You ever look back on something and think, “Wow, if only I knew then what I know now…”? Yeah, quitting my 9-5 was definitely one of those moments.
I’d love to tell you that the second I handed in my resignation, I rode off into the sunset, laptop in one hand, cappuccino in the other, living my best freedom-filled life.
But the reality? It was more like a bumpy bike ride with no training wheels—and lots of spilled coffee.
So, today I’m going to spill the beans (coffee pun intended) on what I wish I had known before I said goodbye to my cubicle.
Consider this your crash course in what to do—and more importantly, what not to do—on your own journey to financial freedom.
Lesson 1: Your Time Is Your Most Valuable Asset
When I quit my 9-5, I thought I was gaining all this free time, but it turns out, freedom without structure is just chaos in disguise.
There were days I’d wake up, glance at my to-do list, and end up doing nothing but refreshing my email 20 times and wondering why Netflix kept recommending crime documentaries.
What I wish I knew? Structure your day like you’re still working for a boss—except this time, you’re the boss. Block out time for important tasks, and stick to it.
That way, you can actually enjoy your freedom without feeling like you’ve been “busy” but accomplished nothing.
Lesson 2: It Won’t Always Be Smooth Sailing (But That’s Okay)
I went into this whole thing thinking once I was out of the 9-5 grind, everything would fall into place.
Spoiler alert: it didn’t. There were days when I was crushing it, and then there were days when the Wi-Fi cut out, the coffee machine broke, and I seriously questioned if I had made a terrible mistake.
Here’s the deal: bumps in the road are normal. If I could go back, I’d tell myself that those tough days are just part of the process.
It doesn’t mean you’re failing; it means you’re growing. So, when you hit those rough patches, just remember—you can always buy more coffee. (It helps, trust me.)
Lesson 3: Diversify, Diversify, Diversify
You know how they say not to put all your eggs in one basket? Well, that’s also true when it comes to income streams.
In the beginning, I relied almost entirely on one income stream—my freelancing gig on Fiverr. It was great, but when client work dried up, so did my income. Oops.
What I wish I knew? Start diversifying your income streams as soon as you can.
Whether it’s launching that digital product you’ve been thinking about, investing in a new skill, or even renting out that dusty bike in your garage—having multiple streams of income keeps you afloat even when one slows down.
Lesson 4: Learn to Love the Hustle (But Don’t Let It Take Over Your Life)
One of the biggest mistakes I made was thinking I had to hustle all the time to make this work.
I was convinced that if I wasn’t grinding 24/7, I was failing. But you know what that led to? Burnout—and probably more takeout pizza than I’d like to admit.
What I wish I knew? It’s okay to take breaks. You don’t need to hustle every second of every day to be successful.
In fact, taking time off to recharge will actually make you more productive in the long run.
So, enjoy the journey. Hustle hard, but remember to live a little. (Yes, even if that means binge-watching crime documentaries. No judgment.)
Lesson 5: Believe in Yourself (Even When You Don’t)
This one’s a bit cheesy, but it’s true.
I can’t count how many times I thought, “What am I doing? Who let me quit my job?!” Imposter syndrome is real, and it likes to pop up right when you’re getting into your groove.
But the truth is, if you have the guts to quit your 9-5 and chase financial independence, you’ve already got what it takes to make it work.
What I wish I knew? Trust yourself, even when it feels like you’re winging it. Because guess what? Everyone is winging it to some degree.
Keep pushing forward, keep learning, and eventually, you’ll look back and realize you’ve built something incredible.
So, there you have it—everything I wish I’d known before I quit my 9-5. If you’re thinking about making the leap, or if you’ve already jumped and you’re currently mid-air wondering what’s next, just know that you’re not alone.
It’s a wild ride, but it’s worth every single coffee-fueled, chaotic moment.
Next, I’ll be sharing my secret sauce for balancing multiple income streams—without losing your mind (or your sleep).
In the meantime, join my newsletter ‘The Coffee Shop’. 8 years ago, i went to my local coffee shop to formualte my 9-5 escape plan… and it worked. Join my at my virtual coffee shop by clicking this link here
Until then, keep hustling, and maybe start a “lessons learned” journal of your own. You’ll thank yourself later.
Catch you next week,
Warren (Hustle from home dad)
Recovering 9-5er & Full-Time Freedom Chaser
Provide & Protect 
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