A series of articles I’m considering is a focus on the creative and technical journey I’ve experienced over the past five years.

It’s during this time where I was tasked to build a digital team and capability set for an advertising agency. I can equate the journey to an Everest ascent, ultimately “losing” several team members and experiencing countless periods of self-doubt, before reaching the “summit.” The summit became a virtual marker for change and not the “pinnacle” I had originally foreseen.

This “history” is important to document and fully understand, as it’s the education I gained from this journey that is materially more important than the end-result, not to mention the countless design and technical artifacts created during this timeframe.

This latter point is worth emphasizing. Things that one creates rarely stand the test of time. This is particularly true in the digital space where a project’s half-life is typically between 6 and 12 months, with a complete dissolution of the original product within 3-4 years. Design artifacts have an even shorter half-life, and project artifacts represent a blip on the radar.

Given this context, it’s important that one take a much broader perspective into one’s work. Focus less on the final outcome, and more on understanding, and refining the methodology used to realize that outcome. In time, the level of effort required to achieve a similar outcome will be less, and the resulting quality and content will be substantially greater.

But this is just one level of refinement. There are, in my view, countless levels that go beyond this, which I’ll do my best to explore in the weeks and months to come.

I recently completed the book entitled “Ai Weiwei Speaks” curated by Hans Ulrich Obrist. I have been interested in Ai Weiwei for several years now, having been primarily exposed to him via the film “Never Sorry” by Alison Klayman. Through the interviews captured in this text, I’ve come across several quotes that reflect my own thoughts. Here, Ai Weiwei talks briefly about the writing process:

“I like writing the most. If I have to value it against all human activities, writing is the most interesting form, because it relates to everybody and it’s a form that everybody can understand. During the Cultural Revolution we never had a chance to write, besides writing some critical stuff, so I really like to pick up on that, and them blog gives me a chance. [..] So in the blog I did over 200 pieces of writing and interviews which really put me in a critical position – you have to write it down, it’s black and white, it’s in words, and they can see it, so you really have no plan to escape. I really love it, and I think it’s important for you, as a person, to exercise, to clear out what you really want to say. Maybe you’re just empty, but maybe you really have to define this emptiness and be clear.”

When I first started writing in 2007, many of the ideas that I captured in my blog were ones that related primarily to events and things I was experiencing during that time. Ultimately, the posts focused primarily on building and increasing my overall sense of awareness. Having no other way to manage the emotions and thoughts that were effectively “running my life,” writing, to me, seemed to be the best way to manage them.

In the excerpt above, Ai Weiwei talks briefly about the “emptiness” and defining it through the writing process. There are times in which I’ve been challenged to begin writing anew, and this is due primarily to a feelings of mental emptiness – what is it I’m supposed to write about? Having read Ai Weiwei’s thoughts about this, it’s now increasingly clear – obvious perhaps – that writing helps one define (make visible) this emptiness.

This post is a good example of this. The emptiness I have been feeling is now a bit more defined. It’s very similar to drawing on a canvas or blank sheet of paper. It’s important to get something down on paper so that the creative process can truly begin. The blank paper is the emptiness. It’s up to me to fill that emptiness and create something anew.

“npm is not a typical product, and we are not a typical “work hard/play hard” startup. We are responsible adults with diverse backgrounds and interests, who take our careers and our lives seriously. We believe that the best way to iterate towards success is by taking care of ourselves, our families, our users, and one another. We aim for a sustainable approach to work and life, because that is the best way to maximize long-term speed while retaining clarity of vision. Compassion is our strategy.“

This past Saturday I completed my fourth marathon. I was four minutes slower than last year’s time (3h 24m), but I was still pleased.

While I have always been active, the desire to improve my strength and endurance began nearly ten years ago. At present, I can report hundreds of miles of running, cycling, and swimming, hours of strength training and at least one 1st place finish (in my age group; sixth overall).

However, it’s only recently where I’ve considered the broader picture. I realized it’s not really about the individual event or accomplishment; it’s about the timeline the event is contained within.

For example, if I only ran one race in my lifetime, it’s simply a “blip” on my radar. In contrast, if I run a race every year for the rest of my life, it becomes a key marker in my personal history. And this marker is likely to contribute to other experiences outside of running:

• Improved appearance
• Improved confidence
• Connections with new people
• New professional opportunities
• New interpersonal relationships
• Etc.

Furthermore, as new accomplishments are added, the timeline and its embedded behavior become stronger and more resilient to potential interruption. Consistent achievement eventually powers itself.

To harness this energy “surplus,” three additional components require explicit development (and their own collective timeline):

• Concentration
• Memorization
• Meditation

In a future post, I will share some of the progress made within this training timeline and what my future plans entail.

I reach a point at least once a year where I pause to re-evaluate my life. Every several years, I go through a similar exercise, albeit in greater depth. The “evaluation” exercise I’ve just completed is perhaps my most exhaustive yet.

As part of this exercise, I recently completed Peter Thiel’s book “Zero to One.” In the text, Mr.Thiel writes briefly about controlling one’s future:

“You can expect the future to take a definite form or you can treat it as hazily uncertain. If you treat the future as something definite, it makes sense to understand it in advance and to work to shape it. But if you expect an indefinite future ruled by randomness, you’ll give up on trying to master it.

Indefinite attitudes to the future explain what’s most dysfunctional in our world today. Process trumps substance: when people lack concrete plans to carry out, they use formal rules to assemble a portfolio of various options. This describes Americans today. In middle school, we’re encouraged to start hoarding “extracurricular activities.” In high school, ambitious students compete even harder to appear omnicompetent. By the time a student gets to college, he’s spent a decade curating a bewilderingly diverse resume to prepare for a completely unknowable future. Come what may, he’s ready – for nothing in particular.

“A definite view, by contrast, favors firm convictions. Instead of pursuing many-sided mediocrity and calling it “well-roundedness,” a definite person determines the best thing to do and then does it. Instead of working tirelessly to make herself indistinguishable, she strives to be great at something substantive – to be a monopoly of one.

“[…] Optimists welcome the future; pessimists fear it.”

Using this categorization scheme as a basis, Mr.Thiel goes one step further and postulates four main categories of human existence over the past fifty years:

• Definite/Optimistic: U.S., 1950s-1960s
• Definite/Pessimistic: China, present
• Indefinite/Optimistic: U.S., 1982-present
• Indefinite/Pessimistic: Europe, present

While my mood/demeanor may sometimes reflect otherwise, I consider myself an optimist. However, the two associated subcategories intrigued me; which one did I fall into?

“To an indefinite optimist the future will be better, but he doesn’t know how exactly, so he won’t make any specific plans. He expects to profit from the future but sees no reason to design it concretely.

“Instead of working for years to build a new product, indefinite optimists rearrange already-invested ones. Bankers make money by rearranging the capital structures of already existing companies. Lawyers resolve disputes over old things or help other people structure their affairs. And private equity investors and management consultants don’t start new businesses; they squeeze extra efficiency from old ones with incessant procedural optimizations.

”[…] To a definite optimist, the future will be better than the present if he plans and works to make it better.“

Not surprisingly, it’s difficult to place me in a single category.

On one hand, I always take steps to ensure next year is better than my last. On the other hand, I’ve frequently taken advantage of opportunities available to me without a clear understanding of how it fits within my personal “grand design.”

It’s fortunate I have reached a point in my life where I can transition to a belief system that revolves around “definite optimism” while continuing to recognize the future is, in fact, truly random.