A taste of freedom can make you unemployable
What Naval Ravikant got right, and what stepping off the corporate track actually feels like a year in.
There’s a line from Naval Ravikant that I have been turning over in my head for about a year now.
I read it for the first time sitting at my desk in a corporate job, telling myself it was clever but did not apply to me. I read it again a few weeks later and thought maybe there was something to it. I read it a third time, handed in my notice the next month, and have been living inside the sentence ever since.
In March 2025 I walked away from a career in the kind of company that gives you a laptop, a pension, and a performance review cycle. I have spent most of the time since then moving. Istanbul, Bali, Vietnam, Thailand, Malaysia, Singapore, Australia. Airports, apartments, long walks in cities I did not know in the morning. Some of that time has been building things. Some of it has been doing nothing in particular, which turns out to be the harder skill.
This is a newsletter about why Naval’s line is true, what freedom actually feels like when you have it, and the boring financial decision that made the whole thing possible in the first place.
Why the quote is accurate
The reason a taste of freedom ruins you for employment is simple. Once you have felt what it is like to own your time, going back to renting it out to someone else feels absurd. Not noble-absurd, not brave-absurd. Actually, physically absurd. Like trying to wear shoes two sizes too small after you have spent a year barefoot.
For the first couple of months after I left, I kept checking my calendar out of habit. There was nothing on it. I would feel a flash of panic, then remember, then feel something closer to embarrassment. I had spent years believing I was busy because my calendar was full. It turns out my calendar being full was the whole problem.
The thing no one tells you about corporate life is how much of the pressure comes from other people’s urgency. Your boss’s priorities become your priorities. Your team’s deadlines become your deadlines. A good manager makes this feel meaningful. A bad one makes it feel frantic. Either way, the shape of your day is not yours.
When you remove all of that and replace it with nothing, you meet yourself for the first time in a long time. That is the taste Naval is talking about. Once you have it, the idea of giving it back becomes genuinely hard to imagine.
What freedom actually feels like (the bit nobody warns you about)
I want to be honest here because most of what you read about leaving the corporate world online is either cope or sales pitch.
Freedom is not a permanent high. It is a vacuum. A good one, but a vacuum all the same. For the first month or two you are running on the euphoria of having escaped. Then the euphoria wears off and you are left in a cafe in Chiang Mai at 10am on a Tuesday with an entire day ahead of you and nobody asking anything of you, and you have to figure out what you actually want to do with your life.
This is the bit that a lot of people do not handle well. They fill the vacuum with busywork. They start five projects to prove they are still productive. They doomscroll job listings at 3am even though they know they are not going back. They build elaborate Notion systems to optimise a life that does not yet have a shape to optimise.
What I have learned, slowly, is that the vacuum is the point. You are supposed to sit in it. You are supposed to be a bit bored, a bit aimless, a bit scared. That is how you find out what you actually care about, as opposed to what you have been told to care about.
The moving around helps. Every new city strips away another layer of the old routine. I thought I loved going to the gym every morning, and it turned out I just liked the identity of being someone who goes to the gym every morning. I thought I needed a lot of stuff, and it turned out I needed a backpack. I thought I was an introvert, and it turned out I was just tired.
Travel is not the point, to be clear. You can do all of this from your home town. Travel just accelerates it because every familiar anchor disappears and you are forced to rebuild from scratch.
The building and the failing
The other thing freedom gives you is the room to fail.
In a job, failing is expensive. It dents your reputation, your bonus, your standing on the team. So you play it safe. You ship things that are fine, not things that are interesting. You stop pitching the weird ideas because the weird ones get shot down and the safe ones get promoted. Over years, this calcifies into a kind of quiet mediocrity that feels like excellence from the inside because everyone around you is doing the same thing.
When you leave, that incentive structure just evaporates. Nobody is watching. Nobody is grading. You can try something, have it not work, and the only consequence is that you learned something. That sounds obvious written down. It is completely different to live inside.
Since March I have started things, abandoned things, picked things back up, changed direction, written stuff that went nowhere, and shipped stuff that surprised me. None of it has the clean narrative arc you get when you curate a LinkedIn post about it. Most of it has been messy and unglamorous. But the compounding is real. A year of genuine attempts beats five years of safe bets, and I feel that in my bones now in a way I did not before.
The boring decision that made this possible
None of the above happens if the money is wrong. This is the part most people skip when they talk about freedom, and I think skipping it is slightly dishonest.
I moved to San Francisco in 2017 and that is where it started, though not in the way you might expect. I did not get rich there. I did not ride some unicorn IPO or cash in on a lucky bet. What happened in San Francisco was simpler and, looking back, more important. I was surrounded by people who thought about money differently than I did.
Back home, money was something you earned, spent, and hopefully had a bit left over at the end of the month. In San Francisco, the people around me treated money as something that should be working. Every conversation at a dinner table or a bar eventually wandered into what someone was investing in, what they thought of the market, what they were building on the side. It was in the water.
So I started investing. Nothing clever at first. S&P 500 index funds to start, then Bitcoin, then XRP, alongside a handful of other positions. I made mistakes, I held through volatility, I bought more when everyone was panicking, and I kept going for eight years. That is it. That is the whole secret, which is why nobody wants to hear it. Time and consistency, not genius.
But the decision underneath the investing is the thing I actually want to talk about, because anyone can open a brokerage account. Fewer people do the harder thing. I bought assets instead of nice things.
That is the whole principle. It sounds too simple to be useful. It is the actual mechanism.
Most people, when their income goes up, scale their lifestyle with it. Bigger flat, newer car, nicer restaurants, a wardrobe that reflects their seniority. This is called lifestyle inflation and it is the single most effective way to stay employed forever. Every upgrade raises the monthly floor you have to clear. Every new recurring cost is another reason you cannot say no to your employer.
The alternative is to let your lifestyle stay roughly flat while your income grows, and to push the difference into things that either pay you back over time or grow on their own. For me that was the S&P 500, Bitcoin, and XRP, alongside a handful of smaller positions. The specific mix will be wrong for you. The principle is the thing.
Assets buy you optionality. A nice car buys you a nice commute. Over a decade the gap between those two choices is enormous, and the gap is literally the difference between needing a job and not needing one.
I am not anti nice things. Life is short and you should enjoy it. But if you want Naval’s taste of freedom, you have to be honest with yourself about whether the nice things you are buying are actually making you happy, or whether they are making you a more reliable employee. A lot of people would be shocked how much of their consumption falls into the second category once they look.
So what do you do with this
If you are reading this and something in it resonates, I am not going to tell you to quit your job. That is a decision you get to make with full context on your own life. What I will say is this.
The taste of freedom is real and it is one-way. Once you have it you cannot un-have it. So if you think you might want it one day, start laying the groundwork now. Not in a panic, not in a dramatic gesture, just quietly.
Spend a bit less than you earn. Buy assets. Resist the urge to upgrade your life every time you get a pay rise. Get clear on what you actually want your days to look like, separate from what sounds impressive at a dinner party. And maybe, eventually, take a week off and do nothing. Just sit in the vacuum. See what comes up.
You might find you love your job and come back energised. You might find something else. Either way, you will know, and knowing is most of the battle.
I will write more about the specific building and the specific travel in future issues. For now, I just wanted to sit with Naval’s line and tell you it is even more true than I thought when I first read it.
Good luck
Stephen