in the 5+ years I worked for my ex-boss Dinesh (@dineshraju), he constantly would ask me about my goals & desired outcomes. He would ask things like,
- “What do you want to get out of this?”
- “How will you measure your progress?”
- “What’s the next step?”
- “What’s the limiting factor?”
He would ask these questions with a casual intensity – he really wanted to know the answers to these questions, with a persistent curiosity that I inherited. I’ve since internalized that stuff so thoroughly, and found it so useful, that I now almost struggle to remember what it was like before I installed Dinesh’s “instrumental thinking module” into my mental suite.
The wack thing is, once you internalize this, or a version of this, you look at the world in a completely different way than people who haven’t internalized this. And you look around and you see that very few people really internalize this. You can get whiplash from the contrast.
Here’s what I think I’ve observed:
1. Lots of people don’t know what they want. They don’t really try very hard to figure out what they want. Many don’t really believe it’s even possible. Amongst those who try, many aren’t very systematic about it, or they “try too hard” and agonize about it unproductively. There are many ways to fail on this front.
2. Suppose you don’t fail too hard on (1)- you now have some sense of what you want. Cool! Lots of people then aren’t very persistent about translating this into manageable projects and actions. Some might come up with a big grand plan that’s insurmountable, like “write epic novel”. This sort of thing is doomed to fail, because you can’t make much progress on this. Some people call talk about “SMART goals”, that does come into play here.
3. suppose you did ok with (2)! people will always find ways to fail 😂. They’re like, okay, “I have a plan, I want to become good writer, by writing a lot, write some tweets everyday, a blogpost every week” – pretty good plan! But then they struggle with managing their psychology/emotions and get jaded. Trying to do any substantial project is a struggle, and you have to slog through a significant period of time where the reward for the work you put in isn’t tremendous. Super loosely, I’d say most meaningful, reasonably-well-scoped projects seem to like 3 months of meh before they get you anywhere really interesting.
Managing your psychology is basically THE HARD PROBLEM in LIFE. (h/t Ben Horowitz’s book The Hard Thing About Hard Things). everything else is pressing buttons and pulling levers. a novel is one word after another. a marathon is one foot in front of the other. but how to keep going?
To keep going you have to know your motivations. You have to know your WHY. WHY are you doing this? What is it all FOR? It helps to examine your own life to see what are the things you’ve cared about in the past. Ask your friends & family what got you passionate riled up the most.
Because we are each a bundle of competing motivations, competing interests, there’s a whole Game of Thrones going on inside your head every day (ppl are different, YMMV). In a way you are kind of like the boss of your brain. Or maybe not even THE boss, but like, the SVP of your brain or something. So. A lot of people are shitty managers of their own brains. I’m sorry, its true! It’s not even really your fault, particularly if you weren’t taught better. This species is a fractal of shitty management all the way up and down. And all the cliches of bad managers apply internally as well:
“My manager doesn’t listen to me, keeps making promises of me he can’t keep, drives me too hard, never gives me a break, doesn’t praise me when I DO get things done, infinitely critical, is somehow both paranoid and clueless, is no help at all, keeps increasing my workload…”
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This post on product-market fit is also pretty much downstream of my on-going conversations with Dinesh.
My friend Tasshin did a zoom call with Dinesh that’s on his YouTube channel:
I did a call with Dinesh myself: