Heron catching a fish, This file is licensed under the Creative Commons Attribution-Share Alike 2.0 Generic license.
Heron catching a fish, This file is licensed under the Creative Commons Attribution-Share Alike 2.0 Generic license.
Attribution: Kenneth Allen

It has now been 4 months and 14 days since my job at IBM dissolved, and on August 18th, I accepted a contract role to become a Principal UX Designer for PayPal, started yesterday (September 14). Big sigh of relief for me.

On Twitter, I noticed a designer (https://twitter.com/rodrigotellom) post about a list of companies that had rejected him for the past 6 months, and it made me reflect on my experience. I’d like to share some stats, insights, and talk about some of the tactics that kept me going for the last few months.

The Approach:

The way I approached every…


Vol. 1: Fear & Pivoting in Silicon Valley

Drawing by Ralph Steadman of Dr. Gonzo and Hunter Thompson driving
Drawing by Ralph Steadman of Dr. Gonzo and Hunter Thompson driving
Illustration of Dr. Gonzo and Hunter Thompson, ©️Ralph Steadman

My manager and I had just sped out of the San Jose airport, when I looked at him with a hint of fear in my eyes. The entire car was shaking, and I couldn’t tell if it was his driving skills or the fact that Hertz had given us the modern day equivalent of a Geo Metro circa 1996.

As we hit the top speed of 63.5, semi trucks blew past us, each truck shaking the car even more.

“So if we both die today on this freeway, all of Watson Design…


When I was 15, my father took me muzzleloader hunting. For those who don’t know, muzzleloaders are rifles that use black powder to fire, much like an old timey musket. We went with my uncle and one of my father’s employees, Walter, who is a Navajo native. The hunting days were repetitive…scout out animals, wait, and on occasion, fire. Muzzleloaders sound like explosions going off…much louder than a traditional firearm. I think it was supposed to be a bonding moment for myself and the men. …


A reflection of a friend & mentor

Abdullah Shaikh (1967–2020), a good human.

When I first met Abdullah Shaikh, I was at first put off. He was boisterous, loud, and would interrupt you at a moments notice. But there was something magnetic about him…his knowledge, his humor, the ability to connect himself to the people he referred to as “super heroes”.

On May 16th, he left this world during his second fight with liver cancer, and I miss him greatly.

This is a partial reflection of Abdullah and myself, a most unusual friendship…halfway through writing this, I realized that there’s so much I could write about…


NASA Picture of the Day, December 26, 2016

I’m terrible at taking compliments.

I found myself thinking about that subject today because a colleague gave me some wonderful compliments earlier. They included the fact that I listen, I empathize, and I’m a weirdo, just like her. (I won’t go into details)

She recalled a moment last year, when my manager compared me to a celestial body during a group feedback session.

What my manager was referring to back then was the fact that I have a gravity about me, which draws others in, and they get caught up around it, and that it’s fun. …


Courtesy Dilbert

Last October, I visited my alma mater, the School of Visual Arts Masters in Branding program, which teaches graduate students about the intersections of business & design. Whenever I visit, there’s always students that have questions about what I do, both as an IBM’er and a Design Strategist. Most recently, I was asked by a student “How does design strategy work within a large enterprise like IBM”?

In order to answer that question, you need to consider the context. IBM isn’t just one organization or company, it’s a company within a company within a company, ad nauseum.


(or, what’s it like when you join a new team)

Image from The Next Web

Cat’s out of the bag. I’ve joined a new team at IBM. After spending nearly the last two years working on various cognitive developer experiences within Watson Core, I needed a change, which has taken me to the world of Watson Health, where I will be focusing on Empowering Heroes, by Transforming Health through the usage of cognitive technologies in the healthcare field (where necessary).

Naturally, joining a new team has it’s own series of challenges, so I will detail a few of these challenges I’ve come across in the last three weeks, and how I’ve overcome them.

  • Handling the…


What is a portfolio? Is it an opportunity to show finished work? A way to convey process? The life and death of a project? Is it a Dribbble account?

Over the course of my career, I have redesigned my portfolio to reflect new skills or new work, and I have reviewed hundreds of portfolios for IBM’s design initiatives, provided advice to growing designers about their books for the AIGA, helped IBM Talent iterate on their design hiring program, and I base all of this on the training & mentorship of two people: Debbie Millman (Design Matters) and Michael Beirut (Pentagram)…


Lately, I’ve been reflecting on my life and career…primarily because I’m building a case for my next journey at IBM, to be a Design Principal.

I started to think about how Creativity comes and goes…for me, it’s something I actively decided to stop pursuing, because it results in half finished projects, stress over making, and lack of fun.

Instead, I think that Creativity emerges as a result of other stimuli.

Lately, my life has been chaos. Work has increased tenfold, and I’m surrounded by a group of individuals who aren’t too thrilled with the project’s politics, which doesn’t help my…


Because of Black Friday, I, like many people now have a cognitive enabled assistant sitting in our homes. It’s name is Alexa.

I say Cognitive Enabled Assistant because Alexa isn’t truly AI yet. Here’s why:

  1. Request based: All inputs are treated as requests…if you ask Alexa something that isn’t a direct request, it responds with “I didn’t understand that question.”, minus jokes of course, and custom programs from Skills. This is exceptionally hilarious when my girlfriend asks Alexa about her ties to the NSA, or if I ask her about her opinions on Siri.
  2. Pronunciation issues: A favorite christmas album…

Randy Gregory II

Principal UX Designer / Design Strategist in Austin, Texas. Forever weird, always curious.

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