What Happens When You Tell the Truth About Failure
Spoiler: You don’t lose credibility. You earn trust, build connection, and lead like it matters.
He didn’t set out to become a writer. He simply got tired of watching leaders struggle in silence while the real conversations stayed buried beneath slide decks and status reports.
So he opened a blank page, told the unvarnished truth and built a community around what no one else was saying out loud.
Meet
Q: What's the story behind your Substack?
The story behind my Substack is simple: I saw a gap in the content available for tech program managers and delivery leaders. As someone deeply embedded in the tech and PM world, I realized that while there’s plenty of content for the basics, there’s a lack of nuanced, real-world insight—especially around the complexities of leading teams, managing stakeholders, and executing large-scale projects. Substack became a platform to fill that void and offer actionable advice grounded in my own experiences.
Q: What's the most courageous creative or personal risk you've taken since starting your Substack—something that pushed you far beyond your comfort zone?
The most courageous step was deciding to put myself out there publicly—sharing not just my professional expertise, but also my personal experiences and challenges.
I’m used to speaking at conferences and in professional settings, but writing for an audience that isn't directly engaged with me on a daily basis felt much more exposed.
I realized that taking those risks, like sharing struggles or lessons learned the hard way, created stronger connections with my audience. It's been an uncomfortable but rewarding leap.
Q: The blank page can feel like a judgment waiting to happen. For those writers sitting on the sidelines, paralyzed by the fear of criticism or failure, what would you say to help them take that first brave step into sharing their voice?
I’d say: Don’t let perfectionism paralyze you. The fear of judgment is natural, but it’s also self-imposed. Start by writing for yourself, not for an audience. The first draft is always messy, but it’s better than not starting at all. You might surprise yourself with the impact you can have when you focus on sharing what’s real and raw, rather than worrying about how others will judge you.
Q: Reading can be passive, but transformation requires action. What's the most courageous step you believe a reader can take after being moved by something you've written?
The most courageous step a reader can take is to take the concepts or insights I share and put them into practice, immediately. Transformation is only meaningful when it’s tied to action. Whether it’s changing how they approach their day as a project manager, or taking a hard look at their leadership style, applying the lessons will lead to real change. Don’t just read—act.
Q: There's a fine line between authentic vulnerability and emotional exhibitionism in public writing. How do you navigate sharing your truth while protecting your inner sanctuary?
It’s all about balance. I share personal stories and lessons learned, but I do so with purpose. Every piece of writing has a reason for being shared—either to educate, inspire, or spark reflection. I always ensure that I’m sharing enough to be authentic and relatable, but I don’t overshare in a way that risks compromising my emotional well-being. Protecting my boundaries means being mindful of what I share and ensuring that it serves the bigger picture of my journey.
Q: Every meaningful piece of writing contains an element of risk; whether it's challenging popular opinion, revealing personal truths, or exploring uncharted territory. What's the biggest creative or personal risk you've taken through your writing, and how did it change you?
The biggest risk I’ve taken was writing about the struggles and failures I’ve encountered in my career, especially in leadership. People expect polished stories of success, but sharing the unpolished truths—like the moments I doubted myself or failed—was tough. But it opened doors to deeper conversations with my audience and helped them see me as someone who’s been through the same challenges they face. It’s made me more connected to those I aim to help, and more comfortable with imperfection.
Q: Reinvention requires dismantling the comfortable cage of who we used to be. For established professionals or thought leaders feeling trapped by their own success but afraid to evolve, what wisdom would you offer about the courage required to start over?
I’d say: Don’t fear reinvention, embrace it. Growth requires shedding old identities and embracing new ones. Just because you’ve built success in one area doesn’t mean you’re stuck in it forever. Starting over doesn’t erase your experience—it builds on it. If you’re feeling trapped, that’s the first sign that it’s time to evolve. The courage comes in taking that first step into uncertainty, knowing that it’s part of a much larger journey.
Q: If you could sit across from yourself on the day before you published your first piece, knowing everything you know now about this journey, what essential truth would you share?
I would tell myself: Stop overthinking and start doing. The journey won’t be perfect, but it’ll be worth it. Don’t let the fear of making mistakes hold you back, because each mistake will be a learning opportunity. Trust the process, but also trust yourself to adapt and evolve as you go. If you wait for the perfect moment, you’ll never start. Just begin. And be okay with not having all the answers.
If you enjoyed this interview, and resonate with
way of being, subscribe and reach out! He would love to hear from you.
👉 If you enjoy reading this post, feel free to share it with friends! Or feel free to click the ❤️ button on this post so more people can discover it on Substack
This is another wonderful interview, Magdalena. Thank you for introducing Rajesh. I will follow his insights soon. You are so good at uplifting others with your servant leadership and community spirit.