Welcome to the Deploy Yourself Newsletter, where I gently provoke you to show you your own power. This newsletter is an invitation to your leadership. You can also read this issue online.


Can you let go of the 3 bananas? (that traps most leaders)

It has been 2 weeks since I came back from leading a wonderful leadership retreat in India. I will share more about the retreat later, but today I want to reflect on something I witnessed years ago during my time living in Jaipur, India.

Jaipur is overrun with 🐒 🐒 monkeys. They cause all sorts of trouble for locals and tourists alike. To deal with the nuisance, the authorities set up “monkey traps” around the city – they place bananas in a small box with a hole just big enough for a monkey to slide its hand in and grab the 🍌 banana. But once the monkey grabs hold of the banana, it can’t pull its clenched fist out of the hole.

The monkey struggles, fighting for its freedom. But the only thing holding it back is its unwillingness to let go of the banana. The freedom is right there for the taking, if it would only open its hand and release its grip.

I confess this monkey trap has been an all-too-accurate metaphor for me at certain points in my leadership journey. I’ve found myself struggling against ⛓️ invisible constraints, fighting for a freedom 🔓 that was mine all along. The only thing limiting me was my refusal to let go of certain “bananas” I was clinging to.

What are these metaphorical bananas for leaders like us? Based on my experience, I see three common ones:

  1. The illusion of control. We want to control outcomes, people, and situations. But true freedom means accepting you can’t control everything.
  2. Playing it safe. Taking risks is scary, so we avoid failure at all costs. Yet real freedom means embracing the fact that failure is part of growth.
  3. Knowing it all. We go into situations convinced of what will and won’t work. But freedom requires humility, openness, and a willingness to be proven wrong.

I won’t claim to have this all figured out. I still find myself grasping those bananas from time to time.

monkey trapped chasing the bananas

Here are 5 practical steps I have found useful to finding the freedom that eludes so many leaders:

  1. Let go of the need to control.
  • Delegate tasks and trust your team to handle them.
  • Set clear expectations then give people flexibility in how they meet them.
  • Focus on guiding the vision and values, not micromanaging the details.
  1. Take calculated risks.
  • Start small, such as allowing a pilot project to launch before it’s fully polished.
  • Set aside a portion of resources/budget for experimenting with bold new initiatives.
  • Celebrate lessons learned from “failures” as much as successes.
  1. Actively seek opposing views.
  • Bring contrarian voices into important conversations and decisions.
  • Read articles/books from sources you disagree with. Stretch beyond your bubble.
  • Ask for blunt feedback on weaknesses and blindspots. Listen without defensiveness.
  1. Admit when you’re wrong.
  • Thank team members who point out mistakes and show you other perspectives.
  • Verbally acknowledge when others prove you wrong. Model openness.
  • Demonstrate the courage to change course based on new information/input.
  1. Replace “knowing it all” with curiosity.
  • Approach issues with inquisitiveness rather than assumptions. Ask, listen, learn.
  • Value curiosity, growth mindset and humility in your hiring and promotion practices.
  • Inspire others’ curiosity by sharing your own learning journey, questions and self-reflection.

The freedom we seek starts with letting go of false securities. By taking these steps, we can loosen our grip on limiting mindsets and boldly embrace the growth that comes with true freedom.

The choice is ours. What “banana” will you release today?

Hit reply to share your responses or insights from the above.

I read and respond to every reply.

Fascinating Articles & Stories


New interviews on the Choosing Leadership podcast

Since I have not written to you in almost 3 weeks, here are all the interviews that have been published since then on the podcast.

Bookmark them and listen at your leisure.

  1. I learned from Ajay Tiwari that “Pain brings you closer to reality”
  2. I learned from Blake Hutchison that “Transparent communication and customer centricity are essential for effective leadership”
  3.  I learned from Ranjan Kumar that “The more you worry about the outcome, the more corrupt you become with your efforts”
  4. I learned from Karoli Hindriks about the value of a powerful morning routine – her is 2.5 hours long
  5. I learned from Afraaz Masters that “The most important thing is to keep moving forwards”


Curated resources for your leadership

Here are my best finds from all over the internet for your leadership. Make yourself tea/coffee as you read, listen and learn.

Pro-tip – Listen and read the below about YOU – not about the author. (reply back and ask if you do not understand what that means)

That’s it for now. If you have any questions or feedback, or if you are new and want to introduce yourself, hit reply. I read and respond to every reply. All the best,


P.S. – I am looking to interview more inspirational leaders on my podcast. If you know anyone I should interview, make an introduction.

(Twitter) @SumitGupta
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