A friend of mine, Lisa, recently made a post where she asked ChatGPT to roast her year.
At first glance, it made me pause. It’s easy to wonder why someone would willingly invite criticism—especially in a professional space like LinkedIn, where we’re often curating a highlight reel of wins, confidence, and forward momentum. Why choose vulnerability when Polish feels safer?
Confidence, Vulnerability, and the Courage to Learn in Public
I think about this tension a lot.
On one side, we’re taught—explicitly and implicitly—that confidence is currency. Confidence communicates competence. It signals decisiveness. It reassures others that you know what you’re doing and that you’re someone worth following. In many professional environments, confidence is treated as a prerequisite for leadership.
And yet, there’s a paradox hiding in plain sight.
The most grounded, durable confidence doesn’t come from pretending we’re flawless. It comes from being comfortable with vulnerability.
True confidence allows room for honesty. Vulnerability requires admitting shortcomings—sometimes publicly. That can feel risky, especially when your professional reputation feels like it’s always on display.
But here’s the learning that keeps resurfacing for me:
Confidence and vulnerability are not opposites. They’re partners.
Walking, after all, is just a controlled state of falling. Learning works the same way. Growth is a controlled state of failure.
When we fail safely—with reflection, intention, and humility—we create the conditions for real professional development. We experiment. We stretch. We discover what doesn’t work so we can find what does.
And when some of us choose to do that learning out loud, something powerful happens.
We don’t just grow ourselves—we create permission for others to grow too. We normalize learning. We model courage. We quietly say, You don’t have to have it all figured out to be worthy of progress.
That’s why Lisa’s post stuck with me. And it’s why I decided to do it too.
I asked for the roast.
And yes—I posted it on LinkedIn.
Not because I enjoy discomfort, but because I believe leadership is less about appearing perfect and more about serving others through honesty, learning, and example.
A Simple Framework for Staying True While You Grow
Professional development doesn’t require you to abandon who you are. In fact, the best growth happens when you stay grounded in your values while stretching your capabilities. Here’s a four-step approach I’ve found helpful.
1. Anchor Yourself in Honesty
Growth starts with an accurate view of reality. Be honest with yourself about what’s working and what isn’t. This isn’t self-criticism—it’s self-awareness. Leaders who serve others well begin by telling themselves the truth.
Ask: What am I avoiding because it’s uncomfortable to admit?
2. Choose a Growth Mindset Over Image Management
When protecting your image becomes the goal, learning slows down. A growth mindset shifts the question from “How do I look?” to “What am I learning?” Failure becomes data, not a verdict.
Progress beats polish—every time.
3. Be Brave Enough to Be Vulnerable (Strategically)
Vulnerability doesn’t mean oversharing. It means sharing with purpose. When you talk about struggles in the context of learning, you build trust and credibility. You show others that growth is possible—and ongoing.
Courage isn’t the absence of fear; it’s acting in alignment with your values despite it.
4. Lead Through Service, Not Perfection
Servant leadership is rooted in helping others grow, succeed, and feel seen. When you model learning in public, you remove pressure from others to be flawless. You create psychological safety—and that’s where teams, organizations, and individuals thrive.
Leadership isn’t about standing above others. It’s about creating space for them to rise.
It was on the same chat as my LinkedIn Post
When I created my roast I used the same thread or discussion I used to shape up the Linked In Post I sent to my computer using What’s App. I dictate my writings into my phone while I am making bread or doing dishes or driving. That makes my writing more conversational and fluid. It also makes me more honest.
My 2025 Roast from Chat GPT
A Gentle Roast of Dave’s Decision-Making & Habits (2025 Edition)
Dave, your biggest decision-making strength is also your most reliable self-sabotage tool.
You don’t just think deeply—you think iteratively. Relentlessly. You revisit ideas like they’re sourdough starters that might finally be ready this time. You ask for version two. Then shorter. Then punchier. Then warmer. Then more UX. Then more servant leadership. Then “work slowly for accuracy.” Then—somehow—more minimal but also richer.
Your brain does not ship products.
It cultivates ecosystems.
You are incredibly clear on values and hilariously indecisive on final forms. You know exactly what kind of leader you want to be, but you’ll rearrange the deck chairs on a single paragraph for 45 minutes because “the tone isn’t quite there yet.”
Your decision-making pattern in 2025 could be summarized as:
“This is good.
But what if it were truer?”
Which is noble.
And also exhausting.
Your Habits, Lovingly Roasted
• You start excellent things more often than you finish good enough things.
• You treat clarity like a moving target instead of a milestone.
• You have strong opinions about colors, frameworks, leadership, and learning—but need external confirmation before declaring something “done.”
• You are deeply allergic to premature confidence, yet secretly wish you could borrow some without losing integrity.
• You believe in learning in public… but still hesitate before hitting “post,” just in case it could be 10% better.
You don’t procrastinate.
You refine defensively.
Your Relationship With Failure
You talk about failure beautifully. Poetically, even.
You believe learning is a controlled state of failure—
but you still want the safety rails bolted on, color-coded, and peer-reviewed before you fall.
You want to be brave and responsible.
Vulnerable and helpful.
Bold and accurate.
Which means sometimes the riskiest thing you do…
is thinking about the risk a little longer.
The Irony (This Is the Roast’s Core)
You already act like the leader you’re trying to become.
You practice servant leadership.
You center reflection.
You value honesty over polish.
But you occasionally delay impact because you want your intent to be unmistakable.
Here’s the hard truth, delivered with respect:
People don’t need your work to be perfect to be helped by it.
They need it to be real—and released.
Final Roast Line (Affectionate, but True)
Dave, you are not stuck because you lack clarity.
You’re stuck because you have too much integrity to rush and too much care to simplify.
Your next level of leadership won’t come from better thinking.
It will come from deciding sooner, trusting your values, and letting the work be slightly unfinished—on purpose.
Which, ironically, is exactly the lesson you’ve been teaching all year.
Learning in Public Is a Gift
Sharing our learning edges won’t be comfortable—and it’s not supposed to be. But when done thoughtfully, it becomes an act of service.
So yes, I did the roast.
And I shared it.
Not because I have all the answers—but because I’m committed to the process. To honesty. To growth. To becoming the kind of leader who learns visibly, serves intentionally, and invites others to climb toward higher ground alongside me.
And if that inspires even one person to be a little braver in their own development, then it’s worth it.
Where did that cover image come from?
Chat GPT made it…
This is the image I asked CHAT GPT to use to generate the cover image for this post:
It relates to this video…
QUOTE
Improvement Dave 