The Obstacle Is The Way

I recently finished reading The Obstacle Is The Way by Ryan Holiday. I was a little skeptical at first – since most self improvement style books are pretty much the same – but I heard great reviews so I jumped.

I don’t typically highlight books or take notes but I couldn’t help myself. There were so many gems. Here are a few of my favorites.

There is no good or bad without us, there is only perception. There is the event itself and the story we tell ourselves about what it means.

Holiday has anecdotes of people being genuinely excited to practice patience or calm in the face of negative experiences. Like most people I often cannot take make this connection right away, but now I’m reminded to practice. And practice makes permanent.

And what is up to us? Our emotions, our judgements, our creativity, our attitude, our decisions, our determination. This is our playing field, so to speak. Everything there is fair game. What is not up to us? Well, you know, everything else. The weather, the economy, circumstances, other people’s emotions or judgments, trends, disasters, et cetera.

While this seems obvious it’s shocking how many people (including me!) forget this point. I always find that taking a step back from the problem, asking myself why I’m stressed or angry, and reminding myself that I can’t control other people’s reactions almost always helps stay me on course.

Certain things in life will cut you open like a knife. When that happens—at that exposing moment—the world gets a glimpse of what’s truly inside you. So what will be revealed when you’re sliced open by tension and pressure? Iron? Or air? Or bullshit?

I thought this quote was a perfect summary of all the lessons and stories in the book. When everything goes to hell, how you react or get back up is truly how we’re all measured. I know I don’t want to be full of bullshit.

Service first

One of my favorite companies — Automattic, creators of WordPress — recently hired design heavyweight John Maeda. With a resume including the Rhode Island School of Design and working with entrepreneurs at venture firm Kleiner-Perkins, Maeda sounds like an amazing hire. While reading the Wired article announcing his move I found this great tidbit…

Maeda’s description of the new role is still vague, but his first few days at Automattic see him sweating the details. He’s doing a three-week stint as a customer service rep (Automattic calls them “happiness engineers” and requires every new hire to spend time in the role). If a WordPress user has trouble, say, navigating a menu, Maeda receives the ticket and replies with instructions—a baby steps approach to becoming acquainted with a service’s overall user experience. It’s a departure from his gig in VC, where he focused on the big picture.

While I’ve always known of Automattic’s new hire philosophy it’s amazing to see someone of Maeda’s status go through this process too. This is a direct reflection of the company’s commitment to community and customer support. I’d love to see more companies adopt this approach. How can a design leader truly craft an amazing product if they aren’t in tune with the challenges and concerns of their audience?

Web trends

I love the HTTP archive. For people who work on the web it’s a great way to see long term progress, especially if you’re just focused on the day to day.

Here’s one of my favorites — web font usage.

Screen Shot 2016-06-02 at 10.31.31 PM

Back in 2010/11 when Typekit was growing this percentage was in the single digits. Over the years it’s grown to a new average of 60%. When you consider the size of the web it’s a massive change.

So what does this actually mean? Adding web fonts to your site means using your brand’s typeface across all mediums (print, tv, web, etc.). It means removing flash and other rich media that take light years to load (especially on mobile) and make it tough for search engines to index. It means improving the accessibility of your site so people with visual, audio or other disabilities can view your content. It means browsers can easily translate your text into other languages so your content can reach new audiences.

This is progress. It’s always fun to look back and see how far we’ve come.

Shipping makes you better

David Cancel, the former head of product for HubSpot, has an excellent post about shipping your work to make gradual progress. While reading the post one of his comments really hit me..

When you’re constantly shipping, you’re constantly learning. But here’s the other benefit of always shipping — it makes you a better teammate too.

Shipping equals showing your work, and showing your work creates an environment of transparency and shares your thought process with everyone.

While working in business development and sales it’s pretty easy to communicate your progress. Closing deals for revenue, new users or product growth is a version of shipping. You can quietly go about your work as the results are measurable daily. The numbers don’t lie.

After moving towards marketing and product management it’s been a complete change. It’s so easy to let a couple weeks go by without communicating progress — however small — with your colleagues. You can’t expect everyone pick up on what you’re doing and why it’s important. The best leaders and product builders not only ship, but also get everyone bought in on the goal. Reading this was great timing for me personally.

Asking for feedback

At some point in our professional lives most of us have been coached on delivering quality feedback. It’s a critical skill that people of all ages and experience levels need to develop and hone. But delivering feedback is only one half of the equation, the other half is asking for feedback, and depending on your role at a company odds are you probably need to ask for feedback way more than give it.

In asking for feedback I believe there are two important components — context & constraint. Let’s unpack those words a little bit. Context is critical because it helps the giver understand what you’re hoping to achieve. Without context they don’t know if you’re looking to brainstorm ideas, or stress test a single idea. By providing the feedback giver with adequate information they know how to best help you.

Constraint puts the power back in your hands. By constraining the feedback to a specific focus the feedback receiver can block off topic comments and realign focus to the task at hand. There’s nothing worth than starting with a simple brainstorm exercise then crashing off course into an implementation discussion. When off topic comments and questions come up, politely decline to answer stating it’s not the focus of this discussion and get back to the objective.

In short, tell people the type of advice you’re looking for. They will feel helpful, and you’ll get the answers you need. It’s a win-win situation.


Success and failure

On my last day of college one of my professors passed around a small slip of paper to everyone in attendance. It read,

Never let your successes go to your head. Never let your failures go to your heart.

I have no idea who the author is but for the last six years I’ve had this quote pinned to my desk at home. To me it packs a similar punch to Steve Jobs’ “stay humble, stay hungry” line. Most of the time I forget it’s there but every now and then my eyes glance over and I’m immediately grounded. I’m reminded that life is a marathon and that we should all enjoy the journey.

Working remotely

It’s taken a while for corporate culture to change, but change it has. More and more employees — from startups to large corporations — are starting to work from home or join distributed teams. If you’re thinking about transitioning to this type of work environment I’ve written down a few pieces of advice to consider when pondering the next move.

First, some qualifications. While limited, I do have some experience working on both sides of the remote team concept. At Typekit our team of 20 was located in San Francisco with remote offices in New York and Chicago. During the independent days of Typekit I was located in our San Francisco HQ of 13 employees. Even though our HQ was small in size San Francisco was the official home for the company.

After leaving Adobe / Typekit for Zemanta the situation was completely reversed. At Zemanta we have offices in San Francisco, New York and Slovenia. Slovenia is home to our product and engineering teams, and New York holds down sales and account management. I hold down the fort for product management, partnerships and marketing. An office of one.

Last year, I also had the opportunity to live in London for 3-months while my wife Emily was on rotation at Google. We were extremely fortunate and privileged to have that opportunity but once again another example of remote work. An office of one in London with the rest of the Zemanta teams still in New York and Slovenia.

After working through each of these situations over the years I’ve found a handful of tips that I believe people should keep in mind if they are thinking of working for a distributed company, or they work from home full-time.

Set a schedule. Depending in your time zone it’s easy to wake up for a 7am call, work til noon and completely forget to shower or eat breakfast. Even if you’ve been super productive in your work — if you’re like me — it’s hard to feel like you’re having a good day if the essentials like eating and bathing aren’t on schedule. Whether you’re a morning person or night owl I’ve found it helpful to set designated work hours so you have some guidelines built into your day.

Offline means offline. This goes hand in hand with #1. If you’re living in Europe and communicating with a team and clients in the United States it’s very easy to wake up to a full inbox and end your night with a flurry of instant messages or meeting invites. Letting others know your hours of availability will lead them to be more conscientious when communicating with you. It also gives you the mental freedom to stop checking your email and messages when you’re supposed to be spending time with friends and loved ones.

Have a designated work space. It doesn’t matter if it’s your couch, the kitchen table, an office space or a local coffee shop. Wherever you choose to work make sure you make that space your own. Maybe it’s an extra monitor, custom notepads or just a comfy chair, these subtle changes enable you to focus directly on the work rather than trying to get comfortable every 10 minutes.

Tools bridge the distance. I’m not going to tell you which tools are the best, that depends on the type of work you do, the company you work for, and how you personally like to organize and work. That said, it’s important to choose tools that help you communicate effectively and collaborate with your colleagues. Great tools make you feel like everyone is sitting in the same room, and poor tools will leave feeling even more cutoff than you already are. My advice is to do your homework on the types of tools and services you believe will help you be more productive, and then constantly evaluate them. Why continue using a service if it’s not providing you and your team value?

Get outside. For anyone working from home full-time, this is a requirement. Even for introverts like myself staying in the house all day is not healthy long term. We all need to get some fresh air, see our friends and experience life beyond the computer screen. Whether it’s going to the gym, having coffee with friends or seeing a movie, schedule regular outings so it’s easy to get out of the house at least a few days a week.

Working remotely often has a lot of benefits — flexible schedule, independency, and much more — but if you’re not careful it can really put a strain on your personal and professional lives. Make the necessary preparation and then dive in. Good luck!