This article is part of Failure Files, a special series conceived by India Development Review in partnership with Acumen Academy, where social change leaders chronicle their failures and lessons learnt.
This failure story has been a hard one to put down; mostly because the shame and guilt caused by this failure are still alive. Through this piece, I hope to reflect honestly on what went wrong and find closure—perhaps it will resonate with others struggling to find the words.
It was 2017. I was in my late 20s, and based in Bengaluru. I had been in the development sector for more than seven years, and had a couple years of experience in the corporate sector. With two fellowships to my credit and a decent trajectory through a mid-management leadership role, I was ready to make the next move. When I was offered a senior management role in Mumbai, I was more than thrilled to accept.
And that is how I landed up as the executive director (ED) of a nonprofit working with children from low-income communities. When I joined, my vision was to grow the programme by at least three times in a year, and lower our cost per child by at least 50 percent. Innovation and scale at the lowest cost are very close to my heart. I was ready for this! Moving to Mumbai—a city with multiple funding opportunities, that would offer a lot more independence, access, and exposure to a female entrepreneur—was the cherry on the cake.
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I was not prepared for what came next
A month into my joining, two senior team members left, which is not unusual when there’s a change in leadership. Our organisation was also struggling with funding and partner delivery—something that all nonprofits have to go through, apparently. Initially, the founder was available to help me ease into the role, but with a full-time job of her own, it was always hard to get more time from her. Soon, I was the only ‘senior leader’ on the team, with a dysfunctional board and an inexperienced team.
I worried constantly about ‘What will go wrong next?’
On my part, I did not trust the team’s abilities, and did not have the bandwidth to help them build the necessary skills. To make sure that work never stopped, I kept adding more to my plate without delegating, blurring the lines between my weekends and weekdays. I thought I was protecting the team by taking on their tasks. But the result was that they often felt incompetent, unheard, and eventually disengaged (in retrospect, I can see why), often going to the founder to feel heard. I worried constantly about ‘What will go wrong next?’ which made it hard for me to listen to and connect with the team, or to make space for dissent.
Personally too, I had a lot going on. I ignored the overwhelming feeling that Mumbai brought. Soaring rents, hard commutes, dire, visible poverty, and fewer support systems. Mumbai was (and is) a sensory overload in every way. This went on for about ten months. In the midst of all this, I took exactly one week off to get married, and with no break after, jumped right back into work. After all, isn’t that what entrepreneurs are supposed to do and enjoy?
By March 2018, I had raised enough for the organisation to survive for a year and half, had a second line of leadership, and potential partnerships in place. We were in a much better place to achieve scale—the reason why I joined this organisation. I felt like an entrepreneur, albeit, one who was lonely, sad, and burnt out. My top-down approach meant that the vision and these achievements had little to no buy-in from the team or the board. The effort it had taken to get there (mostly alone) left me with zero emotional energy to enjoy what I had achieved or form meaningful relationships. I had come far, but I was alone.
Within a year of joining, I put my papers in
There were many, many things wrong in the system, and by not calling them out, I enabled a broken system to stay broken. The combination of my perception of lack of skills in the team, my inability to invest in them, and overworking to compensate while not taking care of myself was the perfect recipe for a bad burnout. When I left the organisation, I was probably in one of my lowest phases ever, despite all that I had achieved. I was struggling with confidence, had stopped reaching out to my friends, felt like a bad person (I was confusing being a bad manager with a bad person), gained about 15 kg in six months, and had no idea what had hit me.
Two years and many leadership experiences later, I owe this phase many lessons. The three most important ones are:
I learnt the importance of building allies who are rooted in a shared vision. One of the activities I spent the least amount of time doing was connecting with the board and asking for their help, simply because I never realised the importance of it. In my 14 months as ED, we (the board and I) never co-created the vision for my role or the organisation. As a result, I constantly felt lonely, was stuck in ‘operations’, and never had a thought-partner to work through the many challenges I faced.
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There is nothing heroic about loneliness and working alone.
With the growing number of nonprofits and number of people available to join boards of organisations, it’s tempting to have ‘big names’ on the board. The questions that I wish I had answered as the ED are: Who do I want on the board? Why do I want them? How will I hold them accountable? How will I build and partner with the board?
They say leadership is a lonely journey, but I think this loneliness is over-glorified. I now realise that it takes more strength to do whatever it takes to build a collective vision and work together to get there. There is nothing heroic about loneliness and working alone.
My experience taught me the importance of having tough conversations, with kindness. I recall an incident of a team member who expected to get promoted. I didn’t think she was ready to make the jump, but the founder thought that she should be promoted immediately or we would lose her. My inability to have this conversation objectively impaired me and eventually left me with a disengaged employee. The same thing happened when I made a wrong hire and I could not give her feedback on her work. Or when I had to ask someone to leave for non-performance.
One of my biggest learnings is that tough conversations are themselves never hard, doing them with kindness is.
Asking hard questions, making tough decisions, and giving feedback with kindness are skills that I undermined. Thanks to non-violent communication, resources from Adam Grant, and sheer practice, I no longer avoid these conversations. One of my biggest learnings is that tough conversations are themselves never hard, doing them with kindness is. Going in with the intent to be kind and retain the other person’s dignity does more service to them than not having the conversation at all. I remember this, always.
My biggest takeaway from this experience is that work is not life. Work is an important part of life, but it is not life itself. I had defined myself as the ED to such an extent, that it left no room for any other identity to surface. In my head, the ED had to ‘have her act together’ all the time.
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Performance at work became the singular definition of my self-worth. This not only suffocated me, but the pressure that I put on myself never allowed me to be a full version of myself. It did not help that I had moved to a new city and was going through so many changes in my personal life. Burnout was on the cards. I, however, did not see the signs—my confidence dropping, resorting to stress eating, not returning calls from friends, and most importantly, not listening to my gut.
Usually successes get us closer to who we want to be. For me, however, this failure did that.
Of all the things that I did wrong that year, the one I regret the most is silencing my gut. My gut felt that something was wrong in the system, that there were factors beyond my control that were causing things to go wrong—my journals scream of this. I did not allow myself room to experiment, laugh, or have fun, and punished myself for making mistakes. I never shared my vulnerabilities with the team. Having fun is integral to work—especially as a leader. But I wonder if it is harder for young, female leaders to do it and still be taken seriously? Looking at gender dynamics in leadership roles has been another lesson for me. If I could go back, I would tell myself to take a break, to know that sometimes hard work is looking in the mirror and accepting your shortcomings with kindness and humility. I wish I could be kinder to myself. Leaders are often hard on those around them, and harder on themselves. Female leaders, maybe the hardest.
I failed in many ways that year, not just as a leader and colleague, but as a daughter, friend, and partner. I lost friends, and formed very few bonds at the workplace, despite working with great people. The part of my identity that needs to care for people never got expressed that year. Usually successes get us closer to who we want to be. For me, however, this failure did that. It brought me closer to myself, and most importantly, reminded me of all that I want to be.