The Lie of Having It All Together

Over coffee recently, a founder I was chatting with said something that stuck with me: “Other leaders look so successful and seem to know exactly what they’re doing. Is that really true?”

As someone who works closely with founders and leaders, my answer was immediate: No. In fact, most people—whether they’re founders, professionals, or anyone navigating life—are mostly just figuring it out as they go.

This question reminded me of my own journey as an entrepreneur and of a leader I used to mentor. He was brilliant, ambitious, and had a sharp vision, but he struggled with one thing: ambiguity. He wanted answers, clear plans, and certainty in every situation.

But here’s the thing: leadership—like life—is rarely that tidy. I used to tell him, “You don’t have to know all the answers. Your job is to embrace the ambiguity and be comfortable with it. Lean into vulnerability, and don’t be afraid to be human.”

It wasn’t easy for him to hear at first. But over time, he realized that not knowing everything wasn’t a flaw; it was an opportunity to listen, to learn, and to connect.

The Facade of Success

Why does it feel like everyone else has it together? Part of it is the curated nature of modern life:

• Social Media Highlight Reels: We see the wins, the milestones, and the polished moments—not the messy behind-the-scenes reality.

• Cultural Pressure: There’s an unspoken expectation to project confidence and success, even when we’re unsure.

• Comparison Trap: It’s human nature to compare our struggles to others’ successes, creating an illusion of being behind.

This illusion creates a false standard that’s exhausting to live up to. It makes us feel like we’re failing simply because we don’t have all the answers, when in reality, no one does.

The Reality: Ambiguity Is Where the Magic Happens

In my life as a leader and my work as a coach, I’ve seen the reality behind the facades. Even the most accomplished individuals have moments of doubt, uncertainty, and trial and error. The truth is, the greatest leaders and most fulfilled individuals aren’t the ones with all the answers—they’re the ones who embrace ambiguity and lean into it.

Here’s what I’ve learned:

• Ambiguity Sparks Innovation: When you accept that you don’t know everything, you’re more open to new ideas, perspectives, and solutions.

• Vulnerability Builds Connection: As Brené Brown says, “Vulnerability is not weakness; it’s our greatest measure of courage.” Admitting what you don’t know doesn’t make you weak—it makes you relatable and human. It invites collaboration and deeper relationships.

• Clarity Emerges from Uncertainty: Progress isn’t about avoiding ambiguity; it’s about navigating through it and trusting that clarity will come.

If you want to learn more about vulnerability, I highly recommend exploring Brené Brown’s incredible work here.

Lessons for All of Us

This isn’t just a lesson for founders or leaders. It’s a reminder for anyone navigating life:

• Stop Chasing Certainty: Accept that some questions won’t have immediate answers—and that’s okay.

• Lean Into Vulnerability: Be honest about what you don’t know. It’s an invitation for others to support and collaborate with you.

• Reframe Uncertainty as Growth: Instead of fearing the unknown, view it as a space for discovery and possibility.

A Call to Reflect

What if the pressure to have it all figured out is what’s holding us back? What if the real strength lies in admitting that you don’t know and being okay with that?

As we step into 2025, I invite you to rethink how you approach ambiguity. Instead of resisting it, try leaning into it. The answers you’re looking for might just emerge from the questions themselves.

As Brené Brown reminds us, “Leaning into the discomfort of vulnerability is how we turn uncertainty into possibility.”

This is exactly the kind of conversation we explore at ReAmbitioning—how ambition can be redefined and aligned with authenticity, values, and purpose.

What do you think? Have you ever felt pressured to have all the answers? How did you navigate the uncertainty? Let me know—I’d love to hear your story.

About Me

Nick Cakebread is a business and founder coach, as well as the creator of ReAmbitioning, a platform dedicated to rethinking ambition, redefining success, and helping individuals build purposeful lives.

If you’d like to learn more about Nick’s work or explore coaching opportunities, visit nickcakebread.com.