In July 2010, Paul Graham—Y Combinator co-founder and one of my favorite essayists—published “Self-Indulgence”. He wrote it because, after selling his startup in 1998, he realized something scary: you don’t lose your fortune by spending it on Ferraris. You lose it by making confident, terrible investments.
He then connected this to time, and honestly, it hit me hard.
The most dangerous way to waste time isn’t having fun. If you sat on the couch watching Netflix all day, your brain would scream at you by noon. You’d feel guilty. You’d know you were wasting your life.
The real danger is fake work.
It’s spending six hours answering emails, reorganizing Trello boards, or having “sync calls” that resolve nothing. You end the day feeling exhausted, so you tell yourself you worked hard. But you didn’t actually do anything. You didn’t build, you didn’t learn, you didn’t ship.
As Graham put it: “The most dangerous way to lose time is not to spend it having fun, but to spend it doing fake work.”
Why this matters if you’re targeting FIRE
In The FIRE Paradox, I wrote about the courage it takes to finally quit. But nobody warns you about the void that comes after.
When you’re working a 9-to-5, your time is managed for you. You have deadlines, bosses, meetings. You might hate it, but it gives you structure. Once you reach Financial Independence, that structure vanishes. And if you’re not careful, you’ll replace it with busywork just to feel useful again.
I see people preparing for FIRE by obsessing over withdrawal rates and asset allocation. That’s important, sure. But almost nobody prepares for the Tuesday morning when they wake up with absolutely nothing on the calendar.
If you’re on this path, you need to build a new operating system before you pull the trigger.
1. Install new alarms
When saving for FIRE, your alarm is: “Do I really need to buy this?” It protects your money. Once you’re free, you need a new alarm for your time: “Did I actually accomplish anything today?”
If the answer is “I cleared my inbox,” that’s a red flag. Fake work is sneaky because it feels like duty. It’s not. It’s procrastination in a suit.
2. Schedule deep work (or deep play)
Start blocking out time now. Two hours of deep study, coding, or writing is worth more than eight hours of low-level busyness. And when you’re not working? Be really off. Go for a run. Cook a complex meal. Read a book.
Real work is good. Real play is good. The grey zone in the middle—where you’re kinda working but mostly just distracted—is where dreams go to die.
3. Pick a mission, not a job
Reaching your FIRE number is a huge quest. Once it’s done, you’ll need a new one. Not a job, but a mission.
Maybe it’s learning a language, building a SaaS, mentoring, or mastering sourdough. It doesn’t matter what it is, as long as it’s hard and you chose it. Without a mission, entropy takes over.
4. Audit your time like an investor
Graham noticed rich people lose money on bad investments they don’t understand. Post-FIRE, the risk is doing the same with time.
Don’t say “yes” to coffees, boards, and projects just because you’re flattered to be asked. If you wouldn’t do it for free—or if you wouldn’t do it if nobody was watching—don’t do it. You’re buying your freedom. Don’t sell it back for cheap validation.
The bottom line
Paul Graham ended his essay saying: “Avoiding pleasure is no longer enough to protect you.”
For anyone chasing FIRE, avoiding the 9-to-5 isn’t enough either. You have to actively fight against the drift into emptiness.
You need the courage to be unproductive when you’re resting, and the discipline to be effective when you’re working. Anything else is just a fancy way of wasting the freedom you’re working so hard to earn.