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.


Why creativity is the fuel for 21st-century leaders?

I wanted to get real about something I’ve been working on lately – getting more creative as a leader.

Early on, I bought into this idea that leadership was about having all the answers and executing plans. But as my teams grew, I hit a wall.

No matter how smart my ideas seemed, they didn’t spark that energy and inspiration I longed for. My technical expertise wasn’t enough.

I realized I needed to lead with creativity. But having spent years in analytical roles, this didn’t come naturally to me.

In one company, I led multiple software and AI teams. When we had a big failure, morale crashed fast. I scrambled to course-correct but nothing revived the team’s spirit.

That failure taught me leaders need creative thinking (not just new plans) to reframe setbacks into learning opportunities. We need to imagine possibilities that feel out of reach.

Once I noticed my developers struggling to innovate on an outdated tech stack. My solution? I assigned them the latest coding tools to learn after hours.

But my “efficient” solution backfired. Resentment grew as their personal time eroded. I failed to see that creativity can’t be forced through sheer effort.

That humbling moment revealed I needed to cultivate imagination more organically by sparking inspiration, not giving orders.

These mistakes taught me creativity must flow through everything leaders do—it can’t be compartmentalized.

Now as an entrepreneur, here are a few ways I’m trying to lead with more creativity:

  • I make time for activities that ignite my imagination outside work – writing, tinkering, photography. This fuels new connections.
  • I’m getting comfortable with half-baked ideas, sharing early sketches and embracing wild questions. This keeps me nimble.
  • I regularly invite creative talent from other companies into strategy sessions to mix things up. Fresh perspectives reveal breakthroughs.
  • I’m letting go of rigid agendas when inspiration strikes. Following energy unlocks our best thinking.
  • I celebrate failure and encourage experiments that fizzle. This gives people permission to play.
  • I make space for improv, prototyping, and other playful ways to unlock creativity, not just status updates.
  • I share my own creative struggles and ask for input. This models that creativity is vulnerable, collaborative work.

Creativity lives in everyone, not just “innovators.” It reveals itself when people feel safe to play, take risks and voice half-formed ideas.

But leading with creativity means letting go of the illusion of control. Here are a few key mindsets that help:

  • Seek surprise over certainty.
  • Value imagination as much as practicality.
  • Embrace play and whimsy alongside rigor and analysis.
  • Get comfortable with ambiguity and not having all the answers.
  • Stay open and responsive rather than rigidly attached to “the plan”.
  • Trust your team’s creative genius even when the path is unclear.
  • Know creativity gets messy but bears fruit when persevered through.

This remains a journey for me.

But the more I lead with creativity, the more ideas, energy and solutions flow. It feels aligned, joyful, and fulfilling.

I’d love to hear how you are embracing creativity in your organization!

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

I read and respond to every reply.

Fascinating Articles & Stories


I interviewed 5 more inspirational entrepreneurs

I am now close to interviewing more than 150 entrepreneurs on the Choosing Leadership podcast. Here are the few episodes that have gone live since the last time I emailed you – almost a month!

This is what I have been learning from these inspirational leaders:

  1. I learned from John Cherian that “You build skill when you get your hands dirty”
  2. I learned from George Huff that “There’s no substitute for experience”
  3.  I learned from Deepti Prasad that “It’s okay to fail, but it’s not okay to not try.”
  4. I learned from Derren de Jong that “Freedom is the biggest driving factor behind everything I do”
  5. I learned from Sanket Nadhani that “A sabbatical helped me discover myself, build confidence, and open my mind”


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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