Have no idea WTF you're doing with your life? Read these.


Springboard is a book written by a guy who teaches at UPenn's Business School. He was son of army guy and was expected to join the army then in his late teens became pacifist / didn't want to go into army. He ended up being in existential angst, not knowing what to do with his life until mid 30s when he realized he loved teaching. He teaches Negotiation at Wharton AND he teaches the coolest course I've heard of called "Success".

The book is a book format of the "Success" course. In first half of book he talks about what Conventional Success looks like -- fame, money, reputation, etc. And he talks about how these are not the greatest things to strive for -- i.e. Hungry Ghosts. In second half of book, he talks about how you can figure out what you TRULY want and how to get that.

The second book is called Designing Your Life and it's written by 2 Stanford tech/design professors. I really like this one because it is very, very practical and actionable -- it gets you to do stuff so you can "test" ideas you might have for career. So we test by doing informational interviews. Once you're ready to commit more, you test again, maybe by doing a 3 month trial with a company where you can opt out at the end of 3 months OR they can opt out at end of 3 months.

Most important thing from both of these books... MAKE SURE YOU ACTUALLY DO THE ACTIVITIES IN THEM. It's a complete waste of time if you just read them and they go in one ear, out the other. You need to reflect on them, come up with a plan.

In my mind, the goal with doing these activities is so that you can try to build a rubric or criteria for evaluating routes to pursue with your life.

Let's say you figure out that there are 3-5 values that are very important to you. Then you can use those values (and maybe even their respective importance) against any opportunities that come your way and make a rational and strategic decision.

I think people who are confused tend to jump at whatever comes to them first, even if it's not the best thing for them long term (with that being said, I do realize that people do need to make money). They get desperate.


Furthermore, people get carried away with rose-coloured glasses. Let's say that they get a job opportunity at a company that's very popular right now (Tesla, Shopify, etc.). Many a people will jump at the opportunity to work there — even if it's not the best long-term thing to them — because it's currently what's sexy. Trust me on this one because I've done it before.

Written: September 21, 2020 (originally written for a few friends and repurposed)

Additional resources:

  • Haven't read the book but done exercises from it. The Happiness Trap by Russ Harris is very similar.
  • Smart Choices

From Naval:


He says we usually just lean on "what you do" but recommends we also give good amount of time to think about "where you live" and "who you're with".

From email to Sabrina:

I love Springboard; however, I do think I like "Designing Your Life" better as advice, at least for me. I owe a TON to Springboard and it's arguably one of the most impactful books I've read in my life. I think about tons of its concepts all the time.

With that being said, I am an overanalyzer/overthinker. There's a quote in Sprinboard from Socrates, "The unexamined life is not worth living."

While I agree with this and I don't think very many people really think hard about this until midlife or some crisis, I tend to OVERindex on this. I think about my life too much, which leads to existential angst. A quote, at least for me, to balance out Socrates' is "The unlived life is not worth living."

I've seen a counsellor / therapist whatever for just over 2 years now. I started working with my current psychologist about 7 months ago and she does CBT, DBT, ACT, etc. Prior to that, I was seeing a counsellor and it seemed very psychoanalytic --> why am I the way I am, what can I do to rectify that, etc. This was aligned with Socrates' quote and examining your life. However, it actually led me into a deep spiral of anxiety and then depression because I couldn't figure out "what I was meant to do", if that makes sense.

With my current psychologist, the objective is action. Even though things might have happened in the past that have made me the way I am, I need to commit to taking actions forward rather than stewing and overthinking what I'm meant to do, why I am the way I am, etc. (generally speaking, from what I know, this is why psychoanalysis has fallen out of favour because the clinical research shows that CBT -- i.e. action based behaviours -- lead to better results than psychoanalysis)

Anyways, that's why I find Designing Your Life very useful. It is very practical and action oriented. Sort of the premise behind Designing Your Life is "Hey, you might be interested in X. How can we come up with little investment experiments and test out your hypothesis for what you're into." Versus, for me, Springboard kind of makes me think "Am I doing the RIGHT thing?" and then with my perfectionism, I worry about doing the right thing and don't do anything...