Why I Keep Losing All The Time

And How I Deal With That

I have lost much more in my life than I have won.

If you followed me for some time, you already know that. And if you haven’t read me yet, well, there are a lot of failures in my past.

I went broke twice. Once playing poker and once gambling on sports. I failed to graduate university twice and I co-owned a start-up that went bankrupt.

And that’s only the short list. There’s much, much more. Loyal readers know that.

But there’s one thing I never did.

I never gave up.


The M-Word

Take money for instance.

I have gone broke so many times, that my family and friends probably thought for the longest time that I was incapable of managing money.

Some of them probably still think that.

But my dream was to be a trader, despite the money issues.

And nobody could talk me out of that dream. I was ridiculed over and over again by said friends and family for even having such ludicrous goals in life.

by Joshua Earle on Unsplash

But I kept on learning, reading and trying. I struggled for the longest time.

But now I’m a profitable trader and money is no longer a problem.

I went broke trying a lot of ‘quick rich schemes’ until I found something that really works for me.

That’s how you win in the long term.

By losing in the short term.


The Writing Game

The same thing happened for my writing.

I always thought of myself as being a decent writer. But there was one slight problem: I never wrote a single sentence.

Apparently, I just liked the idea of calling myself a writer.

Photo by Dmitry Ratushny on Unsplash

That changed drastically too.

First I wrote a manual on Magento, an open source e-commerce software product, as a freelance writer.

Then, a couple of years later, I wrote a little book on asset allocation and wealth preservation in my spare time.

And finally, on October 29th 2017, I started writing every day on Medium.

I wouldn’t call myself the greatest writer in history.

But hey, I’m a writer.


No More Coasting

The next thing is probably podcasting.

Aleesha Lauray and I are revamping our daily ‘On the Rise Show’.

We’re on a two week break in order to return with a vengeance. And frankly, our brainstorming sessions are really promising.

We’re going to make an epic dent in the universe.

Photo by Greg Rakozy on Unsplash

The brainstorming sessions made me realize that I wasn’t really pulling my weight.

I was coasting. I was talking too much about easy subjects, as a writer and as a podcaster.

But we’re at a critical juncture in history and coasting is no longer an option.

That’s why I want to create even better content from now on.

The world needs my A-game.


It’s possible that writing doesn’t work out.

And maybe even the podcasting thing doesn’t work out. Because there are no guarantees in life.

But I don’t mind losing if I truly gave it my all. After all:

You win even when you lose.

It’s only losing when you didn’t even try. And trust me, I will definitely try.

Thank you for following my journey.

Good luck on yours too.


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