Playing Catch Up

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April 24, 2020

(9 min read)

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“If you don’t improve your math grades, I will take your class president position away.” Those were the words that my seventh-grade teacher told my crying young self as I received yet another C on a math test in China. Now a college student in California, I still vividly remember that pivotal moment years ago, both for its role in prompting me to pursue an education abroad at twelve and mark for the beginning of a journey of constantly trying to catch up. Although my skills in math improved over the years, I’ve found myself trying to match my peers in other areas. Whether it is struggling socially in an unfamiliar culture during my first years in the United States, competing on the basketball court as a short and skinny player in comparison to my opponents, or now as a budding tech entrepreneur who’s noticed the distance that he has to make up behind many others.


I do want to stress that my problems and challenges are minute when compared to those in more strenuous conditions. There are still people around the world without adequate access to education, family support, or even food and shelter, having to run in a much more difficult chase in life just to be on an even playing field. However, the reason why I’m writing this essay is that many people may also feel that they are behind in their fields when they compare their own progress to others who’ve been mastering certain skills for a much longer period of time. I want to explore, using my personal experiences, what we all can do when we’re feeling or are indeed behind and still be productive in this position.


I was fortunate enough to grow up in an environment where I got to discuss entrepreneurship and business with people around me and felt that I was making substantial progress in my learning. Having completed six years of secondary education on the east coast in rural locations, where the population was not consistently conversing about the tech industry or honing their skills in hacking and building, I ignorantly thought that I was amongst those who gave the most thought to tech and business at my age. But attending college in California in a metropolitan area gave me a reality check; I soon came across and feel fortunate to have befriended computer science students who have been coding since they were kids, design students who already have magnificent portfolios, or very professionally driven individuals who can seemingly name every VC in the state… Then I evaluated myself. Despite my prior internship experiences including one at a VC, my only exposure to technical skills was my computer science classes in high school where I did not come close to mastering or appreciating the beauty of CS.


Some may call my reaction irrational—and in some sense it is. Here I was, with a VC internship experience under the belt before college, yet I was still feeling behind. This is probably a perfect example of a “first-world problem”. However, this type of feeling is not uncommon, which is why it’s important to address. While you may define it as “imposter syndrome”, I do not want to completely eliminate the possibility that some of us who are feeling behind are actually correct. For example, it is true that my coding skills are lacking in comparison with a lifelong coder or for the sake of building complex software. And it is also true that I cannot draw anything with my hands for the life of me. So what do we do when we feel or are in fact trailing? Through my personal experiences so far, I have narrowed down some useful lessons and thought processes to follow when I find myself in situations where I am behind in my learning or skills compared to others around me. Please also keep in mind that I am also just another ignorant college student who is trying to figure out many more aspects of my own life, so read on with a critical lens knowing that I am still in the process of polishing myself:


Underdog mentality helps, only when done right.

Tom Brady, often considered the greatest of all time in American football, has said that he still keeps an underdog mentality as he approaches each day in his career. When you tell yourself that you are the improbable star or that the odds are against you, you may feel an extra boost of energy and motivation to grow. Some people also strive to “prove the doubters wrong”, and it may help, but I have not leveraged this mentality much and cannot vouch for it personally. The underdog mentality technique works and has been proven to work as long as you don’t feel defeated or hopeless when facing the knowledge or skills gap between you and who you want to emulate. When you choose to have an underdog mentality, it is crucial to stay confident in your ability to improve. Once you stop believing that you can grow, the only thing you’ll see is this expanding gap without any hope of bridging it, and this is a calamitous zone that you don’t want to be in. So if you do choose this mentality, handle it with care and confidence.


Think of the unique value that you can provide and objectively evaluate your shortcomings.

When you’re feeling behind, it’s easy to fall into a trap of only focusing on your weaknesses or lack of skills in certain areas, and this attitude will hinder your capacity to clearly evaluate yourself and your position when compared to others. Taking mental notes about your own strengths that may contribute to a field can help bring yourself back to a more balanced emotional state that prepares you to logically think through the required steps to catch up. In my personal experience, I knew that, despite my rudimentary coding skills, I owned a relatively good sense of product and user experience, in large part due to my conversations with founders and evaluations of pitches, demos, and beta tests. From retelling myself these strengths of mine, I developed more confidence in my ability to contribute to projects and ultimately provide value to businesses. The good news is that you can always find strengths within yourself that you can rely on to contribute if you try hard enough. After knowing your strengths, it is much easier to objectively list out the steps that you need to take to catch up with others in a field or skillset. In my case, after reminding myself of the value that I could already bring to the table, I became more enabled to think of the specific steps needed to learn coding and design in order to be prepared for further entrepreneurial pursuits. Overall, this specific thought process is geared towards having the right mental state to pinpoint specific weaknesses and address them without shame or disappointment, which are unproductive.


Do a cost-benefit analysis.

In some cases, it may be better for you if you just develop your existing strengths further instead of trying to catch up with others in a high-barrier field or skillset that requires years upon years of mastery. An extreme hypothetical scenario that I can think of is a 60-year-old trying to break Usain Bolt’s sprint records. If this person’s metric of success is solely whether they actually break the record and not their enjoyment of the process, then it is probably in their best interest to pursue something else. To be clear, I do not mean to discourage anyone from reaching for the sky. If the 60-year-old track star wannabe aims to redefine human limits, I am fully supportive of this aspiration, but they need to know the costs and sacrifices on the way to accomplish that goal. We can all sleep better at night knowing that the growing availability of information and knowledge in the present day helps to lower the barrier to learn most skills and shorten the time frame that it takes to master them. It is ultimately up to each individual to make that decision for themselves—whether to dive fully into their existing strengths or try to improve and catch up to others in another—and sometimes it could be a mixture of both.


Be confident in your strengths but stay humble to learn.

As you can probably tell by now, confidence plays an important role in dealing with the feeling or fact that you are behind. If you utilize an underdog mentality correctly or think of the unique value that you can create, you’ll develop some of that much-needed confidence. But staying humble after you’ve developed confidence is just as important. Contrary to some people’s actions, confidence and humility do not exclude each other; it is not an either-or choice between the two. Humility allows you to put yourself in the role of an eager student, who knows and is excited for the specific work that they have to complete in order to get better at their craft. Reminding yourself that you can already contribute greatly to software engineering or sales is great, but that doesn’t mean you can’t become a more well-rounded contributor by emulating the best marketers that you know.


These are the lessons that a naïve college student can summarize thus far in his life in regard to being in a position where we have to catch up to others. I want to conclude by stressing that, although comparing ourselves against others can evoke motivation at times, the true “progress bar” that we should rely on to judge our skills and experiences is ourselves. In the end, no one has had the same upbringing and is in the same situation as anyone else. We can’t choose to have been mesmerized by painting, mathematics, or computer science since we were kids like some others around us; we can’t choose to be born in Silicon Valley, having learned to use different API’s and SaaS platforms since middle school. What we can choose though, is what we do and how we react, now knowing the existing gap between us and where we want to get. In truth, “playing catch up” just depends on how you choose to run and where you want to go.