Pillaging My Ego to Become a Better Pirate In 100 Days

Batten Down the Hatches!
There’s no point in denying the challenge and frustration of learning a new skill. Improving can be even harder. Mastery takes time and effort.
Remember the first time you drove a car? The initial few turns were either too sharp or too wide. You either scraped the side of the vehicle or finished five feet from the curb when parallel parking (okay, some skills may never get mastered…).
But you got better. Or are getting better. The point is, difficult skills become less difficult in the DOING. As they say, “you can’t eat a recipe.”
As simple as this concept appears, I still take it for granted. I relearned this lesson recently after completing a 100-day design challenge (via Daily UI). This reinforced my core beliefs and introduced new insights about learning skills in life and approaching the creative process.
Quick background on how Daily UI works and how I conceptualized the challenge.
It’s simple enough: they send you a daily design prompt. You interpret it. Put together a design. You share it on social media with the hashtag #dailyui. They give surprise rewards to lucky participants. Rinse & repeat for 100 weekdays in a row.
The main objective is to get motivated and inspired, all the while honing skills.
It should be noted that my personal goals for the challenge were:
- find a way to develop design thinking as well as my technical skills.
- work my creative muscles.
- compare my creative abilities against other hardworking UI (and UX) designers.
Daily UI is a slight misnomer since I wasn’t designing for users or testing for usability. I was designing to a prompt. I knew that my technical chops and visual patterning would develop over time so my primary objective became: design for creativity’s sake rather than for users’ sake.
Note: I hope to follow this post with an article about more specific topics from my 100-day challenge. These might include: did I get lazy, how I kept going, fluctuating skill levels, the good and bad of it all, etc.
For now here’s a rundown of key highlights I learned. Let me introduce you now to my Pirate Principles.
RRRRRRRR, matey!
This is my journey to become a better pirate. And these are my RRRRRRRRR’s of creativity, improvement, and progress. Get the pirate theme now?
During the 100 days I built skills, addressed blockages, worked within constraints, and was as creative as possible. I thought deeply about how to approach creativity. I’ll share some of my design examples to illustrate each R of the Pirate Principles.
I hope this helps you on your endeavors, design or otherwise!
1. Repetition
This one is simple and crucial. We’re all familiar with the old saying, “Practice makes perfect.” Working on daily designs was no different than riding a bike or playing an instrument. I kept at it and saw improvements in quality and efficiency. This was most evident in simple tasks like finding the right text shadow or spacing out elements.
As I performed tasks my steep learning curve gradually plateaued. I also found ways to automate or speed up repetitive tasks through Sketch plugins, symbols, default settings, etc.

The harder I worked, the smarter I worked.
Here’s my two cents on positive “reinforcements” (which can be an “R” under “Repetition”). Every time I completed a design, I felt pride and satisfaction from the creative output. I was happy from the experience of creating something. Whether it was good or bad was secondary to the positive feeling of accomplishment. This positive reinforcement (and chemical release) fueled me, excited me, and kept me going.
2. Routine

Like clockwork, each daily prompt arrived in my inbox at midnight, every night, for 100 straight weeknights. I felt like one of Pavlov’s dogs around 11:59pm. I was anxious…err, curious to see what the day would bring. On some nights, I’d even read the email, hit the hay, and dream of potential designs. For example, on Day 19 the task was to design a leaderboard and I came up with a beauty: a leaderboard that tracks how often people appear in my dreams!
For the most part my design process was consistent. Each day, I’d give at least two hours to work on daily UI. The routine was:
- meditate for 10–20 minutes (more on this in #5 below)
- search for #dailyui on Twitter and Dribbble to get inspired and see the types of submissions for that day’s prompt
- conceptualize / ideate the design, including theme, layout, and color palette
- hand sketch (optional)
- list out the standard design elements from a usability standpoint (for example, if the prompt was “landing page,” I knew I’d need to include a header, sub-header, description, call-to-action button, and maybe a main image)
- design!
I adopted this design schedule early on and it was helpful to ensure I stayed on task and ended with an optimal output.
3. Ritual
This one is important and an extension of Routine. I’m a big fan of Joseph Campbell and his teachings on trials, rituals, and all things myth. Rituals attach wisdom and potential to practice. Each day’s design process could be a spiritually insightful or solemn experience. The meditations helped of course. Pairing this mindfulness with Realities (see #6 below), the practice of design each day felt more elevated than just a boring exercise.
I did my best to release myself from what I know and what I think I know. I did my best to release myself from my realities.

Much is written about rituals that calm nerves, decrease anxiety, and help you perform at your best. They assist us mentally, emotionally, and spiritually for what’s ahead. Malcolm Gladwell’s “Outliers” is a great book on habit and ritual.

Several videos helped me appreciate the importance of rituals from a religious or cultural perspective. This one talks about proactively doing rituals every morning.
4. Restrictions

The daily designs gave me the framework I craved. It was like the difference between sculpting a castle inside a sandbox vs. an entire beach. Each has different size constraints, obstructions, sand quality, viscosity, moisture, weather, tools, ground depth, distracting flora and fauna, etc. You get the idea.
I loved the specific themes and design patterns to play with. These were the parameters and rules which I could push or break if I wanted.
But having restrictions does not imply abiding by rigid rules. Although, some might argue that having strict rules forced filmmakers in the 1920s to 1950s to be extra creative to get around the Hays Code (censorship rules imposed on Hollywood films in the 1920s — 1950s). Without them, I’m not sure that we would have gotten the genius of screwball comedies or the covert and subversive storytelling devices. This isn’t an endorsement of censorship so much as it is a hindsight observation of how artists get creative when they’re restricted.

Creativity often arises out of restrictions and restraint. The daily prompt confined me to a specific requirement and I had the flexibility to be as innovative (or ridiculous) as I wanted within those boundaries. The restrictions represented the lines I needed. At my discretion, I could color inside or outside of them.
There are plenty of examples where restrictions breed creative output: freestyle rappers riding the beat, improv actors taking suggestions from the crowd for scene topics, competitive scrabble players who must race against the clock to find the perfect word (yes, these tournaments exist!).
Completely unrestrained and boundless creative expression can sometimes be overwhelming. When we are paralyzed by unlimited options, it’s hard to take that first step.
We all secretly love guidance and structure so Restrictions, coupled with Ritual can keep you going.
5. Risk
The stakes weren’t high since I had free reign to design anything I wanted, as long as it fit the prompt. I could work at my leisure since I had 24 hours to create and post. Provided I kept within the boundaries of accepted UI and visual design principles.
I chose to take risks in conceptual and thematic designs.
Some risks were departures from standard artistic patterns and usability standards in favor of a design that reflected an idea or theme. I tend to improve my skills when taking calculated chances.
Whether you think so or not, calculated risks almost always lead to a reward. The real prize will be intangible and/or gained in hindsight, regardless of whether you “win” or “lose.”
I pushed myself as much as I could to avoid the easy route during these 100 days. I tried to bite off more than I could chew or move outside my comfort zone.

We all have ideas that block us, such as insecurities, anxieties, self-consciousness. I didn’t set out to reject these obstacles but rather to accept that these elements are as much a part of the process as creative epiphanies and breakthroughs. I meditated on them all.

We all end up pleasantly surprised how high we can climb with a little grit and perseverance to take risks.
6. Realities

I’ve meditated for a few years and with every daily design I challenged myself to dig deep for inspiration. With my helpful routines (see #2 above), I started each work session with a meditation to see what would surface. These raw ideas — once cultivated and expanded upon — could be applied to the daily design challenge. Is today’s project a To-Do List app? I’ll try a Kill Bill / Lady Snowblood theme since I watched it the day before. Yesterday’s challenge a Pricing List? Oh that’s right, I had a Walking Dead marathon, so I’ll make a survival weapons catalogue.
Sometimes I had to challenge my cognitive dissonance and my pre-wired realities. To push through I had to acknowledge my biases and step outside of myself at times. There is tremendous value in questioning our own realities, cognitive dissonance, and belief systems. Call it empathy. Call it compassion. Just make sure we identify it and call it out.


I’m not saying my designs were profound life-changing statements on existence and technology. I just wanted to make sure I was trying to push the boundaries of my comfort zones and realities.
7. Rob?
Imitation is the sincerest form of flattery.
As Kirby Ferguson says in his fantastic TED Talk on creativity, nothing is original and everything is a remix. With that in mind, there were days when I didn’t push myself to be as creative as I could be (usually from laziness). That was OK. In those cases, I simply looked at other designs and unabashedly mimicked certain elements; doing the bare minimum to meet the challenge at hand.

At times I resorted to remixing existing designs. What about the lyrics from Pirates of the Caribbean song?
“Yo ho, yo ho, a pirate’s life for me. We pillage, we plunder, we rifle, and loot”
Now I’m not saying we should all plagiarize because that’s definitely not cool. Just like a good pirate, we can “plunder” for ideas, “rifle” for inspiration, and “loot” for solutions. Then we make it our own. After all, everything is a remix of a remix of a remix of a remix of a remix. One person’s stealing is another person’s inventiveness. You have the right to Tarantino the heck out of your work. Just don’t make it an obvious, blatant, outright, malicious copy. Embrace the remix.

Couldn’t I have called this section ‘Remix’ instead of ‘Rob?’ Sure, I guess. But where’s the risk in that?
8. Relationships
I technically wasn’t designing for the purposes of actual use and usability. So I set my own parameters and goals with each prompt. I wanted to add an extra layer of trickiness for myself, whether it to make a design with something as benign as a gradient or something as ambitious as a set of concept trading cards.
Designing for the purposes of creativity and my own parameters gave me free reign to be as wildly creative as possible.
Taking this approach, I confidently owned my ideas and shared them publicly — welcoming feedback and criticism wholeheartedly.
I didn’t want to design inside a vacuum. Otherwise, they’d all suck (last joke, I promise 😊).


Suma-rrrrrr-y (okay, that’s really the last one, I promise)
Do things.
Do them regularly.
Do them often.
Do them with meaning.
Do them with others and share them freely.
Do them recklessly.
Do them replicatively (someday that will be a word).
This isn’t an exhaustive list of course. There are other R’s like research, resilience, reflection, rejection (giving and receiving are both valuable), reason (WHY you’re putting in the work), release (share your creations with the world already!), reloaded, revolutions… but these were the key components to develop my skills.
Thanks for following along and I hope you got some value from my experience. Feedback, thoughts, comments, and questions are very welcome.
Oh, a few more things, before you go…
I want to send a huge thanks to a friend of mine, Brian Stefan, for helping me organize my thoughts for this post. If anyone is interested in a free, friendly, cheerleading copy-editor, contact him on Medium!
And if you want to see all my 100 designs and the occasional food macro du jour (mmm, the textures), peep my Twitter or Instagram.
Lastly, if you like this post, please Like — err, applaud — and Share to show your support!
Originally published at https://www.linkedin.com on August 25, 2017.