The vastness of curiosity

I have been thinking deeply about this quote from the author of one of my favorite books, The Little Prince.

"If you want to build a ship, don’t drum up people to collect wood and don’t assign them tasks and work, but rather teach them to long for the endless immensity of the sea."

— Antoine de Saint Exupéry

Though this also applies to my personal life, I often reflect on this in the work setting and with design teams. This quote always finds me looking back at Kimber Lockhart's post about fostering a sense of purpose. Everyone has a different drive and motivation, and when you can find people who are purpose-driven, there is an infinite amount of energy because it is their human need to explore and be curious.

If you can find people who are in love with the process and are curious, they will lead you all over the ends of the earth.


Take California

It’s been almost two years since I moved back to Seattle for the second time. The city of New York is a really special place in my heart and it was difficult to move away from there, but the motivation was the be close to family. I moved to Capitol Hill and re-united with my my mentor at HTC. A year later I then joined Black Pixel, the one company I sought after for several years. It was the dream job. After leaving Black Pixel I spent months exploring to figure out what I would do next.

From that I exploration I met a mentor who really changed the way I worked and thought about ideas. I worked in the heart of the Mission District in San Francisco California. As I worked, I also started contracting at One Medical, where my friend David (another designer named David H. with a slightly smaller cat) works. He told me that I would love it and there is this great new CTO who has been taking charge for a while and thinks I’d get along. That person is Kimber Lockhart. I remember when I first talked to her on the phone after a panel interview she did, I felt an instant connection and resonated with this person. As I contracted, she and I began doing 1:1s and the rest is history. I decided to join One Medical’s product team as the last decision I made in 2015.

2016 turned out to be a _really_ odd year. A lot of us can feel that once David Bowie died we knew this year was going to be a bad one (I’ll let you fill in the rest). In 2016 some personal events made it really important for me to remain in Seattle. I found myself on the Monday 7am Virgin America flight every week…so much that the staff and flight attendants all knew me. I’d fly to my first meeting and work there until Thursday evenings to fly home to Seattle.

Here’s the kicker…I didn’t officially have a place to live. I crashed with my aunt down in Redwood City and spent a lot of quality time with her. She is the one who taught me to be curious, live a simple life, and always travel. In addition, my friend Rob and his wife Emily took me in for several months with me crashing on their couch and occasionally feeding the cat. Their sacrifice made it possible for me to continue flying back and forth. By the middle of Summer I realized I needed a more steady arrangement and reached out to my friend who serendipitously was looking for someone to rent her place while she was traveling. It really reminded me of when my friend Damon was staying at my place while in Europe. His presence did such a favor for me to have someone trusted in my apartment.

This year has reminded me a lot of the power of community—a word that is often thrown around as a buzzword but yet so obviously necessary. Community for me is the tribe I’ve found in Seattle Xcoders and the Cocoa Community, my Destiny clan, and the Brunch Crew in San Francisco. As friends have sacrificed to accommodate me while I achieved a goal, I found that I wanted to pay it forward and have friends stay at my temporary place instead of paying hundreds of dollars for a hotel room. It also gave me the chance to catch up with them and spend some quality time.

2016 also brought constant change in my life and willingness to embrace change. The time feels right for a change, yet again. At the end of the year I will be moving down to the San Francisco Bay Area. The difference this time is I will only be living in one place—something I have not done in several years.

I would be lying if I said there wasn't any initial reluctance to moving down there. In fact, I still do. Of course, there is the myth that rent is $800 billion a month for a studio…okay, that is slightly exaggerated. Just slightly. That actually wasn’t my concern.

My concern about San Francisco is that it is losing its sense of purpose and reality. There seems to be a focus on making the world easier, not better. You could not tell the difference between an episode of Mike Judge’s Silicon Valley and real life. The tech scene in San Francisco is very much often “the scene” and superficial. It seemed like more of a lifestyle instead of a privileage to make such an impact, and with such great power comes a great responsibility to do something meaningful.

However, my concerns were addressed with a sense of hope, meeting people who were truly authentic about their mission and was looking for the signal through all the noise. I met people who were part of a continuos narrative of some of the great pioneers of the bay area. I feel I have ties with people I look up to here. Similar to the connection I felt in Brooklyn with Adam Yauch, I have ruthless innovators who taught me to “just win baby” and be a crazy one.

My goal is to chase the big dream and finally do something really meaningful…be a living proveocation. I’m looking to put that dent in the universe. My commitment is to stay true to a mission in using technology to empower and enable humans, not exploit them.

I want to be a better community member, and really be present in one city. This starts with simply being a great host. I’ve traveled the world for so many years visiting friends, and as they have hosted me with wide arms open, I want to return the favor.

I will miss Seattle a lot. It is the city that where I have spent most of my adult life and I will always have ties here. Ever since moving back from New York I have appreciated it so much more than I ever did. I will miss most the Seattle Xcoders community—a place where I really found my tribe and sense of purpose. However, I know it is just a hop and a skip away to come home and visit friends.

When I was young our family friend, Mrs. Pulliam, once told my dad “David’s life is like an unwritten book. You’ll never know what the next chapter will contain.”

Here is to the next chapter.


- Yes, Wilson is moving
- The title is inspired by the Propellerheads song “Take California”, which was the song used in the original iPod commercial

Abstract For My New Talk: Making Together

Talk Title: Making Together: The Need for Organizations to Have Internal Studios


The practice of design, engineering, and product management has been see as the foundational aspect for building products. However, as product roles continue to evolve with ever-changing problem spaces, the lines of responsibilities have blurred. This talk challenges the notion of ownership and function with the intention to break the barriers and friction by building together synchronously. A world where a PM cares as much about design as much as a designer cares about working with engineering directly to get it shipped.

One approach to this problem is building a work culture and space that fosters a studio model within organizations, whether you are a small startup or large corporation.

This talk covers:

  • Why current processes are broken
  • The importance of having a space focused on collaboration
  • Work approaches and tools needed
  • Seeing the problem together

Note: The focus of this talk will vary based on the conference/audience. I plan to dive very specific in process and proposed work structures for more technical conferences for engineers and designers.

Assembling Your Personal Board of Directors

It is quite common for a company to have a board of directors who act as representatives to stock holders.

I have written a lot about the importance of mentorship and these type of relationships to help you grow as a practitioner in your career, and there is no reason you should limit yourself to just one. As in other forms of relationships, you will find that you gravitate around certain people for specific things.

Assembling your own Board of Directors (BoD) for you as a person can be beneficial in getting the hard questions answered. Though family members and friends have good intentions when giving you advice, they can often be too affirming and support you in what you want to hear, and not necessarily what you need to hear. With your personal Board of Directors, these are (or should be) constructed with people who will give you a dose of reality in each of their respective practices.

An example of some people who sit in my personal BoD:

  • Adam: One of my best friends since I was 10 years old and former co-founder. He knows my habits personally and professionally and has a channel of communication with me that’s the realest.
  • Alan: The ex-Apple engineer and inventor who teaches me about shipping, ideas, discipline and getting things done.
  • Dylan: The UX Designer who used to teach web design/development. He encourages my writing and generously edits it.
  • Jaimee: A seasoned UX Director who expands beyond that. The person who really encourages me to speak at conferences and publicly share ideas.
  • Joris: My Dutch friend, a software engineer who chats with me about every month or so about our side projects.
  • Kimber: My new manager with industry knowledge of building and running product teams in the bay area. Not only do we have 1:1s professionally in my role but she gives amazing insights personally in my growth as well.
  • Marie: The first mentor who taught me the skills of design and has seen my progression from the very beginning. I go to Marie for everything but she has the most knowledge of my career historically.
  • Natalie: The proven executive and company builder who has really mentored The Rock Tumbler Collective and advices particularly on my innovation projects.
  • Laura: A former VP of Strategy who helps me focus on…surprise…the strategy of my career; where I am now, where I want to be, and how I position myself to get there.
  • Lesli: The Canadian Creative Director who I met sitting next to each other one day. A peer mentor who is going through similar growth challenges as I am now in a leadership role.
  • Rich: A former colleague and VP of Engineering. He loves to tinker, code, and has encouraged/helped me throughout my quest to write better Swift code.

(This is not everyone but a sampling of the range of conversations)

After reading that you may think, “Wow, that’s a litany of mentors.” It definitely is, and each person voluntarily shares so much value with me.

A Google Hangout with Lesli.

How to Assemble Your BoD

This is simpler than you may think. Design the structure around your BoD and it will take form. You can formally ask each person for their time, but I’ve often found these relationships form naturally. If they cannot commit to it, they will tell you or it will be very apparent. The cadence in which I meet each person varies on who they are, what they do, and what their schedule can be like.

Put it on the calendar: Treat your Personal BoD like a real board and make time for it other on the calendar. Otherwise it is at risk of getting pushed back or becomes secondary. The BoD provides value for you and your future so you must carve time to do it.

A conventional BoD typically meet synchronously, but it is not necessary in this instance. In fact, I do not think anyone in my Personal BoD has ever met one-another. Just know what information you want to tell them.

How you should meet with your BoD:

  • Set time to meet with them on a cadence. It can be quarterly, weekly, or even annually
  • Give a clear update of what you have been doing. This isn’t a time to impress anyone. Let them know what is going well and what is going bad
  • Ask for specific advice and insights about what you’re going through, and what your goals are
  • Take notes and write down your follow up plan. I like to write on physical paper and then add it in OmniFocus as an actionable item.
  • Most importantly, don’t waste their time. These people clearly are invested in you and care about you. Make sure you follow up and update them with what happens after you meet.

If you have a BoD, make sure they get a return on their investment. In this case, it is not financial (though it possibly could be), but the return is on you as a person. There is no gratification a seasoned vet in the industry gets more than seeing someone they coach and mentor grow exponentially.

Set the expectation for yourself, not that you’re afraid of letting them down, but strive to make them proud.

Who is on your Board of Directors? Is it time for you to reach out to people who you trust that will push you to get the best ROI on yourself?

The Career Holy Trinity

It takes some time to get there or figure it out, but here is your career Holy Trinity: Loving what you do, getting paid for it, and being able to make a living off it. If you can find these three things, you will find that there is no need for a work/life balance in the traditional sense, but you're constantly living what you love.

The will to ask and the will to act

This week I had the pleasure of meeting my friend's cousin who was visiting New York. Clare is a recent college grad and flew out to New York to meet with potential companies and people.

I had coffee with her and she picked my brain and told me what I can do to help her. She asked me a lot of great questions and was taking notes the whole time. What pleasantly surprised me was she asked a lot of really specific questions, such as my process from getting from one career to another. I was really impressed to hear such detailed questions.

Clare was probably the most proactive college grads I've met in a long time. She has a vision of where she would like to be and asked questions to connect the dots between where she is now to where she wants to be.

It reminded me of this video I saw of Steve Jobs:

"Most people never pick up the phone and call, most people never ask. And that's what separates, sometimes, from the people who do things and the people who just dream about them."

People cannot help you and sometimes will not help you if you do not tell them you need help with. You will be surprised how many people are willing to help you, but they have to know you need something.

How to confront people

I posted this status on Facebook about Passive/Aggressiveness it it drove some pretty good insights from friends and colleagues. Here is a conversation between myself, Daniel Pasco of Black Pixel and Curt Clifton from The Omnigroup on Twitter:


Professional, I've always been put in a position where confrontation occurs a lot. Personally, living in New York City has taught me that confrontation is a very good thing, and should be done a lot.

Roughly translated based on our conversation on Twitter: Call attention to but don't be an asshole about it.

Here are some thoughts about how to confront people.

Do not confront people in public

I have yet to see a situation where public confrontation is a good thing. It is usually never a good idea to call someone out publicly because it is embarrassing to the other person and it opens up a lot of opportunity for people around the situation (but not in it) to misunderstand what is going on. If the issue can wait for later, opt to talk to the person privately.

Talk to the person directly first

Unless it is a very particular situation where someone needs to be address with someone else, it is best to start with the person. You owe it to the person to call attention to it before involving other people. Donglegate is a perfect example of how a conflict could have been resolved between the parties, but it spread like wildfire.

Hypothetical situation: There is a team member who talks extremely loud during Skype calls with clients, and it is disrupting everyone in the office.

Here's the thing—this person probably has no idea that they are disrupting the office. She is probably focused on the call and possibly wearing headphones so cannot hear ambient noise.

What I would do: Talk to this person privately and say something like "I've noticed that some of the other colleagues are having trouble focusing when you're on your Skype calls with clients. It gets a bit noisy. I know you're not doing this intentionally, but would you consider going to a conference room or just be a bit more aware of the volume when you are having your meetings?"

You will find one of these things will happen:

  • The person will appreciate that you brought it to his or her attention, and there is resolution.
  • There will be resistance, but at least you brought it to their attention.

Define the perception

Whether it is fair or not, a lot of life is based on perception. You don't have to pay attention to it all the time, but in collaborative situations, it is important to define it.

Hypothetical situation: An engineer is working on milestones for the next deploy but has not updated the rest of the team.

I would say something to the engineer like: "Hey, I know you're working hard on this deploy, but can you update our client just to let them know what you're doing? I know it takes a little effort for you to stop what you're doing but the client does not know what you're doing with your time so we just want to update them and let you know what you're doing, even if it is a brief note."

The hypothetical client just might be concerned and their perception may be different if someone goes radio silent. Everyone has had to wait for their UPS package to arrive and we know how much a quick update can eleviate any perceived concern.

If you are the leader, then you call attention to it

It is the responsibility of the leader to care for who the people he or she is working with.

Hypothetical situation: Let's say a team member is underperforming and has been delayed on his projects.

It is our job to call attention to this without making any assumptions, especially if the person is a bit sensitive. I might say something like "Hey, I've noticed that you have missed some of your milestones recently. Is everything okay? Is there anything you are struggling with on this project? What can I do to help you?"

A person should never feel like they cannot ask for help. However, that is in an ideal world, and in the real world, some people are just afraid to ask for help—as if they let someone down.


Remember that confrontation does not have to be a negative. In fact, it is very positive to increase the contrast in things. When you do not confront, it allows built-up animosity that might be misconceived from the beginning. My advice to people, especially in the work situation, is to call attention to things and confront in the early stage.

How to talk to your clients

I've had the pleasure of working with many clients ranging from individuals who want to build a product and enterprise clients as well. In every role I've had for the last six years it has been client-facing. I've learned a lot during my days at ExactTarget and now at Xhatch.

How was your day?

The most important thing you need to remember about your clients is that they are human just like you. This blog is focusing on human interface (for now). Clients have good and bad days, just like you, whether it is at work or at home. Take a few minutes to greet them and ask how things are. It is a nice way to set the tone of the conversation.

Do not expect the client to understand everything

This is probably the most frustrating thing for me. When I hear someone complain about a client not understanding something, I think "Well, they shouldn't. That's why they paid you to consult and help them build it." Now of course, there are limits, but try the best you can to explain to your client what you are doing in different ways.

If it is too technically complex for comprehension, then draw diagrams or use analogies so there is some mutual understanding before diving deeper.

Repetition is okay. Repetition is okay.

It is never a bad idea to repeat yourself. Often when a client will explain something or provide feedback, I will wait until he or she is done and say "Okay, I just wanted to repeat what you said to make sure I understand. The features you need in v1 are..." to make sure that no assumptions were made incorrectly. You will rarely see a client get upset about you wanting to make sure you understand.

When closing a meeting, I will repeat the overview of what was discussed to make sure that nothing was left misunderstood.

"This town is a part of us all... a part of us all... a part of us all! Sorry to repeat myself but It'll help you remember!" —Marge Simpson

Never say "no" or "we can't"

I need to jump out right away and say this does not mean "always say yes" or "yes we can" to your clients either. The reason this is important is just the communication between people. When you say "no" it immediately dismisses the question/request. However, if you say things such as "Yes, but ____" or "We are not sure, but can take a look" it instills that you are listening to their needs and taking such actions. Now, the result might be that you cannot do something in the circumstance, but at least the client felt they were heard.

Does this make sense?

This is probably the phrase I say the most on a call with a client, especially in the beginning when we are doing discover and requirements gathering. Never assume a client completely understands what you are presenting so it never hurts to have checkpoints during your meetings to make sure everyone is following. Most of the time things make sense but it is good to see that nobody is falling behind in the conversation.

When in doubt, over-communicate

I travel a lot and work with a lot of clients remotely. Even though it does not matter where I am, I like to give them the courtesy of updating them. I tell them when I might be traveling so they know I will be out of reach.

My rule is "try to answer their question before they even ask it." If a phase of a project still needs more time, I email the client to let him or her know that we're still working on it and we will reach out if we have any questions. If the client sends an email with a lot of questions and I am busy working on design work, I just write back a quick email acknowledging I received it and will take a look later.

Think of it as a long-distance relationship. It is better to over-communicate to ensure everyone understands the context of actions so nobody misunderstands something like delayed responses.

Again, try to answer the questions before they even ask. I do not think most of my clients even expect this, but I think they appreciate that you are thinking of them.


I have rarely had a client from Hell, and I think most are actually enjoyable. The most important things are to remember that they are people trying to work on a project and may not understand it. Take time to make sure they are getting it and over-communicate.

See how I repeated myself?