My 10-year vision: Systematizing decision-making

High-level summary: My 10-year vision centers around creating a company or series of companies aimed at improving decision-making on 1) an individual level, and 2) an organizational task/process level.

I believe that when we actually set an intention and write things down, that significantly increases the chance that they will become reality. I’d like to write out my 10-year vision for the future, as it stands right now. I recognize that this is still quite broad, but I wanted to write it down nonetheless.

I. What I would like to focus on

One of the biggest challenges that I have in my own life is making decisions – deciding what decision to make, criteria by which to make the decision, and when to actually stop deciding and to consider the decision made and locked. As such, my 10-year vision focuses on improving decision-making, both in an organizational and in a personal context.

I envision doing this in two main ways:

1. Systematizing personal decision-making at an individual level

2. Systematizing decision-making and automating complex tasks at an organizational level

II. Improving personal decision-making at an individual level

I envision simplifying decision-making at a personal, individual level. Human beings are inundated with information and decisions everyday, and it can get tiring and overwhelming at times. I believe that if we didn’t feel like every single decision was so uncertain and unclear and novel, it would minimize a lot of the stress we face, because we would realize that we have done this many times before and have an approach for dealing with this sort of problem.

Thus, I would like to create tools that enable people to sort through the chaos of this information and recognize the similarities in the situations that they face, and therefore, the similarities in the decisions that they must make. I would like to provide and facilitate the self-creation of frameworks to help individuals analyze the pattern of their past decisions and approach new decisions in an informed and clear way – by understanding what they did before, why they made certain decisions, why it did or did not work, and what they can do now that they are faced with a slightly different, but still archetypically the same, sort of decision. That is, I would like to provide individuals with the tools and frameworks to make new decisions in a confident manner.

Of course, this goes hand-in-hand with increased personal awareness and understanding of our emotions. After all, how can we know what the “right” decision may be, if we don’t know what tends to drive our personal happiness or unhappiness? (if we are solving for happiness, that is)

In order to make good decisions, we need to be very aware of our own personal strengths, weaknesses, sensitivities, biases, and more. We can only understand our emotions through careful reflection of our reaction to certain situations and decisions. We need to be aware of who we actually are. Therefore, part of the process of facilitating personal decision-making also involves a heavy element of facilitating increased personal awareness.

III. Improving decision-making and automating complex tasks at an organizational level

As I have written previously in some of my posts, I believe that there is significant opportunity to systematize certain complex tasks and decisions, many of which are currently done by humans, but which could be simplified and automated by embedding sets of logic into the workflow.

I would like to start a company, or maybe series of companies, to drive innovation in decision-making and knowledge work systematization. I could see this taking place in several ways.

1. Systematizing/automating complex knowledge tasks: As I wrote in one of my previous posts (linked here), I believe that when we think of the bigger picture of complex tasks (e.g., writing memos, making certain types of presentations, making financial models, eventually other even more complex tasks), there is opportunity to take a bigger-picture lens and identify the “archetypes” of certain types of the task (e.g., type of memo, type of presentation, type of model, etc, all further codified based on context and situation), identify the common elements across them, and create a system or process that creates an ~80% version, based on the archetype, customized as needed. I envision creating something in this space, likely for complex knowledge work-based organizations, such as consulting, investment banking, private equity, and other such firms. The starting step for this would be to pick a specific task and create a very robust logic-based system creation for this particular task. If this worked, others would follow.

2. Systematizing work-related decisions through prediction and recommendation engines: As part of this, I also envision systematizing decision-making and prediction in some of these areas. I believe that this includes

1. Stipulating what sort of data will be necessary to consider when making a certain type of decision (e.g., if making an investment decision, identifying what will be most important to consider in making the decision)

2. Gathering data on these elements in previous such situations (e.g., previous similar investment decisions of this “archetype”)

3. Gathering a record of the relative success/failure of these past decisions.

This would help to build a predictive engine for this type of decision, based on analyzing the factors and variables that led to success or failure in past such situations, with the output being a recommended decision and prediction of outcome/level of success (as per defined “success” criteria) based on the decision taken. From there, it would be a matter of, every time this type of decision came up again, gathering these data variables, incorporating them into the model, and reviewing the recommendation that would be provided (while, of course, applying human decision-making and judgement in parallel). As more and more decisions are run through this decision-making engine and the feedback is looped back in (positive, negative, etc, and why), the engine itself would be continuously refined and improved. Of course, there would sometimes be situations of mismatch between human/system recommended decision or prediction of success, and we may realize that there are further variables that would need to be built into the system for better decision-making. As we continuously built in new logic, variables, and information, the questions to be asked and refined include:

-How important is this information?

-What specific factor would it impact?

-With what magnitude would it change the decision?

-In what direction would it impact the decision?

-Would it change the decision or not?

Of course, I know that variants of this are already being done across a variety of different fields. Nonetheless, it is still not systematically applied in a majority of work situations, and I could envision that tools such as this begin to be embedded in a much wider array of situations, down to more daily tasks (e.g., writing certain sales emails, determining strategic priorities based on market sizing/growth rates, etc). This definitely needs to be made more specific in order to be successful (i.e., down to the very specific decision level). I would begin by focusing on something more concrete, and once again with this, I would start with something that I am more familiar with (e.g., consulting/banking/private equity contexts), and expand from there.

IV. Post-10 year vision: Creativity using data

Later on (not necessarily within the next 10 years, but still part of a longer-term vision), I also envision expanding my decision-making facilitation to more creative endeavors. As I have mentioned in a previous post, I would like to enable the development of novel creations based on something like comprehensively tagged databases of “building blocks,” (e.g., such as in dance, figure skating, art, cinema, music, etc) which could then be used to develop something new through unique combinations of these building blocks, aimed at optimizing for what the creator chooses to optimize (e.g., most likely to succeed with certain type of audience, or optimize around a certain style, etc) and along certain parameters (e.g., certain length, budget, etc), with the predictions of success being based on the success of past combinations (contingent upon a large enough database having been created).

This would be a decision-making framework applied in a unique way to more creative fields. Even though on the surface it seems very different than solving for things such as highest-success investment decisions with predicted success based on financial metrics, this would, in some ways, be the parallel to that for creative endeavors (except that it would be decision-making for creation, rather than just for the purchase/sale of existing assets). For example, these proposed creations could optimize for things such as highest expected ticket sales, highest expected audience attendance, etc, which would be similar to the “highest ROI” sort of decision-making done in financial settings.

V. My own path and role in all of this

I’m at the very beginning stages of doing all of this, but the above is a high-level version of what I would like to work toward in the coming 10-15 years. Of course, I recognize that I will need to get much more specific with my vision each of these areas in order to pursue it, and I would do this by picking very specific, discrete problems to solve and beginning there.

I also wanted to think through how I could go about doing this in the next 10-15 years. I would start by creating a company in one of these areas, focused on solving something relatively specific (i.e., a thin slice of a much larger problem). I imagine that this may start more on the individual decision-making side, as that is the more easily accessible challenge to solve, given that I don’t have technical skills in the area. I imagine that my first company would be a challenge, but I’m also sure that it will provide a variety of lessons.

Over time, I would also like to start several other companies, all related to certain areas of decision-making. Through multiple iterations, I would like to learn the skill of creating something from nothing and building it up to success. I imagine that I’ll fail many times in the process of this, and I accept that as part of the learning journey. The failures will be inevitable, but the important point will be to simply get up and continue toward the longer-term goal and vision.

Ultimately, I envision creating some sort of growth ventures fund, in which my team and I start, incubate, and grow  companies in these spaces (task-based decision making/automation and personal decision-making). I could envision it being organized a bit like the below:

Decision Fund [growth ventures fund]

Branch 1: Personal/life decision making

Branch 2: Task/process/automation decision-making

Some of what I would like to build into the culture of my company/companies includes (as a first hypothesis, as I’m sure this may adapt as I get actual experience):

  1. Being ruthlessly results-oriented
  2. Building a learning organization (always learning and iterating)
  3. Building a meritocratic organization in which the best people can thrive, grow, and continue gaining opportunities

In the meantime, a couple of skills that I also want to learn include: data science (at a high level) and investing (in-depth – I think this will come partly through the experience of starting/running companies, and partly through the trial and error of actual investing, both before and during my envisioned growth ventures fund).

Now that I have put it out into the world, I hope that it’ll help me get there by keeping this clear vision in my mind. 

Freedom and responsibility of shaping our reality

High-level summary: Having the ability to shape our own path is an enormous freedom, but we also have the responsibility to ourselves to constantly be aware and continue questioning what is right. It is important to maintain a relentless approach in cutting that which we realize is not, while incorporating our continually increasing self-understanding to decision points in the future.

I was recently thinking about the freedom that I have had in shaping my life and my reality – both out of circumstance, but also because I made it so. I wanted to share some of my thoughts around this in terms of how this has come about, but also the responsibility that this also brings about.

I. Shaping of freedom

As I thought about it, three main things set the stage for freedom in my life from the very outset.

  1. New country: My family and I immigrated to the United States when I was a child, which meant that there was no precedent set for me in terms of what to do – this country was as new for my parents as it was for me, and the old ways of doing things did not hold true here.
  2. Oldest child: I was the first child, so I was my parents’ first experience with parenthood, and I had no siblings to look up to or compete with.
  3. No rooted family traditions: Finally, given that most of my family is relatively independent and non-religious, I have never really had any strong family or religious traditions that rooted me into any set routines or processes.

All this to say – I have had a lot of freedom from the beginning of my life. This meant that as I grew older and began to make decisions, there were no expectations, precedents, or footsteps to follow, from my parents or any family or siblings. What my parents did give me, however, was a guiding light – they pushed me to always strive for the highest and best that I could do, while also keeping in mind my happiness. Despite an unclear exact path, I internalized, from a very young age, the ever-present pursuit of excellence and achievement – and also of happiness.

Over the years, I have shaped my path very independently. I have felt free to explore, try things, fail, try again, and keep trying, across a variety of different areas. I had no expectations to meet other than my own, which tended to be far higher than those of others around me. At times when I felt that I had limited freedom or felt stuck in a “box” of some sort (stringent expectations from others around me that were not aligned with my own), I often distanced myself from this as well. Overall, this freedom has meant that I have taken a relatively unconventional path at times, and likely will continue to do so. However, the freedom to shape my path as I want, combined with my relentless pursuit of excellence, has also come with a certain responsibility to make sure that I am doing the right thing for myself in the decisions that I take.

II. Sensitivity = awareness, which also requires ruthless decision-making

For me, this responsibility has meant constant analysis and a certain hypersensitivity to the situation in which I find myself. I am naturally a sensitive person, but as the weight of my decisions has become increasingly higher over the years, my level of sensitivity has also increased. With sensitivity comes a high level of awareness.

I constantly assess how I am feeling and try to determine what is causing me to feel a particular way. I track (in my head or in written format) the specific emotions that I am feeling at particular moments, the situation, and the factors that may be leading to these feelings. I try to be very specific about it, down to getting an understanding of what types of people I tend to get along with (down to personality type), what sorts of work situations I enjoy (down to particular focus areas, tasks, and team situations), where I tend to enjoy living, and more. Doing this over time has enabled me to develop a very keen understanding of the small factors of the bigger-picture situations that lead me to have positive or negative experiences. With enough data points, my level of certainty increases, and I am able to form a relatively clear picture of what it is that I like or do not like.

When I realize that something is wrong or right with a high level of certainty, I try to act upon that (whenever possible). That may mean changing course, cutting ties with certain people, changing work direction, or other such measures oriented around change and decision-making. It may also simply mean that next time such a decision comes about, I am more aware of my preferences, and can make a more informed decision that will likely provide a better experience.

Over the course of time, I have realized how important it is to take steps to cut out that which we know is not right, and to take steps toward that which is right (or at least toward the unexplored and unknown, if we already know that what we have tried is, at least, not right). We need to be ruthless in cutting things out or making better decisions, because that is the only way that we can create the empty space to fill with something that has the potential to be better.

It is only in taking these decisions that we actually get the feedback to continue making more decisions that are increasingly more right – tailored toward increasing the good and decreasing that which is not right.

Over the course of my life, I have tried to become increasingly active in making these decisions for myself, even though it can be hard sometimes, and I have not always perfectly followed this. Nonetheless, in business and in life, it is an important mindset to take. In shaping our reality, we need to be both aware, but also relentless in acting upon this information.