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Deep Dive #12 Khe Hy on Quitting Wall St., Self-Worth and Leisure

Khe is a teacher, coach, and speaker who has been called the “Oprah for Millennials” by CNN and blogs about transforming our relationship with time, work, money – and ultimately ourselves

Ali Abdaal
Ali Abdaal

Khe is a teacher, coach, and speaker who has been called the “Oprah for Millennials” by CNN and blogs about transforming our relationship with time, work, money – and ultimately ourselves. He worked in finance for fifteen years before quitting his job in 2015 with a quest to understand “what it means to live an examined life”. We talk about the question of what is enough, issues of validation and status and why the concept of leisure has been overturned by modern society.

Here are some of the highlights from our discussion:

Working in finance is a very easy way to get you out of the bottom but once you get there any feeling of success is short-lived. Equally, any feeling that you belong or are accepted isn’t long lasting either as you become just one of many employees within huge organisations.

The question of ‘what is enough?’ clouds the judgement of many people in modern society. Just because other people can do it doesn’t mean that you have to do it as well. Being accepting of what is enough for you has become almost a skill that we need to consciously practice. The key thing to ask oneself is – do you derive your confidence and happiness from within or do you derive my happiness from other people?

If one’s self-worth is driven by what you accomplish, we end up chasing achievement at the expense of leisure, love and relationships. Achieving is not ostensibly bad, but to seek achievement just because it’s filling an emptiness within us is an unsustainable way to approach our lives.

“We have it all backward. We go on vacation or meditate in order to be well-rested in order to be better at work - that's all wrong”

The concept of leisure has been completely upended by modern society. Culturally we’ve said that leisure is not virtuous – watching Netflix is not seen as productive. Yet for the Romans the amount of leisure time was a show of wealth and status. Today people view leisure in a patronising way or simply a chance to recharge before heading back into ‘more meaningful’ work – busyness has instead become a measure of importance and status.

“We become prisoners of our own expectations”

Seeking validation is not necessarily a bad thing. Trying to create a legacy or trying to succeed in a certain area or industry are not, in and of themselves, harmful aspirations to hold. The key is to be honest with yourself about why you are doing it rather than deceive yourself with laudable reasons that you don’t really hold.

The whole issue with status is that it requires someone else to impart it on you. Status requires some form of external judgement or validation – we might strive to achieve a certain status but ultimately, we are defining ourselves, and being defined by, external measures and other people.

“The more self-aware you become, the more you will begin to understand intrinsically what makes you happy”.

If you want a routine or structure, try to impose a constraint which helps force you into action. For example, if you want to set up a routine around writing a weekly newsletter, a constraint might be imposing an artificial deadline or planning something on the day that you are releasing your newsletter so you know that you can’t wait until that day to write it.

Deep Dive

Ali Abdaal

Junior doctor, YouTuber, web designer, aspiring musician. Trying out this blogging thing.