On October 21, Brooklyn Roasting Company announced it was filing for Chapter 11 bankruptcy protection and closing all if its brick-and-mortar locations in New York City. During the time of the COVID-19 pandemic, this is too common as business are struggling to stay open.
I grew up in the Pacific Northwest but Brooklyn was the place I found a sense of home. Brooklyn Roasting Company (BRC) was my third place that I would stop in before starting the work day. At the time I was running my own company and it often was the workplace for me. I’d spend hours there filling up on the Maple Shay Almond Latte or Cortados as I worked on client projects.
It’s impossible to get someone from Manhattan to come over to Brooklyn. Since the coffee shop I went to in DUMBO was right along the F stop, the occasional miracle would happen where someone from Manhattan would come over to meet me since it was the first stop into Brooklyn. Anyone who lives in Oakland can understand how this feels with their friends in San Francisco.
BRC was the gathering place for old and new friends. Many people I’d sit next to were freelancers and I have made life-long relationships from being present there.
BRC was a metaphorical Brooklyn Bridge. I hope we can pull off one more miracle and that BRC opens up for business again. Regardless of the outcome, thank you so much for the memories, forged friendships, and a third place to call home.
A year ago today I started my journey as a team member at Webflow. Before I joined, I took a small sabbatical to really spend time finding something I wanted to do meaningful for a very long time. I recently left One Medical, a place where I stayed for four years—the longest place I’ve worked aside from my own company. One Medical taught me that as a leader it takes long-term commitment to build something great, and I was looking for something that would be that. My gut was telling me to start a company again. I have many interest in industries (health tech, fashion tech, consumer apps, travel, SaaS, etc.) but the one that is unrivaled is design and developer tools. Many years ago I interviewed with the Xcode team at Apple and always felt I missed my opportunity on tools that enable people to create and build. My noodling and doodling led me to think about taking a crack at a startup to enable people to build apps without code. During my break, I met with my good friend Alissa who mentioned Webflow to me, and the rest was history.
Domm Holland, CEO at Fast tweeted about what you can learn from scaling a startup. After experiencing that at One Medical and having so many fond memories, I simply couldn’t resist doing it again. I’m so grateful to join Bryant, Sergie, and Vlad to work with them in the journey they took several years before as co-founders to make Webflow become real.
In many ways, it’s the perfect product and space. For years I’ve obsessed over the infusion of design and engineering. I also love building tools for people to create, build, and dream big.
Most importantly, the people. From the first hour I started I felt so welcome by this remote team and it’s a pleasure to serve them on a daily basis.
2020 has not been the year anyone expected. Despite all the challenges we are facing in the world, my purpose at work is something that remained constantly optimistic. There is so much more we need to do, and I feel like my journey is only beginning—feel grateful to simply be a part of it.
Is there any better way to dunk on Virgos than writing about subverting perfectionism in September? (Narrator: There is not.) I’m kidding, Virgos. My cat, who just celebrated his 18th birthday, is also a Virgo.
The refusal to accept any standard short of perfection has its benefits and major challenges is a common theme among Virgos and other humans. The benefit is it can motivate you to do top quality work. However, this can be counter-productive, inducing a lot of anxiety, fears, and insecurities.
Perfectionism is a personality trait characterized by a person’s striving for flawlessness and setting high-performance standards, accompanied by critical self-evaluations and concerns regarding others’ evaluations. This can create analysis paralysis and you may never put your idea in motion. Psychologist David Burns once said, “Reaching for the stars, perfectionists may end up clutching at air.” People often don’t launch their ideas because of what they might face as it transitions from idea to reality as a result of this fear. Sometimes you’re trying to refine something so much in your head that you later learn that someone else went and did your idea.
Sharing ideas is extremely hard. It puts you in a vulnerable space. When you keep ideas to yourself, there is no risk of critique or reaction. It’s perfect in your mind. When you create something and put it out to the world, you face critique. It’s tough to launch that app idea, only to find out it’s something nobody wanted and failed. It’s also hard to put yourself out there in a world where things are portrayed in the most idealistic. Open Instagram and within seconds you’ll often encounter perfectly staged narratives. How would you ever reach that standard?
Becoming the imperfectionist
In 2006, the world was introduced to blonde hair and blue-eyed James Bond in Daniel Craig. For those who are familiar with the Ian Fleming character, James Bond has always been portrayed as hyper-masculine, smooth, and suave. Aside from the ocean-blue eyes and blonde hair, Daniel Craig’s portrayal of Bond was different. It was brutal, rugged, and inelegant.
Bond: Vodka martini Bartender: Shaken or stirred? Bond: Do I look like I give a damn?
This is a rough cut of Bond. He doesn’t care about being smooth; that the job is done (In no ways am I saying Daniel Craig is imperfect). I’ve always looked at the Daniel Craig James Bond as a metaphor for being more real and unrefined in order to achieve results. Though I care about doing high-quality work, I am far from a perfectionist. My style of getting there is very rugged and often by brute force. As the saying goes, “A ship in harbor is safe, but that is not what ships are built for.” This is what Proof of Concept is about; encouraging you to get those ideas out to exist in the world so you can refine it.
The other end of the spectrum of a perfectionist is often defined as an Optimalist. This comes from the Latin word Optimus, which means both “best” and the fearless leader of the Autobots in the Transformers series.
Filling the white space
In art school, I was trained to get rid of all the white space on the canvas. In my oil painting classes, I’d apply the techniques of the artists of old like Titian to complete an underpainting, a very low fidelity pass of the entire canvas to shape up the composition. Once you mess it up, you can then refine it. This helps me cope with any sense of perfectionism that might creep in.
There is more hesitance to make a mark on a blank white piece of paper because each stroke can feel like a mistake. When it’s filled, you have less to lose.
The key is you do not have to attain perfection in one iteration.
Iterate the momentum
As Dr. Julie Gurner recently said on Twitter, “What most won’t tell you? It’s not knowing what to do that it is hard…it’s actually doing it, and not allowing yourself to get in the way.”
Building momentum is the most challenging part of doing anything. One of my favorite quotes is from Pixar’s 22 secrets to storytelling: “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.”
Similar to my painting style, I approach writing the same way; creating mind maps of ideas and unstructured writing to help me get started. The blank canvas often the biggest blocker.
Especially now during COVID-19 where we seem to be perpetually on screens, I take my sketchbook as a way to plan my action. Whether it’s a book idea or a quick note, I scribble on paper to hash the ideas out a bit before focusing on any digital computation. I’ve also found putting thoughts on paper has put my mind at ease and makings me less anxious about any work I do. Since I spend seconds doing quick thumbnails, there is such low risk for me to re-do the work in a better way.
Sharing your drafts to the public
I’ve been so inspired by people on the web who have been sharing concepts out in the open, and I’d like to share two who come to mind. Paige Doherty is a software engineer who is working on a children’s book about venture capital and has been sharing her pen and paper pages of the book. She used Loom as a way to create an intro video to solicit feedback. I cannot wait to see where this book goes! Jordan Singer, a product designer at Square Cash with a background in computer science, has been building his ideas for many years. He created an app called Airport which lets people browse different TestFlight builds of iOS apps that people are building.
These are two of many examples of people putting work out there to get feedback and providing early access. People don’t create things out of thin air like magic. We often feel like it is so because often we don’t see the drafts and iterations. The reason someone has achieved more success is often likely they’ve failed more than you.
Non Finito can be therapeutic
The word “Non Finito” means “not finished” in Italian. I find a lot of benefits doing a “brain dump” of all my thoughts. This type of journaling has helped provide some mental relief by making it tangible and a source to start new ideas.
You don’t even have to show your imperfections to the world if you’re not ready for it, or if you ever are. Putting these thoughts down can help you look at things head-on and be accepting of the imperfections.
“What if I mess up and break something?”
Who cares.
Kintsugi, the art of repairing with gold is the Japanese art of repairing broken pottery by mending the areas of breakage with lacquer dusted or mixed with powdered gold, silver, or platinum. As a philosophy, it treats breakage and repair as part of the history of an object, rather than something to disguise.
It is in our imperfections and fragments where we can find a long-lasting beauty we can appreciate in an authentic and sustainable manner. Take a moment, put that idea out there. You might inspire someone to do the same. Together we can iterate more and share it with the universe.
As the artist, Salvador Dali once said, “have no fear of perfection – you’ll never reach it.”
P.S. In the spirit of idea generation on early drafts, I’d love your feedback on what you’d like for me to write about. Simply reply to this email with your idea. I appreciate any suggestions!
It became official during this virtual WWDC, you were officially deprecated. I never thought my heart would ache for the deprecation software. However, to be honest, I owe so much to you in my life, and it’s no exaggeration. Is this a love letter, or a farewell letter? Like many great loves that aren’t meant to last forever, it’s a bit of both.
We met many times, but you weren’t my first love. To say you were my first love would be a lie. Before we met, there was HyperCard and Dreamweaver. With visual programming tools like this in my life, I could do something I never thought I could…build what I imagine.
We had encounters at times in college, where I remembered you as primarily a graphics app that my music friends loved using. It was a way to create trippy visualizations along with electronic music they produced. You weren’t the first visual programming language (VPL) tool I was introduced to, but were there for the most formative times of my life and career.
I met you again later in my career. It was 2013 and HTC just announced their new phone, the HTC First, AKA the Facebook phone. People were talking about the chat heads interaction that appeared in the device. Julie Zhuo wrote about how the design team prototyped the interactions in QC.
This was at the cusp of my iOS design career. I remember having coffee with my friend Robert Eickmann at Caffe Vita in Capitol Hill. He showed me a video of a designer recreating the chat heads using QC. When I finally joined Black Pixel, one of my dream companies, I was responsible for doing a lot of prototyping work for client projects. I really relied on you to tell stories through inspiring interactions.
A while after, Facebook released Origami, a plugin built on your software. Like many designers, I was obsessed with building every interaction out using it. You once inspired me to give a talk at the Seattle Prototypers meetup, where I met Stephen Crowley, one of my good friends to-this-day.
You helped me ship the most impactful projects in my career and helped me build rapports with some of the engineers I worked with. You gave me the language, the rhetoric, and the conversation. You enabled me to become a curious explorer and prototyper. I have to be honest, you were the reason I felt I needed two Thunderbolt Displays to see my work. From prototyping a camera app for a social networking app people use daily to creating our first experience of video appointments at One Medical, you were there for all the big moments.
There were others similar to you that came, such as Form (what a great tool and Google did nothing with it) and Noodl. You will always remain the original to me, and the one that sent me on a path of curious prototyping, which really changed my career; the one that invoked endless possibilities.
Thank you, Quartz Composer. I owe so much to you, and as we embark on the next evolution of visual programming, you will not be forgotten and your place in history will forever be remembered.
David (forever known as “That designer who is obsessed with QC”)
Earlier in the year I had the wonderful opportunity to be interviewed for the CodeNewbie podcast. I am truly honored to be interviewed and you can check it out here.
In the midst of the pandemic of COVID-19, many lives have been impacted in so many ways. Unfortunately many people have felt the impact of layoffs throughout the industry, including design. I’m offering up some of my personal time to review portfolios and resumes for those who find it helpful.
Disclaimer: Please note this offer is me as a person and not that of my role as Director of Design at Webflow. This means if you’ve applied to a role at Webflow I am not reviewing your application as a part of this rather free coaching/feedback.
If you're a designer and affected by a layoff at or working on your first role in brand, product, or UX, I'd love to offer my time to review your resume and portfolio.
My email is david[at]https://t.co/p8ja6Yst9Y. Let me know if there is any specific feedback you're looking for.
I studied Art History in college and find the liberal arts to be one of the biggest influences in my design career. One of my favorite eras to study is Baroque art. It often brought high contrast, strong asymmetry, aestheticized violence, and remixed symbolism in its works. It’s the Tarantino era of art history. One of the artist who first caught my attention at an early age was Michaelangelo Mersi, better known as Caravaggio.
The Catholic Church at the time were huge patrons of the arts and commissioned artist to create paintings of famous scenes during the counter-reformation. Caravaggio, is what you wouldn’t necessarily call a religious man, which made his works so fascinating to me; an amoral man and sinner in the views of the church, being commissioned by the church. He often left a lot of room for interpretation in his paintings. One of the famous ones is that of “The Calling of St. Matthew”.
The 10.5×11’ oil painting in Rome depicts the moment when Jesus Christ inspires Matthew to follow him and become an apostle. In the painting, it’s not clear which one is St. Matthew. Is it the young man hunched over the coins? What about the main pointing at himself to ask “me?” Art historians have often said Caravaggio left it open ended for the viewer to interpret that the calling can be for anyone.
I use this piece of art not as religious evangelism but perhaps career evangelism. This painting often reminds me of how people get called into management, and how ambiguous it can be where great future managers come from. Perhaps it’s the 10x engineer who points at himself and clearly assumes it’s him. But what if it’s the average senior designer who has a great emotional intelligence (EQ), organized, and really cares about people?
The current state of management
Since it’s what I have the most experience and observation in, the purview I’m going to share is primarily design management, though I believe this applies to many other functions and disciplines as well.
The industry sets up wrong incentives for people to become managers
The candid truth is that there are a lot of managers in positions who shouldn’t be. It’s not to point fingers as they come in many forms and they come in many forms. Perhaps it is someone at an early startup and fell into management as the company grew. Some pursue management positions for personal gains and have more perceived influence. As we ponder who would make good managers, we also must ensure that people who have a desire to thrive as individual contributors and leaders have incentives to do so.
The system often incentivizes people to go into management for the wrong reasons. There’s often a pay bump in becoming a manager. I believe that’s the wrong incentive, but that’s a different blog post.
At Webflow, we have individual contributor (IC) designer tracks that have parity with manager tracks, both in pay and influence. Leadership is a trait both managers and individual contributors have. If we’re going to fix the management pipeline, then we need to ensure individual contributors have clear and equal tracks. Buffer has a great article about their individual contributor career track.
Lack of a succession pipeline and development process
“There is no success without a successor.” — Peter Drucker
The core problem I view is that there is a substantial gap in the management pipeline for new managers. As experienced managers and leaders in the industry retire (and they will at some point) there needs to be a clear investment for new managers to take the mantle.
A lot of managers transition into lateral positions at different companies. Roughly put, the same people are getting the management jobs, and not all of them are good managers. At this state, these managers will continue to fail up if there isn’t any dilution of the talent pool.
While this is happening, some of the best potential managers may be neglected from pursuing management, both by external forces and perhaps themselves. The biggest problem I see is the lack of encouragement from others for them to pursue management. In a land of bad-to-middling managers, sometimes people who would be great managers don’t see themselves in management positions because the people they do have as models aren’t who they want to be.
The industry needs good managers, which is not necessarily managers who have been doing it for a long time. The management pipeline needs to be refreshed from time-to-time with new people to take on the responsibility.
Companies are looking at historical data to de-risk
Hiring is important to get right at a company. Make the right move and you might find the person who is going to shift your team and elevate them. Make the wrong hire and it can be costly and dire. The impact is felt even higher for management and leadership roles. It’s no surprise then that companies are seeking methods to de-risk the hire.
The desire for more “influence”
I’ve often heard in many conversations with people considering management state that they want to pursue it to mentor and have more influence. It’s understandable how people might feel this way, however, it’s not good motivation to enter management. When you are in a higher leadership position, your role is more motivation and coaching than influence.
The calling of ICs
I firmly believe that some of the best new managers are currently individual contributors who have not considered management or shied away from it.
If you would have asked me a decade ago about people managers, I would have laughed. Never would I have imagined taking on a role as an introvert where the majority of the responsibility is dealing with people. My motivation then was to strive to be the best individual designer.
What makes a good manager?
Though this clearly varies based on company and industry, I’ll try to boil it down to the essentials based on experiences I’ve had and observed. At the core, a good manager is someone where their highest impact is focused on developing people, processes, and systems that provide farther value than what they can achieve as an individual. Your focus transitions from heads down to heads up.
Your focus shifts to the success of others
Clearly individual contributors also care about other people, however, the success of others is one of the core performance indicators in management. If you find joy working with people to enable them to be better at their job, management is a great place to do that.
The turning point for me was when I realized that focusing on spending time with other designers to help them get better brought me so much more joy than heads down time to explore a new project or prototyping tool, which I was very much in love with. Seeing where people started and witness their development became what I cared most about.
People-centric approach, team-oriented outcomes
You care about people but your mission is that of the team. The team is your metaphorical product and you’re responsible to strategize, unblock, and scale. Empathy and advocacy for your people is the natural start of being a manager. However, to be a strong manager, you will have to thoughtfully balance the needs between every human and the team.
Enabling people and systems
As a manager, you are now a builder and maintainer of people and systems. The responsibility of a manager is not to be good at everything, but to ensure the team is effective at everything.
The greatest system design challenge in the history of humanity is getting people to work together effectively.
I’m interested. So how do I get in?
If I’ve peaked your interest, here are some things to think about to prepare for the calling.The trick is to distribute your impact and influence as you’re a high performer to transition into a higher scale role. There is no shortcut to management. Be sure you’re a consistent and high performer at an IC level. The trick is to convey that your time can be maximized as a force multiplier.
Remember, if you don’t like management, you can always go back to being an IC in your career. There is nothing wrong with that. There are different layers of management, and you don’t have to keep climbing the ladder. Find the purview that gives you the most joy. If you enjoy first-line management, you don’t have to climb all the way up to executive. They have different roles and responsibilities.
Even if you have never thought about it, I encourage you to dip your toe and get some taste of management. You may find it be the calling you never expected.
It’s often said “the best ability is availability.” In order for people to champion your management track, you must make it known to people you’re considering it. This sounds obvious, but crucial. If you never speak up, people might assume you prefer to be an IC. Here are some ways to dip your toe into management.
Start taking on process projects
The hardest gap to fill is to show people you would make a good manager when your resume has only been as an individual contributor. Identify a gap and volunteer to take it on with an action plan. An example of a process project could be a proposal to improve a design review process during critique or drafting a standard operating procedure for the team (SOP). As you take on process and team tasks capture impact metrics on the return on the time invested in you working on such things.
Advocate for junior people and do it consistently
Note that I didn’t say mentor. If you don’t have any, mentor ones externally. There is no shortage of new designers looking for a great mentor and sponsor.
If you want to get a taste of management, then you have to do it consistently and be involved. Mentorship is great, but it’s a different type of focus. To get a taste of day-to-day management, coach someone more junior for them to take action, follow up and keep track of progress.
If you don’t have junior people on your team or company, work with people externally. I assure you people will be thrilled for the time you offer up.
Prepare for the calling, give yourself time
It’s not too soon to start thinking about a management track in your career. However, give yourself time for the opportunities to form for you. Your career is a marathon, not a sprint. Start prepping for the opportunity and it’s not too soon to commence.
Ask the question and perhaps answer the call
Pretend this isn’t all white guys. Which one are you in this painting?
What does your heart and intuition tell you? If you sense a signal, dip your toe into management. Reach out to leaders to get their advice. If you’re interested in talking about it I’m happy to discuss personally or connect you with an advocate.
Remember, you don’t have to make a decision right away, though I encourage you to start exploring those capabilities. Accrue evidence as you begin the management dialog.
Take a moment and ask yourself, “What if the future cohort of great managers and leaders includes me?”
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