James's Blog

Sharing random thoughts, stories and ideas.

Internalizing Wisdom

Posted: Nov 11, 2019
◷ 3 minute read

Despite constantly consuming various books, articles, and speeches about how to more effectively run a team, how to be a better person, how to live a happier life, etc…, I don’t believe that there are shortcuts to wisdom. All the things that truly matter are hard, and as as a result, much easier read than done. Wisdom is nothing more than mere ammo in the intellectual status game if it is not internalized and applied when it is really needed.

The clichéd advice of “never give up, no matter how hard it gets” is commonly given by experienced startup founders and venture capitalists to people looking to start companies. Ben Horowitz spent an entire book on this in The Hard Thing About Hard Things, which is considered as one of the must-read “entrepreneurship-101” textbooks on starting a business (along with Peter Thiel’s Zero to One)1. Countless other people have said similar things, and the notion is almost considered gospel. Yet it is something that’s very difficult to truly internalize, even though anyone can parrot the idea. Personally I don’t think I’ve really internalized this bit of wisdom until recently, despite having been a founder for nearly 8 years.

When things are going fine, it is an easy notion to think and talk about, after all it is of little consequence during these times. It’s when things are going to hell, when everything is on fire, with seemingly no outs, that founders need this piece of wisdom the most. But this is precisely when one is least likely to think of and apply this advice! Reflecting back on the numerous occasions that I’ve been through a crisis, or filled with frustration and burnout, in the worst moments it always felt like an all-consuming sense of despair. All the readings about how hard things can get and how you should never give up were nowhere to be found in my mind. Luckily, I have managed to successfully pull through all of these periods (so far), thanks to peer support from my co-founders and other helpful team members. This is a testament of how important team camaraderie is for a company’s success, but it still shows that knowing about some wisdom does not necessarily mean it’ll be effectively used in practice.

I don’t think this particular startup advice is unique in this regard. Most useful, consequential pieces of wisdom are similar, in that you are least equipped to apply them when you most need them. This is why internalizing the ideas behind the wisdom is so important, so that in those moments of crisis you are able to utilize them automatically. Can this be done by mere reading? Perhaps, but I am generally skeptical. Experience followed by reflection is usually the more effective way to become wiser.

And to all the founders or team members of startups who are currently struggling with some catastrophe, or feeling burnt-out: remember to think about this bit of advice in this moment of darkness. Do reach out to colleagues, friends, and mentors for help of course, but also don’t forget to apply what you undoubtedly have seen countless times: don’t give up. This is the moment that all those books, articles, and speeches about entrepreneurship were preparing you for.


  1. These pair of books are often recommended together, because they compliment each other very nicely: Zero to One gives you the what and why, while The Hard Thing About Hard Things gives you the practical how, on starting a company. ↩︎