of the creators of the PIXAR 3D animation engine… In normal circumstances I would have hung up the phone but there was something about Jose’s dream that captured me. I could hear it in his voice… this kid was going places and he meant business. Looking at the raw files he sent over.. it quickly became evident that he was the real deal. He and his co-founders were developing some serious tech And the fact that he was prepared to invest thousands (to be fair I think he was seed funded) on a guy like me to help him tell his story just so he could ask for.. mentorship? I was enamoured.

So at 1am we agreed to a rush delivery premium and I took the job. I worked through the night and delivered what has turned out to be one of my favourite decks of my career.

Jose Mendes and his VR Dream Inc. team is the reason I love my job. Visions like his are too cool to not help share with the world. I should check up on him and see if he ever closed Elon as a mentor…that is one story that is definitely to be continued…

What a kid.

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