Why quitting your job won't make you happier

Why Quitting Your Job Won't Make You Happier: Here's What Will

Have you ever found yourself daydreaming about quitting your job? Maybe the thought crosses your mind every Monday morning as you trudge into work, or maybe it's a recurring fantasy throughout the day as you deal with endless tasks and meetings. It's easy to fall into the trap of thinking that quitting your 9-to-5 is the key to happiness and freedom. But here's the reality: for most people, quitting their job won't magically solve their problems. In fact, it often leads to even more stress and financial instability. So, what's the real solution to finding freedom and happiness without making such a drastic leap? It might be simpler than you think—discretionary income.

The Real Problem: Not the Job, but the Lack of Income

Many people believe they hate their jobs. But more often than not, it isn't the work itself that drives dissatisfaction—it's the lack of financial freedom. You don't make enough to do the things that make you happy, and the daily grind feels like it's just enough to keep you afloat, without room for growth or enjoyment. When I started out in the corporate world, I landed a job as a junior copywriter making $40,000 a year. Coming from an internship where I made $12 an hour, that $40k felt like a huge leap. But once my student loans kicked in, rent was due, and the bills started piling up, I realized that my "big salary" didn't go as far as I thought it would.

I found myself in a cycle that so many people are stuck in—living paycheck to paycheck, just getting by. And that’s where the urge to quit comes from. You start dreaming of doing something different, thinking maybe another job or even entrepreneurship will solve everything. But the harsh truth is that quitting your job without a solid plan often leads to more stress, not less.
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The Irony of Quitting Without a Plan

Quitting your job sounds like a dream—until the reality hits. You leave your steady income behind, and suddenly you have no guaranteed paychecks, no health benefits, and no 401(k) match. Instead of being free, you become responsible for everything. You eat what you kill, as they say. The stress that comes with having to make your income every single month can be overwhelming, especially when your expenses don’t take a break.

According to the Bureau of Labor Statistics, about 20% of small businesses fail within their first year, and 50% fail within five years. The truth is, entrepreneurship is tough. It requires you to constantly hustle, make sacrifices, and deal with uncertainty—and it certainly isn't for everyone. For most people, the goal isn’t necessarily about running a business but about having the means to enjoy life without financial worries.

Discretionary Income: The Key to Happiness

If quitting your job isn’t the answer, what is? The real game-changer is discretionary income—money left over after covering all your essential expenses, which you can use for things that bring you joy. It's that extra $1,000 to $2,000 a month that can give you the freedom to travel, dine out, or pay down debt faster. This kind of financial buffer doesn’t just make you feel more secure—it also dramatically boosts your happiness.

I learned this first-hand. At one point, I started playing guitar in a cover band on Austin’s 6th Street, just to save enough to buy a guitar amp I’d been eyeing. My regular salary covered my basic needs, but the dream of owning that amp was out of reach without something extra. After countless nights playing for $50 in tips, I finally saved up the $3,000 I needed. I can still remember how happy I was when I walked into the music store and bought it. That experience taught me something crucial: my salary alone was never going to cover the things that brought me true joy. I needed something extra.

How an Extra $1,000 to $2,000 a Month Changes Everything

For many of us, even a small amount of additional income can make a big difference. According to the American Psychological Association, 72% of adults report feeling stressed about money at least some of the time. Imagine reducing that stress simply by finding a way to earn an extra $1,000 or $2,000 a month—that’s enough to cover a vacation, pay off a chunk of debt, or splurge on a nice meal without guilt.

When I started Airbnb as a side hustle, I didn’t imagine it would change my life as much as it did. My goal was simple: cover some basic expenses. But soon I was making $1,500 a month in profit, all while still working my 9-to-5. Suddenly, that extra income opened up possibilities I hadn’t even considered before. I could take my wife out to dinner without stressing about the bill. We could book spontaneous weekend trips. In one year, I visited 13 different destinations, something I never thought I could do on my regular salary.

The most incredible part of this journey wasn’t just the money—it was the mindset shift. For the first time, I felt like I had control over my finances and my future. I realized that I didn’t have to wait for a raise or a new job to improve my life. I could create the extra income I needed on my own terms.

Why You Shouldn't Fear Side Hustles

I get it—starting a side hustle can seem intimidating. But let me tell you, it doesn’t have to be complicated or risky. Before I stumbled into Airbnb, I tried other side gigs. I made furniture in my basement, flipping rustic industrial tables for $800 a month. I even flipped VCRs on Craigslist for extra cash. One time, I got paid $50 to taste-test Doritos—not the worst gig in the world, honestly. But none of those side hustles compared to the cash flow and scalability I found with real estate.

Airbnb allowed me to earn passive income while keeping my day job. It wasn’t about getting rich quick—it was about creating that discretionary income that let me enjoy life more fully without taking on the massive risk of entrepreneurship. Real estate, specifically Airbnb, became my pathway to financial freedom without sacrificing the security of a stable job.

The Path to Real Financial Freedom

The truth is, you don't need to quit your job to unlock financial freedom. You need to find a way to add that extra $1,000 to $2,000 to your monthly income. It’s about covering your base expenses with your stable job and using your side income to cover your happiness expenses—the things that make life enjoyable. This balance is a far less stressful way to find freedom and fulfillment.

Imagine owning just one rental property. The moment you start seeing those rental payments or Airbnb deposits hit your bank account, something changes. You’re not just working to pay bills anymore—you’re investing in your future. That first property is more than just a source of income; it's a confidence booster and a mindset shift. It shows you that financial freedom isn’t just something other people achieve—it’s something within your reach too.

What Comes Next

If you've been thinking about quitting your job, I encourage you to reconsider. Instead of jumping ship, focus on building a source of discretionary income that can give you the freedom to do the things you love. You might be surprised at how much your life can change with just a little extra cash flow each month. If you’re curious about how real estate, specifically Airbnb, can help you achieve that, check out my latest video where I dive deeper into how owning just one rental property can transform your life—without the stress of quitting your day job.

👉 Watch the full video here.

Let’s unlock the 2.0 version of yourself together.

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