Two weeks ago I gave notice to my job that I would be leaving at the end of the year. On January 5th, I am moving back to Chicago to start a business with some friends.
Time for Change
Sometimes we find ourselves in an uncomfortable spot in life, needing to make a change even though the motivating forces are blurry. This happened to me a few months ago. It had become increasingly clear to me that my job wasn’t right for me. More specifically, it was the role that I played in the organization and how it was no longer providing me with the skill growth I was hoping to gain.
You see, I studied graphic design (and, laughably, music business before that) in Chicago. But before I studied graphic design, I had this intuitive sense of what made good software products and how one could use software to solve problems. I also had an uncanny knack for getting in touch with people who had no reason to talk to me. Becoming a designer was a small step to start building the hard skills I needed to be able to look at myself objectively, as if I was starting a business, and say “I want to work with that guy”.
The goal at the time, as a 19-year-old college sophomore, was to find a way to work for a technology startup in San Francisco. There was little else on my mind; I had to get to San Francisco and get my foot in the door. Nothing else felt like it would prepare me to someday start my own company more than to be “in the middle of it all”.
Right before my final year of college, I found a way to get in touch with Twilio. Not long after, the stars aligned and they had an opening for me. Almost exactly two years ago, I left Chicago and moved to San Francisco. Over the past two years I have played the role of a product manager, and I have enjoyed almost every moment. My time there has been truly great, and even though we have had our disagreements over process and other things like that, the company treated me extremely well. I gained everything from the job I was hoping to gain, plus some much needed clarity of purpose.
Cheating My Way In The Door
The problem is that I cheated. I snuck my way into a job at a great startup because I thought that was what I wanted. In my mind, the only thing that mattered was to be working at a startup. The role I sought out was product manager, mostly because my design and programming skills were too thin for someone to hire me to do either of those fulltime. I thought that would be okay. I could get my foot in the door and slowly move from a product manager role into a product designer role, which is the role I preferred.
Thus, as time went on, I continued to feel unfulfilled. My projects were exciting and I had autonomy, but I wasn’t playing the role that I needed to be playing. Too often I found myself not caring deeply enough about the output of the product because I didn’t have a direct hand in crafting the code. My input was always from standing behind the engineer, which if you are a builder, is a sad place to be while giving advice.
Toiling in Obscurity
So far, the best analogy for my situation is one based on another love of mine: standup comedy. Imagine that you are a young standup comedian. You have only been performing for a few months. However, you know that if you are going to make comedy into a career, then some day you need to move to Los Angeles to be in the thick of the scene.
One day, you take a job as a associate producer on a sitcom in Los Angeles. You think this is the break you needed to get your foot in the door. You’ll be able to do standup shows at night, and work as a producer during the day. Then a few months or so later, you’ll be able to quit your producer job and become a full-time standup comedian.
The problem with this situation is that you rarely find the time or energy to practice your craft at night. You never write new material and rarely evolve your existing act. You can’t quit the producer job because you need the money to survive in Los Angeles, but the job is the primary thing holding you back from progressing. You realize the only way for you to work as a comedian is to jump ship. You must toil away in obscurity while you hone your craft. Only then, once you accept that you can’t get past doing the long hours and hard work, can you really start to make progress.
Clarity of Purpose
It has become clearer than ever what I desire to accomplish in the next stage of my life. That is an important part of all of this. In the past, my actions felt like they were driven mostly by ego and the desire to be known in the startup community. If being out here has taught me anything, it is that none of that stuff matters (obviously). It is okay if I don’t fit in and if other people don’t understand my motivations.
My problem is that I also took a job that wasn’t exactly what I wanted to be doing so that I could be in San Francisco, instead of staying where I was and honing my craft. I wouldn’t change any decision I have made so far, but I do think it is worth evaluating those decisions over time. I have learned and grown immensely while working out here in San Francisco, but the time is right for me to move on.
One last thing…
Words could never express the thanks I owe Jeff Lawson, CEO of Twilio, for taking a chance on me two years ago. He gave me an opportunity nobody else had up until that point. I can only hope that I provided a fraction of the value to Twilio that he provided to me. To observe Jeff leading the company and product team was inspirational and hugely impactful on me.
Thank you to everybody who I worked with the past two years (particularly you, Thomas). You’ve been phenomenal friends and an invaluable support structure. The founders of Twilio (Jeff Lawson, Evan Cooke, and John Wolthuis) have built a truly special company. I am incredibly proud to have been there during some of the foundational years. It will be particularly exciting to watch from afar as everybody drives the company to new heights.
Even though I’ve seen most of Stanley Kubrick’s films and read a fair bit about him, I was surprised to recently discover that he always did the hand-held camerawork for his films. It was less a surprise to the extent that he, famously demanding and meticulous, had a specific vision which needed to be realized, but more-so a surprise that he would take on the task himself instead of delegating to his crew.
Why would a director like Stanley operate the hand-held camera for all of his movies? By this point, Kubrick had released many critically and commercially successful films, so he could likely hire any camera operator he desired. Actually, that is exactly what he did. Stanley only worked with the best on his films. So then why would he, needing to manage countless tasks while on set, choose to operate the camera over his best-in-the-business cameraman?
Yes, all of the hand-held camerawork is mine. In addition to the fun of doing the shooting myself, I find it is virtually impossible to explain what you want in a hand-held shot to even the most talented and sensitive camera operator.
You see, Stanley started his career as a photographer in New York City in 1946. Soon after, in the early 1950s, he began making films. His first few projects had minuscule budgets which required him to fill almost every duty, including director, editor, lighting, sound effects, and cameraman.
As Stanley’s film career continued, he operated on a different frequency, dictatorially controlling even the minutia in a manner which surprised and frustrated most crew members. As such, he could see every shot in his mind’s eye so clearly, it was seemingly impossible to delegate. It’s not that he didn’t trust his camera operator, but Stanley was legitimately the only person who could do the task in the way it needed to be done.
Craftsmanship and Execution
Lately it has started to feel like our society respects “vision” more than the actual craft of execution. We believe that we can hand off orders for someone else to execute upon. As long as we guide them to complete our vision then everything will be fine. It is sometimes desirable as we become successful or start working on teams to start delegating seemingly basic, inconsequential tasks, yet we should be careful to not fall into this trap.
Whether we’re filmmakers, designers, product managers, photographers, software engineers, or something much different, we should try to be aware of and cultivate most of the skills required to finish any project. We easily forget that the crux of a project comes together in the details, and the person executing on the vision is in the strongest position to have an impact here.
Many people want to become the director, the boss, the one who gets to sit back and tell everybody else what to do. Forget that. Let us be the ones who help execute the vision while also setting the vision. Strive to continue executing for yourself, and only hand over the reigns of a task when you absolutely cannot do it yourself any longer.
You will hopefully notice that this approach requires us to do less overall and to increase our focus on each unique task. Our surroundings have pressured us to believe that doing less and moving slower are negative characteristics, but I see them as a obvious advantages. We could all use some more pacing and care in our work, particularly in this era of overabundance.
Remember, even Stanley Kubrick got down in the dirt with the camera in his own hands, because if he let go then he would have lost control. Stanley knew that life was long, and compromise is an unfortunate game.
Marco Arment wrote a short and interesting post about creating lasting value during his lifetime. It is something we should all aspire to do. With my posts here I try to capture truths which I feel are not beholden to this moment, but can be referenced at any point in time and still be informative and valuable.
Here Marco says it in his own words:
Most of my favorite writing over the last few years was about specific products or technology companies. There’s a place for that, but in one year or three years or thirty years, who’s really going to care about the politics of technology and the nuances of gadgets in 2012? My primary outputs, professionally, are software and writing. This is what I’m contributing to the world. None of the software I write today is likely to still be in use in thirty years, but if I write a truly great and timeless article, that could be valuable to people for much longer.
Why is it that in most instances we are our own biggest obstacle in the way of making progress? We tend to care only about big, world-changing, important problems. We talk about projects which we deem unimportant as if they are without merit. However, the solutions to important problems seldom have such ambitious beginnings. Instead, most important problems are solved by projects which had humble beginnings and only became important over time.
On his blog, Yossi Kreinin, a software developer, argues that we should instead work on unimportant problems:
Working on unimportant problems can create important side-effects. A whole lot of mission-critical, world-changing and even life-saving tech is a by-product of “unimportant” things - time-wasting infotainment products, or personal pet projects started without a grand noble cause.
Industries with heavy regulation are also often the ones which have the most important problems (healthcare, transportation, education, etc). Regulation is supposed to protect these industries. However, innovation is stifled due to the huge expenses and man-made obstacles in the way of bringing a solution to market. Yossi goes on to explain why so much progress in these industries has actually come from other places:
The same is happening in the automotive market, the healthcare market, etc. There’s progress, of course, just nowhere near the progress in more frivolous areas - and much of the progress in “important” areas is a byproduct of progress in frivolous areas. As in, the best system for managing patients’ records may well be Google Docs that doctors access from their iPads.
To overcome this we should hope to inspire more frivolous experimentation. When we experiment, we ask questions of the world and we try to find answers quickly. Experimentation often allows us to find answers in places we weren’t even looking. Encouraging playfulness, both for yourself and in those around you, might solve more important problems than you expect.
So if you ask me - by all means, work on unimportant problems. They’re often more fun to work on, and ultimately you never know how important they really are.
When I moved into my current role as a product manager at Twilio, I chose to focus on building internal tools for the company. The goal is to empower my coworkers with the tools and knowledge they need to build better products and provide better service to our customers. I believe strongly that companies should be cognizant of their limitations, and that they should provide themselves with the internal products to overcome those limitations.
Knowledge can be dangerous
We all know that knowledge can be powerful. However, when knowledge is owned by a single person or a small team then it is dangerous. Your company should minimize any individual or team specific knowledge. It’s hazardous and will likely shoot you in the foot someday. If you have pieces of the company that are managed by any small group of people, find time to train other employees to understand those systems or business processes. You should worry about the potential damage that can be done to your business if something were to happen because not enough people were knowledgeable or had the right tools to do their job.
An individual’s fear and cynicism can permeate quickly through teams and inspire irrationality in actions. Fear and cynicism are destructive to companies. For example, I’ve often heard engineers refer negatively to certain parts of a company’s codebase. They say “I don’t know what goes on over there” and reject any notion that interacting with those systems could ever be easy. In reality, these engineers are more than capable. Their response is totally irrational and based essentially on fear.
“Beware of the guy in a room”
A few months ago, J.D. Hildebrand wrote about seeing Jim McCarthy speak at the Software Development Conference in 1989. McCarthy spoke about his experience managing teams who ship software projects, and he focused primarily on building healthy teams. Looking back, Hildebrand’s favorite lesson from McCarthy was about the “guy in a room” phenomenon.
Hildebrand recounts:
Many projects, he explained, have at their core a challenging bit of code that is assigned to the development team’s acknowledged superstar. This programmer takes custody of the crucial module and retreats to his office. The team spends the next weeks tiptoeing past his door so they don’t interrupt his intense focus.
Having superstars on your project is always a blessing, but as I discussed earlier, allowing any individual to solely own a crucial piece of any project is very dangerous. Then McCarthy continued on to make his most alarming statement of the talk:
His code will be ready when it’s ready.
Empower the individuals, empower the team
Try to imagine what happens if this employee, for any reason, is no longer with the company. How will you finish the project? How will you maintain this this core piece of the project in the future? The other engineers will look for every way to circumvent working with this section of the codebase. If you empower individuals from the start, then the team will always be able to function properly, even if it loses the people who once owned important systems or processes.
How do you overcome this information silo conundrum? First you need to make sure that you are aware of all potential pitfalls in your organization. Once you discover which areas need to be operationalized, start to map out how you can best spread this knowledge amongst your employees. Do you have training sessions? Do you rotate employees between teams? Do you build tools which help break the information silo? At Twilio we ensure that almost every system, business process, and carrier escalation path has its own runbook. This has worked for us so far, but a company’s abilities and needs change as it grows.
Tools of the trade
In my role as product manager for internal tools, my focus is solely on improving the way that our employees do their jobs. We build the tools which help a customer support rep diagnose audio quality issues in an individual phone call. Other tools give our sales and marketing teams the reports and metrics which inform their strategies. There are numerous projects like these which empower our employees and make them increasingly more effective in their positions. Twilio’s ability to think at scale and do more with less will continue to be one of our defining characteristics.
Every profession has tools which empower the craftsman or craftswoman. We are lucky in the software and technology industries to have the ability to create our own tools. We are also fortunate that our tools are easy to tailor to fit the exact needs of the task infront of us. Beyond that, it is incredible that so many people in our industry take the tools which they built for themselves and share them for free online.
Finding value
It is basic human psychology to enjoy the feeling of other people needing and relying on you. However, as soon as you realize that your colleagues are constantly relying on you for information or to do a common task, you should realize that this is a problem. Find a way to share your framework for thinking and solving the problems with them. Build the tools which allow them to get the job done without you. Only when other people don’t rely on you will you be able to focus your efforts on the work that really matters. Make yourself irrelevant, and you’ll discover that you are now valued more than ever before.
In today’s world, where we are hyper-connected to one another in more ways than ever, it seems that we often forget that humans are the primary consumers of the products and services that we all provide. We regularly release things to the world that we wouldn’t recommend to our own friends, and provide service and support to other people in ways which we would be offended to receive. We are now equipped with more tools and knowledge to produce the best products ever possible, and provide the most human interactions ever possible, directly to people all over the world. So why don’t we act like it?
Habit
Sometime last week, as I was sitting on my couch at home and winding down for the night, I noticed that there were updates waiting for apps on my iPhone. I am fairly religious about updating apps, so I did as usual and downloaded the pending updates. This particular night there were updates for two games waiting: Circadia and 1-Bit Ninja.
Normally I skip reading the release notes for an app, but if it is an app I particularly care about then I try to peek at them to see what’s being updated. Most release notes for an app update plainly list what is being updated, and that’s about it. For 1-Bit Ninja, there were three short items, the first stating that the developer, Ben Hopkins, was releasing an entire new world full of levels. “This is awesome!”, I thought to myself. For a game purchased for $1.99 last summer, it is incredible to continue receiving significant updates months later.
When looking at Circadia’s release notes, I was greeted with a letter from the developer, Kurt Bieg. I was intrigued, as almost all release notes that I’ve seen from iOS apps up until now are usually just a checklist of the updates. There might be a blog post online somewhere, but usually the details are “1) bug fixes 2) a small new thing 3) another small new thing”, and that’s about it.
Unexpected
This was a shocking experience. I felt like Bieg had written a letter directly to me, the player. I felt connected to him, and was now particularly excited to try out all of the new stuff that he built for me. At least, it now felt like it was built specifically for me, but in reality I was one of many thousands of people who had purchased Bieg’s game. The truth of the situation, and what makes it particularly magical, is that very few users update their apps on a regular basis. Then, even when they do update their apps, the number of people who decide to click through to read the release notes is undoubtedly small.
This left me giddy and, frankly, a little dumbfounded. I decided to reach out to Bieg on Twitter to tell him how much I appreciated the letter. It was informative, kind, and most importantly, unexpectedly human. We had a quick back-and-forth about how important it is for game developers to show love to the little details of the entire experience and to be human to the people who play their games. Once we moved the conversation to email, he said this:
I think if someone takes the time to try my game, I owe it to them to spend time on them.
For an independent developer like Bieg to take the scarce time that he has to be thoughtful and informative about something which almost nobody will view is meaningful in itself. It reminds me of the dedication to craft which the original Macintosh team took such care to cultivate. Steve Jobs drove them to the edge of sanity by requiring that the inner guts of the Macintosh be as beautiful, if not more so, than the external shell. Now every original Macintosh has the signatures of the original team engraved inside. This device was just as much a piece of each of them as it was a piece of machinery.
Many people are so intensely dedicated to their craft. It’s why I believe that your personality informs your craft, and that you should use that to your advantage. Whatever you create should be treated as a piece of yourself shared with the world. The people who interact with or purchase it should be treated with respect, gratitude, and admiration for giving you their time.
Communication, Identity, and Vulnerabilities
Recently I attended a screening of Indie Game: The Movie, a documentary about indie game developers. The documentary follows the development of two different games as they near their release: the soon-to-be-released Fez and the already successful Super Meat Boy.
Edmund McMillen and Tommy Refenes, the creators of Super Meat Boy, spend a large portion of their time on-camera discussing the personal struggles they have gone through to get their game finished and released. It’s impossible for the viewer to fail to realize that this game has consumed their lives, and more importantly, that their lives have become a piece of the game. You cannot have Super Meat Boy without Edmund and Tommy.
Jonathan Blow, the developer of Braid, makes many appearances in the movie and had this to say:
Making it was about: let me take my deepest flaws and vulnerabilities, and put them in the game.
Most telling, however, is the time you spend with Phil Fish, the designer of Fez. In the movie, Phil states bluntly:
It’s not just a game. I’m so closely attached to it. This is my identity. It’s Fez. I am guy making Fez. That’s about it.
It is truly incredible to me that someone can create something so personal, yet share it widely with the world. Having played both Braid and Super Meat Boy, I can tell you that the joy and smiles I share with those games are something I’ve only experienced during indie titles. That’s also why I am eager to play Fez once it is released.
At Scale
Each person I’ve referenced so far is an indie developer, working alone or on a very small team. You’ll probably argue that the human approach can’t be scaled to work for a major corporation, or even a mid-size game studio. However, back in the 90s particularly, Nintendo was incredible dedicated about responding to kids who wrote letters to them with ideas or questions.
For example, there is an entire blog full of scans of one fan’s childhood letters to Nintendo. Most important is the incredibly thoughtful and personal response that a Nintendo representative sent to the blog’s author, who was a kid at the time. Notice how direct and human the interaction is, and imagine how inspired and connected you would feel if you received this from a company which you admire so deeply. We should all hope to create products and services which consumers connect with, but the career-defining goal should be for them to grow a deep connection with our company and our company’s purpose.
There is a great talk by Simon Sinek about how great companies and leaders inspire us to join their cause. The premise is that you should “start with why”, meaning that you should always question the purpose or reason for doing something before you decide what it is you are going to be doing. Use this concept to help frame your thinking when you are making decisions. If the “why” behind any decision isn’t a positive one for the experience of your users or customers, then it likely isn’t the right decision.
Make It Personal
Let’s go back to Kurt Bieg and Circadia. He crafts each game with such care that he treats the entire experience of playing his games as if they were hand-delivered himself. He writes a letter to his users for each update. You can probably imagine his devastation when he receives a support request from someone having an issue playing his game. Each email or tweet from a customer is a chance to have a personal connection and deserves a genuine emotional response.
He remembers that he is human, and that the person at the other end of the iPhone/tweet/email is human. He makes it personal. It’s the indie way.
“It’s a very rare thing, where you answer to no one at all as a comedian,” said Aziz Ansari
The newest movement in entertainment is upon us. Standup comedians are finally taking full control of how their material is consumed outside of live performances. The beginning stages of this has comedians self-releasing their standup specials online, the first being Louis C.K. back in December, and continuing earlier today as Aziz Ansari self-released his newest standup special in the same way.
Allowing comedians to stay in charge of their product has hugely positive effects in the comedy ecosystem. See Louis C.K.’s comments:
“I don’t have to go, ‘Here’s this product,’ to whatever company,” Louis C. K. said, “and then cringe and shrug and apologize to my fans for whatever words are being removed, whatever ads they’re having to watch, whatever marketing is being lobbed on.”
It’s also worth noting that Louis C.K. has an unprecedented deal with FX which provides him full control over his superb television show Louie, which is currently taping its third season.
These comedians have proven that great entertainment can be made on a budget and without the interference of media executives. More importantly, however, is that consumers purchase and support these shows with incredible enthusiasm. My gut tells me that this trend will continue onward.
It’s on sale now. You can buy it on his website for $5.
The $5 price appears to have become the magic number which conveys value, yet still allows the convenience of an impulse buy. Louis C.K released his standup special at $5 back in December, Jim Gaffigan is releasing his in April for the same price, and now Aziz Ansari jumps into the fray today. This is a trend I can get behind.
Being allowed the opportunity to wander deep into the mind and career of a living comedy icon is an audacious task that can be easily fumbled. Yet Amy Wallace’s August 2010 profile of Garry Shandling still holds true as testament to the affect he has had on standup as a craft and on the comedy industry as a whole.
For the past five years especially, the 60-year-old comic, who counts both George Carlin and Johnny Carson as mentors, has devoted himself to mentoring others. A generation of people at the top creative rungs of Hollywood credit Shandling with shaping both their material and their careers.
Not everybody begins on top. Garry once drove two hours to a George Carlin show to ask the comic to review some bits he wrote:
After that night’s show, Shandling recalls, “he takes me into the back room, which is like the clubs where I work now, and there’s my material on his little table with marks on it.” Carlin walked him through the twenty or so pages one at a time, and then he said, “You’re very green, but there’s something funny on each page.” Very earnestly Carlin added: “If you’re thinking of pursuing this, I would.”
Both of his landmark shows, It’s Garry Shandling’s Show and the truly extraordinary The Larry Sander’s Show, paved the roads for some of TV’s biggest hits like Seinfeld, The Office, and 30 Rock. You won’t find another living comedian who has constructed the under-pinnings of the current state of American comedy as fully as Mr. Shandling.
Apatow says the main lesson Shandling taught him on Sanders was that the curtain that separated backstage from onstage was just a metaphor for how we all hide our true selves. “He always talked about how it’s incredibly rare for people to say what they mean. People are lying a great deal of the time.” That was the root of the show’s humor, Apatow says: the disconnect between “what people are trying to project versus what they’re actually feeling.”
Read the profile on GQ.com here. You’ll be glad you did.
