A tapestry of possibilities, but no progress without choice

I think there’s something about “possibilities” that makes us excited — looking at a map and seeing all the places we could go, looking at a list of classes and seeing what the semester ahead could entail, walking into a library and seeing all of the books that we could read next….but that’s the key – “could.” We see a multi-faceted, many-colored tapestry in front of us, and we become excited.

But ultimately, we can only choose one reality. We can only go down one path. And if we try to do all of the things, we may end up with nothing. Or if we take too long to choose, we may also end up with nothing. The longer we stay at a crossroads, taunted by the multitudes of possibilities in front of us, but afraid to let them go by choosing only one, the more they begin to slip away from us. Not choosing means wasting time, and the more time we spend choosing, the more time we’re spending not pursuing any of them.

So, it’s better just to choose one, even if we’re uncertain. Choose one and then try it, and even if it doesn’t work, that doesn’t mean the others are all off the table. We can try one path, decide that it’s not what we want to pursue, and take a decision to go in a different direction. The key is to not stand still and wait. We’ve got to take action, and only through action do we actually learn what we want and don’t want.

And the key thing about this is that, as long as we truly are listening to ourselves to understand what we like and don’t like and taking action accordingly, at each inflection point or fork in the road, the tapestry of possibilities in front of becomes increasingly more tailored to what we actually may want…more tailored to us. So the choices in front of us become better and better.

The key thing is to simply do something. Take action to gain information. There is no right or wrong, only the gain of information with each step.

Remember that feedback is aimed to shape us to the system we are in…so take it with a grain of salt

Shaping us to the system

One thought I’ve been having recently is regarding feedback. We often receive a lot of it, from many different sources and directions. However, it is also often inconsistent, and the key is to find the consistent patterns within it, while taking some and leaving some (ideally, taking that which anchors on the consistent patterns).

Moreover, I think that there is an important recognition to be made that feedback is meant to shape us to the system that we are currently in, without necessarily helping us to become the way that we want to actually become (i.e., that depends on the answer to how we actually want to be shaped, and whether that is aligned with the current system that we are in — is the direction that the system is shaping us actually how we want to be shaped? )

For example, we may be working at a particular company that has certain values, culture, and vision – the feedback that we will receive will be geared toward making us more aligned and fit in more with that company’s values, culture, and vision. If we were to switch companies, the feedback that we would now receive would be far more tailored to now getting us to become more like the culture, values, and vision of the company that we have joined. In a sense, although the feedback we would now receive would have some similarities, there would be many differences – and simply because we would have switched companies, not because we would have become a fundamentally different person.

I’ve also noticed the same pattern when I work with different people — with one person, I’ll receive one point of feedback, and sometimes with another person, I may receive the exact opposite. Again, not because I’m different (because I haven’t changed that much in the span of a few weeks or a month), but because different people have different perspectives, and in working with us, the feedback is coming from their perspective, and people inevitably give feedback from their own perspective (which is aligned with who they have become), and in this way, subtly try to shape us to become more like them, so they give feedback aligned with that. However, this often leads to inconsistencies.

All this comes to say that although we should listen to the feedback that we are receiving (especially the patterns, because that is what is actually consistent over time and may be worth considering), we should nonetheless take it with a grain of salt. In the end, when we work for a company or person,  we are part of their system, we are part of their system, and the feedback that we receive will be aimed to try to shape us to operate smoothly within the context of this system. The managers of every system want it to run smoothly, so they will try to shape the elements of the system accordingly — and employees are part of this system. As Ray Dalio recently said in a post about his philosophy of providing constant feedback: “Remember that you are responsible for achieving your goals, and you want your machine to function as intended. For it to do so, the employees you supervise must meet expectations, and only you can help them understand whether they are stacking up.” So, indeed — feedback is meant to shape us to a system.

What this means for me

What does this mean for me? I listen to and recognize the feedback that others give to me, but I always try to remember that it is coming from their point of view, and although I do try to implement the actionable and relevant feedback that I agree with, I also do not always fully trust certain points until I’ve heard a particular point come up more than once. If it has only come up 1-2 times, then it may be due to idiosyncrasies of a person’s perspective, rather than a true pattern.

However, beyond this, I also ask myself if the system that I am currently in is actually what I want to be shaped to – and I have consistently come to the answer that I want to create my own system, rather than remain in the system that someone else has created. I would rather be the creator of something, than a “system element” for someone else.

And when we run our own system, or company, to say it more clearly, we certainly cannot do without feedback. Rather, we will consistently have many points of feedback, and we may even seek out more feedback because it is critical to growing the business successfully. However, if this is our system, our company, then we know that the feedback is fully aligned with what we are trying to accomplish – build a product or service that others want. All the market and customer feedback on our product/service, as well as the feedback on our own management and work style, is highly valuable, and will help build our own company into the best it can be, while also shaping ourselves and our management style around that as well.

So, it is worth remembering that although consistent feedback is valuable, we need to remain cognizant of the fact that most feedback is aimed to shape us to a system, and we have to constantly ask ourselves, “is this actually how I want to be shaped?” And if not, maybe it is worth stepping out of that system…maybe to find another with which we are more aligned, or to create our own. 

What does good look like?

High-level summary: As we progress in life, leave our structured university and job settings, it becomes more difficult for us to assess where we are, and what the benchmark for “good” actually is. I’ve thought through three methods of gathering guidance or feedback on where we are (i.e., top-down guidance, sideways peer comparison, and looking up at successful individuals/companies that we hope to emulate). My thoughts are that while retaining the big-picture perspective that comes from “looking up” is most important in guiding us, we can and should leverage all three methods to get accurate guidance and feedback on our progress toward our goals.

I sometimes think about how hard it can be to determine what good actually is or looks like. For example, when we are still studying in a school or university setting, we have very clear guidance for what good looks like – good grades, good test scores, and so on. Beyond this, we also have our peers to compare against – we can see who around us is considered good (i.e., in terms of intelligence, grades, having the right answers in class, etc), and we can take that as an implicit measure in our minds. As we progress and enter our first jobs, which often tend to be in larger and more structured organizational environments, we also often have very clear indications of what “good” is — we have ratings, reviews, and more.

However, as we progress forward, leave the realm of our academic pursuits and structured job settings, the question arises: what does good actually look like? As we branch out and have a less standardized path to follow, with less clear direct comparisons to ourselves, that answer becomes more unclear.

We no longer have our classmates or colleagues from work to compare ourselves against. We may or may not have crystal-clear guidance from work that tells us what good actually is. And we may not even have a view of what direction to actually turn to find the clear examples of what good is.

I’ve been thinking about these things as I consider starting my own company in the future, and branching further off the relatively clear path that I have followed thus far. I see three primary methods to getting input on performance and path (both on a personal level and as a company): guidance top down, sideways comparison against peers, and looking up. My thoughts are as follows (and by no means necessarily correct):

1) Receiving guidance top-down: By this point, I mean receiving feedback and guidance from someone who has done something similar before, or has input to provide from a stance that provides a bigger-picture view than what we may current see (i.e., for a company, this may be an investor; for an individual, this may be a mentor or manager).

-Pros – Personalized: Because we are receiving this feedback from someone who knows us or our situation well, this method can provide more personalized feedback, with direct and actionable input that is applicable and tailored for our unique situation and where we may be at the time.

-ConsMyopic and reactionary: However, it is worth noting that the feedback received via this method is limited to the knowledge or experience of the person providing the feedback to us, or of the mental model that they have of what good looks like, and therefore may be too myopic. Furthermore, this sort of feedback can sometimes be more reactionary (i.e., “you did this, and this didn’t work well from my perspective, so my advice for you is to do this differently next time”), rather than proactive.

-Overall: While personalized, this method of feedback can sometimes be too myopic, and therefore, it is important to receive feedback from multiple points of view when following this method, so as to avoid the bias of only receiving one point of view.

2) Looking to the side (Comparison against peers): By looking sideways, I am referring to referencing what other individuals or companies are doing that are at a similar stage or point in progress as us.

-Pros – Not falling behind: By looking sideways at our peers, we can get useful, real-time information for not falling behind, in the sense that we remain aware of what others around us are doing, and make sure to emulate that, or at least, not stray too far away from that. If we can identify who is doing best out of the peer set we are comparing against, we can also try to follow that path more closely

-Cons – Limited-term information, and regression to the average: While a comparison against peers provides real-time input that is useful for not falling behind, I believe that it is less useful for helping us to become the best. After all, if we are comparing against others alongside us, we would get a more “average” view, which is helpful for remaining average, but not for rising above this. Beyond this, sometimes we don’t even know whether our peers are actually good or not, or whether their methods are actually working – that information often comes over time with feedback from results, and is hard to gather in the moment. Unlike in a school setting where we receive grades very shortly after doing work or taking an exam, feedback loops in the real world often take much longer. Furthermore, a pure peer comparison can turn into more of a competition (a race to stay ahead), rather than something that actually guides us in the direction that is most accurate or productive, because as mentioned, we often simply don’t know what actually works or doesn’t until more time has passed. 

-Overall: While a peer group comparison can be useful for helping us remain “in the range,” it will not necessarily take us beyond this, so it is important to have a bigger-picture view than just looking sideways at what our peers are doing.

3) Looking up: By looking up, I refer to finding someone (or a company) who has done what we aspire to do, or is at a point that we would hope to get to (can be quite far ahead of where we are), and using them to provide some level of guidance. It may also be more than just one person or company — it can be multiple — but the key point here is to look for individuals/organizations that are farther ahead than we are.

-Pros – Big-picture view, and incorporating longer-term success criteria: I believe that this method works best for enabling us to look up to someone or an organization that has truly had success over time (rather than looking at peers, who may or may not achieve success in the long-term). Of course, our vision may be different, but we will adapt it to ourselves as we go, and having this far-off “guiding star” can help keep us centered on what it is that we most what to achieve and what the best actually looks like. Beyond that, I believe that the value of looking so far ahead (and maybe getting advice and input from such a person or set of people, who have managed to get so far ahead) is more useful than looking to the side, because someone who has already walked this path has far more experience with trial and error than our peer set does. Our peer set simply knows what is the current reality, and will, of course, learn over time, but does not have the big-picture view that someone who has already gone down this path would have. Thus, keeping this “guiding star” view will also help us  to actually understand what it may take to get there, in a more real rather rather than hypothetical way.

-Cons – Not always directly relevant for the present – While extremely useful for providing a big-picture view, this method sometimes does not take into account the current reality, because sometimes current situations have changed significantly from what worked when the “guiding star” example(s) were starting out, or at a similar stage in growth or development. Thus, this method sometimes doesn’t provide the best “current” situation guidance, which is where peer comparisons can help.

-Overall: I believe that this method works best for enabling us to take matters into our own hands, retain a bigger-picture view of what has worked for truly successful individuals/organizations in the past, and retain the perspective of what we can do to actually get there as well. However, we should keep in mind that we should still look to our peers or closer mentors to give more real-time guidance.

Overall, I think that as we leave the structured path, there are actually more ways than initially come to mind to gather the feedback on where we are and how to get to where we want to go. We likely would benefit from a mix of all methods mentioned above, with each of them providing different points of input — feedback “from the top” provides some level of direct input, but is limited to the feedback giver’s own point of view, looking to to the side prevents us from getting behind, but doesn’t help us to become the best, and looking up gives us a “guiding star” to keep in mind and big-picture guidance on how to get there (although of course, our own path will still be unique). Ultimately, I do believe that “looking up” toward someone or a company that has accomplished what we hope to accomplish provides the most unwavering guidance for us to progress towards, while supplemented by the other methods. This provides intrinsic motivation, and is a better benchmark for excellence. 

Staying flexible without spinning in circles

Staying flexible without spinning in circles

I’ve recently been thinking about the spectrum of flexibility and adaptability and where the optimal level lies. I’m going to share my thoughts here as I think through this.

On one hand, I think it is important to be highly flexible so as to be able to adapt to the situation and adjust actions, behavior, and  decisions as new information arises. On the other hand, there has to be a certain level of stability so as to not be jumping, changing direction, and spinning in circles with every single new piece of information. There is likely an optimal level somewhere in the middle.

I think that to maintain this “optimal level,” it helps to have a bigger-picture goal and perspective in mind. This can ultimately help with minimizing the spinning, because with a bigger goal in mind, the smaller details matter less and do not derail us as much. Having this goal also helps to keep us focused on finding the best way to get there, which means remaining flexible enough to pay attention to the feedback points on what is and is not working, and adjusting based on this. These points are more informative when we pay attention to the patterns that arise over time rather than each individual one-time occurrence, helping us to remain flexible to adjust to bigger themes but not constantly changing based on every single new data point.

How do I handle this? I tend to have my bigger goals in mind (e.g., start a company, find a place where I’d like to live more permanently, etc), along with plans on how to get there, but I am very willing to adapt these plans based on new information. As part of this, I am extremely clear on what I know and do not know (for example, these days I’m quite clear that I do not know where exactly I want to live). I am transparent about these points of uncertainty, both with myself and with others, because it enables me to more easily seek and gather other perspectives, which often help me to gain clarity. This helps me be especially adaptable on these open points, because these are exactly the areas that I should be changing as I get new information to test what works and doesn’t work and eventually move toward having a stronger perspective and making decisions that move me closer to my goals.

As I run more “tests” by trying a variety of things and continuously gathering opinions, I begin to develop stronger perspectives across multiple areas, and these areas become slightly more fixed. As I gain higher “certainty” in my opinions and hypotheses, I still remain willing to adapt with new information, but the bar for the level of information required cause me to change those points becomes increasingly higher – i.e., for areas with high points of certainty, I would need materially new information to change my perspective. Of course, this should all be taken from the perspective of understanding that we definitely don’t know everything, and should always remain highly open-minded. 

I believe that I am somewhere in the middle in terms of my adaptability. Above all, I maintain a bigger-picture goal that I try to work toward, which helps me to keep all of the more minor points in perspective. I’m highly adaptable for areas in which I am less certain (and therefore I explore these a great deal), but I become somewhat less adaptable as I develop higher confidence levels in my perspectives and certainty (based on feedback) that this works to help me move toward my goals.

So, I suppose that I answered my own question. There is not really a right answer on the “optimal” level of adaptability, but what does help is keeping a bigger-picture goal in mind to serve as a guidepost for what matters and doesn’t matter (i.e., patterns rather than one-time data points). We should start out with a “hypothesis” plan, but be clear on where we are more “uncertain,” and be open to gathering information on what works and does not work. Even when we are more “certain,” maintaining open-mindedness over time is still very important. 

As we gain more information, we should look to increasingly “fill the gaps” on the uncertainties, and become more certain, point by point. We should still maintain flexibility to change the approach based on materially new information, but not spin in circles with every single minor detail.

What does home really mean?

“Remember that wherever your heart is, there you will find your treasure.” – Paulo Coelho

For me, movement has always been a part of life. However, whenever I have found stillness in the midst of all of this movement, the question has always arisen: what is home, really?

The uncertainty around the concept of “home” has been something that I have been thinking about for most of my life, but something that came up more recently as a bigger question.

Home as a blank canvas

I moved around a lot from a young age, coming from Bulgaria to the United States as a child, and then living in several places around the US as I grew up. I spent my childhood across both countries, with school-years spent in the US and summers spent in Bulgaria. “Home” had no fixed meaning, although Bulgaria was the place that I associated with carefree fun, and the US was the place that I associated with work and school. I often felt somewhat unanchored, with no fixed roots anywhere.

As I grew older, attending boarding school, and continuing to feel like I was in perpetual motion, I made up my mind that I would “find the place that would be home.” I figured that the world was big, and I had only experienced a very small portion of it. Home could be anywhere, right? I took a “blank canvas” approach to the matter – I could paint my canvas in whichever way I chose, creating my home as I chose to define it, wherever that may be.

So, I began to travel quite extensively and to pursue opportunities to live and work in different parts of the world. During my university years, I spent extended periods of time living in France, Italy, the UK, India, China, and several other countries. I continued this exploration as I entered my early working years, living in New York, Los Angeles, New Zealand, Bulgaria, and then moving to Germany, France, Singapore, and back to France for some time, before finally returning to the US (where I currently live in San Francisco).

At first, the travel and various experiences were fun and exciting. However, as the years wore on and I kept moving, I began to feel oddly restless and somewhat homeless. Although the places were interesting, none of them felt fully right. I kept thinking that “this place just wasn’t right for certain reasons, but there is still so much to try, eventually I’ll find the place.” I traveled and lived in over 80 countries. However, it seemed like every place felt somewhat off for some reason or other (although I felt more at home in Europe than in many other places). I began to realize that maybe a perfect place simply didn’t exist, and I was looking for something that couldn’t be found.

Creating, rather than finding, home

What I’ve come to realize is that maybe we don’t find home, but rather, we create it. “Home” can be anywhere. It is not a place, but rather, a mindset.

When we don’t have any strong connections, as fun or as pretty as a place may be, it simply does not mean much. A home is defined by the people more so than merely the location, and that starts with ourselves. We are our own homes, with the need to feel fully comfortable with who we are and what we do. After all, we can’t escape from our own minds, so the feeling of “home” has to start there. Over the course of time, as we find people with whom we want to surround ourselves, we may begin to feel a more full sense of comfort, stability, and eventually home. In realizing that this is what it takes, we may realize that we can find like-minded individuals – and therefore, home – in many more places than we initially believed.

Beyond that, as I’ve seen very clearly, every place has its positive and negative sides. It is difficult to just go to a place and feel immediately that it is the right place. Instead, that feeling grows over time. Rather than finding a home, maybe we actually create home by choosing a place and deciding to accept it for both its challenges and its strengths. Over the course of time, as we choose not to escape in the face of the difficulties that inevitably arise, it begins to feel more like home because we have chosen to make it home. Overcoming the challenges is what makes it our own.

I believe that by giving myself a “blank canvas” approach, I have given myself the enormous freedom of choice, but also the incredible burden of responsibility. In the desire to find perfection, we put extreme pressure on ourselves to sort through the options and “find the best one.” However, maybe in the pursuit of future perfect, all of that pressure takes away from being happy in the present.

Freedom to embrace the present…because home can be anywhere

All this to say that I’m starting to believe that maybe when we fully surrender to the reality of the present, we can actually be happy in many places – far more than we may believe from the onset. Of course, we should still listen to how we feel, in terms of things that make us happy and unhappy, so as to guide our choices. We should still pursue our larger goals and make changes when we feel that we should. However, maybe we should not hold out “being happy” just for the future, or simply in the pursuit of a new place or goal. Rather, it is important to also live in the present and find fulfillment where we are now.

And you know what? That realization also dissipates the fear. It means that we are capable of being happy and finding home in many places. It is simply about accepting that maybe there is no “perfect place” or “right answer,” and seeing that no matter where we are, or where we choose to go, it can eventually become home if we want it to become home and invest the time to make it home. It means that maybe we can let go a little bit, and it’s okay.

It is the understanding that things will all fall into place somehow, and this provides freedom to live on the edge and ride the waves of life that will take us to where we need to go, without so much rigid planning.

In the end, what is home? Maybe it is just ourselves – and eventually, the people and places that we choose to accept over time that also become a part of us. The world is our canvas, but we don’t have to worry about painting every single stroke perfectly, because it will paint itself, as long as we follow what feels right.

So, I’m telling myself to let go, be flexible and let myself experience without being so afraid of not following a plan. I will trust that things will somehow fall into place.

A series of auditions, not failures, for what should have a place in our lives

High level summary: Everything that we try can be thought of as a “test” or “audition” for it to be in our lives, and it’s okay if certain things don’t work out. By letting one thing in, it means that we are not letting in everything else, so we should be picky about what we let in.

I’ve recently been thinking about things that I have tried and failed at…or at least things that haven’t worked out the way I had planned or hoped. I tend to have a lot of these, as I imagine most others also do.

Throughout the course of time, we try many things – some work, and some don’t. Some play out out in unexpectedly good ways, and others that we thought would have worked, don’t work out at all.

It’s easy to think of these things as “failures.” I often feel like that in my case – whenever something doesn’t work out with a project, person, friendship, experience, or something else, I feel a profound sense of loss and sadness. I often start wondering why it went wrong, what I could have done differently, and why I did what I did. I question if it was my fault.

But as I’ve thought about it, maybe that isn’t the case. All of these “trials” are like auditions in different aspects of life (and not us auditioning for things, but rather, auditions for these things to be present in our lives). Each “audition” provides us with information on what does and does not work for us, and gives us valuable data points for future decision-making.

Ultimately, it is all part of the process of figuring out what belongs in our lives – that is, what deserves our effort and mental space. Every single thing that we let in means that we don’t let in the whole universe of other alternatives. That means that we should be picky, because by saying yes to one thing, we are saying no to everything else.

And so maybe we should be thankful for, rather than sad about, the things that don’t work out. They save us time and effort.

Think of all of the things that we try, people we interact with, as auditions, not failures on our end. They are simply auditioning to be in our lives – and some will pass, while the majority will not. And that’s okay.

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.

Modularization of knowledge work

[I know my posts are long, so I’m going to start adding a high-level summary if you want to get the main point without having to read the full piece]

High level summary: Even within the complex domain of knowledge work, there are certain processes that can be increasingly standardized when we take an archetypical, big picture view. This is already being done in ways both big and small, ranging from tagging/labeling, to bigger-picture process automation in recruiting, investing, and other decision-making. In the future, there are multitudes of opportunities for increasing knowledge work automation.


In some of my other posts, I’ve talked about finding patterns and archetypes in tasks, decisions, and processes. I believe that when we have enough experience or knowledge about a certain area or topic (either through direct experience or through thorough studying examples and history), we can begin to find and form patterns, and then to begin to apply them to new instances of the same situation.


In particular, I’m interested in exploring and understanding how certain tasks (increasingly complex tasks), can be defined into a coherent, standard process, and ultimately automated (or at least, 80% automated, with a human reviewing, adjusting, and adding to this to get it to 100% completion). In a previous post, I gave the example of due diligence research for private equity firms, and the potential to modularize some aspects of it (e.g., interview planning, survey planning, modeling). In this set of research, I’d like to look into the future of work modularization for knowledge work, explore examples of how this has already been done, and then explore how this could be taken further.


I. Future of knowledge work

First of all, what is knowledge work?


Some scholars have defined it as work focused on “non-routine problem solving that requires a combination of convergent and divergent thinking.” (1) According to Wikipedia, it is: anyone “whose line of work requires one to think for a living.” (2) Essentially, we can think of knowledge workers as people whose jobs focus on significant amounts of unique, case-by-case thinking, problem-solving, decision-making, and non-routine tasks with non-linear processes. In terms of careers, some examples include bankers, consultants, lawyers, accountants, scientists, engineers, professors and academics, and more.

However, I’d like to test the common assumption here and ask if this is really the case – is knowledge work truly non-linear and non-routine?

Although it seems that way on the surface, I would actually take the stance that maybe that’s not fully the case. Rather, maybe it’s just that we have to zoom out a bit and take a much bigger-picture view to to be able to see the patterns in what is being done across the work of knowledge workers. There is definitely a lot of independent thinking that does need to be done a case-by-case basis, but for many roles, there is still a level of process that is followed in the big-picture. For example, in private equity, there is a somewhat standard big-picture deal process that takes place, in consulting, there is a big-picture process for running projects, and in academia, there is a big-picture process for doing research and publishing papers. At the detailed level, this work changes because there are nuances to every single thing that takes place (i.e., types of consulting projects vary vastly, private equity deals have a large amount of variance, and academic research and publishing is never fully the same). However, if we accept the fact that there is similarity at a big-picture level, then we can begin to explore how we can take this further, by finding similarities across cases in levels of detail of a second-order, third-order, and below.

To do this, we can consider archetypes. For example, what are the different types of consulting projects that there may be? For example, we could break them down by industry – those would have more similarities among each other. Then, we could apply a functional filter on them (i.e., strategy, diligence, transformation, etc) – those would have even more similarities with each other. Then we could think about what type of company it is for (i.e., corporate BU in a large multi-national, or a small/medium enterprise, etc). The further we segment and apply filters, there more the subset that we reach actually has increasing levels of similarity, and therefore, the more that there may be opportunity to apply some level of standardization across (e.g., maybe there are certain types of analyses that are more or less standard if we do a go-to-market study for a medium-sized B2B software company focused in the retail space). When we segment and break down, we find similarities in how we can approach each of the cases.

The point is, when we actually try to apply logic-based categorization to each situation, we may find that there are more similarities than we see on the surface, and this is true across topics and industries. What it takes to find them is to think at a high enough level and then begin to break down the mass into specific areas that have similarities among each other – archetypes.

II. Examples of where this can be possible

Today, a lot of progress has been made in terms of modularization across a variety of areas. I’d like to go through a few examples of where I see it or could see it being done. This is not meant to be exhaustive, but simply to be a starting point of examples of where this can be and is being used.

Atomization of work units: At the very base level, there is significant movement toward “atomization” of work. What I mean by that is the breaking down of work into very small components. I see this happening in terms of labeling and tagging. As AI and machine learning become increasingly important decision-making tools, there is also an increasing need for data to train these machine learning algorithms. As such, human minds are being used to label, tag, or identify objects and meaning in images, text, videos, and more. A wide number of companies has emerged to meet this need, the largest among them being Amazon Mechanical Turk, with others including Scale, Hive, Labelbox, Cloudfactory, and Samasource. In practice, what they do is outsource thousands of small tasks (e.g., identifying all of the stoplights in an image, saying whether the meaning of a sentence if positive or negative, etc) to human workers all over the world, the output of which is used to train machine learning models to do the same.


What does this mean and why does it matter? It matters because it shows that at a very core level, tasks which have been are traditionally human-led (i.e., thinking, identifying, recognizing, predicting), are now being systematized and given to machines to do. Thus, labeling is simply a smaller example of something much bigger – soon, whole thought and decision-making processes will be (and are being) systematized.


Recruiting: Recruiting is one area which has seen and will continue to see a great deal of automation. It can take place in many ways. For example, it could be determining what specific skills will be needed for a specific role, but also going beyond that into thinking about what personality types actually may perform well in this role (Bridgewater and many other companies have done this), and also into what other qualities will be important for success in the role (e.g., level of curiosity/desire to learn, propensity to work hard before giving up, need for autonomy, etc).
On the candidate side, it would then be important to determine where they actually stand across all of these data point dimensions – i.e., skills, personality types and dimensions, and additional categories. This data can be gathered via a variety of different methods, from self-reporting, to formal test-taking of certain personality tests, to even web-scraping based search methods.


Ultimately, the automation and systematization in this area is and could come from determining what the right fit is across a variety of data points (as well as where the levels of tolerance are – i.e., critical vs. nice to have), determining candidate positioning across the data points, and then identifying top matches based on this, with the system ultimately creating a more systematized process for recruiting.

Training: To continue on the human capital angle, I could also envision that training would also become more modular, in that there could be services with a variety of “base case” trainings available for a variety of roles (e.g., likely starting out with roles that have some level of task similarity across companies, such as customer service representative, delivery person, driver, etc). There could be a base case training that is available for certain roles, with additional elements added in as “customized modules” based on more specific elements of what is needed for a specific company or role.


Financial modeling: Already, many financial modeling processes are automated, with tools such as Capital IQ. However, many more complex models such as LBOs, market growth models, and others, are still being largely done by financial analysts (of course, with exceptions). I could envision that by integrating with data sources (such as Capital IQ, Bloomberg, etc – which is already possible), and building in more complex rules around how to model certain events, forecasts, or scenarios, much of this could also be made more automated and made more modular, such that we could build in certain parameters (i.e., type of model, data sources, some assumptions), and an 80% version of a model could be created, that could then be reviewed and edited by a human.

Writing legal memos/PR/marketing/business documents: Writing certain legal, PR, marketing, or other business documents could also be modularized to some extent. Of course, the specific documents to be written would depend on the field and area, but I could imagine that certain more standard memos, press releases, or overview documents could be standardized in format (across archetypes – i.e., memo used for x, y, or z topic/situation), each with a different format and typical information included, and then users could provide the information needed to “personalize” the document with the information that is required based on the archetype.


Decision-making and prediction processes: Ultimately, I also see automation and systematization being useful in a variety of decision-making process, including investing (PE, VC, hedge funds), acquisition planning, and more. The methodology would involve each decision-making party systematizing their decision-making process by determining the standard criteria to be considered in every decision and minimum requirement across all criteria, and then assessing options across these. I could envision that there could be various archetypes of decisions set up (i.e., different types of investments, for example, maybe depending on industry/geography/size/goal), which would each have a different methodology and criteria for reaching the decision. The user could then fill in the required information to reach the necessary archetype, be prompted to provide additional information needed for this specific decision (or this would be pulled in from other documents), and then receive a recommendation.


III. What this means going forward

Ultimately, this means that as we move increasingly in this direction, we will be more able to move beyond pure task automation, and into more complex work automation that typically requires thinking and complex decision-making. The key is to realize that everything is ultimately built off of logic, even human decision-making, but that this logic is simply very complex. However, if we can try to systematize this complex and multi-layered logic, we can begin to build modular processes across a variety of areas that have thus far been primarily in the domain of human thinking.

Once “thinking processes” are able to be systematized, the systems that we trust to do the initial thinking for us would ideally be able to create ~80% versions of whatever task we are doing, with humans then stepping in to review and adjust as needed. This could be like a “turbo tax” tool for businesses, in that work is increasingly made modular with clear steps or inputs, with a first version output that can then be adjusted.

What does this mean? Having such tools would enable us to focus our attention on the even more complex work that requires our full attention, and away from lower-level tasks that are more able to be systematized (with increasingly more seemingly complex tasks being added to this category over time).

IV. Sources
1.  Pyöriä, P. (2005). “The Concept of Knowledge Work Revisited”. Journal of Knowledge Management9 (3): 116–127. doi:10.1108/13673270510602818  .https://www.emerald.com/insight/content/doi/10.1108/13673270510602818/full/html


2. Davenport, Thomas H. (2005). Thinking For A Living: How to Get Better Performance and Results From Knowledge Workers  . Boston: Harvard Business School Press. ISBN1-59139-423-6.

3. Deloitte University Press, The Future of Knowledge Work, https://www2.deloitte.com/content/dam/insights/us/articles/the-future-of-knowledge-work/DUP416_The-future-of-knowledge-work.pdf

4. https://www.nintex.com/blog/will-automation-knowledge-work-really-mean/

5. https://www.researchgate.net/publication/270771273_The_process_of_atomization_of_business_tasks_for_crowdsourcing

Creating order out of chaos: Archetypes and systematization

How can we create order out of the chaos that is our disorganized world? Recently, I’ve been thinking about two concepts that can help us to do this, related to organizing ideas, systems, and businesses: archetyping and systematizing.

I. Identifiying Archetypes

A couple of years ago, I read Ray Dalio’s book, Principles, which detailed his principles around life and work, and among many topics, one stood out to me in particular: his focus on finding patterns, or archetypes, in the world around him. He explained that he applies this principle across much of his work and life, including hiring, investing, and making predictions. For example, Dalio applies personality testing in his hiring process at Bridgewater in order to determine what potential hires’ natural strengths and weaknesses are, and what sorts of roles people are best-suited for. As another example, he studied the history of the rise and fall of empires to determine what the high-level patterns are that take place before, during, and after an empire’s rise and fall, thus being able to apply forward predictions for our world today.

In his belief, most things in life can be categorized into archetypes – people, problems, situations, and more. The concept is that even though problems/people/situations in our lives may seem unique to us, once we have enough experience or information over time, we can see that certain sorts of these problems are actually repeated multiple times, many people fall into certain archetypes of personality, and patterns of events and situations repeat over time (ex: debt crises, rises and falls of empires, etc).

Once we realize that these patterns exist, it opens the door to actually start looking for these patterns in our own personal work, interactions, and experiences. This concept was quite interesting to me, and since then, I’ve been looking at things from that perspective as well. Around me, I see various experiences, but I constantly ask myself – what is the big picture behind this? What is the bigger pattern underlying this? How can it be systematized?

We can take the chaos that is the constant influx of ideas, situations, conversations, work, events, and more, identify a pattern, and then create a narrative and understanding of it.

For example, I’ve recently been looking at my own work and trying to identify areas that may seem different and varied, but actually have a variety of similarities. What came to mind was due diligence work. Private equity firms often do a large number of diligence efforts as they analyze a variety of acquisition targets, and they often hire consulting firms to run them. Although each target and diligence effort may have differences, when we zoom out and look at the bigger picture, there are actually a variety of similarities. For example, they often require building a market model, doing a customer survey, running ex-employee/ex-competitor interviews, identifying trends/growth areas, and more. When we think about these elements, there are many opportunities to standardize and maybe systematize. I’ll continue with this analogy in the next section.


II. Systematizing

Building upon a concept in Michael Gerber’s E-Myth Revisited, it is important to build in standardized sets of practices and systems for conducting certain processes. Once an order or pattern has been identified, I believe that this is where there is a lot of opportunity to address it by creating systematized solutions for the situation at hand. For example, let’s say that we have identified a set of archetypes for a particular problem, situation, or type of person that we may interact with. Once we have the archetypes laid out, we can determine how to go about appropriately addressing each archetype based on the bigger picture and unique circumstances/requirements of each, and can create a more standardized solution approach.

Let’s return to the due diligence example. As we said, there are often a variety of types of analyses that need to be run in due diligence settings, regardless of the type or topic. Let’s go deeper into one of them – conducting interviews. There are often a variety of types of interviews that need to be run, for a variety of topics. However, maybe if we think further into the types of interviews that we need to run (e.g., ex-employee, ex-competitor), the particular topic (e.g., understanding competitive landscape, understanding key buying factors, understanding trends, etc), we can think of the types of questions that may need be asked for each, and how they would differ (by leveraging past successful examples of each type). We could then construct a base set of questions that would be asked based on the particular type of interviewee, topic, and add further specificity as needed.

Now, we could argue that this wouldn’t be useful because we would need to adjust the questions that we are asking in real-time as per the interviewee’s response. However, maybe we could actually build that in. Let’s say that we anticipate that a particular question would have response type A, B, or C – we could then actually create a set of follow-up questions based on the response that the interviewee provides, dig deeper into that area with several questions as long as needed (maybe as long as we have specified as per the parameters), and then go back up several levels to the overall set of questions.

Ideally, we could create this base skeleton of questions to be asked as per several parameters set at the beginning (i.e., length of interview, type of interviewee, type of topic, level of detail desired which could govern the depth we enter for follow-up questions, and more), with certain data plugged in to customize to the situation (e.g., name of competitors trying to assess, key buying factors we are assessing between, etc).

In this way, we could actually create a customizable skeleton of questions for conducting interviews across a variety of situations. Of course, all this isn’t to say that we can create a perfect guide 100% of the time. However, what we can do is at least minimize level of effort expended to create new solutions every time, and rather, get the team ~70-80% there with little effort by creating a base case version customized to the situation, which can then be further adjusted.

This is a very particular example, but the concept is applicable in a very wide variety of ways. For the diligence example, we can create 70-80% skeleton versions for the other areas as well, including for building a market model, building a survey, and finding growth opportunities. Outside of the diligence example, we can think more broadly within consulting about the archetypes of projects that come up, and the standard elements that may be included within each.

Thinking more broadly, we can also find countless examples in other domains, from writing an essay, to putting together a brief, to designing a building as an architect, to doing a company valuation, and more. In every single situation and domain, there are currently many complex tasks that require a great deal of mental energy because people often start from scratch for the creation process, when in reality, there are countless past similar creations to leverage, and complex thought from scratch may not be necessary. If we could create 80% versions as a first step with very little effort and then only some minor adjustment required thereafter, we could take out the requirement for heavy thinking in these areas, and instead focus our and our employees’ mental energy on more complex tasks.

III. What this means

I think that as we progress as a society and continue in our desire to grow and enter into new areas, thinking about our work and experiences from the perspective of archetypes and systematization can be immensely powerful in simplifying much of our current mental load.

I’m going to continue thinking through this in my work, experiences, and daily life, and I encourage anybody reading this to do so as well, because there is an immense amount of potential within this.