Why Your Plans Will Always Fail

Why Your Plans Will Always Fail

why your plan will fail

Back in the day, I was the man with the plan.

When I started a new business, I always performed thorough market research to make sure there was a demand.

I always made sure the idea got validated. I always did the math to get an idea if it could make a profit. And I always crafted a plan to make sales and generate repeat customers.

But every time I ended up failing. Not always because I couldn’t accomplish the tasks needed to accomplish my goal. Sometimes I learned that I didn’t even want to achieve my own goals.

Eventually, this caused me to throw away the concept of “plans” and settle with a more powerful method for dealing with life.

Hear me out:

You don’t know where you’re going

Take any successful person for example.

Let’s say Elon Musk. Now, he’s on a mission to populate Mars.

But in the 90s, he dropped out of university to found Zip2, a software company that served newspapers and eventually sold for $340 million. He then founded a company which would later become Paypal, and his entrepreneurial career proceeded with its regular ups and downs.

Turn back time to when Elon just founded Zip2.

elon musk

He spent his days in a room which could be described as the average computer nerd’s. And his wall was not covered by a whiteboard where he in detail planned his way to eventually become the colony king of Mars.

His focus was on Zip2. To build it into a good product.

Surely, he was an ambitious guy who thought of doing great things after his stint with Zip2. But he didn’t know what in detail, all he had was ambition and the will to detect new opportunities.

No one, not even the great Mr. Musk, knew the future.

But now when it’s all said and done…

You watch all the documentaries and read all his biographies. Everything in the past has already happened, so it’s easy to look back and connect all the dots.

In hindsight, it’s easy to point out the signs of what Elon Musk would do after his lucrative exit from Zip2. “The market was in its infancy and growing”… “the need had just appeared”

But most people didn’t at the time, and not even the confident Elon knew for sure albeit he had his hopes.

Let me make it clear to you:

Others didn’t succeed in the past by knowing where they were going. You didn’t know where you were going in the past, and you won’t magically start doing it now.

And if you don’t know where you are going, it’s pointless to have a detailed plan that won’t pan out.

The only successful plans are laid out in hindsight.

You are a flaneur walking through life and smelling at the flowers. You don’t know where you’re going. So instead of pretending as if you do, you better prepare to catch every desirable opportunity when it appears out of thin air.

Go in the general direction

Let’s get back to Elon Musk. He was an entrepreneur from the get-go of his life, just not an entrepreneur with a thriving business.

He was driven, knew that he wanted to be great in some capacity. Because of that, his mind began to see all these opportunities that everyone else was blind to. He was like a psychic that could see dead people.

Where everyone else would see an annoyance, like how you in the 90s had to physically mail money to buy something online, Elon saw an opportunity.

Do the same. Know kind of where you want to go, because you will become aware of opportunities leading that direction. But don’t open Google Maps and expect to get to the exact coordinates.

Tinker around

A big benefit of just going in the general direction is that you get the opportunity to tinker around.

If you were to go for the exact coordinates of a location, you’d have to get every street right until you’re there. But in the case of going a general direction, you can take a look at every street you come by and decide if it looks like somewhere you want to go. If you arrive at a dead-end, you can just turn around and keep going.

You use the oldest, most time-proven method of becoming a successful inventor, businessman or scientist:


If you get an undesirable result, you just rinse and repeat. You use the knowledge learned from your previous error to succeed better next time.

You may be scared by the thought of errors and mistakes. Don’t be.

When it comes to flaneuring, to trial-and-error, your undesirable results will be many. But you will quickly notice them, which mostly means they will be small and easy to deal with.

If you were to follow a plan, on the other hand…

You would fumble around in the dark. The feedback loop, the time it takes for your action to get a positive or negative response, will be longer.

And that means you’ll have executed several steps of your plan until you know if they even work or not.

Not only do you get more infrequent feedback from your actions:

The feedback you do receive will be much more drastic.

If your plan would succeed, it would be a gigantic success.

But if it doesn’t… the negative feedback, the damage, will be much more serious than if you lived by trial-and-error. Maybe you lose out on your live savings or pour years of your life in a fruitless business.

You absolutely MUST understand this:

Plans never work.

Sure, in movies there is always a secret king who followed his ingenious plan all along.

Sure, the inspirational videos highlight some entrepreneur or athlete and make it seem like he walked a straight, beaten path to where he is today.

But reality just doesn’t work that way. It’s less glamorous.

Don’t bet your life on a plan. Be confident in yourself, tinker around and win at life with the trial-and-error way of life.

Until next time,

— Alexander Contrarian

PS. Of course I don’t know for certain what Elon Musk thought at different points of his life. But let’s use his story as a mirror to more easily understand ourselves.