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. 

Burnout. From Denial to Understanding

Upon listening to the longer form of the popular Buzzfeed article How Millennials Became The Burnout Generation on Audible, I wanted to add onto what I think is a crucial step towards finding a solution. For background, this book was a 2 hour Audible exclusive where the author interviewed ~5 out of the 7 million readers who live in different parts of the country, are from different backgrounds, work in different industries but have all experienced their own version of burnout.

Burnout has many sources, but a lot of them, come from the changing societal dynamics of our Millennial generation, which also explains why it’s become more pervasive than ever.

It’s about social media pervasiveness, and the need to continuously build and maintain a profile that adds so much superfluous tasks to our everyday lives. It’s due to the mounting student debt some of us have, way above that of graduates in generations before us.

Everything is more demanding and less stable. It’s truly the flip side of the coin to the “gig economy”– where one can work whenever, almost wherever, but not stably. As Uber’s victory in the contractor vs. salaried employee case has shown, also with fewer benefits, organization and room for personal development.

My personal experience with burnout is of the more traditional sort. Albeit, I am somewhat affected by another overarching theme the author comments on–the lack of focus and having to do too much on a regular basis (errand paralysis). I work 80+ hour weeks and barely have time to take 2 – 3 weeks off fully. In fact, I’ve never had a vacation longer than 2 weeks in the 5 years since I started my career in finance (investment banking and private equity).

I have been in denial of my own burnout. There were definitely moments over the last few years when I just wanted everything to stop. The e-mails to stop blaring, the calls to stop, and the instant need to respond and crunch numbers, fly to faraway places for 3 days at a time–to come to a halt. I wanted peace. I turned to meditation. Nothing was even that interesting anymore and everything (no matter how small the task) felt like a nuisance.

A classic case of burnout here, you think? Well, I didn’t think so. I and many of my colleagues and friends who complained of the same frustrations thought of just two resolutions (fixes to this shockingly common problem): 

1) TAKE VACATION (usually a few days off spent flying around in Europe so you can get a nice Instagram shot looking like you are finally getting to “play hard” and not just “work hard”); or

2) FIND A NEW JOB. The advice I hear, “something or someone must suck at where you are at now. Maybe you are just bored. A new place will jolt your energy!”

Why the denial of burnout? I think it’s because we find “accepting it” to be an act of failure–the fact that we can’t keep up with the hard work, or the mounting amount of stress. When others among us seem to be able to, this just shows us how even more of a failure we are! I remember telling myself that burnout is just for people who grew up in European societies where people worked to live and were used to balanced 9 to 5 lives, or that since I was making decent money, I really can’t complain.

How to begin to accept? Author of the Buzzfeed article, Anne Peterson recognized that “The problem with holistic, all-consuming burnout is that there’s no solution to it. You don’t fix burnout by going on vacation. You don’t fix it through “life hacks,” like inbox zero, or by using a meditation app for five minutes in the morning, or doing Sunday meal prep for the entire family, or starting a bullet journal. ” And yes, I have tried all of the above. I know I’m just not an inbox zero person in that I will read everything but I don’t have the patience to sort through them all and meal prep I can only do a few weeks in a row at a time before I start giving myself food poisoning from the lack of attentiveness. None of those things have helped me–in fact they probably added more “MUST-DO TASKS” to my already overloaded list, which to my detriment, actually left me with more errand paralysis.

The understanding” Part. It’s truly part of the solution. Instead of being gung-ho and unrealistic about timelines, how much work can be compressed into them and making “magic time” in each and every project as one consultant told me when I commissioned a 4-day deal turnaround workstream, we should make it part of the everyday vocabulary to recognize when these things could lead to burnout. To catch ourselves from 10+ item priority lists and trim them down to 1-2 must do’s and maybe 1-2 optional tasks. To recognize that the world won’t end if we don’t get to some on the list today. To accept and communicate when we have competing priorities that will make completion and our satisfaction challenging. Better yet, make our satisfaction a KPI in the project deliverables. Increasingly I have helped my group and firm make the team’s enjoyment in the staffing/project, a priority, a constraint, an important factor of consideration.

Not only do we individually need to part with our shame when we hear of or associate ourselves and/or colleagues and friends with the word “burnout,” but also society as a whole needs to accept that this phenomenon is indeed commonplace, and especially amongst studious, not lazy, members of corporate America.

Written by Anna Wang

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. 

On Investing: Greed, Pride and Optimism

Is it like a rondeau that never ceases or an intricate Mozart which one willingly plays on repeat to be stroked by its melodious intrigues?

Investing has taken on so many forms, with strategies evolving from both psychological and technological innovations. Whether it is behavioral methods of predicting the next black swan, market turning event, or optimizing the arbitrage that exists between two very similar stocks in pairs trading, the goal remains, to make more money by outsmarting the market.

And what exactly is this market? Its constituents consist of sophisticated and highly unsophisticated retail investors. On one spectrum you have the PhDs pitching complex strategies set to exploit some underlying market inefficiency and on the other you have retail investors strapping on old and new names, or picking based on one metric, or being wooed by investor presentations. When an investor thinks about a stock, are they really thinking about the underlying company that share of ownership represents, the management, the board, the strategies, and employees? (I reckon when said unsophisticated investor thinks about the word stocks, they could be alluding to real apples and pears or that cash tree which will grow under the right sunlight conditions or whither away if an untimely long winter freezes its growing capabilities. It’s merely a seasonal effect, just got to pick the right tree in the right place and extradite its roots before the winter hits).

The underlying principles are the same and they are A) the market is indeed inefficient, despite the theoretical arguments back and forth as it is something that practitioners acknowledged whether they grew fat or poor from the fact and B) there is both real and perceived randomness.

A) Is just how the real world differs from what economists and finance academics believe is true about this non-physical financial world of money that we have created.

B) Now that I’ve worked with a dealer and on the buy-side in private equity, I know how some news can move prices in ways that are much unbeknownst to the knowledge or care of the general public. Intraday trading and technical trading merely try to capitalize on some of this signal in the noise.

To say that the world is but a stage and we are all merely actors in it would be an understatement. We are merely puppets. The real puppeteers are our own, very raw human emotions of greed, pride and optimism. 

All of these three emotions must be infused together in one. One can’t be called greedy just for chasing high returns. Especially if the stock is down 20% and the person still doesn’t sell, well that just pride. Now, hoping it will go back another 40% to reach the initial 20% upside if everything goes right, now that’s just optimism.

When all is said and done, what exactly do I want to do with this money built upon greed, pride, and optimism?

There are only two choices. Reinvest it into the economy or hoard it.

The hiding of wealth under the mattress (literally, and completely out of the system not even in a bank) provides that luxurious safety net the size of a small country for the few. After all, if the world turns upside down who wouldn’t want their own country to jet back to?

And does this hoarding really sap and suck from the economy?

Won’t what is sapped just be displaced by more free printing? Hey, people won’t even notice this 50 billion missing once it’s injected on the other end by some central bank. Aren’t they the true equalizers of the world, redistributing the invisible clinch as that excess will only be noticed in the future, once it’s spent on the funding of a whole new country.

And by then what’s a minor economic quake of unspent excess when the whole world has already been hit by the magnitude-9?

That’s only the traditional sense of Robber Barons and their style of wealth creation.

What about the venture capitalists of today and the budding entrepreneurs?

Devoting their undying love to impact creation and bringing the world to more sophisticated promises of the future.

Again, greed, pride, and optimism.

That 200 million dollar valuation from the mere $20k savings, scraped during college or the first few years thereafter, represents merely a byproduct, an additional benefit of introducing a popular app to the world?

What of the celebrity status that comes with having been enormously successful at having sold your “company” which has yet to make a buck. As if almost an extraordinary Van Gogh was auctioned off with the promise that the artist will soon die upon the signing of the change in ownership on the dotted lines.

The hope that Google or whoever buys your company will even continue its operational legacy passed the first year is the optimism you need to have.

Thus, the real music that drives the beat of investing is really that of a Ba-roque (n.) record. Refrain and repetition followed by high shrieks and baritones designed to steer the crowd of lavishly dressed into cathartic outpours of their primordial emotions.

The above is a satire on the world of public markets investing and venture capital investing.

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.

Demystifying Disengagement at Work

Over 85% of people are not engaged at work, yet we can spend 100,000+ hours (50%+) hours of our waking lives at work. Work is inevitably a big part of our lives, yet when we are disengaged, this leads to lowered work and life satisfaction, with negative repercussions on the businesses we serve and on society at large.

I know it’s possible to lower this lack of engagement statistic dramatically—most of the methods and research are out there. However the delivery of effective methods, to more people, can be improved.

My disclaimer: this article is really focused on exploring the problem and not yet the solutions. “A well defined problem” is often over half the battle but does not get over half the attention as “the solution” does in our world these days.

Why does this matter to me?

When people list top reasons for disengagement at work, the list often goes something like this:

  1. They believe it’s just a temporary or stepping stone job. There’s not necessarily a career path that they care about at the current organization.
  2. Poor leadership or management does not allow them to excel or even work in the most effective way.
  3. Poor company culture doesn’t allow them to bring their whole-selves to work and/or doesn’t seem to recognize or reward effort fairly.
  4. Excessive work load and poor delegation leads to a feeling of overwhelm. Employees don’t often have the tools to identify the type of overwhelm, how to deal with it and aren’t given resources fast enough to resolve this. We know what comes next when this happens–burnout.
  5. Lack of training, resources or support to actually do the job properly.
  6. Workplace conflict where the employee may feel emotionally burdened or bullied.

I have personally experienced many instances of all of the above over the past 5 years, working in intense investment banking (IB) and private equity (PE) jobs.

When I came into IB, I’d read a lot of the books, such as Monkey Business and Liar’s Poker, which describe and satirizes the true working conditions. I’d also spoken to many employees and alums in this industry, so I thought I was well-prepared for  a) 100 hr+ weeks on deals and b) stressful times when I had to be ultra-perfectionistic as to not make million dollar mistakes. Thus, I was expecting to suffer a bit of #1 and #4 from the list above.

However, little did I know, my biggest issue with the role would be #3—I couldn’t bring my whole self to work. I had to constantly pretend I was some IB Analyst Clone! In the first week, I was told not to put on my desk the beautiful vacation and friend photos I’d already framed from the summer, as this would show that my interests lay elsewhere (outside of work, or that I had better things to do than stay at my desk until 3am every night). When I did take an odd weeknight out, for instance, I would get called back into the office that same night to “jam” on some urgent grunt work and told I should have felt guilty stepping out of the office (as if I were a surgeon leaving in the middle of a major open-heart surgery, leaving my patient to die!)

Following close behind is #6. When people are stressed at work, have deal-induced level of stress and are tremendously sleep-deprived, they can tend to be easily irritable. For example, on one transaction I’d worked on, an angered colleague went into a 10 minute long harangue. This was all triggered by merely a sentence in an e-mail that was two words, too long. And no, those two words were not some obscenity! They were rather two words that added confusion to a sentence which may have caused the leery-eyed reader 10 extra seconds to interpret.

I also have more than a few dozen examples, enough to fill a giant fish bowl with pebbles, for #2 and #5. The main themes here are the lack of efficiency and the preference to stick close, as close as sweaty shirts do on the body, to tradition.

Some things have improved since I left IB 3 years ago. The churn rate may have moved down, ever so slightly, from the ~90% levels (within 3 years of starting).

This can’t be the way how the rest of my ~77,500 hours of work life should go!

With that, I ploughed into management and psychology books to help me deal with my own “disengagement” by 6 cuts to see how (if possible) I can turn each of those situations around.

What is the problem? Getting more specific

Now, what is the definition of work engagement anyway? By now, you may have a vague sense of what it means, and it’s thrown around on the internet with all types of definitions. Work engagement is commonly defined as the extent to which employees feel passionate about their jobs, are committed to the organization, and put discretionary effort into their work.

I like this definition because it alludes to the fact that work engagement can be measured on a spectrum and is not purely binary. Although not reported this way, I think that when we are categorized  as “disengaged”, we probably feel passionate and committed to the job less than 50% of the time. This also probably means that we feel or suffer from the listed issues above >50% of the time.

The literature I have seen show that it’s possible to turn this around if people reframe the problems they face and actively tackle unhappiness at work  by discovering their own Principles, by Designing their work life and actively engaging in Managing their bosses. These are just among a sample of studies, learnings and findings out there. Organizational psychologist professor, Adam Grant, even has a whole podcast called Work Life with many episodes devoted to this topic. 

  1. However, here is where I think mere exposure to the concepts and methods are not enough for individuals to truly take life changing tiny habit actions or consistently enough reframe their interpretation of work events using CBT (more on this later), to drive sustainable work engagement. Recall our target is to go above 50% of the time per person! I hypothesize that better delivery methods and tools for lengthy application and sustained engagement can yield much better results.
  2. Adoption needs to be much more pervasive. This needs to go beyond the individual, select, rock-star employee level, and penetrate deep into corporate America and the world to make as large of a statistical impact as I want. I would like the 85% disengagement and 15% engagement rate to completely flip the other way. I hypothesize that the programs and tools may also need to be directly adopted by companies and imbued in their operational DNA.


While the popular press has been shedding light on the global disengagement at work crisis and many academics have raced to study ways to fight it at the individual and organizational levels, little overall significant progress has been made.

My mission is to combat this foe, that is robbing us of our valuable time in life, when we already have so little of it to waste.

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.