Things You're Allowed to Do
Milan Cvitkovic's sprawling catalogue of unconventional but legitimate things people overlook -- from hiring grad students for research to cold-emailing famous people to treating parking fines as convenience fees. The central message: most constraints are self-imposed.
Key Quotes
"In general, just ask for things, even if you've never heard someone ask for them. It's okay if the things are crazy. You can always mollify afterward by saying 'I know that's a crazy thing to ask for, but I have a rule that I always ask.'"
"You'd be surprised how cheap most of the things on this list are."
"You won't make people mad if you're polite."
Key Themes
The essay works because it's specific. Not "think outside the box" but "hire a graduate student to research a question for you" and "host a small conference on a topic you're interested in" and "bypass job postings with direct pitches to decision-makers." Each item is actionable and, when you think about it, obviously fine.
The meta-insight is about permission structures. Most people don't ask for things because nobody told them they could. Cvitkovic's list is a permission slip. The recurring pattern: the thing costs less than you think, the social risk is lower than you fear, and the worst case is someone says no.
The professional section is especially sharp. "Negotiate job offers (easier leverage than raises)" is advice that's worth thousands of dollars to anyone who acts on it. "Request signing bonuses equal to stock option exercise costs" is the kind of specific, non-obvious tactic that separates people who've been around from people who haven't.
Critical Analysis
The list has a clear socioeconomic bias. "Hire a coach" and "use laundry services" and "treat parking fines as convenience fees" assume disposable income. Cvitkovic acknowledges this partially with "hire can often be replaced with barter for or DIY" but the framing still assumes a certain economic floor.
That said, many items cost nothing: say "I don't know," cold-email someone, ask for a raise, drop out without being kicked out. The free items are arguably the most valuable because the only cost is social courage.
Connects to Happiest I've Ever Been -- both essays are about noticing that the constraints on your life are more flexible than you assumed. Wallace discovered he was allowed to find happiness outside tech; Cvitkovic catalogs hundreds of things you're allowed to do that nobody told you about.
A productive tension with A Pattern Language (Christopher Alexander): Alexander argues the opposite — that good design comes from imposing constraints (light on two sides, four-story limit, 9% parking max) because constraints form a grammar that produces better outcomes than unbounded freedom. Both are right. Cvitkovic removes constraints you didn't know were optional; Alexander names constraints you should choose because they work. The skill is knowing which kind of constraint you're facing.
Sources: Things You're Allowed to Do Last updated: 2026-05-14