From a horrendous failure, I ironically learned how to never fail

Until 2012, I had gotten every job I wanted, and cracked every exam I had written. And then, finally, I failed. Miserably. My luck had finally run out.

What followed was years of misery and frustration. And yet, from all that pain, emerged this beautiful truth: You can fail in exams, jobs, or even startups. But if you have the right mindset, you will NEVER fail the biggest exam of all – life itself.

Today, I want to talk about that mindset, which can help us conquer any failure or self-doubt, no matter how depressing things are. I hope this story will stay with you in your most difficult moments.

So here is what happened.

When I launched my first startup in 2012, I was on a high. Even before I had formed the company, a VC was pursuing me to invest in my venture. His exact words – “Boss, just take the money and keep it in the bank. You never know when you will need it.”

But I was so confident that I declined his investment.

However, as soon as I started building our product, problems started raining. Every single thing that could possibly go wrong, went wrong.

Each day, I was haunted by how much money my startup had lost that day. Had I been in my previous job, I would be earning a handsome salary. Instead, I was now writing checks every other day. Every month, my bank balance dwindled.

At that time, I was living in a spacious house in Mumbai’s posh locality of Pali Hill – my neighbors were Dilip Kumar and Sanjay Dutt! But soon, I did not have the money to afford the rent.

I now moved to an apartment half the size, but over time, even that became unaffordable.

I then moved to Trivandrum, lowering my cost of living, but the struggles continued.

However, despite all this, I resolved to myself, “Till there is a drop of life in me, I am not going to give up.”

But life had its own plans. Things kept going from bad to worse. I raised a few crores investment for my startup but we spent it all. Customers did not want our product – there was no product-market fit. Every successive day was more depressing.

When going through this hell, I would get all kinds of thoughts and self-doubts. Why was I doing this, when I could be easily earning truckloads of money, working for a private equity fund? Look at my classmates – they are doing amazing things, living a fancy life, in the world’s biggest cities. And here I am, in the small town of Trivandrum, barely surviving.

But through all this, there was one thought that kept me going: I have not failed until the game is over.

When you play football, the game is over only when the referee blows the whistle. But in the game of life, there is no referee – you are the referee. It is only over when you say it is over – when you blow the whistle – when you quit.

While the game is on, you may have fallen behind – so what? You failed an exam – no matter. Your job did not work out – no matter. Your startup failed – no matter. Remember – the game is still on. The score is not final.

And until the score is final, there is no defeat – your losses don’t count. Don’t teams come back from being down under to win? It happens all the time.

That is how I fought back my self-doubts. That is how I lived through unending failures, losses, and frustration.

I knew I would win not because I was smart or rich or capable – I would win because I was not going to blow the whistle before that.

In my mind, it was ok to change my startup idea. Had I totally run out of cash – and I came pretty close to it – I would have taken up a job. But I would have come back to do another startup.

But thankfully, with HabitStrong, I did eventually find success. Today, at HabitStrong, we run bootcamps to build life-changing habits. And thanks to your support and goodwill, we are doing well. We are not a unicorn or anything fancy but are financially independent without having taken an additional penny of external capital.

However, even that is not the best thing. The best thing for me is that I love doing what I do. In the HabitStrong bootcamps, we train people to do the right thing, even when it is hard – no shortcuts, no fluff. I get to share and teach my life lessons to others.

So in my mind, all the losses I suffered in the past don’t matter anymore.

Going forward, we will hopefully grow HabitStrong and be very successful. But that is not the most important thing.

The most important thing for me is to serve you. Therefore, let me end with this message.

Whatever your life goals are, I can guarantee your success but I have one condition – you have to promise me this: You will not blow the whistle until you win.

Can you do that?

If you can, here is my counter-promise: If I am still alive even at 85 or 90 or beyond, and if my mind and body are still working, you will find me working and doing something useful. I will never blow the whistle. Just as I hope, you also won’t.

Thank you for reading this. Stay in touch. Your goodwill means so much more to me than you imagine!

I hope that in your most difficult moments you will remember this newsletter and remind yourself that all setbacks are only temporary – the game is still on!

Rajan

HabitStrong Newsletter by Rajan Singh

In this fortnightly newsletter, Rajan shares inspiring lessons and stories from his career as an IPS officer, McKinsey consultant, investor, and now, as a startup founder. Join 25,000+ subscribers.

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