On Mentorships

A long time ago, I came across Ellen Chisa’s post on mentorship. The gist is that instead of focusing on finding mentors to show you the path, focus on what you are interested in learning, and see who can help you learn more about it.

Diana Kimball has also written about the dynamics of mentorships. They work when mentors and mentees are able to express their mutual vulnerability. She also talks about the unnaturalness that comes with defining a mentorship relationship before it exists.

So here are my takeaways on how I currently think about mentorships:

  1. Forget the idealized version of a life mentor that is your coach. No one person should have all that power over you. No one wants that responsibility.
  2. The range of questions and challenges you will face are better served by a set of individuals rather than one person. Build relationships where you can talk about the different challenges you will face.
  3. Experience and perspectives are relative. Mentors don’t need to reach a universal threshold of success to be mentors. As long as the person on the other side is providing a new perspective, that should be enough to help you unblock your immediate challenge.
  4. If experience is relative, this means that you have the potential to help someone else with less experience. To figure out how you can help others, look back to the work you’ve been doing in the past year. Think of the challenges or difficult decisions that you’ve come across. Whether you’ve solved them or not, sharing your thought process is enough of a starting point to offer support.

Internal and External Motivations

I want to think about information flow this morning and how it affects our motivations.

We have plenty of feeds that push information to us, but not enough sandboxes to reflect. Notifications, emails, social feeds are always producing, and they serve as variable rates of reward systems.

We also have a limited amount of time to consume this infinite amount of information, so how do we select what is interesting to us? We rely on publications and friendly recommendations to point them out to us.

The downside of relying on the push of our feeds for information is that it overemphasizes a variable rate of rewards. They represent external sources of motivation.

The information we find in our feeds have evolved to be engaging for the short term. They only have an awareness of immediate views and comments, but know nothing of longevity and impact.

Is there a way to identify the information that is meaningful to us? If we have the concept of nutritional value for food we consume, is there a similar sift for the media, entertainment, and information we consume?

Which sources of information make you feel better in the long term after you consume it? Which sources emphasize variable rate rewards the most? How do we carve out space for internal motivation when the world has a constant stream of information from everyone else?

The irony is that in the process of exploring and capturing my own thoughts, I’m also adding to the feeds and pool of information. Creating content in itself has a separate set of rewards.

What is a healthy ratio of push/pull of information? The difference between, I am interested in X, so I’ll seek it out, versus scrolling through feeds, coming across a rabbit hole, then following the trail for too long.

The Difference Between Envy and Inspiration

I had a conversation today about the difference between moments of envy versus moments of inspiration. Both emotional states are triggered by an outcome that we want for ourselves. The difference is in how we perceive the path required to achieving that outcome.


When we see someone else achieve something great, but we don’t see how they arrived at that place, then we are in a state of envy. We assume our circumstances are different from theirs. Our approach, skill set, and personality is different from theirs. I see what I want, but I don’t see how I’d get there with what I have now. Envy is yearning without resolution.

Seeing another person’s accomplishments without a clear path to attain it for ourselves shifts us into a zero-sum mindset. I don’t know how I could create the same outcome for myself, so I want what is yours.


When we see someone else achieve something great, and we see the path forward, we are inspired to act. I see what they did, I see how they did it. My circumstances are similar to theirs. I still have work to do, but I can see how I’ll get there. Inspiration is a preview of where I could be.

Seeing a path forward creates a sense of possibility, which places you in a mindset of plenty. I see something I want, I can figure out a way to get my own version of what you have.

I hope my work inspires action rather than envy.

What is Design Pairing?

I learned about pairing when I started working at Pivotal. It’s a way for two people to collaborate on a single problem at the same time.

The main benefits of pairing:

  • Short feedback loops: By working with someone through a problem, you have someone else’s feedback helping you course correct as you are solving the problem, rather than after you have solved it.
  • Focus: Having someone else there helps you keep your direction and scope in check. Are you solving for the most important thing now? Or can those issues be solved separately at a later time?
  • Knowledge Transfer: Working closely with someone else creates a shared understanding of the problem space and how you arrive at a solution. Along the way, you also get to learn about other ways to think about the problem, and other ways of crafting a solution.

How does it work?

The key to pairing is externalizing your thinking and receiving feedback while working through a problem together.

If my pair and I are designing a screen inside Sketch, we would be sitting next to each other, using one computer. To make pairing easier, we attach two sets of keyboards, mice, and mirrored displays to that one computer.

Only one person is controlling the computer at any one time, while the other person is either listening or providing feedback on what he/she sees on the screen.

Even though only one person is actively using the keyboard and mouse, the other person can start to drive the computer at any moment. The two sets of keyboards, mice, and displays makes switching easy enough to happen dozens of times during a pairing session.

While working through a problem, you might have discussions on the scope of the problem you’re solving, approaches to solutions, and ways to execute the solution.

Common Questions About Pairing

  • Isn’t it slower to have two people working on a single track of work than two people working through two separate tasks?
    • It depends on the task. If it’s a rote task, and all you need to do is to execute, then it’ll be faster to have each person churn out their own widget. However, if you’re working on problems where there are multiple possibilities, tradeoffs, and solutions, the outcome will be better with another person.
  • What if I work faster by myself, and I need space and time to think?
    • This is probably true for a lot of us, since we have only worked at the two ends of the spectrum, by ourselves or in groups. There aren’t a lot of places where we articulate thoughts in progress. We work alone, and present in public. Pairing flexes a different set of muscles, where you externalize your thinking and intentions. It brings the dynamics of day-to-day conversations to problem solving. There aren’t many places to practice this, and the skills you pick up while pairing also improves how you work by yourself.

What I’ve Learned Through Pairing

  • You practice communicating your intentions more clearly. Ideas crystalize faster because they need to be understood by someone else.
  • You come across unknown unknowns and learn a lot of things that you didn’t think to ask. This happens when you see another person think through a problem differently than how you would’ve tackled it. Outside of pairing, our thinking is mostly invisible to ourselves and others. When we pair, we see the contrast of all the things we take for granted.
  • You learn to disagree and find paths forward. It’s useful to separate whether you disagree on the problem, goal, priority, or solution.

How to Try Pairing

  • Find someone else that is interested
  • Work on a problem together.
  • Spend 1 hr to 1.5 hrs pairing
  • After the session, spend 10 minutes talking about how it went. What you would do differently next time.

If you would like to try pairing, send me a note. I’m interested in meeting new designers and introducing pairing to more people.

Design Tools

A few years ago when the design team at Facebook launched Paper, there was also a lot excitement around the tools they built to explore new interaction patterns for the app. This is when I first heard about Origami and around the same time, Framer.

The idea that certain teams build their own tools stuck with me. It makes sense and seems to be the type of productivity advantage that you’d want your teams to have.

I’m interested in tooling, because it is such a direct route to be a force multiplier for individual or team outcomes. You can have an impact on your team by improving the process; experimenting and sharing how something can be done differently and better. Tools are another venue for having an impact on teams.

I’ve heard how designers at Apple have a similar tool to Principle. There are design systems and style guides that are internal (AirBnb) or open sourced (Bootstrap, Tachyons). There are Sketch plugins that help designers share their document styles, prototype, and design with content and data.

We usually think of tools as a category that only includes hammers and other hardware. Outside of the interaction design domain, I’ve heard of spoken and written language be described as a tool. It’s used as a way to capture and spread ideas. A tool, technology, or concept, fundamentally changes how you work and what you create.

Without innovating on our toolset, the possibility of our output is limited by the tool’s range of possibilities.