Should ambitious young people follow the conventional linear career path or deliberately step off it?

Miki Kuusi · Nov 28, 2022

A life spent off the prescribed track — taking risk, doing something unconventional — is more interesting than the standard uni-to-promotion path

He was on the conventional track and got 'misdirected' into startups, which made his life far more interesting than it otherwise would have been

Scope: conventional paths are fine if genuinely chosen rather than driven by others' expectations

55:57 20VC: Wolt CEO, Miki Kuusi on Leadership Lessons Scaling to a Reported $8.1BN Exit to Doordash, Building Teams not Families, The Difference Between Trust and Safety Within Companies, How To Use Compensation to Create Culture & Why You Should Not Be Lookin

Keith Rabois · Nov 27, 2023

Joining a demanding startup in your twenties is by far the better move than a comfortable large-company job

You have the energy then, and a job where you can put in 50% effort on Zoom with no fear of layoffs wastes a decade without pushing you; growth comes from the hypertrophy model of putting yourself in situations that challenge you and surprise you with what you're capable of

33:36 20VC: Keith Rabois and Mike Shebat on Creating an Olympian Mindset to Work Ethic, Why First-Time Founders are Better Than Serial Entrepreneurs, Why Remote Work Does Not Work, Why the Best Founders Always Start in their Teens & Why Companies are Cults?

Lucas Swisher · Feb 23, 2026

Young people building careers must get off the linear path

Linear decisions (SAT, Harvard, Insight) are easy and comfortable; growth came from stepping off that path into an unfamiliar, uncomfortable role

Scope: framed as advice to young people early in their careers

59:30 20VC: Inside Coatue's $70BN Machine: Why Price Matters Least | Why Mega Markets are the Most Important | How to Assess Durability of Revenue and Margins in AI with Lucas Swisher

Harry Stebbings · Feb 23, 2026

The safe career path is less safe than it appears and the risky path is less risky than it appears

60:26 20VC: Inside Coatue's $70BN Machine: Why Price Matters Least | Why Mega Markets are the Most Important | How to Assess Durability of Revenue and Margins in AI with Lucas Swisher

Emilie Choi · Aug 23, 2021

If you leave a comfortable role, you should choose something unlike what you just did — the next technology frontier — rather than an equivalent role at a similar company

The point of leaving comfort is to get out of your comfort zone, so replicating the LinkedIn experience elsewhere would defeat the purpose

4:06 Leaving comfort should mean chasing a new frontier not an equivalent role