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By Lenny Rachitsky · lennysnewsletter.com · @lennysan on X · YouTube · LinkedIn
Lenny Rachitsky shares five strategies from his own early career for people in their 20s deciding on roles, quitting jobs, and new ventures. He argues against over-optimizing for resume checkboxes, follows interests while creating value for others, shakes things up before getting too comfortable, prioritizes the people around you, and keeps learning. The core message is that career paths are only clear in hindsight, so act on interests and stay intentional.
Subscriber post — summary only01Key takeaways
- Don't over-optimize for resume checkboxes; the pressure to build credentials never ends.
- Pursue interests, but pair them with creating real value for others or they become a hobby.
- Notice which work gives you energy and gradually steer toward it.
- Change roles, teams, or companies when comfortable for too long; pivotal moments often followed long stretches.
- Evaluate future colleagues and company culture as carefully as the job itself, and keep learning for its own sake.
“Passion is not something you follow. It's something that will follow you as you put in the hard work to become valuable to the world.”Cal Newport · Lenny’s Newsletter
“You can't connect the dots looking forward; you can only connect them looking backward.”Steve Jobs · Lenny’s Newsletter
02Frameworks mentioned
Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.