Why work at a startup?

I have been pondering for a long time – Why is startup experience invaluable? How is it different from working at a big corporation? I have a good vantage point on this as I have been part of many startups, traditional process-driven enterprise corporations, and in-betweens. I knew the benefit of the startup experience. I was finding it tough to put it into words. It clicked when I listened to conversations with David Epstein, author of the book Range.

David Epstein makes a case for generalists. He also talks about Kind and Wicked learning environments.


A kind learning environment is one where all the information needed to make a decision is available. In a kind learning environment, you get timely and accurate feedback.

A game of chess is a kind learning environment. You have at your disposal the complete information needed to make a move. Once done, you get to know whether the move was right or not.

A wicked learning environment lacks all the information needed to make a decision. The feedback that you get is hazy and inaccurate. Luck plays a role in the outcome.

A game of poker is a wicked learning environment. You do not know the card your opponent has up her sleeves. Even if you play your cards right, you can end up a loser if lady luck frowns on you.

Working at a startup is more like a game of poker than chess. You are operating in a dynamic resource-constrained environment. You have too many things to do and not enough people to execute. You have to play the role of jack of all trades and master of none or one. You need to step out of your comfort zone. The business strategy is still evolving; you tweak it as you go – nothing is crystal clear or black and white. There is no one to guide you step by step. You need to make decisions with half baked information. Someone said – all startups are train wrecks inside.

Operating in such an environment is a fantastic learning experience. It is like packing a lifetime’s worth of education into a couple of years. It also forces you to look deep into yourself and check your biases and decision-making process.

Herminia Ibarra, an organizational behavioral specialist, says – “First act, and then think.” The reason being – “We learn who we are in practice, not in theory.” Startups give you a platform to do this.

Startups need generalists – people who can move up and down the technology stack as well as carry out many functions as and when required. In a startup, you get to work on the entirety of a product rather than a tiny weeny bit. You get a ringside view into what it takes to build an organization and run the day to day operations.

Being a generalist forces you to adopt the spiral method of learning. You learn enough to get your job done. You go back to it as and when needed and broaden your expertise. As a generalist, you get comfortable with not knowing everything and taking calls with the available information. You become comfortable with being uncomfortable.

Being able to don many roles lets you develop a broad mental model and good judgment – it gives you intellectual range. Also, it engenders curiosity – you want to learn more and more about a variety of subjects. When you are aware of many fields, you can borrow ideas from one and apply it to another. Charlie Munger calls it a latticework of mental models.

Please do not consider this as a case against working at a big corporation. The title of the post is – “Why work at a startup?” not “Why not work at a big corporation?”. All experience is valuable. In the future, I will write a counter post on why working at a big corporation is valuable.

If you like this, you should also read my old post on “What a startup is not?

Do not miss the next post

Photo by Samuel Scrimshaw on Unsplash.

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