What happens when you can feel yourself digging in?
You know the situation is going nowhere. You know you’re becoming more entrenched, yet somehow you keep pushing in the same direction. The harder you try, the heavier the atmosphere becomes.
In this episode of the Women Emerging Podcast, Julia Middleton explores that familiar experience with Uthara Narayanan, who has an unusual answer: sometimes, the way out is wit. Not humour for humour’s sake, but the ability to think differently, shift the conversation and see a problem from another angle. Together, they explore how wit can change the energy in a room, loosen an entrenched conversation and help someone leading move from a dead end towards a different possibility.
When the Answer Is to Draw Another Line
Uthara begins with a story that has stayed with her since childhood: the story of Akbar and Birbal. Akbar draws a line on the ground and challenges his ministers to make it shorter without erasing or covering it. Nobody can solve the problem. Then Birbal simply draws a longer line beside it.
Suddenly, Akbar’s line is shorter.
For Uthara, the lesson is not about being clever for the sake of being clever. It is about recognising when we are too focused on the problem directly in front of us to see another possibility. If we keep trying to make the original line shorter, we remain trapped inside the terms of the problem. Birbal changes the terms altogether.
Uthara explains that she carries this story into her work because the same thing happens in conversations. We can become so determined to make someone understand our point that we keep returning to it, arguing it from slightly different angles, without noticing that we are no closer to where we want to be.
Sometimes the answer is not to argue harder. It is to change the level of the conversation.
“If you keep looking at the problem and trying to solve that, which was the line that the emperor had drawn, you will never be able to do it.”
That distinction feels important. There is a particular kind of determination that looks admirable from the outside but is actually keeping us stuck. We call it persistence because we are committed to the outcome. But persistence without flexibility can become doggedness.
Julia captures the shift when she describes what Uthara is doing as using her wits “not to carry on so doggedly down this path, but to jump to a different one.”
The point is not to abandon the issue. It is to stop assuming that the only way forward is through the route we have already chosen.
Lightness Can Move a Heavy Conversation
There is another kind of wit that runs through Uthara’s approach: humour.
Julia describes her as someone who can “reframe the conversation, change the atmosphere, make people smile”while still leaving people thinking differently. That combination is important. The humour isn’t an escape from the serious issue. It is a way of making the serious issue easier to engage with.
Julia offers her own example. She remembers negotiating situations in which she knows she needs to ask someone to put something in writing, but saying, “I don’t trust you, so please put that in writing” would immediately make the conversation defensive. Instead, she uses an expression her father taught her:
“In God, we trust. Everybody else in writing.”
The message is exactly the same. But the way it is delivered changes the energy in the room. People smile, the tension lifts, and the practical point gets made.
Uthara recognises the connection immediately. What Julia’s father was really saying was, I don’t quite trust you, so let’s put this in writing. The joke simply allows everyone to hear the message without forcing the conversation into confrontation.
This is where wit becomes more than charm. It becomes a tool for maintaining a relationship while still saying what needs to be said.
Leading often involves moments where the truth is uncomfortable. A decision needs to be challenged. An assumption needs to be exposed. A boundary needs to be established. The question is not always whether we should say something, but whether there is a way of saying it that allows the other person to hear it.
Sometimes a little lightness creates that opening.
Wisdom Through Wit
Uthara’s stories are full of humour, but she is careful about what she means by wit. She isn’t talking about being the funniest person in the room.
For her, the important thing is that there is wisdom within the wit.
She tells another Akbar and Birbal story to illustrate this. A man spends a freezing night standing in cold water and is promised a reward for doing so. When the ministers discover that he had been looking at a distant lamp in the emperor’s palace, they argue that the lamp gave him warmth and therefore disqualifies him from receiving his reward.
Birbal doesn’t lecture them about their faulty reasoning. Instead, he invites them to dinner and then leaves a pot of food hanging high above a tiny fire. When they protest that the food could never cook from such a distance, Birbal simply points out the contradiction: if the distant lamp could provide enough warmth for the man in the water, surely this should be enough to cook their dinner.
The lesson lands because the ministers discover it themselves.
Uthara explains why she prefers this kind of wit. “For me, I always like the wit which has wisdom in it.”
That is an important distinction for anyone leading. Wit isn’t about making people laugh at the expense of the point. It is about finding a way to make people see something they could not see while they were inside their original way of thinking.
Sometimes the most effective challenge isn’t a direct confrontation. It is a story, an analogy, a question or an unexpected comparison that allows someone to arrive at the conclusion themselves.
The wisdom is not removed by making the conversation lighter.
It can become easier to see.
Changing the Energy in the Room
Julia takes the conversation into something that sits at the heart of Women Emerging: energy.
She observes that the organisation has become increasingly convinced that leading is about generating energy. But energy can also become stuck. A conversation becomes stale. A team becomes frustrated. A person leading gets their head down and tries harder and harder, only to become more entrenched.
Uthara’s response is wonderfully physical: sometimes you have to “shake it up a bit, jiggle it a bit.”
She connects it to facilitation, where sometimes the answer to a stuck group is simply to get people moving. Stand up. Change position. Move around. Do something different.
The underlying idea is simple: when the energy is stuck, more of the same energy won’t necessarily solve the problem.
“You have to change the kind of energy.”
That may mean changing the question being asked. It may mean bringing in humour. It may mean introducing a story. It may mean stepping away from the immediate problem and looking at it from a wider perspective.
The physical movement is only a metaphor. The real shift is cognitive.
We often assume that difficult situations require us to become more serious, more focused and more determined. Sometimes they do. But sometimes seriousness itself becomes part of the problem. The more tightly we hold the issue, the harder it becomes to see beyond it.
Wit creates movement.
It gives people permission to look again.
The Value of Having Someone Who Pokes a Hole
The conversation then takes another fascinating turn.
Julia asks Uthara about another story, this time involving Tenali Rama, the court jester of King Krishnadevaraya. The king is convinced that nobody in his kingdom is corrupt. Tenali Rama decides not to tell him that he is wrong. Instead, he creates a situation that exposes the flaw in the king’s assumption.
For Uthara, the lesson extends beyond the story itself.
A person leading needs people around them who will “poke a hole in the system once in a while” so they can see what is really happening.
This may be one of the most important ideas in the whole conversation.
Wit isn’t only something the person leading needs to practise themselves. A healthy team needs people who can change the energy in the room, challenge assumptions and expose what isn’t working.
Julia picks this up immediately.
“So it’s not only you who changes the energy in the room, but you have in your team people that you know will change the energy in the room for you.”
Uthara agrees, adding that this has to be modelled. If you want people to bring lightness, challenge and different perspectives, you have to demonstrate that those things are welcome.
That requires a particular kind of confidence.
If everyone believes that the person at the top must always be serious, certain and right, nobody is going to risk being the person who says, Hang on. What if we’re looking at this completely the wrong way?
But if wit, questioning and challenge are part of the culture, someone can play the role of Tenali Rama.
And sometimes that is exactly what the team needs.
The Courage to Stop Taking Yourself So Seriously
Perhaps the most revealing part of the conversation comes when Julia and Uthara talk about why so few people use wit in their work.
Uthara suggests that people working for social change often become serious because the work itself matters deeply to them. There is also a fear that if you are too playful, people will stop taking you seriously.
She believes wit often comes later, once you have proved something to yourself.
“As you have proven yourself to yourself first, then you feel confident enough to joke about it.”
That is a subtle observation about confidence. Wit requires enough security not to treat every moment as a test of your competence.
Julia recognises something of herself in Uthara’s approach, observing that perhaps part of the reason they connected so quickly was that neither of them took themselves too seriously.
That doesn’t mean taking the work less seriously.
In fact, the opposite may be true.
The work can matter enormously while we remain able to laugh at ourselves, question our assumptions and recognise when we have become too entrenched. Taking ourselves seriously is not the same as taking the work seriously.
And perhaps that is where wit becomes a form of wisdom.
It creates just enough distance for us to see ourselves, the conversation and the problem differently.
Don’t Get Stuck
Towards the end of the conversation, Julia returns to the idea that began it: digging yourself in.
Uthara admits that she still does it. She can think back to situations and wonder whether she really needed to be so hard, whether she could have approached something differently, whether she had missed the opportunity for a little laughter.
It is an honest admission because the episode isn’t offering wit as a magic solution. It is a practice.
There will still be moments when we become tired, serious and entrenched. There will still be negotiations where we lose perspective, conversations where the atmosphere becomes heavy and decisions where the easiest thing is simply to keep pushing in the same direction.
The invitation is to notice.
To recognise when the line in front of us has become the only thing we can see.
And then to ask whether there is another line we could draw.
Julia’s final reflection brings the whole conversation back to that original story:
“Do not just fixate on the line that’s in front of you. Think of the other line, that other line.”
Perhaps that is what wit gives us when leading: not an escape from difficult situations, but another way into them. The ability to lift a conversation when it becomes too heavy. To challenge without humiliating. To make a serious point without making the room more serious. To recognise when persistence has become entrenchment and to find another route forward.
And perhaps, most importantly, to remember that getting unstuck does not always require more force.
Sometimes it requires a different way of seeing.
Excerpt from the Episode
Julia Middleton: What happens when you’re leading and you can feel yourself digging in? What happens when you do feel that sense of digging in and you know you’re keeping on digging in? You’re sort of inevitably going down a sort of dead end. You know you’re doing it, but you’re almost unable to stop. What do you actually do?
I talked to Uthara about this and she talked to me about the role of wit in dealing with that sense of being in a dead end when you’re digging yourself in. She talked about wit in the sense of quick thinking, and she also talked about wit in the sense of sort of light humour, both of which have often been her method of undigging.
Uthara Narayanan: It is the story of Akbar and Birbal. And in India, we grew up hearing a lot of those stories and in the context of wisdom and taking some moral out of it. So one day, Akbar basically drew a line on the ground and called on all his ministers and he wanted to test their wisdom. And he said, how do you make this line shorter? You can’t rub it, you can’t cover it up, but you have to make this line shorter.
None of the ministers were able to do. Of course, Birbal came up and he said, he just drew another line, which was longer than this particular line that Akbar had drawn on the ground. And he said, there you go, emperor. Your line is shorter now.
And that story I’ve always carried with me because I feel in any situation, especially where you are trying to make a point, it could be with your board, it could be with also your team members. And if you keep looking at the problem and trying to solve that, which was the line that the emperor had drawn, you will never be able to do it because you’re like, oh, I can’t rub it, I can’t cover it up, I can’t do anything about it.
But the moment you say, can you do something in parallel, which makes this look like a smaller problem.
I use this also in the context of in conversation, you actually take your conversation to the Uber level. And this was with a Kenyan friend of mine, we’ve had this long conversations about why we’re speaking with somebody and you’re not able to get your point through. You take your point above where you’re speaking right now. And you take it to a point where they’re like, oh, they don’t even remember where they began by the way.
Julia Middleton: It’s a really good example, isn’t it? That you use your wits to, not to carry on so doggedly down this path, but to jump to a different one. And in so doing, you lighten the situation.
Uthara Narayanan: Yeah, also using your smartness, I feel. Just be smart about it. Even during conversations, I feel, sometimes when you keep on arguing on a certain thing, and you’re getting nowhere with it. And I know some of, most people say, okay, let’s just agree to disagree. But then that dark cloud sort of remains, right?
When you say that, I feel rather than that, it’s just moving to making this conversation about something bigger than what it is already.
Julia Middleton: It makes me think of an expression my father taught me, because sometimes you get into those negotiations and over, I don’t know what it is, anything, you’re negotiating, you’re negotiating, your head is coming further and further down into the situation as you lead a negotiation.
And you get to that sort of point where you don’t want to say to somebody, I don’t trust you, so please put that in writing. But you know that you have to.
And my father had a wonderful expression, which was, “In God, we trust everybody else in writing.”
And whenever I use that expression, everybody then smiles and immediately puts it in writing.
And it’s sort of, your point is firstly, you lift people away from getting too entrenched. But my father also had this thing of doing it with a bit of a joke.
Uthara Narayanan: And it works. Actually, what your father was trying to say is that, I don’t really trust you, so let’s put it in writing, but rather than saying it that way. It was just a wink, wink.
Julia Middleton: Absolutely. Absolutely.
Tell me more of these stories, because I love them.
Uthara Narayanan: So the other story that I remember is again, of Akbar and Birbal, where Akbar announces that anybody who can stay in water, in the cold water in winter for the whole night, he’s going to reward them a certain amount of money. And a person is able to do it.
When that person comes to collect the reward, the minister sort of jump in and say, oh, but how were you able to do it? How did you do this? And this person says that at night, I looked at the lamp in the emperor’s palace and I got the confidencebecause of that.
And they said, oh, this is cheating. This person actually got the warmth from this lamp, which was almost a kilometer away.
And they said, no, emperor, you can’t give the reward to this person.
And that person was very disappointed and leaves. But Birbal had this idea of saying, how do I make these people see, in a way almost give them a lesson and invites them all for a meal to his house.
All of them reach and Birbal is not serving them the meal. So they get impatient and say, what’s going on, Birbal? How come the meal is not yet ready? He says, oh, it’s still cooking. And he makes them wait for hours together.
And finally they all lose their patience and say, we want to see where it’s getting cooked. And he takes them to a place where the pot of food is actually on top of a tree and the fire is below.
So all of them pounce on him saying, how dare you? How could you do this? Are you nuts? How will it get cooked? It’s so far away.
And then Birbal says, oh, but you said that the person who was in the cold water, looking at the lamp from the emperor’s palace, that he was able to get the warmth. I thought that could apply here as well.
So in a way, all of them, they understood their mistake.
Uthara Narayanan: So making it lighter to give the lesson, rather than, Birbal could have easily said, what are you people saying? Do you think this person who deserves the reward could have got the warmth a kilometer away? Rather than just saying it out loud that way, the way that your father also made it light, Birbal decided to show it in a different way.
Julia Middleton: And how does all this translate into how you lead Uthara?
Uthara Narayanan: I feel sometimes, rather than just saying things constantly and being dogged about it, you have to bring in a little bit of humor. You have to become a little light and also have to give examples outside of the box and also trigger people to think differently. And it’s very situational.
It could be while you’re talking to your team members or while you’re with your board members or anywhere, any situation that how do you bring in a different perspective so that people remember these stories also.
Julia Middleton: It’s interesting, isn’t it? Because we’ve become so convinced everybody involved in Women Emerging that leading is about generating energy.
And what you say fits it too, doesn’t it? That there comes a point where energy sometimes gets sort of stuck. It becomes stuck or stale, and you get your head down and you just try harder and harder and harder and you get more and more stuck.
And the argument here is that you have to change the kind of, you have to generate a different kind of energy.
Uthara Narayanan: Yeah, you have to shake it up a bit, jiggle it a bit, saying, okay, you know, shake it off. And I feel we also do this in our facilitation, right? When people are in groups, sometimes we say that, shake your body, just get up and move around. Movement is important, that you move it around rather than just getting stuck at that point.
And these are the kind of stories that you have in your back of your mind to just bring out and say, are we thinking differently? Are we doing things differently than what we were thinking about?
Julia Middleton: But the danger with leading is that you dig yourself in, isn’t it?
Uthara Narayanan: Of course, all the time. You get so serious about it.
Julia Middleton: I don’t know if it’s with you, but certainly I get more entrenched if I’m tired.
Uthara Narayanan: Well, sometimes it happens. If I get really tired, I also tip over. So it’s even this that I’m so exhausted that I start laughing for no reason as well. And I can see only the humor in it.
Julia Middleton: So there isn’t much weight at all then. So don’t get stuck.
Uthara Narayanan: Don’t get stuck, yeah. I’m still practicing it. I don’t think I’ve done it yet. It’s still a practice. It takes time to get there.
Julia Middleton: Because you always get that sense of, yeah, you got me, okay, let’s do it then.
Uthara Narayanan: Yeah, exactly. So that’s also, then it comes in many, many situations. And I think it’s situational in the moment with, right?
Julia Middleton: But the danger with leading is that you dig yourself in, isn’t it?
Uthara Narayanan: Of course, all the time.
Julia Middleton: Or shift the conversation?
Uthara Narayanan: Shift the conversation, yeah. I mean, I use the word joke there, but it is about shifting that conversation, moving it to a level where you can make the people see what you mean.
It’s a practice, it takes time, it’s a journey. I know very few leaders who can do it from the beginning.
Julia Middleton: Thank you so, so much, Uthara, that was wonderful. The two lines are firmly in my head. With that sort of message, do not just fixate on the line that’s in front of you. Stare at the line that’s in front of you. Think of the other line, that other line. It was fantastic.
