Some questions to ask yourself when confonted with major decisions about your life.
Find your inner compass
This goes by many names: “gut feeling”, “deepest impulse”, “instinct” or “intuition”. I think everyone has it, to some extent, but listening to it is a practiced skill. Instead, one tends listens to their “thoughts” - a narrative or some conversation going on in their heads. But these tend to obscure the inner compass.
Thoughts feels like the voice in your head. The voice in your head is formed by your recent experinces (think: availability bias), by your concern for comformity and convention, by negative emotions like fear or anger or jealousy or envy, by your acquired vocabulary, by habit.
The inner compass is more visceral. It feels like freedom. It comes from your free and unhindered will. It is honed with inquisitiveness, curiosity, integrity, presence.
And it is abundant. The inner compass exists in the space and life beyond thoughts. It is vast and infinitely more expansive than the mind’s ability to think.
Speak to yourself in the third person
When faced with a difficult problem one trick is to ask how you would view your choice in hindsight a year later. I’m able to make clearer judgments about situations, when someone else is going through them. It’s much harder when I’m the subject of the story. Your mental context is so much more developed when you’re thinking about yourself (not in the 3rd person). You have skin in the game, maybe it’s that you’re worried about the outcome of the situation, or it’s just stressing you out, or you’re thinking about how it will affect your friends/family/the rest of your life. So when you view it from an outsider’s perspective, and throw away all that mental “noise”, you have a clearer head and can make better decisions with the long-term in mind. Alternatively, if you’re going through something, you could try imagining someone else in the same situation (make up someone if you have to). What advice would you give to them? Then use that advice for yourself.
Separate the idea of something from the lived experience of it
There’s a difference in having something and looking like we have the thing. There’s a difference between what you like, and what you’d like to like; between love, and the idea of love; being aware, and being aware that you are aware. One is the the map, the other, the territory.
Some examples…
The experience of actual programming something is quite different from the romantic vision of a hacker.
Living the life of a nomad travelling around the world seems enticing. But visualising yourself at awesome places is a fantasy where you usually leave out your own inner psychology: imagine as you are, right now. If you were transported to your dream vacation place, would you be happy? Imagine the anxieties you will feel: being jobless and aimless in life and not adding meaning to anyone else’s, of not making a lasting impression on the world etc. Who would take care of your family? Does it still seem enticing?
Seperate the feeling of lived experience from the memory of it
There is a difference between the remembering experience and lived experience. If something was not enjoyable, do you want to do it despite suffering?
“I don’t like writing, but I loved having written”
What were the experiences of other people who followed this path?
Preemptively avoid the mistakes they made. As an example, this is how I decided against academia.
What are the worst criticisms of doing this?
Does the things that can hold itself against the worst criticisms that you would come up with?
Is it intrinsically meaningful?
Why is it meaningful? Is it intrinsically meaningful, or are you doing it because of social validation? What is your benchmark for social proof - is it your immediate circle, national, or international?
This has helped me decide against some of the opportunities I have walked away from: BRCA GSec elections, any event management gigs, jobs in finance etc.
What are you giving up?
Life is tragic. There are opportunity costs.
Let’s say you have to make a decision about what job offer to accept. If you take up a prestigious career, say working for a big law or management consulting firm, what would you be giving up? Would you find time to pursue health and physical fitness, or hobbies like writing and music, or pursue dating opportunities and obligations to family? Would missing out on all these for spending extra time debugging code or fixing excel sheets be worth it?
In your old age, would I regret the time spent on this?
What is your legacy going to be? What are the stories people are going to tell when you’re gone? What is your obituary going to say? Is there anything to say at all? If not, what would you like it to say? How can you start working towards that today?
Does this express who I am?
Some decisions are not a matter of what leads to a better outcome or what does not, but instead are expression of identity (“this is who I am!”)
What’s true about you today that would make your 8-Year-Old Self cry?
The funny thing though, is that if my 8-year-old self asked my 20-year-old self, “Why don’t you write anymore?” and I replied, “Because I’m not good at it,” or “Because nobody would read what I write,” or “Because you can’t make money doing that,” not only would I have been completely wrong, but that eight-year-old-boy version of me would have probably started crying. That eight-year-old boy didn’t care about Google traffic or social media virality or book advances. He just wanted to play. And that’s where passion always begins: with a sense of play.
Man reveals how chosing comfort in his 20s led to a life of emptiness and pain
Whenever you are making a consequential decision, write down what you decided, why you decided as you did, what you expect to happen, and if you’re so inclined, how you feel mentally and physically.
Writing itself makes you realize where there are holes in things. The analysis part of you kicks in when you sit down [to write]… You think, “Oh, that can’t be right.” And you have to go back, and you have to rethink it all.
How we make decisions at coinbase?
Accept reality as a gift. You don’t know anything.
Lastly, maybe just stop taking decisions so seriously. Just go with anything.
I was incredibly sad about my first job out of college - which was not my first choice, but by accepting it I walked into a gold mine of friendships that I wouldn’t have found had my elaborately thought out plans worked out.
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