The People Who Keep Us Productive

When I reflect on the moments in my past when I was the most ambitious and productive, I notice a pattern among the people in my life. Whether it was applying to universities, angling for internships, or recruiting for private equity, the types of relationships were actually quite similar.

I’ve come to believe that in order to sustain elevated levels of ambition over long periods of time, it’s extraordinarily helpful to have a few specific characters in our lives. I would identify them as:

  • Competitive and transparent peer
  • Mentor / role model who has achieved desired outcome
  • Comfort and psychological support

When we have these relationships in our lives (and when we are working towards clear goals), we are well set up to be productive over the long-term.

In essence, we need a combination of tactics, inspiration, and emotional health to effectively achieve our goals.

Competition with a Transparent Peer

Competition has consistently proven to be the most accessible and easily renewable source of motivation for me. It must be evolution that throttles our tiny brains into wanting to be better than those around us, but I think we can all relate to being motivated by competition, whether it’s over grades, wealth, sports, or innocuous games of Taboo.

I’ve found that having a transparent peer – ideally someone with roughly the same skills and goals as you – is the best way to keep yourself on track to those goals. Conversely, I think that competition with a non-transparent peer will very quickly lead to resentment and “toxicity”, particularly when scarcity is involved (e.g., a finite number of jobs).

A peer chasing after the same goal as you will be eager to talk about the nuances and specifics of how to achieve that goal, which your significant other or mentor likely won’t want to do.

It’s extremely helpful to talk to someone who is tackling the exact same problems as you, as you can improve on each other’s ideas and watch out for each other’s blind spots. Certain aspects of skill development are so technical and so mundane that unless you’re paying for a coach or teacher, only a peer chasing the same goal will have the patience and understanding to help you with it.

Being competitive with a peer of similar aptitude also helps you have reasonable expectations of progress, which I think is fundamental for maintaining self-esteem.

Nico Rosberg and Lewis Hamilton! (Via: @f1.turkish) : formula1

The storied rivalry between childhood friends and teammates Lewis Hamilton and Nico Rosberg in Formula 1 feels like an example of competition pushing peers to maximize their output. But when rewards are finite, the competition often leads to hostility and toxicity

Comparing your own abilities to someone too much ahead or behind you can make you evaluate yourself unfairly. It’s very tempting for us to compare ourselves to people who have put much more time or energy into their craft than us and be jealous of their success, which is why transparency is vital.

In my own career, I definitely observed the benefits of competitive transparent peers when I was studying hard and recruiting at Ivey. I benefited a lot from living with housemates who all also wanted to recruit for finance because we were able to share notes, mock interview each other, and keep each other apprised on opportunities.

I had a very similar experience in high school, when me and my nerdy friends would play Counter Strike and then meticulously game plan for Mr. Sheikh’s physics tests.

More recently, I’ve found my music production (and chess) progress to be a lot more sustainable when I engage with people who started around the same time as me.

It’s really demoralizing talking to people who are significantly better, but it’s helpful talking to people at a similar level of skill. You can talk about extremely nitty gritty stuff (e.g., What the hell is multiband compression doing? Which pawn breaks do I target in the King’s Indian?) without it coming off as annoying or dumb.

Mentor / Role Model Who Has Achieved Desired Outcome

While the competitive peer helps you deal with tactics and knowledge, the mentor / role model helps you develop your judgement, helps you see the big picture, and ideally inspires you. The ideal mentor is someone who understands your path and who has achieved exactly what you want.

The ideal mentor is going to be an expert who is willing to give you conscientious feedback and who is concerned with your development. It’s hard to understate the value of an expert, which is articulated in Peak:

And finally remember that, whenever possible, the best approach is almost always to work with a good coach or teacher. An effective instructor will understand what must go into a successful training regimen and will be able to modify it as necessary to suit individual students. Working with such a teacher is particularly important in areas like musical performance or ballet, where it takes ten-plus years to become an expert and where the training is cumulative, with the successful performance of one skill often depending on having previously mastered other skills… Finally, a good teacher can give you valuable feedback you couldn’t get any other way. Effective feedback is about more than whether you did something right or wrong. A good math teacher, for instance, will look at more than the answer to a problem; he’ll look at exactly how the student got the answer as a way of understanding the mental representations the student was using.

Anders Ericsson in Peak: Secrets from the New Science of Expertise

An expert will help you save hours spent drudging their YouTube by answering your specific hard-to-Google question in the matter of minutes (though I still love YouTube teachers). I try to apply these principles and I have a music production teacher as well as Chinese teacher.

I think it’s extremely important to rely on case studies when we make life decisions because it often articulates the scope of what is possible. If you can’t find anyone else who has achieved a specific goal of yours, it’s possible you have an unreasonable goal. If you can find many people who have achieved a specific goal, it’s likely that there is a discrete number of steps to achieve that thing.

For career matters, I’ve always studied precedents when planning how to get certain jobs. A huge benefit of being involved with university clubs is that it exposes you to older students who have oftentimes achieved exactly what you want. And when I was writing my university supplementary in high school, I made sure to reference successful examples.

Anders Ericsson, Psychologist and 'Expert on Experts,' Dies at 72 - The New  York Times

The legend Anders Ericsson, Swedish cognitive psychologist and author of Peak (passed in 2020)

When I was deciding whether to leave finance, I was extremely inspired by a couple of people who had left finance and were doing something entrepreneurial. Honestly, the golden handcuffs are secure as hell in finance, which made my search kind of difficult, but I still found a handful of people who more or less had the life I wanted to have.

I’m not sure if I would’ve had the confidence to leave finance had I not had many conversations with those people (notably Khe Hy from RadReads, who I found through his blog; Ibs, from my hometown; and Prabh, a school alum).

Comfort and Psychological Support

Lastly, I think the great majority of us need some form of emotional support or relief to sustain ambition over long periods of time.

I do think you can perform at an extremely high level if you just have a competitive peer and a role model, but in my experience, ambition starts exacting a taxing mental toll if you don’t have good support or a proper reward system.

We typically find support in our significant others, parents, close friends, and therapists. People who understand us and who remind us of what is important when we fail.

Sometimes we just need someone to complain to or to remind us that our value isn’t tied to a specific outcome. Sometimes we need people to remind us to get sleep and take breaks. Sometimes we need someone to party with on the weekends with so life doesn’t feel so dull.

This might be overly cynical / judgmental and probably doesn’t apply to everyone, but I think people without support end up leaning too heavily on themselves. I don’t doubt that people can still thrive under those conditions, but I do think it can be unhealthy.

Speaking from personal experience, if you don’t have quality support, the defeats can feel absolutely devastating. When you don’t have someone to rely on for comfort or to console you when you cry, it’s natural to obsess over unhealthy narratives to pick yourself back up.

I’ve met some extremely successful people who tightly clutch onto feelings of pain and inadequacy in order to make sure they remain perpetually motivated.

I definitely did this when I got to university, immortalizing and constantly reminding myself of my failures from high school as the reason for why I needed to be “the best” in university. It was effective, but it wasn’t sustainable. I think the flimsiness of that kind of thinking is partially why I ended up burning out in finance.


As I think about this mental model, I do feel like I’ve been a little lazy in my post-finance career.

I don’t intentionally interface with other digital entrepreneurs very much, which makes me think I’m not optimizing large parts of my business. I also don’t know any lifestyle-oriented entrepreneurs who have succeeded in art, so my efforts sometimes feel a little rudderless.

That’s OK though, I no longer feel the need to always be at maximum ambition and productivity.