The Bold Ones: A Conversation That Took Me Behind My Own Book
Recently, I had one of the most fun and revealing conversations about my book The Bold Ones and it wasn’t with a journalist or a podcast host. It was with my good friend Jennifer. She’s one of the fastest, most dedicated readers I know, and she also happened to be the very first person to read the book.
Jennifer finished it in just two hours. (I’m still trying to figure out if she’s secretly a speed-reading cyborg.) She told me it felt accessible, engaging, and full of practical takeaways and that made me incredibly proud.
What I loved most was that our conversation wasn’t formal. It felt like a behind-the-scenes Q & A, part personal reflection, part big ideas and it reminded me why I wrote The Bold Ones in the first place.
Why I Wrote The Bold Ones
One of the biggest misconceptions about boldness is that it requires blowing up your entire life. You’ve probably heard the stories: quit your job, take a massive risk, go all-in overnight. That’s not my philosophy.
I wanted to write a book for people who feel a pull toward more creativity, more impact, more meaning but aren’t ready (or willing) to burn everything down. It’s about taking smart, incremental steps. You can stay in your job and build something bold on the side. Honestly, I think that’s the smarter path for most people.
Incremental Progress Over Radical Leaps
We live in a culture that glorifies all or nothing leaps. But I believe you can make massive changes by starting small side projects, creative experiments, little tests all while keeping the stability of your career. Over time, those small steps compound into something transformative.
The Beauty of Wastefulness
One of Jennifer’s favorite ideas in the book is wastefulness. It sounds counterintuitive, but in a world obsessed with optimization, I think we need to make space for exploration and a little chaos.
That so-called wasted time?
It’s where creativity lives.
It’s where unexpected connections happen.
It’s where you stumble on your next big idea.
If your life is so streamlined that every moment is accounted for, you’re not leaving any room for the magic.
Find Your Number Two
We also talked about the idea of the number two in an organization: the person who might not be the face of the brand but holds real influence.
It’s not always the CEO calling the shots. Often, it’s the strategic thinker, the trusted operator behind the scenes. If you want to make bold moves within the system, build relationships with these people. They can open doors you didn’t even know existed.
Hot Streaks Are Made, Not Found
Hot streaks those golden stretches when everything seems to be going your way are not just random luck. They can be engineered.
They happen when preparation meets opportunity. You spot the momentum, say yes to the right things, and double down while the energy is high. The catch? They don’t last forever. That’s why you have to keep exploring so you’re ready for the next one.
Failure Is Part of the Deal
I’ve failed more times than I can count. Projects flopped. Plans fell apart. I’ve gone from feeling unstoppable to starting from zero repeatedly.
But failure isn’t the opposite of success. It’s the tuition you pay for it. Every restart makes you sharper, more resilient, and more ready for the next leap.
Bold but Grounded
In the book, I talk about people like Kanye West and Sam Bankman-Fried not as role models, but as reminders that boldness can easily tip into recklessness.
That’s why I believe in being bold but grounded. Take the risk, but surround yourself with people who’ll pull you back if you’re about to cross a dangerous line.
Rihanna: The Ultimate Bold One
Jennifer crowned Rihanna as her ultimate Bold One, and I couldn’t agree more. She’s reinvented herself from music to fashion to beauty and dominated every single industry while staying culturally relevant. That’s the kind of reinvention I want readers to embrace.
Final Thought
The Bold Ones isn’t just a book about success, it's a playbook for staying curious, making room for creativity, and taking calculated risks without betting it all.
Start small.
Stay curious.
Embrace a little wastefulness.
And when your hot streak comes, ride it like it’s the opportunity of a lifetime
Frequently Asked Questions
1 - Why is creativity important today?
We’re living in an age where ideas move the world. Creativity helps you solve problems, stand out, and adapt when things change which they always do.
2 - How can I be bold without taking huge risks?
Being bold doesn’t have to mean quitting your job or betting everything. Start small, take on a new project, speak up in a meeting, share your ideas publicly. Boldness is built in layers, not giant leaps.
3 - What are small steps I can take to start my passion project?
Set aside 30 minutes a day or a few hours a week for your idea. Test it, play with it, share it with a small group. Those small steps add up faster than you think.
4 - How do I balance my job and side projects?
Treat your side project like a standing appointment. Put it on your calendar, protect the time, and work on it consistently. The key is progress, not perfection.
5 - Can I be bold if I’m naturally introverted?
Absolutely. Boldness isn’t about being loud, it's about acting on your ideas. Introverts can be incredibly bold through writing, building, designing, or even having one powerful conversation.
About the Author:
Shawn Kanungo is a globally recognized disruption strategist and keynote speaker who helps organizations adapt to change and leverage disruptive thinking. Named one of the "Best New Speakers" by the National Speakers Bureau, Shawn has spoken at some of the world's most innovative organizations, including IBM, Walmart, and 3M. His expertise in digital disruption strategies helps leaders navigate transformation and build resilience in an increasingly uncertain business environment.