Why I Regret Quitting My Job to Pursue Financial Freedom: The Truth Behind Chasing Your Dream

In the present web-based entertainment-ridden society, it gives you a very slanted perception on the success rate of making it on your own. Let me show you what I mean using this simple [Music] analysis.

**Tony:**
I finally dived in and quit my job to pursue my business full-time.
**Winston:**
That's a bold move, Tony, but have you thought about your finances?
**Tony:**
I have around $100K saved and monthly costs of $1,500.
**Winston:**
I have around $100K saved too, but I will keep my regular job and work on the business on the side.
**Tony:**
Hey, Winston, my business is going great! I made around $50K last year. With costs, I'm worth around $130K now.
**Winston:**
I just made around $10K from my side business, but with costs, that was just about break-even.
**Tony:**
So, you made all that work in vain? You should leave your job and start full-time.
**Winston:**
Man, Tony, unexpected costs are destroying my savings. I've already burned through $50K in just the past year.
**Tony:**
Yeah, it has been tough. I don’t have much left, but my net worth has increased slightly to above $170K.
**Winston:**
$170K? That's crazy! I thought you said you couldn’t save that much.
**Tony:**
Better believe it! That's just after costs. I only had about $116K left, but I didn’t put it into savings. I put $8K into the stock market and $88K back into growing my business. My stock portfolio only grew around 8% per year, but my business income quadrupled. Now it makes me about $5K per month.
**Winston:**
I still have my regular job.
**Tony:**
Oh, wow.
**Winston:**
But it wasn’t all like this. If you want to hear my story when I quit my job and failed, stay until the end of the video.

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If you’re deciding whether to quit your job and start pursuing your dream of building financial freedom, well, you’ve come to the right place. I’m going to tell you my own story today, without the glamorized makeup of social media, so you’ll know what not to do and avoid making the same mistakes I did.

Hi everyone, I’m Tony. I’m your typical 30-something figuring out everything about investing while clearing my way into financial independence and sharing my learnings along the way. I’m a full-time marketer working in corporate tech by day and juggling the world of finance and YouTube at night.

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So, my financial freedom disaster story started when my first daughter was born. I was, what you’d call, burnt out from life at the time. I had been working in my previous corporate marketing job for 10 years, and my motivation was very low. When COVID came about, I mean, I’d say it was slowly fermenting for quite a while already, but when COVID came, the back-to-back Zoom calls, the endless PowerPoint presentations, and the overt repetitiveness of constantly meeting someone else's expectations in an extremely remote setting defeated me.

I mean, I had a good salary and yearly bonuses, business class trips to London, Dubai, and Berlin, and fancy accommodations in Soho House. But no matter how much I benefited, it meant nothing to me in the end. I was mentally drained pretty much every day. Along with finding my footing with an infant at home, I ended up detesting pretty much every Sunday, knowing I had to return to my desk the very next day.

I felt somewhat miserable toward the end and knew I needed to do something different with my life. With all the chatter of social media about pursuing financial independence, now in our 20s and 30s, it became a subconscious pressure. When yearly performance came about, I just told my manager, without really thinking, that I was quitting. In my mind, I said, “It’s now or never! Let’s get out of the rat race and make it work on my own!”

So, I just quit. My motivation was all-time low. I had no more desire to work in an environment I wasn’t thriving in. Against my wife’s wishes and against having debts, being a new father and taking care of my family, I childishly said I’d figure it out. It felt pretty good for about seven days until I started day trading full-time.

For those of you who think day trading is an easy way to make money, please, it’s not. The statistics say 95% of people lose money in day trading, and only 5% of people really manage to make money from the market. That’s pretty much the success rate for getting into Harvard.

That’s how difficult day trading is. Of course, I didn’t mind. I have a specialization in finance. I’ve worked in capital markets before. I’ve made a few trades in the past and profited from them. I even passed two levels of the CFA (Chartered Financial Analyst) exam. I had the knowledge, right? I should have been able to sort this out.

**Lesson number one:** Don’t follow your ego. Without getting too deep into how trading works, the fundamental rule is that timing is everything.

According to your investment horizon, if you get in right when the big players are gathering, you’ll probably get rich as more people start buying, pushing prices up. But if you get in at the very top, well, your chances of making money change drastically. When the market slides down, it can take years for it to return to the level where you initially bought it.

Just to show you, this chart shows my exact timing when I got in and out of the market. April 2022 is when I got in. I essentially started day trading right when the market began its downtrend from all-time highs. I tried making money during the most difficult market conditions. Prices were volatile, slashing up and down for over a year. By June 2023, I had to tap out because I had already lost most of my money or sold my portfolio at the wrong time to cover my daily costs.

I mean, I had no choice but to get out. And what do you know? A month later, after I tapped out, that’s when the market finally decided to climb again. Yes, I’m probably the worst person to time the market in the entire history of day trading.

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I want to circle back to the title of the video, “Why I regret quitting my job to pursue financial freedom.” See, I don’t regret pursuing the dream. I think it’s a very good and very healthy desire to have. But what I do regret is quitting my job to do so. Or, a better way to say it is, I regret quitting my job prematurely.

See, by not having a paycheck coming in while trying to get my dream going, it was detrimental to my mental state. Every trade I made felt like life and death. My entire livelihood was tied to it. This made me really deep on the winning days—I felt satisfied—but on the bad days (and there were a lot of losing days), I was incredibly angry and discouraged. I was cursing, yelling at my screen, breaking things in the house. I was making my wife really miserable as my mood was seriously affecting hers. I even made my baby daughter really frightened at times as, during many nights, I was shouting at the top of my lungs in frustration.

Now, looking back, if I had a paycheck coming in while I was trading, my mood and mental state would have been much better. But that wasn’t the ideal situation for me. Week after week, I saw my portfolio and savings drop. I was getting more and more stressed because now I wasn’t making money and, on top of that, I was losing money every day to the market. I was more in doubt. My confidence was decreasing.

Also, during this time, costs had doubled because of high inflation all around the world. My wife was still on maternity leave, so I was spending our savings to support the family. I stopped going out with friends because I was upset. I didn’t want to incur any additional costs just to socialize.

I’d say after a year, I was broke. I had no money. Mentally drained, bad atmosphere at home with constant fighting with my wife, and genuinely worried about the future for my family and my self-worth. On top of that, all my friends were finding success while I basically lost our entire life savings because I was chasing my dream based on some misguided sense of truth from social media.

Looking back at it, I should have just sucked it up and kept a steady paycheck coming in, and then pursued my dream. Having something stable in your life is also important.

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Even if you had no worries at all about pursuing your dream, if you’re constantly worried about how you’ll pay rent next month, you wouldn’t have the right mindset to do what you set out to do. At any rate, sometimes it’s better to take care of your basic needs first before moving on to bigger desires.

Every day you see entrepreneurs online advising you to quit your job, hustle hard, and create a life worthy of your dream. The possible outcome is painted beautifully: you see the lifestyle—the Lambos, the Rolexes, the luxury homes, and rooftop lounges. But what you see on social media is literally the top 0.1%.

I’m not telling you it’s impossible because it is, in fact, one of my dearest friends has gone through this course and made it. But you must be mentally, physically, and financially prepared for it. It’s not just going to happen because you took the leap. No, you must have a very solid plan, and you have to be ready to go 10x in every aspect of your life to pursue your dream.

And I mean 10x in all aspects—your mindset, your work ethic, and your ability to cope with losses. Because if you end up taking a loss, be okay with it. You know that you’ve learned something from the experience. In the future, you

’ll be better at it. So, it isn’t all time lost.

I’m now in a better headspace, with a load of emotional baggage, knowing what it truly feels like to be bankrupt and discouraged. I actually end up shockingly motivated. I’m working now a regular job, balancing everyday life with two kids, managing website projects, YouTube, and learning about personal finance while keeping up with workout routines. I now truly have way less time than before, but somehow my mindset tells me it’s okay.