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.

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.

Taking an emergent strategy

Sometimes it’s hard to start, and we’ve just got to start somewhere, even if the direction is not yet clear – that’s how it is for me to start writing sometimes. In those moments, I just write, see what comes, and where it leads – and it usually does lead somewhere. It makes me think of a couple of books that I read over the past year, How will you measure your life? by Clayton Christiansen, and Range by David Epstein. In both of them, the authors talk about the importance and benefit of exploration and having a wide range of experiences as we find (and continue to find) our path.


In particular, I like what Christiansen referred to as “deliberate” and “emergent” strategies. If we are absolutely certain that a certain path is the right one, then of course, we should go ahead and follow it – that’s a deliberate strategy. However, as often is the case, we simply don’t know. What to study, where to live, what job to take, and so on – the options are in front of us, but sometimes we don’t know where to start, or even what the full range of options may be (because as is often the case, if we look further and harder, we uncover or create more options). That’s when an emergent strategy works well. Instead of following a clear path, we can try different things. If nothing draws us in, then we can keep moving until something does. Once we find it and finally do feel that something is right, that is when we can follow a deliberate strategy of pursuing it wholeheartedly.


In Range, David Epstein echoes a similar sentiment, writing about the benefits of exploration – and stopping pursuits quickly when we realize that they aren’t a match for what we are looking for. He argues for pivoting quickly until we do find that which is better-suited for us, and he also talks about the benefits of gaining the wide range of experience that is developed precisely through this process of exploration, with which I agree. It is often the case that as we go through a set of experiences, it is sometimes unclear how they all connect. Yet somehow, eventually things come together and become clear. Recall Steve Jobs’ famous Stanford commencement quote about connecting the dots – “You can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future.” He was referring to the fact that he had a varied, often jumpy path, for example taking calligraphy classes at Reed College before dropping out – and yet that interest in design is partially what led to his future Apple computers being so well-designed and aesthetically appealing.

Sometimes having this wide range of experience actually proves to be helpful in unexpected ways. In Range, Epstein gives myriad examples, including those of astronomer Johannes Kepler coming up with discoveries in the astronomical laws of gravity because he was able to apply experiences far outside of astronomy to make analogies, and academic teams finding certain discoveries when they had more interdisciplinary team members who brought experiences far beyond the traditional specialist views. Through the process of exploration that we must often go through to find that which we want to pursue, we gain valuable insights and ways of looking at the world, which may then prove to be useful as we face other challenging problems and situations in the future. Our varied experience proves to be a unique perspective, composed of the many elements that we picked up on our distinctly individual path.


There is, of course, much more that the authors mentioned in these books, but the main point that I wanted to highlight is that sometimes things feel unclear, and we are not certain what path to take or even in which direction to turn. In those moments, it is okay to just try going down a path and see what emerges. Sometimes it is better to just try something, go somewhere, rather than waiting and going nowhere. In the end, we only gain knowledge and information through experience, and we only gain that experience by actually trying something. And that information may be that we like something or that we absolutely hate it, but that is far more than we would have known if we had not tried at all. Therefore, making a choice and trying something is actually a step forward, even if the answer is that this is a path that we absolutely do not want to pursue. There should not be fear of emergent strategies. Emergent strategies will lead us somewhere. As Epstein said “We learn who we are in practice, not in theory.”


This has been on my mind recently as I have thought about my path and life in general. In the midst of the COVID-19 situation and the uncertainty in the world, staying inside has both provided time for reflection, but also been demotivating in some ways. I have found myself thinking at times, “What am I doing? Why? What comes next? What if I don’t succeed?” Despite sometimes not knowing the answers, I am trying to remember that taking an emergent strategy is often okay, and will lead farther than if I were to stay still and wonder, paralyzed by lack of choice. In the end, the feedback from our decisions is what leads us to where we need to go.