TWI Woman of Substance – Nirupa Umapathy


Let’s face it. For most people who are involved in the rat race of life, there is very less or no time at all to self-reflect. We are cogs in a wheel. Or to give a more current and apt analogy, we are like that bus in the movie Speed. If we fall under a certain limit, the bus will explode. How different is that when it happens to us? Conditioned by years of schooling, college years and work life, and to a certain definition of success, what would happen if we veered off the cookie-cutter path? Would we implode, lose it, and find ourselves lost and running after the applecart?

Which brings me to our next guest in the Woman of Substance series. Nirupa Umapathy left behind a lucrative career in Financial services after devoting a big part of her adult life to following the conventional “successful” life. Let’s find out what motivated her to do so, and what path she chose to walk on instead.

AM: Hi Nirupa and welcome to the Woman Inc. We are so happy to have you here! I usually start by asking about your background so we know what you’ve left behind

NU: Boy. In reverse chronology. 14 years in financial services, 13 of which were spent on a trading floor transacting in something called structured products and alternatives. A long, mostly gorgeous relationship of 17.5 years with a partner, who was my rock. Home of origin when I was 18, which is Chennai, India. I was not convinced that my original literature course in Madras was a real education. I dropped two years of college to start a liberal arts education at an all-women’s college in MA called Smith College. I graduated in 2002 with a double major in Anthropology and Economics.

AM: So, would it be fair to say that what you studied led you to what you did at work? Or was that a deviation in itself?

NU: Another deviation. I originally combined Anthropology and Economics so I could pursue development. I always sensed capital was a critical resource- hence, the study of Economics. I abandoned my desire to do good right after graduation for pragmatic reasons- a work visa, wanting to be financially independent. Although the desire to do good burned bright for very long. My degree did not prepare me for Wall Street. Both are soft sciences. They were good windows into studying human behavior. Many, who work on the trading floor, are self-taught because it is its own peculiar ecosystem. You learn by doing.

AM: What was it like working in Financial Services? And what was it that led you to leave it for good?

NU: A wild ride in technicolor. Angsty, exhilarating, intensely competitive and goal-oriented with very high stakes. It was like boot camp for life. It taught me instinct, work ethic, accountability, relationship building and how to get very comfortable with money (dealing with large sums of money that is, not making it).

Once I made Managing Director in my early 30s, I knew I had hit my local maximum. Time for change. But change came to me. My last year at a hedge fund did not work out. They wanted me to leave. The opportunity to switch was presented to me. In 2017 I took a sabbatical to figure out if I could stay away from finance for a year and what else. I realized I could. So I did.

The For Good element was missing from my career. I could not reconcile how what I was doing was creating long-term value for more than the 1%. I still love the markets and stay on top of them and consider myself an investor. So the girl might leave Wall Street, but Wall Street does not leave the girl.

AM: Tell us more about the Life Design Community. How was it formed, and how did you end up being such an integral part of it?

JW Architects Liz-Galen-Nirupa 07122018

NU: The book that emboldened me to take the sabbatical in the first place was by these two Stanford Design School Professors- Designing your Life. How to Build a Joyful, Well-Lived Life.

It was recommended to me by my friend Marni, who started this life design community. We were a book club of 1 book. I took it further and structured my entire year by journeying with the exercises in the book. I am still doing parts of it now. My life is now a series of unending experiments.

I am yet to go back and take the incredible course taught by Kathy Davies at Stanford. It is called DYL for Women.

AM: What was it like to walk away from a successful career in finance?


NU: Terrifying. But I had been fighting malaise for very long- my life values were not coherent with my professional being. This heartburn had started acutely since the financial crisis in 2008. It was incredibly clear when the time had come to leave.

The below was the very confident and euphoric point of view as soon as I hit eject.

In the financial industry it is a known fact that stepping away, even for a year, drastically reduces your shelf life. I determined that I had built up my network, skills, and finances enough to take the biggest risk of all, which was to invest in myself. I was ready to create a blueprint for a well-lived and integrated life, not a canned model that existed for mass consumption.

Since then, I have gone through my peaks and troughs. Sitting where I am right now, close to two years later, I have a glimpse of what really makes me come alive. I am not riddled with fear. My biggest fear I now realize- was I will never find what makes me come alive. Because that is what I am after.

AM: What is one of the main things you’ve learned?

NU: So many things. Dealing with ambiguity and wading in what I call “the sea of no markers.”

With no structure of office time and space, I have to create every day from scratch.

I don’t port a fancy business card although what I do now is incredibly precious and life-giving.

Getting comfortable with no labels. I am no longer Nirupa the finance person, the MD, the married woman. The dog-owner. It has been liberating.

And getting rid of busy-ness. I have complete autonomy of time and space. It is a gift. I try and do a good job of focusing on the essence and the essential.

AM: What are some basic ideas of your take on life design?

NU: Creating a life by design is something that you create almost from scratch. It is not a design someone else chose for you. Although your past is always a good indicator of things that make you tick and thrive. Designing your Life is much about learning a mindset (what designers use and apply when designing products, services and experiences), a set of tools or a process.

For instance, my newly designed life is constantly in flux but it has the sanity of being backed by an intention or a set of values, the desire to feel alive by unpacking all the many facets of me, and to do away with crusty and finite definitions of success and failure or being right. That is so 80s 🙂

AM: What are some approaches you found valuable? 

NU: One of the critical stages that the book talks about is prototyping. Or Experimentation.

It is a framework where you use your own life as a laboratory and go about day-to-day building your way into what resonates and is coherent with you as a person. It comes from a point of view where you become the central actor that you are studying. It comes from a point of action, trying out many different things and giving yourself permission to play, followed by reflection and refining insights as opposed to analysis and pre-determined outcomes. It is a nifty way of teaching yourself how to problem solve. And to have fun doing it. It liberated me from the stranglehold of the fear of failing.

AM: Describe how you hope to change attitudes as you follow your path.

NU: Everyday I live what I talk about. When people meet me they comment on my energy and enthusiasm. For those who have time and are curious, I give them my story. But I also point to techniques and mind-sets and processes that I have utilized. I talk about the What but I also spend a lot of time explaining the Why and the How. And I make it very clear that this is not a finished product. The act of designing of your life is never done really. But why stress about it if you feel alive and are having fun.

I yearn to empower people to believe that they they are their best role models. They need not be experts of anything but their “own wild, precious life” (thank you Mary Oliver). I yearn for people to understand how with self-permission, allowing themselves to think of themselves as creative, expressive beings, they can unlock riches beneath their feet- their own lives. And when they come alive there is a world out there that wants to see more of you.

AM: I’d like to talk to you more about the salons you help create and make happen. Where did the idea for these originate, how do you spread the word and how has the reception been?

NU: The word salon came into my head when I was talking to Kathy Davies at Stanford. Last year, I did a whole series of mind-mapping circles to encourage a small group of people to free-think. These circles became incredibly intimate and story and self were natural emergent themes. I visited India where I met my current partner in crime for work, Mukesh. He was contemplating getting an ambitious arts project off the ground. We are in early stages. I wanted to test the first salon as a forum for patron outreach and engagement and model it off the salons of the French Enlightenment. It happened April 28th and was received really warmly. I have done 11 salons in 4 states to date and each one of them has been received with incredible warmth and enthusiasm and desire to be part of more. Everything is by word of mouth and through the exponential connectivity of the network.

AM: Who do you feature in these salons and what is the general structure of these meetings, or do they typically flow and take their own course?


NU: Artists, storytellers and the audience are featured. Two types of salons have been organized. One explicitly focuses on channeling the arts and artists to activate community and a space for active conversation and reflection. The other focuses on what I call pedagogies of confidence. We explicitly try and learn one technique from the arts and/or the healing arts like yoga and how we can use this in real-life to enrich our lives. Both salon formats derive their vitality from storytelling, active conversation and community creation.

Ultimately, I operate under the assumption that no evening will be the same because those who are in the room are active co-creators of the experience. But there are some formatting guidelines. There is always performance or storytelling. I try to not keep make it too expository. Experiencing and participation are the holy-grail of active learning, which I am a believer in. The audience are very involved in these salons and as a facilitator I always have to engage and maintain a push and pull.

AM: What causes do you believe in, and how do you contribute to these?

NU: The salons are my life project because I live the mindset and framework everyday. I come alive when I am able to help create a safe space where we can not only be ourselves but also thrive.

I believe that the essence of well-being is for us to be the best custodians of ourselves.. When we are good custodians of ourselves we can be good custodians of our communities and the environment. When we thrive we make responsible and sustainable decisions that will contribute to larger well-being.

I donate mostly to organizations that do good work to skill us to live our lives fully- so education, occupation training etc. I donate to my alma mater, Smith College, to my friends, who have started from scratch a school for underprivileged kids in Granada, Nicaragua. An organization called Prajwala, run by Sunitha Krishnan. She is fighting the fight to help human trafficking victims and to rehabilitate them. There are numerous other causes that I do donate to but I believe in systematic giving. The first two are my go-to every year. I am also growing a pool of money that I seeded end of 2018 that I hope can become more a foundation.

AM: Three books/documentaries which are a must-read/must-watch, that you think people in general would benefit from. Especially those contemplating a different life-path.

NU: I don’t watch a ton of TV. So I will give you 5 books instead 🙂


Designing your Life. How to Build a Joyful, Well-Lived Life.

The Power of Habit. Charles Duhigg

Drive. The Surprising Truth about what Motivates Us

How to Fail at Almost Everything and still Win Big

Essentialism: The Disciplined Pursuit of Less

AM: You talk about the mind-body connection. How has Pilates help you achieve that, and what else do you do to maintain your equilibrium, a state that most of us struggle to get to?

NU: The Pilates certification was the first foundation toward personal well-being. It taught me technique and principles on putting your mind-body health at the center of life. Yoga incorporated the deeper inward journey into spirit. I believe that every little micro-process in your life has its own steady state or self-regulation. I am constantly listening to what these micro flows are. Reading and writing have really helped with creating this kind of introspection and space. When the inside is flowing, it becomes so much easier to calibrate with outside demands. I also am very quick now to retreat and incubate if the “noise from the outside” is too much. I have largely gone away from the “must-do, must-have, should-be” mentality to “could be- perhaps- how essential is this- and is this fun” mentality.

AM: Tell us more about the Traveling Pants Exchange. What brought this about?

NU: TPE has a funny starting story.

I am still in the process of shedding a lot of my old life. I literally had 20-25 pairs of blank pants sitting in my closet, many of them not worn from my prior career. So I wanted to create a forum for discussion through clothes. I was also missing my women from Wall Street, all those incredible women that I had mentored and/or been peers with. Instead of donating the pants, I decided to pass on the “intuition, wisdom and energy” endowed in each one of those pieces of clothing to someone who could then use that to endow their career with insights and more confidence. The evening was a success. The name stuck. I kept the pants in the name because all of us can wear pants. This is the second of the Salon series. It is focused on an inter-generational and mixed gender audience.

AM: Truly amazing, you and your story. Before we part, may I ask what else you think your future might hold for you, and for us?!

NU: Thank you for taking the interest to hear my story, Anu. It is important for those of us, who have a platform to also feature unusual, quirky, “oddball” stories.

Honestly, after being such a pre-determined person for so long, I am shocked to say that I have no idea. Short-term, this is what is percolating in my head and heart. The next year, I would like to live in 4 different cities, ideally across 3 continents, 3 months at a time. I am experimenting with this coop-life concept. Ie. I ask a few like-minded friends to join me for each stint and we are roommates in different parts of the world. I suspect that my life from here will be nomadic while always being anchored to this sense of home, which is both a physical space, a voice and a community.

There you have it folks. Thank you Nirupa for sharing your wonderful story and we wish you happiness and success as YOU define it in finding and holding onto your fluid space in this world. Hugs!

One Comment Add yours

  1. Praveen Kumar C K says:

    Congrats Nirupa. We are proud of you. It’s bold decision you took and our support and wishes are with you as a family.

    All the best. Enjoy the travelas always

    Liked by 1 person

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