Should You Quit Your Job? The Two Types of Regret
Should You Quit Your Job? The Two Types of Regret
Should you quit your job for your startup? Here are practical scenarios and experienced advice and points of future regrets to help you make a decision that's not just emotional.
Most people think quitting your job to start a company is a "leap of faith." That’s a romantic way of saying you aren't doing the math, or have even considered all the factors involved. In reality, the decision to quit shouldn't feel like a jump into the dark; it should feel like an inevitable shift in pressure.
The most common mistake is quitting because you hate your job, or your boss. If you quit because you’re miserable, you aren't moving toward a startup; you’re just running away from a boss. Startups are much harder than bad jobs, and for the unmotivated, working for yourself as a boss can be just as bad as working for a bad boss. If you don't have a specific thing you are compelled to build, you’ll find yourself unemployed and uninspired within three months.
The Salary Trap
The harder it is to quit, the more likely you are to be in a "local maximum." If you make $200k a year, the opportunity cost of a startup is massive. This is why many of the best startups are founded by people who are either very young or have just been laid off. They have nothing to lose.
If you are well-paid, you have to ask yourself: Is my current comfort subsidizing my future irrelevance?
A job provides a steady, linear trajectory. A startup is convex - it has a capped downside (you lose some time and savings) but an uncapped upside. The logic for quitting usually boils down to whether you want to play a game with a high floor or a game with a high ceiling.
The Proxy Test: Project vs. Idea
Don't quit for an idea. Ideas are cheap and usually wrong. Quit for a project.
A project is something you’re already doing on nights and weekends. If you haven't been able to force yourself to work on your startup while holding down a 9-to-5, you almost certainly won't have the self-discipline to do it when you have sixteen open hours a day. The "structure" of a job is actually a useful friction. If your idea can't survive that friction, it won't survive the market.
The Regret Minimization Framework
Jeff Bezos famously used the "Regret Minimization Framework." He imagined himself at 80 and asked which path he’d regret more. But there are actually two types of regret you need to weigh:
- The Regret of Failure: "I tried and it didn't work."
- The Regret of Inaction: "I never knew if it would have worked."
For most people who are even considering a startup, the second type of regret is much more painful. You can recover from a failed company. You can usually get your old job back, or one just like it, within six months. What you can’t recover is the window of time where your energy, market conditions, and personal responsibilities aligned.
The Ramen Metric
Before you quit, calculate your "Ramen Profitability" threshold. How much do you actually need to live? Most people overestimate this because they include "lifestyle creep" expenses.
- The Practical Scenario: If you have six months of living expenses saved and a working prototype that someone (even one person) wants to pay for, the risk of quitting is actually quite low.
- The Danger Zone: If you have zero savings and only a slide deck, quitting is just a way to add unnecessary stress to an already difficult task.
Experienced Advice: "The best time to quit is when the opportunity cost of staying at your job is higher than the risk of the startup failing."
Finding Your Point of No Return
If you are waiting for a "sign" or "permission," you aren't ready. The people who succeed at startups usually quit because they simply can't stand not working on their idea anymore. It becomes a distraction that makes them bad at their day job.
If you’re still doing great work at your 9-to-5, you probably haven't reached the boiling point yet. But if you find yourself sitting in meetings thinking about your database schema or your first three customers, you’re already gone. You’re just still collecting the check.
Decision Matrix
The world doesn't need more "founders" who like the idea of having a startup. It needs people who are obsessed with solving a problem. If that obsession is costing you sleep, quit. If it’s just a way to escape your current boredom, stay and find a better hobby.
