Category Strategy


“Those doubting his grand visions have been proved wrong in the past. In 1981 he founded SoftBank to distribute personal-computer software in Tokyo with two part-time employees. On the first day the diminutive Mr Son stood on two apple cartons and announced to those befuddled workers that in five years the firm would have $75m in sales and be number one. They thought “this guy must be crazy”, Mr Son later told the Harvard Business Review, and quit the same day. But Mr Son’s drive and ambition saw SoftBank eventually distributing 80% of PC software in Japan.”

The impact of Masayoshi Son’s $100bn tech fund will be profound.” – The Economist

End Game Analysis: The Performance Spectrum

This article, and the articles that follow analyze my thoughts on what I am calling my “end game.” You can read more about this concept here.

In my recent description of the end game I referred to a (“deep work”) performance spectrum. While my ability to concentrate for longer periods of time is increasing, I’m left to wonder where I fall within this performance spectrum. What equates to maximal deep workability?

The quality of one’s life, if measured along this dimension, relies heavily upon this understanding.

As a starting point, one can argue that corporate life, due primarily to excessive meetings and the prevalence of open office environments, falls just outside this spectrum. To further this point, some of the practices shared below would be considered idealistic, foreign, and at their worst, wrong. For these reasons, let’s classify this as “Level 0” (status quo).

Given this starting point, what do the remaining levels look like?

Levels 1-4: Foundation Building

The challenge at this level is balancing one’s ability to produce efficiently and effectively while remaining reasonably connected with others. The remaining levels omit this internal struggle, at least for now. I will return to this point later on.

Level 1: Utilization of time management tools (e.g., RescueTime) to establish performance baseline; initial email and meeting reduction; greater focus on meaningful work (initial implementation of 80/20 rule).

Level 2: Performance baseline obtained; high-density communications; fixed work hours; further email and meeting reduction (near elimination); hourly time tracking; narrower focus; meditation practice begins.

Level 3: Dedicated workspace and purposeful breaks; work hours aligned with maximum concentration ability; prioritization of projects based on complexity and available energy; explicit stopping points; 80/20 rule fully realized.

Level 4: Utilization of tracking document to monitor training, diet, and work schedule; weekly schedule planned in 30-minute intervals; accelerated ability to produce.

Levels 5-6: Refinement

At this level, what would normally be considered maximal performance is only the starting point for one’s true potential. As of March 2018, I consider myself operating between Levels 5 and 6.

Level 5: Time spent in deep work becomes further concentrated (what would have otherwise been “idle” time is now purposefully omitted to make room for more challenging opportunities); meditation practice increases in frequency and ability; increased journaling.

Level 6: A greater percentage of time is spent on “moderately challenging” or “challenging” subject-matter; weekly schedule takes on increased precision; daily journaling; reading requires greater concentration.

The End Game

The following is an email I wrote to a friend speaking in some depth about what I describe as “the end game.” I will expand upon several aspects of this communication in future posts, but I think sharing the original message here is valuable in itself.

The question you posed – “what is the end-game?” – is one that I have considered for many years. Ironically, you are the second to ask this within a 2-month timeframe (a friend of mine, whose personality is somewhat similar) asked me the very same thing.

I think what I enjoy most in life is the ability to think critically.

The inner struggle that I have been in for as long as I can remember is to “get closer to” sources of complex subject-matter. I think that will pursuit will always be a source of discontent in my life, with varying degrees. At some level, I have learned that this underlying discomfort is normal.

To elaborate, I find myself concerned when things get too “easy” from an intellectual or creative standpoint. In the past, this would equate with abandoning the topic for another. Now, I’ve adjusted my approach in that I will try to stay engaged but do so in a different way. That could be something as simple as getting the work done more efficiently or approaching the topic in a completely different manner. But, at some level, and for certain topics, I feel I am simply pushing the same pieces around on the same board. My goal is to find “boards” that allow for expansion; I have found “design” to be one.

This belief was further reinforced by a quote from Garry Kasparov in his book “Deep Thinking:”

“It’s also a better of opportunity cost. If the focus is too heavily on optimizing, nothing new is created and stagnation can result. It can be too easy to concentrate only on making something better when we might be better served by making something new, something different.”

Two years ago, I went to the GPU Technology Conference in San Jose to explore topics that are beyond my (current?) reach. I went to a talk where the speaker was giving a talk about personal performance. The question I raised in the session was essentially:

“How are some people able to rise to such a level where they are giving talks about complex topics, as discussed in this conference, while others are merely spectators?”

Needless to say, not everyone can be a visionary, but it was a question that I have been thinking about for a very long time. The answer he offered was one in a book called “Deep Work” by Cal Newport.

At the heart of deep work is an intense ability to focus, particularly on challenging subject matter. The book goes into a fair amount of detail in terms of overall strategy and the underlying benefits of “deep work.” Over the past several years (even prior to this talk) I have been steadily working to improve my ability to concentrate and deliver work of increasing quality and depth.

To this point, I recently formulated a deep work “spectrum” to help me understand where I fit within this journey. I have included some early notes about this below.

[Author Note: The details of this spectrum will be discussed in a separate post.]

To bring this email to a close, I fundamentally believe that everyone has untapped potential. As an example, if I look back at my personal training (read: exercise) journey over the past decade, I have made material progress. Surprisingly, I am at a point where I am comfortable with where I am in this space. I could go further on this journey (and likely will), but I have reached a point where I feel I don’t have to.

The difference for me in the intellectual/creative space is that I have not reached a similar juncture. In fact, I feel like I am still far away. Fortunately, I fundamentally believe that the principle of “deep work” is a clear path towards reducing this gap. And while I have made material strides over the past several years, I am really only at the starting line in terms of how deep my concentration ability can go. The benefit of this ability is a greater likelihood of producing new and innovative “work” which is very important to me.

(To be sure, there are other many other (psychological) barriers to realizing “greatness” but I am trying to address those separately, although they play a critical role nevertheless.)

Attention III – Tactics to Strategy

While the previously shared tactics helped improve my raw productivity score, the approach wasn’t airtight.

For example, the use of Evernote helped me distinguish writing from communicating, but was I using Evernote too heavily now? Was the reduction in email traffic somehow giving the perception that I was disengaged? Am I focusing too much on productivity?

As with any shift in approach, there are pros and cons. Focusing too heavily on productivity did pose the potential that I would become further disconnected from the day-to-day reality of the agency. And perhaps I was spending too much time writing, and not spending enough time in other essential creative and technical pursuits.

These were indeed liabilities, but they didn’t reflect my primary concerns. The shift from communicating to writing (read: transactional emails to critical thinking) was a primary tactic. Tactics typically build from a core strategy, and I was absent one.

What does a productivity strategy really mean? Am I interested in further improving my productivity, or is there something else?

One answer came in the form of a best-selling book entitled Rapt – Attention and the Focused Life by Winfred Gallagher.

The book addresses the topic of attention, and how “your life – who you are, what you think, feel, and do, what you love – is the sum of what you focus on.

My focus on productivity is to do more with less. Given the diverse subjects that interest me, and the work required to learn and “realize” the material, transforming what would otherwise be “routine” work into a continuous stream of “high density” engagements is a critical and necessary shift.

If I can refine my focus even further, both in terms of subject-matter and the actual practice, I believe I can accomplish far more than what I’ve accomplished to date and in areas that would have otherwise been left unturned.

Attention II – Realization

While I have always been focused in pushing myself along professional, personal, and physical dimensions, it’s only been recently where I’ve identified the fact that one’s ability to focus is what ultimately matters when it comes to taking on harder challenges.

When I was in high-school, I had a desk that had four small storage areas located towards the rear of the primary work surface. These areas were originally designed to hold small items such as envelopes, tape, and writing instruments, but they frequently attracted many other items that I simply didn’t know what to do with.

While my workspace was fairly well-kept, I found myself distracted by these random items that would find their way within or adjacent to the work area. To alleviate this, I built a wooden structure that encapsulated the work area and allow my mind to focus on the work instead of these random belongings. I also went as far to purchase ear protection headphones (!) in an attempt to eliminate, or at least further reduce, all distraction.

This “physical barrier” strategy had a positive effect on my ability to produce, although I recall struggling internally whether all of this was really necessary. After all, my friends seemed to focus reasonably well void of such scaffolding.

Over the next two decades, I continued to refine my ability to focus and made steady improvements across fairly diverse contexts. However, I always felt that more could be done.

Several years ago, after realizing that the vast majority of my time appeared to be spent compiling and responding to emails, I decided to try a new approach; I signed up with an online service called RescueTime.

The premise behind RescueTime is that it assumes that you spend most of your time on the computer, yet you aren’t really sure how much time you are spending on activities that add real value.

RescueTime monitors the applications that you are using and the time spent on each. It identifies, with your help, those applications that are considered “productive” (e.g., Adobe InDesign) and those that are “distracting” (e.g., YouTube). Further classification ability is also provided for those who wish to dive deeper into the underlying data.

The first year’s score came as somewhat of a surprise: 52% productive

RescueTime confirmed my suspicion, and I felt good knowing that improvements were not only desired but necessary. I decided to take action through two simple tactics:

  • Tactic #1: Send less email. The less email I send, the less I’ll receive. Volume problem solved.
  • Tactic #2: Stay out of email completely, and turn off all notifications. Distraction problem solved.

This didn’t mean that I stopped sending email, but I found that what I was really interested in doing was thinking critically, and I accomplished this through writing. The solution? I replaced Outlook with Evernote.

Now I had a tool for writing versus a tool for communication. Both are necessary, but recognizing this difference is what really matters.

Using these two simple tactics, my productivity score improved nearly 30% over the next 4 years, and I am just getting started.


[This article is part of a series of articles focusing on my professional experiences over the past 5 years.]

In December of 2010, I wrote an article as part of a series entitled “Mental Evolution” where I focused on a topic known as “learned helplessness.” Here’s a short excerpt:

“When one experiences a stream of continuous failures, one’s ability to remain optimistic becomes more difficult.  While there are those that have “bulletproof” levels of optimism, I unfortunately, do not currently fall into this category.

“Crises that I can “plan” for (e.g. burglary, fire, etc.) are easier for me to maintain a high level of optimism than those that I cannot foresee.  Since there will be many challenges that will not display an “early warning signal”, my main challenge is to learn how to develop the skills necessary (i.e., an enhanced explanatory style) to ensure my optimism remains high independent of the crises encountered.”

The applicability of this excerpt will soon become clear, but it’s important to share a brief refresher on “explanatory styles” and how this pertains to feelings of “learned helplessness.”

When examining past performance, it’s important to understand one’s level of relative optimism and pessimism. Pessimists and optimists differ in many ways, but their primary difference involves their explanatory style: (Wikipedia –

Permanence: Optimistic people believe bad events to be more temporary than permanent and bounce back quickly from failure, whereas others may take longer periods to recover or may never recover. They also believe good things happen for reasons that are permanent, rather than seeing the transient nature of positive events. Optimists point to specific temporary causes for negative events; pessimists point to permanent causes.

Pervasiveness: Optimistic people compartmentalize helplessness, whereas pessimistic people assume that failure in one area of life means failure in life as a whole. Optimistic people also allow good events to brighten every area of their lives rather than just the particular area in which the event occurred.

Personalization: Optimists blame bad events on causes outside of themselves, whereas pessimists blame themselves for events that occur. Optimists are therefore generally more confident. Optimists also quickly internalize positive events while pessimists externalize them.

I consider myself a realist, which, for me, is a combination of long-term optimism and short-term pessimism. The former helps me manage the challenges (real or perceived) that I may encounter on a given day, while the latter provides strength and helps me distinguish the “forest from the trees.”

The relative levels of permanence, pervasiveness, and personalization vary depending upon the situation. I’m fortunate to have examined these feelings over the past 6+ years, and thus I’m increasingly aware of these explantory styles & underlying feelings. I also have greater “control” over them, yet this does not equate with true mastery.

When a “negative” situation extends for a lengthy timeframe (in the midst of continuous and purposeful responses to the contrary), one’s explanatory style is likely to drift to that of true permanence, pervasiveness, and personalization. Combined, these equate to feelings of “learned helplessness.”

“Learned helplessness is behavior typical of a human or non-human animal that has endured repeated painful or otherwise aversive stimuli which it was unable to escape or avoid. After such experience, the organism often fails to learn escape or avoidance in new situations where such behavior would be effective. In other words, the organism learned that it is helpless in aversive situations, that it has lost control, and so it gives up trying.” (Wikipedia)

The opposite of learned helplessness is learned optimism. Learned optimism is the idea in positive psychology, coined by Martin Seligman, that a talent for joy, like any other, can be cultivated. Learning optimism is done by consciously challenging any negative self-talk. (Wikipedia)

In my particular situation, and expanding slightly for emphasis, years of adjusted strategies and tactics to realize a natural, and necessary outcome (i.e., increase digital revenue), eventually resulted in a period of non-action, a direct contrast to the continuous investment that I and my team had pursued in the years prior.

Interdepartmental communication and collective understanding, while originally low, now began a steady decline. Our return on investment (real or perceived) was fast approaching zero. Harboring feelings of learned helplessness, my only real alternative was to strengthen the position that was well-understood by the organization (e.g., “run the engine”), and focus less attention in areas that were originally seen as creative and intellectually advancing.

Unfortunately, this behavior and negative mindset reinforces itself to a greater extent over time.

For example, “students who repeatedly fail may conclude that they are incapable of improving their performance, and this attribution keeps them from trying to succeed, which [results] in increased helplessness, continued failure, loss of self-esteem and other social consequences.” (Reference:

In this situation, these feelings of helplessness were also intertwined with feelings of optimism; the feeling and belief that better things were ahead. This contrast, this pulling between two opposing forces, can be challenging to navigate and comprehend. However, expending energy to manage this contrast is a far better situation than one void of such polarity.

Ultimately, and the reason why I’ve re-introduced these two concepts here, is that my explanation for why things happened the way they did is biased and oriented primarily around my explanatory style(s) and personality. Asking an optimist to examine the same events that took place over the same timeframe would likely yield a much different explanation.

One benefit in looking back to 2010 is that I can compare my relative performance in this space. While I still need to respond more rapidly (i.e., fail quickly) to seemingly changeless situations, the time spent in pure analysis and reflection has been significantly reduced.

While possessing a realist mindset goes against “positive psychology,” it affords me a unique perspective to look beyond surface-level interaction and reasoning, and instead dive deeper into alternative mechanics that relate to the events at play. This understanding will enable me to take effective action much more rapidly and purposefully over time.

In summary, what I need to work on at this stage is to learn how to identify “failing” situations sooner and determine whether “first aid” or “surgery” is required to avoid a relapse of learned helplessness. Optimism is useful to a point (e.g., we can do it …), but pessimism may ultimately save the day (e.g., this project is failing, and we need to pursue a different course).

Distillation and Recalibration.

[This article is part of a series of articles focusing on my professional experiences over the past 5 years.]

The narratives surrounding my five-year journey will cover a wide-range of experiences and lessons. The difference I’m hoping to achieve through this exploration is to avoid documenting a simple checklist of “what not to do.” This shallow perspective and outcome will miss the point of such an exhaustive exercise.

As an example, while the strategy may not have attained the end state that I had originally intended, I consider the absence of a strategy in a future endeavor unwise.

What I hope to achieve through this process is a careful distillation of the events, circumstances, and challenges encountered during this period.

Distillation is about refinement, and the “extraction of the essential meaning or most important aspects of something.” When one steps outside of one’s self, which is critical for such an exercise, one gains a perspective that is not dissimilar to looking at a simulation from above. The primary difference is the depth at which one views the activity.

A thorough distillation exercise will ultimately “cut through” the noise in future engagements and continuously recalibrate back to what’s important. This distillation and recalibration process appears to represent two of the most important activities I’ll undertake in the years to come.

Constant Struggle.

“What’s the point?” is a title of an art piece I’m currently designing. The visual design I’m considering is a collection of notes, designs, and other (project) artifacts I’ve created over the past ten years, with an explicit mid-point marker representing my efforts “pre-agency.”

In my view, it’s critical to question the purpose and value of projects/endeavors in which I’ve invested considerable time and energy. Taking the time to examine this creative history can enable one to examine and consider new projects with a much different perspective. It’s a perspective that’s more intelligent and purposeful. This combination enables a greater emphasis on the core “creative” and helps to minimize (not eliminate) wasted energy.

(It’s worth mentioning I’m purposefully omitting the definition of “creative” to open this perspective to projects of all types.)

One goal (I’m also avoiding distilling the number and type of goal at this early stage) is to maximize the “output” or end-result. Maximization, to me, equates with intense concentration and creative contribution, while minimizing the time spent in non value-add activities. These latter activities, while necessary, are “supporting” and thus do not necessarily require the level of engagement the “maximization” activities require.

While I will examine this in greater detail, this is likely to be a constant struggle that will require frequent re-examination.

Considering Strategy.

[This article is part of a series of articles focusing on my professional experiences over the past 5 years.]

The design and development of a core strategy is a large part of who I am and I how I operate. Strategy is about understanding constraints, setting clear expectations, and formulating a vision of the future that other participants can get behind. It’s unlikely, although not impossible, to find someone who is adverse to the articulation of at least a high-level strategy, independent of domain.

In principle, this is an ideal situation. Reality paints a slightly different picture.

First, while everyone appreciates strategic thinking, not everyone thinks with a strategic mindset. On the far-end of the spectrum, if you are action-oriented, you’re less likely to focus your primary attention on a strategic narrative. To you, a strategy is simply a guide; real progress is driven from a tactical/operational approach (“quick action”). Neither method is wrong, but focusing too much attention in one particular area can lead to difficulty.

Secondly, just because someone is supportive of an endeavor, doesn’t mean that they have a vested interest in its success. After all, people have their own agendas and your agenda may not necessarily align. Tying your strategy to a high-level strategy doesn’t necessarily help; the connection helps offer some credibility, but it still does not address the competing agenda issue.

Finally, strategies that are described in a manner that are foreign to the reader, whether that’s presentation length, content, or format, are less likely to be recognized as “valid” and/or “organizationally appropriate.” If your language is deemed too abstract or “complex,” the likelihood of assimilation is substantially less. Participants will take great pains to avoid hurting their self-esteem; “self-handicapping”(+) is one strategy:

Def. Self-handicapping involves the placement of real or artificial obstacles in anticipation of failing performance. In the context of a strategic presentation or follow-up, I’ve witnessed participants use “time availability” has one such handicap.

Ultimately, a strategy is nothing without the necessary action behind it. Convincing others that your strategy is the right one requires the ability to sell your vision. I’ll expand more upon this in a future post

Historical Perspective.

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.