A few years ago I was way more timid than I am right now. The timidness lead to not being able to take small risks, like asking that girl out and let alone taking big risks like dropping out of high school. Now having finished college and learning a few things along the way, I figured a philosophy that helps me take risks.

When I tell myself that “I’m allowed to fail”, I let go of expectations that I created for myself. It was these expectations (or fears) that didn’t let me take risks in the first place.

A task is risky if the the chances of failure are high. It’s hard to take risks because we don’t like to fail. It causes loss of time and energy. It also breaks our momentum and makes us more prone to failure in future. Yeah, obviously, failure is the stepping stone of success, but aiming for failure is not wise.

In the past few years, luck has favoured me and I’ve got a chance to enjoy some successes. In the process, there were some fears, that if I hadn’t overcome, would have stopped me from being where I am. This is how I overcame some parts of them.

Fear of losing money/ expectation of earning more

In the past few years, I rarely experienced a time when I was not making more money than I needed. Not that I was making a ton of money, but because my education was almost free, I lived with my parents which left me with no rent, no food expenses and no bills to pay, and my only expenditure was Uber and eating out.

Having money in the bank is a good thing, but it comes with the fear of losing it and a desire to earn more. This desire is equivalent to a donkey following a carrot stick.

There are two things that helped me overcome this :

Jason Silva’s definition of a Billionaire [video]: This taught me to measure my net worth in amount/effort/energy I have given back and not the number in my bank account &

The fact that money is a by product: I made money because I knew how to tweak systems. Not because I wanted to make money. It came to me when I didn’t care about it. All I cared about was making good art (software).

The great Saint Raheem Daas said :

देनहार कोई और है ,जो देता दिन रेन। लोग भरम मो पे करें ,ताते नीचे नैन।

Translation:

When asked “Why do you bow your head down when you give ?”, Saint Raheem replied that “There is a power bigger than me, helping me earn my means but everyone around me thinks that it’s me who is doing it. Hence my head is bowed down.”

This couldn’t be more true. And because there is someone else helping me earn my living, there is nothing to be afraid of. Go ahead and invest in that new business you always wanted to, or the Bali trip that hasn’t happened yet. The worst that will happen is that you’ll lose your money. No problem. You are allowed to fail.

Fear of staying unsuccessful/ expectation of gaining fame

Somewhere along the passage of time, I tied fame to being a sign of success. Being on TV on the newspaper maybe. It felt like a goal. When I first got myself published in a reputed blog, I realised how broken and corrupt journalism was. Our company wasn’t even operationally profitable and claimed to help our clients get improved ROIs. Liars we were.

It was an eye opener that news is about sensationalism. It’s a vicious circle that will deviate me from what got me there in the first place (making good art). I try not to think about whether I’ll ever be famous or rich or both. The worst is that I wouldn’t be. The best is I don’t need to be.

I really wish it was as easy as I put it, but honestly I do end up thinking about this.

Fear of my friends/ peers earning more than me/ expectation of earning more than everyone in my peer group

This gripped me when I initially started earning. The more I fed this fear, the larger it became. I was literally earning in order to make myself feel important ,due to the fact the I earn the most in my peer group.

This is a pathetic state of mind to be. And I feel guilt (and shame) that I had it. Earning is not bad, but measuring yourself against how much others earned was a terrible unit of measurement.

It meant that I can be only as successful as the most successful person I knew. It also meant that I was not aiming high enough, because no matter what I do, there will always be someone, somewhere, more successful than me.

This one also builds on the anticipation of wanting others to know that you are the richest among the lot.

I overcame this by stopping comparing myself to others. And also by stopping others to compare themselves to me. The rule now is to never tell anyone how much I earn. Nor ask anybody how much they earn. I’m interested in you, your work, your stories, but not in how much you earn.

More than being something internal, this was something I was introduced to. For example, my school measure me against all other students in my class, so did my college. (I’ll write more about this when we talk about the conveyor belt philosophy).

Earning the least in your peer group will not make you a failure. Even if you think you failed, it’s ok, you are allowed to fail.

Fear of being rejected/ expectation to be accepted

The classic. This fear has stopped men and women across the globe far from their actual potential and lures around personal and professional life alike. I was afraid of talking to people, let alone asking them something and getting rejected. And there is no cure for this other than getting rejected on purpose and knowing that it doesn’t define you.

I did this experiment (which I might talk about sometime later) where my job was to get rejected on purpose. And it taught me that it was my expectation of being accepted that held me back. Letting go of expectations makes you an unstoppable beast.

Imagine if you are not afraid, will your chances of getting accepted increase or decrease ?

It’s so obvious that we are rejected by default. Asking only gives us the chance to be accepted. If you have been looking for motivation to talk to that client, or that pretty lady in your college/ office, go ahead, you already have a no and you are allowed to fail.

Don’t fail on purpose

A downside of this philosophy came when I stopped aiming for success and started justifying it with “You are allowed to fail”. No. It doesn’t say “Fail on purpose”. It will be sad to see anyone aiming or justifying failure and I have done this myself, so many times.

You are allowed to fail only pushes you enough to take that chance, with success as the only option.

You have to win. You are allowed to fail.