On Success & Failure

ashwini asokan
2 min readJan 21, 2023


This year I’m reading extensively about failure & success. It seems like there is so much uncertainty in tech, seems like everyone is sitting up & wondering what this all means, where they stand in life, career, and more. More importantly, I have been on a journey myself.

I’ll keep editing and updating this article as I curate and thread this list of thoughts, reads, and lessons on the theme. It feels like a good time to learn to be your own coach. If you guys have ideas or principles you live by or work towards, drop a note here, and feel free to comment here or on Twitter.

1 / So much of success is about how you shepherd your failures

2 / There is no such thing as a failed person, there are only failed actions that serve as rich fertile ground to mold success out of

3 / You haven’t truly tried hard enough or pushed on your capabilities hard if you haven’t failed often

4 / Mistakes are not just part of life, they’re the norm. Mistakes are just another way to refer to failed experiments. And they can turn into meaningful outcomes if you learn from them and not make the same ones over and over again.

5 / Sometimes even when you didn’t do anything wrong, you can fail at something. There are things you can control and things you cannot, if you know for sure you gave it your 100% (and YKIYK). Sometimes failure is simply about luck and timing. And as long as you keep coming back to each day with everything you have, you’ll have just enough hits as you’ll have failures. It’s a game of numbers.

6 / Sometimes when you feel stuck, unable to make progress — you’re likely there because you haven’t learned the lessons that phase has to offer you. Unlocking that phase is simply about making a choice to either leave it or to learn the real lesson it has to offer to solve the puzzle and make progress. It’s like a game. You need to unlock each level to get to the next or abandon the game. Both have consequences. So take the time to register the decision there to learn or leave and then live, embrace those choices.

7 / Learning to associate failure with your actions and not with yourself is the difference between problem-solving to move forward and passing judgment on yourself in a way that can cripple you.

8 / Whose game are you playing? This question determines your definition of failure and success.



ashwini asokan

Founder CEO Mad Street Den, an AI and Automation startup. Musings on life, growth, AI, SaaS, Startups, Design.