5 reads for smart ambitious people between chapters
Yuqi Hou went from Goldman to startup PM to 20 months of figuring it out. Here's what she learned.
Hi, I’m Hannah! Welcome to Nonlinear News, where I write for smart ambitious people with unconventional paths.
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If you've been reading this newsletter for a while (or even if you just found me), there's a good chance you're thinking about making a career move. After talking to hundreds of you about your career transitions, I started noticing the same 4 patterns. I turned it into a 2-minute quiz that tells you your exit type and what to actually do next.
I posted a video this week that resonated with a lot of people - articles for people figuring out what’s next in their career, so I wanted to make sure you didn’t miss them.
I think these resonated because they’re the kind of smart career advice that feels like a rare find for those of us who are ambitious but want to succeed on our own terms, so “normal” career advice doesn’t usually fit the bill. Some of these articles feel tech and startup coded because of who they come from (the founders of YC and a16z), but I think the ideas are bigger than that and applicable to anyone with a nonlinear, portfolio career.
These are 5 articles that shaped how I think about my career post banking and tech - here’s a quick overview of each, who each one is for, and what I took away.
I’m curious: have you read any of these? Which ones resonated most? I’m always looking for stuff like this, so if you have articles or books that helped you figure out your own path, send them my way.
1. “How to Do What You Love” by Paul Graham
Paul Graham is the founder of Y Combinator, and this essay is one of the most-read things he’s ever written. It’s about why smart people end up in careers they don’t actually enjoy, and what to do about it.
The part that changed my thinking was what he says about prestige. When I was in banking, I couldn’t articulate why I’d chosen it beyond “it was the hardest thing to get into.” Graham puts words to that:
“Prestige is the opinion of the rest of the world. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.”
That line is what made me realize I chose my career for the wrong reason. I didn’t love banking. I loved that other people were impressed by it.
Who this is for: If you picked your job because it was competitive to get, or because it looks good on Linkedin (formerly guilty of both…), read this.
2. “Hell Yeah or No” by Derek Sivers
This one is short and it’s a framework more than an essay. The idea: if you’re not saying “hell yeah!” to an opportunity, say no.
This is useful because sometimes we have an easier time knowing what we don’t want than what we do. And if you’re someone who says yes to everything because you’re afraid of missing out on the right thing, this reframes the problem.
Who this is for: The person with 14 tabs open, three job applications half-finished, and a Google Doc of unfinished side project ideas. If you’re spread thin and can’t figure out what to focus on, start here.
3. “How to Pick a Career (That Actually Fits You)” by Tim Urban
This is a long one (it’s Wait But Why, so expect stick figures and 10,000 words), but it’s the most thorough thing I’ve read on why career decisions feel so paralyzing.
Tim Urban has this concept called the Yearning Octopus. The idea is that you have all these different parts of yourself that want different things at the same time. Your ego wants prestige. Your lifestyle tentacle wants comfort. Your social tentacle wants your family’s approval. Your practical tentacle wants financial security. And they’re all pulling in different directions.
The key insight is that you have to untangle which yearnings are actually yours and which ones belong to someone else - your parents, your peers, society. Most people never do that. They just follow whichever tentacle is loudest.
Who this is for: If you feel pulled in ten directions and can’t make a decision, this will help you understand why. It’s especially good for people early in a career transition who feel paralyzed.
4. “Make Your Work Your Calling” by Arthur C. Brooks
This feels like the most pragmatic one on the list, and it’s for a different stage than the others. The articles above are about figuring out what you want. This one is about what to do when you already know your current job isn’t it, but you can’t leave yet.
Brooks’ argument is that you don’t need to wait for your calling to find you. You can turn whatever work you’re doing into your calling by focusing on what’s intrinsically interesting about it and finding ways to serve the people around you.
I know that sounds a little idealistic, but I actually think it’s a good bridge for people who feel stuck. You don’t have to love your job to get something real out of it while you figure out your next move.
Who this is for: If you’re not ready to quit but need to stop dreading Monday mornings while you plan your exit.
5. “Pmarca Guide to Career Planning” by Marc Andreessen
I saved my favorite for last. Marc Andreessen is the co-founder of a16z and one of the most influential people in tech.
His core advice: don’t plan your career.
“Do not plan your career. Instead of planning your career, focus on developing skills and pursuing opportunities. I believe you should look at your career as a portfolio of jobs/roles/opportunities.”
This resonates with me because it’s basically how my career has worked, even though I didn’t plan it that way. I went from banking to tech to startups to business school to content creation, and none of that was on a five-year plan. Each move made sense at the time because I was following skills and opportunities, not a predetermined path.
This is just the first part of Marc’s career advice - the other parts delve into more tactical advice like how to pick degrees and job functions. Great read all around.
Who this is for: Anyone who’s driven and talented but feels behind because their career doesn’t look like a clean ladder.
Reads, Ideas, Tools
2028 Global Intelligence Crisis - the infamous viral “stock market fanfiction” this week
Unoptimized - love these mini essays from Quartermile!
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