Mastering deliberate practice

Issue 62: We're talking about practice

When was the last time you made time to practice skills important to your work or purpose? The answer is probably very little. The demand for work often results in not making time to develop skills in the midst of multi-tasking and doing.

The word “practice" reminds me of my childhood. My parents enrolled my brother and me in so many activities: music lessons, Tae Kwon Do, oil painting, and sports in school. Though I think they wanted to ensure we didn’t get into trouble outside of school, these lessons developed a rigor of practicing. As a child, I did not enjoy it at all. My mental model of practice was "doing the same thing over and over again." That’s not exactly untrue, but there was more to practice than repetition. Practice became a ritual and a place to grow. It forms habits and habits forges mastery.

My practice philosophy

If you're not familiar with the term deliberate practice, there is a great summary article on James Clear's website. Simply put, it's about putting intention to what you practice:

While regular practice might include mindless repetitions, deliberate practice requires focused attention and is conducted with the specific goal of improving performance.

In essence, deliberate practice is setting an intention and building a routine around the techniques you want to improve. Instead of spending 60 minutes shooting the basketball randomly on the court, you’re focused on key techniques that require development.

Evaluate yourself and develop high-value skills.

A former manager once said to me, "Everyone is bad at something." Even top performers have areas they struggle with. I used to think this meant that I needed to get better at everything I was bad at. It can be a low lever to invest in an area you’re not great at if it’s not high-value. To identify what to focus on, ask yourself:

  1. What are skills I’m exceptional at and continued practice will make me differentiated from everyone else?

  2. In the areas I need to improve, which are important for my role and career that need to be improved?

  3. Can some of my skill gaps be filled by other levers such as tools/processes or people who are exceptional at it?

Don't practice your cords during the concert

"Separation is in preparation." —Russell Wilson, Seattle Seahawks Quarterback

The last few weeks at work have been in key executive meetings. Though this isn’t new to me, it can be scary to present. I spent time with my VP of Product to go over our narrative to ensure I was feeling good about the actual presentation. Practicing helps you anticipate and simulate what you’ll go through. As an individual contributor, I'd practice designing user interfaces or writing lines of code. I didn't want to have to think about how to do something when it was time to work on a project. I wanted it to come naturally and familiar. Walkthroughs are a great practice technique of going over the run of show or plan you're executing on. When it comes to the real thing, you'll be more prepared.

A culture of practice

Practicing is an act, but also a culture that focuses on growth and continuous improvement. Your culture is what you prioritize, and it’s very hard to get it right. Over the years, practicing is now a sacred routine. It’s the empty gym where I am away from the world and can focus on my personal growth.

Even today, my mornings start with deliberate practice; drawing pages full of lines to get warmed. Even though I’m not designing in my day-to-day anymore, it’s still important to practice the cords.

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Your creative credo

Issue 61: Writing and refining what you believe

This weekend, I began reading The Contrarian by Max Chafkin, a biography about the billionaire entrepreneur and investor Peter Thiel. Regardless of how you feel about the infamous PayPal co-founder and made a $500k angel check in Facebook’s early days, Thiel’s conviction and point of view are extremely clear. I’m reading this book to explore alternative perspectives and enjoy biographies. In Silicon Valley, many know about the question Thiel made famous: “What important truth do very few people agree with you on?"

Remaining strong in your beliefs is more important than being a contrarian. If being a contrarian is going the other way of the popular crowd, having a strong belief system is standing on the grounds of what’s important to you despite the crowd.

Coming from a Roman Catholic family, "credo" is a familiar word in my upbringing. This Latin word for "I Believe" was the foundational prompt recited every Sunday with the Apostles'Creed. For lay folks, think of it as the pledge of allegiance for Catholics. This isn't a newsletter issue about building a religion or tech cult. It’s about understanding what you personally believe in as a creative person. What is your creative credo? When you have something written down or manifested, it holds your beliefs more accountable. Stacy La recently spoke at On Deck Design in a fireside chat. We talked a bit about how she defined design principles during her time as a design leader at Clover Health. Creating memorable cards that could be top of mind for people is such a genius idea. Being reminded of Stacy’s brilliant idea inspired me to reflect on writing down my own principles and beliefs.

Your belief system will guide how you navigate your work and career. What you stand for likely determines what companies you choose to work with and who you collaborate with.

Iterating on your credo

Crafting a belief system is no small task and requires a lot of thought. Take time to iterate through the ideas. Writing something down is one step. Believing in something comes down to how you act on it. I asked myself the following questions during this exercise:

  • What is it you deeply believe in?

  • Why is it important to you?

  • What has to be true in order for you the belief to stay true?

  • How do your beliefs show up in your life and work? Are you living up to your credo?

I’ll share a few working examples of credos I’m reflecting on; definitely a work-in-progress (WIP):

  • Every human should be able to should have every opportunity to bring their ideas to life

  • The best way to be productive is to reduce the iteration cycle

  • Capitalism can be the most powerful vehicle for fostering creativity

I don’t believe in being a maximalist in anything, so constraints and refinement are important. Let’s take my capitalism claim on creativity and see how I edited it. Saying “I believe in capitalism” is too broad and I wanted to clarify what I think it can enable.

On the right, I created a list of things that need to be true in order for this credo to be effective. The photo above is one of many iterations of notes I’m refining, and I’m still not done. This belief inspires me to fund people’s creative projects from the liquidity I’ve earned over my career. I feel there is a responsibility to re-invest, especially for those who haven’t had the chance to participate in the capitalist ecosystem.

Your creative credo is how you show up in the world

Writing a creative credo doesn’t mean you have to publish it. I don’t know if I’ll ever publish mine fully, but the constant refinement is helpful. If you’re doing it for anyone, do this for yourself. Question it, refine it, and live it.

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You're not that focused. Learn to ignore.

Issue 60: Exploring ignoring as a creative skill

Focus time. We’ve all put that block on the calendar to get things done. The expectations of deep work often turns into the reality of having 50 browsers open while replying to Slack messages during that time. In both the physical and digital world, distractions are abundant, and we’re not as focused as we may think. What's the root cause? You’re not ignoring enough things.

"Ignore" gets a bad rap. The definition of it is to refuse to take notice of or acknowledge; disregard intentionally. I believe people associate ignore with neglect, which is the failure to care properly. Ignoring is not neglecting. The ability to ignore everything around you to focus on the objective at hand is a critical skill. This is why a horse wears blinders during a race to focus on the track.

Ignoring is a creative and professional skill. Focus cannot exist without ignoring things around you. It’s impossible to focus on multiple things. Solving creative problems requires deep focus and thinking, yet physical and remote workspaces are optimized for the opposite—interruption and notifications.

Ignoring people

This skill isn’t about your personal life. You probably shouldn’t give people the silent treatment and ignore relationships. This is about the work. I live with a cat. I learn from the best when it comes to ignoring people. The ability to ignore people gives you the adequate time to solve problems. In the work place, there will be various needs from people vying for your attention. It’s important to triage the ones that need timely responses, but treating all correspondences with the same urgency will overwhelm you. I learned in a former job that not all requests from people are emergencies and there will be an infinite amount of asks. The key is to find times to be responsive and set boundaries of when you’ll get back to people. Learn to ignore people. There are a lot of them.

Ignoring devices

Digital distractions are dangerous because there is no physical manifestation of how it piles up. Imagine having a dozen people surrounding you and chatting. That’s the equivalent of having Slack open. I don’t ever have app notifications on—both my personal life and work. Instead, I opt for times in the hour that I’ll check and see if something needs my attention. I don’t want a notification system to control my workflow.

“You have distracted me from my creative process.” —Kanye West

Ignoring distractions

I personally have an annual quota of Steve Jobs references since it gets overused in tech. However, there are valid lessons from the quotes and experiences. With it being two days away from the 10-year anniversary of the Apple co-founder’s, let's reflect on what Jony Ive told Vanity Fair on what he learned about focus while working with Steve:

"Steve was the most remarkably focused person I've ever met in my life. The thing with focus is that it's not this thing you aspire to, like: 'Oh, on Monday I'm going to be focused,'" said Ive. "It's every minute: 'Why are we talking about this? This is what we're working on.' You can achieve so much when you truly focus."

Focus isn't an activity. It is being mindful of the end destination derived from the intention you initially set. It's driving to the the destination and ignoring is driving past all the stops that could be interesting. Distractions are fun, and hard to ignore.

Creating a focus space to ignore things

It's important to have a focus space in physical and digital environments. I’ve found two hacks to create a space you can escape from the distractions.

Create a separate user account on your computer

You don't need a separate device to create a digital focus space. Create another account on your computer to keep distractions at bay. You can set up apps you need to focus on and ignore others that could distract you. In my focus space, I don't have messaging/chat apps installed or logged into social media...just authoring and creator tools. These distractions not on your machine make a big difference because the friction of having to install apps or log in might be enough to keep you from being distracted. In the same way you might not realize how many times you pick up your phone, the same goes with context switching between apps.

Carve out a physical focus space, make it sacred

I’m working on an exciting home project of turning our garage into a creative studio space. It’s difficult for me to explore projects in my work office because of the stench of Zoom meetings in there. The aura a space contains is critical for doing your best creative work and focusing. Whether it's a corner of a studio apartment, a separate room, or a favorite coffee shop, make that space sacred to focusing—so sacred you're inclined to dip your fingers in holy water upon entering.

Ignoring as a way of saying "not right now"

Focus cannot exist without ignoring. You have to transport to a space of interruption in both the physical and digital realm. In a world of much distraction, it's important to say, "Not now, I need to focus on my creative work."

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Sketching as a strategy

Issue 59: The value of keeping things sketchy

A few years ago, I was interviewing a designer named Xin Xin. The interaction designer from IDEO was interviewing for the first product designer role I was hiring for at One Medical. Xin, whose name means "Spicy Happy" in Chinese lives by her name and gave a wonderful portfolio presentation and is an excellent storyteller. For design and research, stories are the units of data used for qualitative insights. I interviewed her after the presentation in a 1:1. When I asked about how her design process, Xin opened the notebook in her hand and quickly began drawing with a Sharpie. She showed me the notebook and talked through her process. From there we started sketching together on the concept to discuss her process. As a former interaction designer from IDEO, Xin always had heaps of post-it notes and index cards within reach. Her ability to invoke empathy through storytelling in a human-centered way was one of the reasons she became our first UX Researcher at One Medical. She’s truly one of the greatest storytellers I’ve worked with and it was such a joy to be her manager for more than two years.

Designers have a great superpower of being able to visualize strategy, and it is underused. It's difficult to find balance. In some ways, if you come in with too polished of designs, people will accuse it of being "too tactical" and if you don't come with anything, you haven't explored enough. So where is the balance? It's somewhere in the middle. Regardless of your comfort level with drawing, here are three quick ways to get started in sketching in a strategic way.

1. Sketching the vision

To build a design vision people can get behind, it usually starts with sketches and prototypes to develop a proof of concept (Hey, that's the newsletter's name!). It’s interesting to see the sketches that inspired products we use every day. This is the sketch of Twitter.

There was obviously more work to be done than the notepad sketch, but it started with an idea that became longer just an idea. Creating a sketch gives you a visual artifact to discuss a longer-term vision without any concern on the high fidelity detail or cost of creating that work.

2. Sketching a process or framework

When creating processes and frameworks, words can be tricky as it has different interpretations of what people mean. Quick sketches of proposed frameworks help facilitate conversations without feeling too rigid. If you come with a document, it feels too prescriptive. This was a sketch of a product discovery process my friend Dylan Wilbanks and I sketched over coffee many years ago in Seattle. To this day, I reference it a lot.

3. Sketching thumbnails and storyboards

Thumbnail sketches are quick, abbreviated drawings, usually done very rapidly and with no corrections. The namesake comes from the size of the images—about the size of your thumbnail. These tiny drawings can help you talk through the flow of work, whether it’s software or human interactions. Ridley Scott is my favorite director of all time. There’s a great YouTube video of him talking about his thumbnail sketch process. He describes it as the first time of seeing the film—very similar to software.

You don't have to be good at drawing in order to communicate through sketching. When I taught about wireframes and storyboarding at General Assembly, I'd show slides of the storyboard next to the film still to see if students could guess what movie. I'd show Rian Johnson's storyboard from Star Wars: The Last Jedi.

I am not joking. This is the actual storyboard used. Johnson's sketch looks like a kid did it, but it was effective communication to convey the concept.

Happy sketching

Low fidelity visuals invoke high fidelity feedback. Design debt is something we don't think too much about in terms of the cost of maintaining pixels. With sketches, you can easily throw them away if it's not going the right direction. When you invest in pixels and time, there's more attachment, even if it's not the right solution.
In Pixar's 22 tips for storytelling, number 11 conveys why sketching strategies is crucial:

"Putting it on paper lets you start fixing it. If it stays in your head, a perfect idea, you’ll never share it with anyone."

Sketching creates the kinetic energy that turns ideas in the clouds into vision-in-action in a tangible way.

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Exploring intrapreneurship culture

Issue #58: Why the hardest word to spell is so crucial to product innovation

Nearly a year ago, Apple removed the Remote app from its App Store as it introduced the Siri remote. Since most of the remote functionality was now integrated with iOS, Apple felt there wasn’t a need for an app. Alan Cannistraro, the former Apple engineer who created the app, shared his reflections on Twitter about his experience in bringing it to life. For one of the largest companies in the world, many were surprised to learn the first iOS app in the App Store (internally) was an idea developed by one person. Cannistraro often says that Apple works more like a startup and the story of the Remote app is a prime example of that entrepreneurial spirit coming to life. I had the opportunity to work with Cannistraro and consider him a good friend and mentor. Our time collaborating together fueled the idea of always operating like a startup at growing companies.

Intrapreneurship was first coined by Gifford Pinchot III in 1978 and described as "dreamers who do." As the name eludes, intrapreneurship is someone operating like an entrepreneur or founder within a more established company. The best companies constantly reinvent themselves before it becomes too late. It's hard to fathom now, but when Netflix decided to do away with DVDs and focus on streaming services, it was seen as a bad move by many analysts. Once known as Square Cash, this product initiative started as being able to email people payments and evolved into Cash App—a standalone brand and business success within Square.

At the early startup stage, you're the one moving fast and innovating—almost out of survival. If you're fortunate to find product-market fit (PMF), you’re now focusing on growth, market expansion, and continued product development. Suddenly, emerging competitors are able to move faster than you. It's like seeing a speedboat move past larger ships. You want to be the battleship that can deploy small boat operations, being both nimble and supported by the scale. Larger companies need continuous innovators, and this is where intrapreneurship comes in.

Before going back to management at One Medical, I was a lead product designer as an individual contributor. My time at One Medical was a place where intrapreneurship and service design was strongly encouraged. In addition to my core responsibilities with the product area team, I spent time working with other product managers, ops leaders, and people in the company to explore strategies of where we can go next. I don't think anyone ever asked me to do it. I invited myself to the party and nobody ever asked any questions about why I was there. When I'd have coffee 1:1s with colleagues, I'd pull out prototypes I built on my iPhone to share with them; asking them to play around and get reactions. We’d sketch ideas together on paper or the whiteboard and I’d have them walk me through their business problems.

I began building a portfolio of opportunities. They were one-pagers of different ideas we could explore based on the problem and business opportunity. This eventually became a product vision book that helped us build our product roadmap.

Identifying these opportunities internally was not my primary job. It was something out of my passion for it I did in addition to my day job—my internal side hustle. Through hackathons and small brainstorm sessions, some of these were prioritized on the product roadmap and provided clarity on how we'd explore it.

Intrapreneurial Attributes

Not everyone has the entrepreneurial spirit, and that's okay. It’s not something everyone wants to do. Companies need a diverse set of skills and people excelling at what they do best. I'm frequently asked what the common traits and attributes people who have a knack for intrapreneurially work have. These are the five that come to mind.

Thrive in the ambiguity

When you embark on exploring new innovations that people haven't thought of, it's going to be ambiguous. Nobody is going to tell you what to do because there is nobody to do so. When you can take mysterious areas and start making sense of the fog, opportunities emerge.

Ruthless in iteration

There is a finite amount of time to explore new products and services, and the time to iterate is life-or-death on the projects. People who know how to iterate fast on a concept do well in this space. This is where you want to be an optimalist over being a perfectionist.

Inspire through storytelling

Storytelling is one of the most critical skills of a designer. Great storytellers develop concepts, frame the problem and opportunity, articulate their design decisions, and inspire. If you're going to work as an entrepreneur within a company, you need to get really good at selling and pitching; almost like you're raising money for your startup, because, in a way, you are.

Business acumen

We can cover an entire issue on business acumen. Roughly stated, this is the combination of knowledge, skill, and ability in the business. People who understand the business and are aware of stakeholders get things done. Those who do well in intrapreneurship are research-driven and analytical. They understand the business and find gaps that become opportunities. Most importantly, they have strong relationships with people all over the business to bring it all together.


This might be the most important one. Intrapreneurship isn't for the faint of heart. It requires grit, scrappiness, and a desire to do it. Any initiative with intrapreneurship in mind will come with a lot of skepticism, and that's the point. When you are looking for completely new opportunities the company isn't focused on, it's going to come with a lot of questions. I pitched dozens of initiatives at One Medical, and only a handful was greenlit, but those that survived became very high-impact services.

Unleashing the intrapreneurial spirit

Culture is what people do when they're not told what to do. Whether you're a full-time employee, founder, or freelancer, find something you can pick up and run with. It's working within the constraints of the business but requires going a little rogue too. Innovation isn't always about the frosted glass studios where nobody knows what is being designed, it's building publicly at your company and sharing ideas. I believe that the entrepreneurial spirit is a mindset and culture—one that can be applied within a company.

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