The Truth About Becoming Miserably Successful | Debjani Biswas artwork

The Truth About Becoming Miserably Successful | Debjani Biswas

The Midlife Chrysalis

June 5, 2026

What happens when you do everything “right” in life… and still end up unhappy? In this powerful conversation, I’m joined by Debjani Biswas, leadership coach, bestselling author, and TEDx speaker, to talk about burnout, reinvention, identity, and what it really means to live authentically.
Speakers: Debjani Biswas, Chip Conley
**Debjani Biswas** (0:00)
I was laid off from PepsiCo. My personal life exploded. So devastating that I thought that I was down to zero. You have colored within the lines all this time. What has it got you? And I said, screw this world. Here I come.

**SPEAKER_2** (0:17)
Welcome to the Midlife Chrysalis Podcast with Chip Conley, where we explore how midlife isn't a crisis, but a Chrysalis, a time of profound transformation that can lead to the most meaningful chapter of your life.

**Chip Conley** (0:33)
Welcome to the Midlife Chrysalis. This is Chip Conley, and my guest today is Debjani Biswas. Debjani has been a two-time MEA alum, who is one of the leading coaches in the US, and she's been on many lists of being one of the top 10 women business leaders. And what I love about her is that she's got a wisdom. She's got a little bit of a dignified air to her, but she's also somebody who's been in the trenches and had to actually completely change her life along the way. It's not like she just glided into success after success. And in fact, she has a book called Miserably Successful. And I think that you're going to enjoy this particular episode, particularly if you are at a stage in life in midlife where you feel like the path that got you here is not the path that's going to take you there in the future. Quoting Marshall Goldsmith there.
Because what she does for people is in the middle of their life, she helps them to reset what's important to you, what matters, and then how you can get out of the stressful place you're in and actually use your values as a means of exploring who you can be in the future. Hope you enjoyed the episode. I'll see you at the end with my three key lessons.
Debjani Biswas, nice to meet you again. How are you?

**Debjani Biswas** (1:58)
I'm wonderful. How are you, Chip?

**Chip Conley** (2:01)
I'm actually well. It's been warm here in Santa Fe. I think it's probably warm there in Dallas, yes?

**Debjani Biswas** (2:07)
Very warm.

**Chip Conley** (2:09)
Yeah.

**Debjani Biswas** (2:09)
I just got back from New York and this is quite some heat.

**Chip Conley** (2:13)
So you are considered one of the top ten influential business women leaders in business and in life, and congratulations for that. But long ago, why did Harvard break your father's heart?

**Debjani Biswas** (2:28)
It's a very good question. I should say perhaps the blame is more on me than on Harvard, but we ended up breaking my father's heart. So when I finished my engineering school, IIT, I had applied for an MBA in Harvard, and I got in and I declined, and my father was really sad.
And then I did my MBA and I applied for my PhD in the School of Management, and I didn't just get admission, I got a fellowship. So if I taught for a year or two, then everything, it was completely paid for, tuition, staying, everything.

**Chip Conley** (3:06)
Well, so far so good.

**Debjani Biswas** (3:08)
And I said no this time again.

**Chip Conley** (3:11)
Wow.

**Debjani Biswas** (3:12)
Because of personal reasons, I think I didn't understand what Harvard meant exactly. I was also personally, you know, in a stage in my life where it was sort of a choice. I wanted to get married and have kids. So what I did, which broke my father's heart, is I knew he would be devastated. So I lied and I said I didn't get into Harvard. And unfortunately, in those days of snail mail before cell phones, when I sent my rejection letter, it didn't reach them. So they forwarded the entire package with the offer and the fellowship details to my alternate address, which was my parents' address.
He opened it and he realized, not only had I gotten with a full fellowship, I had also lied to him.
And it was really devastating for him. And it wasn't like I routinely lied to my parents or my family. It was just very, very sad. So he passed away some time ago, and my nephew was telling me this story last week. You know, you really broke his heart.

**Chip Conley** (4:25)
God. Okay. Well, we've started with a heartbreak. We're going to get into some good stuff soon. But so you went to IIT, which is the best engineering school in India. It's where Sacha Nadella from Microsoft, the CEO, and Sundar Pichai, how do you say Pichai?

**Debjani Biswas** (4:43)
Hi, Pichai, yeah.

**Chip Conley** (4:45)
The CEO of Google went.
But you were the only woman in your class of 39 boys. You've been breaking through the glass ceiling a lot in your life. What was that like?

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