Leading While You’re Still Figuring It Out
Leading with honesty. Learning as you go. Still showing up.
During a recent discussion with a senior colleague, we explored the topic of leadership, and one of the things we talked about was how no one tells you this early on: leadership rarely comes with all the answers. Sometimes, you’re the person everyone looks to, while quietly Googling behind the scenes, texting mentors for a “quick gut check,” and second-guessing every decision you just confidently announced.
I have had the privilege of leading people in various forms, whether it was leading my class as a high school or college student, or heading entire student bodies, departments, and even organizations. I may not be 30 years old yet, but life has truly given me that level of exposure. You’re expected to steer the ship while still assembling the compass. Sometimes, you might even be building the ship - in a storm - with half the crew asking if we’re really heading north.
I have been there. Leading teams, managing budgets, making hires, raising capital, all while learning, fumbling, adjusting.
There were days I gave a pep talk on focus and strategy in the morning… and spent the evening rewriting the roadmap because something just didn’t sit right.
The truth is, most of us are making it up as we go. Not in a reckless way, but in that honest, uncomfortable, fully human way where we’re doing our best with the information we have, while collecting more as we move.
No book or podcast truly prepares you for the moment a teammate cries on a call. Or when a board member questions your conviction. Or when you realise the strategy you pitched six weeks ago… doesn’t work anymore.
But here’s the thing I’ve come to believe: the ability to lead while learning might be the most underrated skill of all.
Not perfection. Not pretending. But posture.
It’s being transparent without losing trust.
It’s saying, “I don’t know yet, but I’m going to find out.”
It’s inviting your team into the process without making them feel adrift.
And maybe, it’s admitting that leadership isn’t about having all the answers - it’s about making sure the right questions are being asked.
These days, I’ve stopped aiming for flawless. I aim for honest, intentional, and adaptive.
I still make mistakes. I still ask dumb questions in smart rooms. I still wake up some days wondering if I’m the right person for the job.
But I’ve also seen what happens when you lead with humility, when you invite your team to think with you, not just follow you. That’s when trust builds. That’s when momentum compounds. That’s when people show up not just for the job, but for the journey.
So if you’re reading this and you’re in that messy middle, and you’re like me…leading and learning - I’d like to say hang on, you’re not alone. There are many of us, and the world needs us to keep trying.
You’re not behind. You’re just human. And you’re probably doing better than you think.
But before I wrap this up, I’d like to leave you with some books that have helped me on my journey to being a better leader; here’s a simple list:
The Spirit of Leadership - Myles Muroe
A foundational and values-based guide on vision, purpose, and inner conviction.
The Hard Thing About Hard Things – Ben Horowitz
No sugarcoating. Just real stories and strategies about leading through chaos.
Atomic Habits – James Clear
Because leadership isn’t just about big moves—it’s about the small disciplines that stick.
High Output Management – Andy Grove
A practical masterclass in team productivity, management cadence, and scaling performance.
The Five Dysfunctions of a Team – Patrick Lencioni
A leadership fable packed with insight into what breaks (and builds) cohesive teams.
Turn the Ship Around! – L. David Marquet
A powerful story of shifting leadership from command-and-control to trust and ownership.
Radical Candor – Kim Scott
How to care personally and challenge directly — especially when leading people you value.
Leaders Eat Last – Simon Sinek
A compelling case for servant leadership and the biological foundations of trust.
Trillion Dollar Coach – Eric Schmidt, Jonathan Rosenberg, Alan Eagle
Lessons from Bill Campbell, legendary coach to Silicon Valley’s best.
Principles: Life and Work – Ray Dalio
A structured approach to decision-making, self-reflection, and team dynamics.