"It's possible to be very brave and very insecure at the same time."

What might it look like to be “perfectly imperfect”? And to recognize that everyone around us is, of course, also perfectly imperfect?

From the occasional self-doubt to crippling imposter syndrome, we all battle insecurity at various points in our lives and careers. If we wish to play more freely, experiment with abandon, and become better leaders for those who rely on us, we’ve got to learn to accept ourselves—imperfections and all.

Discovering that each of us is perfectly imperfect can be a freeing personal revelation—and a professional rocket booster.

This early October issue of The Leader’s Playground is all about that critical inner voice we hear and the ways we can learn to recognize it, accept it, and grow with and beyond it. And speaking as someone who could be the poster child of imposter syndrome (hello, high-brow-theologian-grandfather and inventor-of-world-changing-ultrasound-technology-father), I have to say: This might be one of my favorite topics yet.

Welcome back to The Leader’s Playground! I’m delighted you’re here. Let’s dive in.

The Leadership Tales Podcast

I loved this conversation. Kris Kelso and I talked about entrepreneurship, leadership, and—you might have guessed—overcoming imposter syndrome. It’s true, even “bold” entrepreneurs experience imposter syndrome! As Kris reminds us, “It’s possible to be very brave and very insecure at the same time.”

Give it a listen! And if you feel like leaving a review (or tips for me on how to become a better host), I invite you with gratitude.

What I'm Curious About This Week

Learning to accept our imperfections, indeed even to love them—can you imagine?!—most often opens us up to operate with less self-criticism and fear of judgment. We can laugh at our mistakes and trust our wonderful competence.

But without understanding our imperfections and the ways they limit us, we’ll have a hard time reconciling them and learning to lean into our better selves.

One of my favorite personality typologies comes from the Positive Intelligence work by Shirzad Chamine. The “Saboteurs” assessment quickly highlights the ways each of us self-sabotages with the help of our “saboteurs,” or those little voices in our heads that combine with our inner judge to move us towards anxiety, fear, control, self-doubt, and more. With nine total saboteur profiles, there are many ways we learn—unique to ourselves—to navigate discomfort, though not always in the healthiest or most helpful way.

These voices are the ones that interrupt our inner “Sage” voice—the voice of reason and calm, which pulls us forward with curiosity, openness, self-trust, and positivity.

I’ll admit: Some of my own loudest saboteurs are the voices of control, people-pleasing, and restlessness. I know, I know… You can’t believe it! (Just kidding 😆) Knowing that these are some of the ways I’ve learned to feel safe in the world helps me meet those voices with grace, and that helps my inner sage prevail more often.

I’ve enjoyed the insight and growth brought on by Shirzad’s framework. If you take the assessment and feel like sharing your results, I’d love to hear them! Perhaps we can practice loving our imperfections together.

From the Lab at P2

As I’ve shared in recent issues, we’ve been focusing a lot of our energy in the P2 Lab on coaching: how to have better mentorship conversations, how to find the right balance between being a “player coach” and a “cheerleader coach,” how to read body language and know when to pivot, and more.

But what I love so much about this particular issue on imposter syndrome is that our insecurities play a huge role in how we coach.

That’s where this concept of “perfectly imperfect” comes into the coaching world.

I must recognize and accept my own perfectly imperfect-ness if I want to be of any service at all to those I coach (and those whom I teach to coach others). If I mistakenly believe I’m perfect—or should be perfect, which is essentially the root cause of imposter syndrome—then I’ll probably also assume my way of doing things is always best.

Then, when I work with another, there’s no room left for me to ask questions and await their answers. There’s no reason for me to explore what they may have to share with me, because I already know best. There’s no way I can authentically pose questions in order to help my clients explore, because I’d only be doing so in order to impose my own “perfect” answer onto them.

But when I can accept that I’m flawed, but still worthy, I leave my ego at the door, shift from a controller into a facilitator, and can support others in exploring their unique talents and expertise.

I’ve always loved this famous quote from Theodore Roosevelt (as does Brené Brown—check out her TED Talk on “The power of vulnerability”) and feel that it perfectly captures the essence of practice leadership and coaching.

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.” —Theodore Roosevelt

I try my best to lean into my imperfections, get into the arena with my clients, share my vulnerabilities, and lead by example first. This approach fosters meaningful connection and real trust, and creates opportunities for unmatched exploration.

Thanks for joining me again, and I hope this issue resonated with you as much as it did me. It’s always a pleasure to have you here with me.

If you have questions or thoughts to share, please don’t hesitate to respond to this email. I’d love to chat with you. And if you like what I’m doing and have someone who might enjoy it too, please forward them this email or invite them to subscribe below.

See you later this month. Be well!

Cheers,Colin

To learn more about my book, Be More Wrong: How Failure Makes You an Outstanding Leader, click here. And if you're inclined to leave a review as well, I welcome you with gratitude.