Lessons I Learnt From My Catastrophic Failure

Space Shuttle Challenger I Catastrophic failure

What I learnt from failure and why it was the best thing that happened to me

I could say I have had an eventful life. I’ve had no problems sleeping on railway platforms or railway coach floors when growing up. Once I had the ‘education’, (read doing that BTech-MBA thing) I was driven to create ‘success’ till one day everything changed to the point where we didn’t have food to eat.

Everything that I write is derived from my personal experiences and my own dissection. You can see a little of the background in this TEDx talk and these conversations on handling stress, failure and about happiness.

Being that low is not a pleasant place that is for sure. Everything that defines you as you — status, name, people are all stripped away. Rebuilding a life along with the daily responsibility of 800+ dogs and 20 staff that I need has not been easy.

I didn’t just need cash to service debt, which was at one stage about $100,000 per month, but I needed steady cash flow for my dogs. That left me very limited room to maneuver. It’s like being alone with your hands tied behind your back and you can only wiggle your fingers.

Now, however, when I look back at it, other than the loss of some of those I love the most and my dogs, I see it as necessary experience. It changed me for the better. In a recent talk that I gave the host mentioned after my talk that, ‘Being absolutely bankrupt should be a necessary experience for everyone’. I agree!

What I think failure is

I personally do not use the word ‘failure’ because it kind of means you got knocked over, and could not get up. I prefer to mostly call it a ‘setback’ or say ‘I fell’.

However, in this conversation I write it in the sense of ‘catastrophic failure’ — to describe a situation such as the one with me (above) and to differentiate it from commonly personal and business contexts, which refer to failure as loss of a client, failure of a project, or loss of a loved one.

I’m talking about the kind of failures that completely alter the landscape of your relationships, finances, and mental wellbeing. Catastrophic failure is when your physical and mental survival is uncertain.

As I began to emerge from catastrophic failure I realised something — nobody wants to talk about falling down, everyone wants to talk about going up. We celebrate success rather than trials, tribulations, upsets, setbacks, and failures even though taking risks and falling down make us into what we call successful.

The other thing I realised is that I’d never really cared to define the essentials metrics of life but was upset on losing what I had not defined clearly (something I reflect in the talk here). When you’re flying forward it feels great and it’s heady.

Falling down caused tremendous pressures and fractures for me. Financial. Social. Psychological. For the first year I kept fighting but with it was a war of attrition and I was not winning. At one time I pretty amazed that I was able to stand up at all as I did ran the steeplechase on empty.

Falling down that hard stripped away every single thing that I thought defined me. But when I emerged, it had given me a brand new mindset. An open-mindedness that balances my aggressiveness. Here are some other things I found that make me think of it is as the most valuable time of my life:

The perspective I developed on failure

After I fell, I was so blinded by anger, grief, self-pity, and denial that I forgot that this is not something that was happening just to me. It has happened to the best of us. What we do after we fall is what defines us. And in the immediate — to help us cope. It took some focusing to see that I needed to keep it in perspective.

It has to be looked at in the eye

My catastrophic failure was the result of a complex set of events that occurred in-step. Understanding what happened provides you an insight into who you are and prepares you for the journey ahead. For most situations — acceptance that you are in it and realising the contours of the problems you face is the single most important step in getting out of them.

Our avoidance of failure is so high that we do not even want to think about it let alone accept or examine it deeply. I learn how emotionally unpleasant it is and seemingly lowers self-esteem. On the other hand, analysing failure required insight and openness with myself.

It is not uncommon

Just like failure, avoidance is built into us so is individual infallibility. We believe bad things happen to others and somehow we are immune to them. That is in direct contrast to the inherent uncertainty in our lives with respect to our professional environment, macroeconomic factors, relationships and biological health.

I learnt that it is not all that you have contributed to — just as success has timeliness as a factor, so does failure. I learnt that my own shortcomings were just one part of it and I do not need to blame myself and that because a particular combination of these circumstances occurred that had never occurred before, it might not again. But the one time it did was catastrophic (for me).

It is the best teacher I have ever had

Of course, my education and the decades of working gave me great professional experience but in terms of sheer learning, enduring and ingenuity this experience was far ahead. You can read case studies all night but until you have had to terminate hundreds of employees whose families depended on you and who still believed in your leadership, you realise you haven’t really learnt what business, people and money are all about. I learnt more about this and relationships while falling down than I had learnt all the years climbing up.

Catastrophic failure is life’s great teacher and it can strip down ego better than in a decade of being a monk. It is also perhaps the only time in your life when you will stop and reflect, take your life into perspective and develop meaning from painful situations. Failing cuts sharp like a razor and deep like a sword and it is precisely the reason why it is a powerful experience. I learnt that failure brought with it important firsthand knowledge which I could use in the future to overcome the very failure that inflicted so much pain in the first place.

It gave me a clean slate

The catastrophic failure took away those things that were the most important for me at the time, but it also took away the greatest millstones around my neck. After working for many years and scoring wins, TWB had become an inefficient company — in quality of delivery to customers, the quality of leadership we had and bloated processes. Most of all, we were not fast enough. We were not reinventing; we were not paranoid.

As much as I was trying to change it, it was not enough primarily because of my relationships with the people who came into the company when it was young. Catastrophic failure brought about a great discontinuity but it also brought the opportunity of TWB being smarter and better without the cobwebs.

I learnt that failure isn’t the end of the road as long as you don’t give up. If you still believe in your goals, you can use the failure as leverage to push past the limitations of your past.

It reshaped my priorities and values

When you fail, it reorders things that matter to you. Through this time I realised I had to re-envision my goals, not revise them. I needed to see them clearer in my mind. I  got an even better perspective than when I started.

It also forced me to look inwards and forced me to make an inventory of my hopes and dreams. I even put that in a graph, which I call the ‘Map of Life’ and that led me to realise the things that mattered to me most. I also realised that this redefinition of priorities was not just a crucial step of overcoming failure — it was a crucial step in building future success.

What I learnt about myself

Catastrophic failure did not just give me an opportunity to see failure in perspective, it gave me an opportunity to meet myself for the first time. Some of the things I learnt were:

How far was I willing to go to succeed

We all know that to get anything significant, you need to endure. The question is how much and for how long? If the goal is more important than whatever circumstance, you will dust yourself and get back to it. My catastrophic failure really tested if I had the strength and resolve to pursue my dream.

Grit, resilience and courage

Grit, resilience and courage are qualities that I have always respected in others but there is no way of knowing whether what you think of yourself is who you really are. I always thought I had the ability to keep fighting on but only when I was tested by catastrophic failure I could learn if you have true grit and real courage. I learnt that the process of getting up and putting up a fight is a quality in itself and I had it in spades.


I went from driving about a dozen cars to not being able to afford autos. I sold all my vehicles and my homes to settle debts. I had to really dive into my pockets to take an auto for Rs 75/ ($1) from where I stay to MG Road, Bangalore. After 2015-16 I was taking buses to get to customers and would have to walk sometimes 2-3 km from the bus stop outside the tech parks to the buildings where they were in.

Once, I walked into a meeting and realised the sole of my shoe had fallen off. I didn’t want to leave it their reception so I picked it up, took off the other shoe as well and walked out barefoot.

From being on top of the food chain, I have had to sit in numerous police stations for days, as I did with tax offices. One day, the bank closed my personal and my company’s accounts as well. I went from very well off to not knowing where the next meal was going to come from. In that time I learnt extremely valuable lessons on humility.

About friends and family

I learnt that failure acts as a “friend filter,” and catastrophic failure made me learn very quickly who my true friends were. When you’re succeeding, everyone wants to be around you but, when you fail, most of those so-called friends disappear. People who knew me well, and knew what happened and knew what a proud man I was, simply stopped talking to me or taking my calls because I might bring up that I needed help.

There were very close personal and professional friendships but at the first sign of trouble, they bailed. It felt very painful at the time as I battled not only a financial disaster but loneliness, hostile debtors and ex-employees. It felt like everyone betrayed me.

At the same time, there were several people I had never met who approached me to help. I was consistently dismissive of them — I had fallen far too hard and lost far too much trust to believe. But they stayed around and helped with their time and expertise. The survival and now the resurgence of TWB_ is a narrative of this help. From the disaster, I learned the value of true friendship.

How it made me better

It allowed me to define ‘success’

When I fell it was a hard fall and while in the short term I had to confront the immediate fallout of money, the lives of my dogs and just surviving — it took the most important part of me away — I thought of myself as successful and now I was not. The conventional definition is that the opposite of success is failure — but if I saw myself as a failure I would never get up. So I started a long process of thinking through was success meant.

I realized that money, and what it buys is not success. Success is being in a place when your values are aligned with your goals. The way I personally define success for myself is that it is a state that allows me to get up in the morning and do the things I love to do. 

Even through my worst time, I was fighting not just for myself — I was fighting for the survival of an idea that was bigger than myself. And while I was broke and millions of dollars in debt, with 650 dogs to feed and take care of every day — in my mind, I was still successful.

I realized that when we’re focused on taking something from the world failure is only a moment away. But when we focus on contributing to the world, giving more than we receive, it changes everything.

Do not get me wrong — wealth is still a priority for me but I’m not married to money. It’s important because it is a byproduct of business efficiency. And it is important because of what it allows me to create. But I am successful without it nevertheless

It made me look to the future

I know from long years of experience that guilt, shame, regret, and embarrassment are powerful forces. It is like getting branded. But I needed to live not in the emotion of the events but focus on outcomes. Catastrophic failure can either make you or break you. And I had a choice to want to not just survive, but survive in the best way possible, so I had the energy and strength to create future success.

In a strange way, I am back to being a bootstrapped entrepreneur on the wrong side of the 40s, starting off with a huge debt. But I saw that as a problem to solve. Come to think of I have more professional and life experience than most people I know, and I still have a solid 30+ years to create the kind of organizations I started to build. After all, in one’s life, four years is just a blip.  

It made me better at handling emotions

That slide wreaked havoc with my emotional state — it was very hard to stay focused and committed when I felt so much pain and betrayal. Many times it was so painful I felt like I couldn’t bear it. But I came away being able to see my own emotions clearly. I no longer define something as a muddy cloud of pain but can see it for its individual elements of where it stems from — and that allows me to resolve it. I’ve learned to focus on what I learn from the experience rather than focus on the emotion.

It made me more empathetic

For the kind of work I do with dogs and children, I would think I have always had empathy. But I realize that most of it came from my ego. It was in some way a continuation of the same theme — of collecting cars or bikes or watches. But with the catastrophic failure, my ego shattered. It was not a priority for me to be concerned with how much money I had or how large was my office building. I became more focused on the cause.

I have a deeper sense of empathy because I understand better the helplessness that comes from having no money to eat or for shelter, or for health. The helplessness that comes from not being able to care for the people and things you care for because you can barely focus on your own survival. As for the other problems — I see them as problems to solve with the wealth that I will create.

It changed the value of money for me

I was never very careful about money. I was fonder of spending it rather than making it. I always believed that as long as I did good work it will keep coming and I never cared much for how carefully I tracked it. That lack of discipline reflected in the people I surrounded myself with — I mean the beancounters were not careful or loyal. They were the ones leading the charge on the gravy train. The core set of people I have today are careful about money and have proven their loyalty without reproach. 

Catastrophic failure led me to re-look my relationship with money. While I focus on making it, I have evolved into a very different person in tracking and spending it. There is a shift in my mind about where money needs to be spent. I’ve learnt to respect it and treat it with care, rather than spending it with disregard. That I see as a stronger platform on which I can create eventual success and wealth in my second innings as an entrepreneur.

It changed the value of time

Some years ago — deep in the four-year period, I realized that I was running out of time. I did not have enough years in my life to do all the things that I wanted to, I did not have enough hours in a day to manage my situation and that ‘time’ is the only real resource I had. That realization alone set me on the path that I became conscious of what I spend time on — and I am much more careful about it than even spending money. I give my time to situations and people that better be worth it because it is the only real thing I have to give.

No matter what advantages or disadvantages one has had in life ‘time’ is the great equalizer. No one has more of it or less than the other. I realize that it was all about what I chose to do with time that mattered, not how much I thought I had. Having learned the lesson I know I am in a great place to create that success with wealth. My ‘Map of Life’ also allows me to categories situations and people that are urgent or important and allocate time accordingly.

The greatest challenge was fighting boredom

Catastrophic failure reset everything in my life. So there are many things I am doing for a second time but there is a problem. When goals are new, they’re exciting. Once the newness wears off, the grind is far more real and I have to fight that because it is boring. With boredom comes complacency and I am more likely to revert to my old ways.

Life goes on only in one direction — forward

Once you’ve suffered a catastrophic event like being absolutely broke, it feels like everything you hoped for is now completely out of reach. It breaks you emotionally, physically, mentally, and spiritually. But what I came to realize was that failure wasn’t the end of the road. Although it hurt more than I care to describe, failure served me more than it hindered me. It helped build me into who I am today.

I would never have gained the perspective I did from this catastrophic failure without it. Nothing of importance can be had easy. It was a way for me to learn the lesson to be a fighter, not a quitter. And for me to discover courage and strength.

The thing about failure is you never actually want to think about it; you don’t want to talk about it but it is one of the possible futures. How we face it is what defines us. Michael Jordan once said, “26 times, I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.”

Stronger with RAKESH SHUKLA is a framework for developing unparalleled mental and physical toughness. It is based on Rakesh’s life, and has helped drive two ‘comebacks’.

Rakesh Shukla slept on railway platforms on his way to creating a world-leading technology company — 
TWB_, which is the choice of over 40 Fortune 500 tech customers worldwide including Microsoft, Boeing, Airbus, Intel, and others. However, at 43, he lost everything within a year. Alone and friendless, he spent the next five years repaying over INR 20 crore of debt and taxes, while building back his company and reputation, and creating and funding VOSD — world’s largest dog sanctuary and rescue.

Rakesh Shukla has suffered heart disease since he was seven years old, had had two heart attacks by the time he was 30, suffers from brain diseases, has broken his back and his kidneys are failing. Towards the end of this five-year period, Rakesh weighed 88 kg and very unfit. Today, at 48 years, he can lift well over 100 kg above his head, run a 10-minute mile, do 2,000 push-ups, and 250 pull-ups. He has never been to a gym, been on a diet, had a trainer, or taken any supplements.

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