You Can’t Win Big Until You Learn to Lose Small

When I first started trading, I had no clue what I was doing. 

After high school, I tried a bunch of random jobs like selling bamboo pillows at the mall, valet parking, and working construction. I even trained to be a firefighter. 

I was just an 18-year-old kid trying to figure out life, and nothing really stuck until I found trading. 

To me, trading represented freedom — the idea of making real money on my own terms and enjoying a comfortable lifestyle.

I thought, This is it. This is what I want to do.

But just because I wanted it didn’t mean I got it right away. 

It was actually the opposite.

When things finally did turn around, the view was better than anything I ever could have imagined.

Here’s how I went from nothing to millions, and you can too. 

Let There Be Light

For my first trade, I lost $54 chasing a random spike, and it happened over and over again. 

Every time I thought I was on to something, the market humbled me. I studied, watched webinars, tried going long, tried going short, paper traded…and still, nothing clicked.

For nearly two years, I was stuck. I couldn’t get anything going.

I didn’t give up, exactly, but finally took a break and went back to valet parking during the Travelers Championship in Connecticut. 

There, I worked long shifts — 4 a.m. to 8 p.m. some days — and after two straight weeks, I had maybe a couple grand to show for it. 

That grind wore me down, and I remember thinking, I’m working this hard for this little? 

Meanwhile, traders were making thousands in minutes.

That was my turning point: the point where I was unwilling to keep spinning my wheels.

I came back to trading more focused than ever. I had studied a lot before, but now I was ready to apply it. 

I understood the patterns. I saw the same price action I had watched in video lessons, and for the first time, I actually started to see the setups happening in real time.

Limit Your Losses

Still, it wasn’t perfect. 

I had periods where I made a little money…then gave it right back

My curve looked like this: tiny wins, then slam! Big red day. Rinse, wash, repeat. 

Eventually, I learned something even more important than how to win:

I learned how to lose well.

That’s when everything started to change.

Instead of taking massive losses, I got better at cutting them small and focused on protecting gains. 

Slowly, my equity curve started to trend upward. It wasn’t flashy or fast, but it was steady.

By late 2018, I had my first $10,000 month. That was huge for me. 

Just a year before, I was struggling to imagine making $500 in a day. But now, I was pulling in $2,000–$3,000 a week, consistently. 

It was the law of attraction at work, except I was finally putting in the real work to back it up.

From there, it snowballed even more: $10,000 turned into $100,000. I stayed in the game, learned from every trade, and eventually crossed $1 million. Then $2 million. 

Fast forward, and I’d made over $12.7 million by age 26.

But I still remember the early days of losing over and over and wondering if I’d ever figure it out.

Personal Growth Cycle

The truth is, most traders lose in the beginning. 

What matters is whether you learn from it. I had to lose a lot before I could win. 

And learning to lose properly — small, controlled, and with a plan — is the only reason I’m still here.

So if you’re in that stage right now, just know it’s not the end. You’re not broken. 

You’re just early in the process.

Lose well, learn, and stay in the game.

Your time will come if you don’t give up.

Jack Kellogg

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