The Turning Point – When I Knew It Was Time to Break Out on My Own
I’d always had that nagging feeling—the itch in the back of my mind that there was something more out there for me. You know the one I’m talking about. It’s like sitting on the couch, flipping through channels, knowing damn well there’s something better to watch but being too lazy or unsure to get up and find the remote.
My life felt like that for years—comfortable, but not satisfying. I was “doing well,” but it didn’t feel like enough.
At the time I was a commission only sales rep. A good one? Nope, but not a bad one either. I think I was just so-so because I didn’t have the drive to do it right. I think to this day, that may be the one trigger I can associate as the “turning point”.
I hated that I wasn’t great at sales and even more so that I had complete control over that. I just didn’t have the drive to fix it.
Drifting in the Routine
Before I made the leap, I was kind of numb. Just going through the motions. It wasn’t that I hated my job. I was making decent money, hitting the metrics, checking the boxes. It was “fine.” But there’s something unsettling about life when it’s just fine. You get caught up in this endless loop of “maybe next year” or “just one more big deal, then I’ll figure it out.”
Yeah, spoiler alert—that “next year” thinking? It’s bull-shit.
It wasn’t like I woke up one day with a grand epiphany, but more like a slow burn that I couldn’t ignore anymore. I started realizing that I was working longer hours. I don’t mean that in the sense that I was working more, but that the hours literally got longer.
Do you know how when you’re enjoying something and time seems to just fly by, well flip that. The clock got slower and slower.
Don’t get me wrong the job wasn’t bad and I got to see quite a few cool things and places, but that damn clock got louder.
I started to imagine what my life could look like if I wasn’t chained to that desk. What if I could be my own boss, make my own rules? What if I could actually design a life that worked for me?
The Internal Struggle
But here’s the thing—they don’t teach you how to trust your gut in school. They teach you how to follow the path, check the boxes, and stay in your lane.
So, even though the thought of breaking out on my own was exciting, I still had that nagging fear.
What if I failed? What if I wasn’t cut out for this? What if everything crashed and burned, and I was left with nothing but a bruised ego?
It’s like being on a boat, drifting toward something better but also fearing the rocks that could tear it apart. I wasn’t ready to make the leap just yet, but my mind was already starting to rebel against itself.
Once you open that door of bigger thoughts, you can’t close it. It’s like realizing you’ve been wearing shoes two sizes too small your whole life—suddenly, you can’t unfeel the pinch.
Breaking Free From the Trap
What really pushed me over the edge wasn’t a grand event or some inspiring speech. It was realizing that if I didn’t do something, I’d be sitting in the same place 5, 10, 20 years later, wondering “what if?” And that thought scared me more than the fear of failing.
The truth is, most of us wait for the perfect time. We tell ourselves we need to save more, learn more, be more prepared. But guess what? That perfect time? It doesn’t exist. It’s a moving target. And if you keep waiting for all the stars to align, you’ll never take a step forward.
What’s that saying, “Aim at nothing and you will hit it every time”. yup!
For me, it was the little things that started building up—the restlessness, the frustration, the nagging feeling that I was capable of more. There wasn’t a single moment that made me leap, but a series of moments that finally tipped the scales.
The Moment I Knew
The night before my third child was about to be born via a planned c-section, I was doing the typical run down to make sure we were ready. My reading material of choice was the book called the 4-Hour Workweek. So I gave it a quick skim and immediately got excited. Probably even more excited then with the kid that was about to come. (Oh stop it, it was my 3rd child damn it)
Anyway, Spoiler alert! The premise of the book is all about designing your life to escape the 9-to-5 grind and live more while working less—by focusing on what really matters.
So the next morning I started to dial in on that book while my wife was getting sauced up on anesthesia. She didn’t even know I was there so I was able to fly through the pages.
Now there were two main takeaways from that book that I still remember to this day some 15+ years later.
- Fear Setting
- and The Mexican Fisherman Story
Fear-Setting
Now Tim does a much better job explaining Fear-Setting if you have the time, but if not, here it is in a nutshell.
Tim encourages you to list out the absolute worst things that could happen if you take a certain risk or make a major decision (like quitting your job or starting a business). Once you identify these worst-case outcomes, you can work backwards to figure out how to mitigate the risks and/or recover from them. By doing this, the fear of failure becomes less paralyzing, and you’re more likely to take the action.
So here’s quick run through.
- Define the Worst-Case Scenario:
- Let’s say you’re considering quitting your job to fully focus on a new business. The worst-case scenario could be that the business fails completely, leaving you without a steady income, and you burn through your savings.
- Preventing the Worst-Case:
- To mitigate this, you could keep a backup income source like freelance work for example. You could also build a financial safety net before you make the leap.
- Repairing the Damage:
- If things really do go wrong, ask yourself: “Could I go back to a similar job if the business fails?” Likely, yes. “Can I move in with a family member?” Probably.
- What Might the Benefits be if it worked?
- Think about the positive outcomes: more control over your time, financial freedom, or the satisfaction of building something on your own terms.
- What Will Happen if I Don’t Take the Leap?
- What’s the long-term cost of inaction? If you don’t leap, will you regret it five years from now? Will you always wonder “what if”?
Once this was inked on paper and visualized, I think it clicked for me. The regret of not trying would be way worse than the failure.
Failing, you can recover from. But regret? That shit sticks with you forever.
The Mexican Fisherman
The second standout was a quick story about a Mexican Fisherman. One that stopped me dead in my tracks and probably will do the same for you. Here it is…
” An American investment banker was walking along the pier of a small Mexican coastal village when he spotted a fisherman docking his boat with a few large yellowfin tuna. Impressed, the American complimented the fisherman and asked how long it had taken to catch them.
“Just a little while,” the fisherman replied. The banker, curious, asked, “Why didn’t you stay out longer and catch more?”
The fisherman explained, “I have enough to support my family’s needs.”
Intrigued, the banker then asked, “What do you do with the rest of your time?”
The fisherman smiled and said, “I sleep in, fish a little, play with my kids, take siestas with my wife, Maria, and in the evenings, I stroll into the village to sip wine and play guitar with my friends. Life is full and good.”
The banker, scoffing a bit, said, “I’m a Harvard MBA and I can help you. If you fished more, you could buy a bigger boat. With the earnings from that, you could buy several boats, eventually owning a fleet. You’d cut out the middleman and sell directly to the processors, maybe even open your own cannery. Soon, you’d control everything: the product, processing, and distribution. You’d need to leave this village and run the business from Mexico City, then Los Angeles, and eventually New York City.”
The fisherman asked, “How long would that take?”
“About 15-20 years,” replied the banker.
“And then what?”
The banker grinned, “That’s the best part! You’d make millions, retire, and live the good life. You could move to a small coastal village, sleep in, fish a little, play with your kids, take siestas with your wife, and stroll into town in the evenings to sip wine and play guitar with your amigos.”
Taking the Leap
Once I digested those two thoughts from the book, it was on. I didn’t have all the answers, and I definitely didn’t have a roadmap. But the fire was lit and wasn’t going to go out until I took a chance on myself.
The first steps were definitely shaky. I’d wake up some days wondering if I was insane for walking away from stability. But then I’d remind myself that stability had been my prison. It kept me in one place when I was meant to be doing much more.
And look, it wasn’t easy. There were times I was scrambling to figure out what the hell I was doing. But I’ll tell you this—it felt right. Even in the chaos, I felt more alive than I had in years.
Every small victory, every hurdle I overcame, felt like proof that I’d made the right choice.
Looking Back
If I could tell my past self one thing, it would be this: you don’t need all the answers to take the leap. You just need to trust that you’ll figure it out along the way. Because, let’s be honest, no one really knows what they’re doing, especially when they’re starting something new.
We’re all just winging it to some degree.
So, if you’re sitting there, feeling like I was—itching for more, but scared to make the move—know this:
the leap isn’t as terrifying as you think. What’s terrifying is staying stuck in a life that isn’t yours.
Take the leap. You’ll figure it out on the way down.
Oh yeah and by the way.. We had a baby boy!
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