- Becoming a Solo CEO
- Posts
- 🏔️ Solo CEO mindset: The Hidden Cost of Playing Small Online (And How Embracing 'Cringe' Transforms Your Entire Business)
🏔️ Solo CEO mindset: The Hidden Cost of Playing Small Online (And How Embracing 'Cringe' Transforms Your Entire Business)
The surprising link between LinkedIn anxiety and business success
Three years ago, I built a TikTok following of 94k people.
I wasn't trying to build a business or a brand. I was just...talking. About life, about the weird thoughts in my head, about the messy reality of being human.
And people loved it. The engagement was insane. Comments poured in from people saying my videos made them feel less alone, more understood, more willing to embrace their own weirdness.
It felt effortless. Natural. Like I'd found this magical place where being authentically me was not only accepted — it was celebrated.
Then something shifted.
The more successful it became, the more I realized something was missing.
I was building a successful business and personal brand on LinkedIn by blending my authenticity WITH my work.
But on TikTok, I was only sharing one slice of who I am — the personal, philosophical, human side.
My work is such a huge part of who I am. How I navigate the world. How I know I can help people. And not talking about it started to feel...incomplete.
I wanted to bring these two worlds together — the personal authenticity that was working so well on TikTok and the professional expertise that was working so well on LinkedIn. But I had no idea how to do it without losing what made each platform special.
So instead of figuring it out, I did what so many of us do when something feels complicated:
I stopped.
I let a voice that had felt so natural get tangled up in strategy and integration challenges until it disappeared entirely.
Fast-forward to today, and I'm rebuilding that TikTok presence — but this time from a place of full authenticity. Not just personal stories, not just professional insights, but the integrated truth of who I am: someone whose work and life and personal journey are all interconnected.
And guess what?
I'm back in the awkward phase.
After years of creating content, after building multiple successful businesses, after teaching others how to find their voice...
I'm figuring it out — again. Rediscovering my voice. Relearning what feels good. Reconnecting to my audience (and myself).
And here's what I've (re)learned: That's not a bug. That's a feature.
Creating content online is always challenging (no getting around that).
But when it comes from a truly authentic place — when it represents the fullness of who you are instead of just the parts you think are "appropriate" for that platform — it becomes infinitely more sustainable.
It's simpler. It feels better. And, fun fact, it actually works better, too.
Because people don't want half of you. They want the real, integrated, whole you.
The Real Reason You're Not Showing Up on LinkedIn
In Thursday’s newsletter, I shared the formula for LinkedIn success. It's deceptively simple: Post consistently. Share your journey. Voice your opinions. Be real.
You've read the playbooks. You've studied the strategies. You might even have a content calendar gathering dust somewhere.
But you're still not showing up. Not really.
Your cursor hovers over the "Post" button, your heart racing. Another draft saved. Another day of silence. Another missed opportunity to be seen."What if my story isn't impressive enough?"
"What if my opinions are too controversial?"
"What if people think I'm trying too hard?"
"What if I sound stupid?"
"What if no one cares?"
"What if I'm just...too much?"
Here's the truth that no one talks about: Your resistance to LinkedIn isn't about time, strategy, or even knowing what to say.
Your resistance about the terror of being seen as your authentic, imperfect, beautifully, uniquely weird self.
And that terror is costing you every-freaking-thing.
Because while you're hiding, your competitors — the ones who are willing to be awkward, imperfect, and authentically themselves — are building the relationships, reputation, and revenue that could be yours.
We talked about the pervasive nature of fear recently and the way it keeps you stuck in an employee mindset. This is just another example of how, whether you’re aware of it or not, fear in one part of your business seeps into other areas of your life, and it’s eating away at you, your confidence and your courage.
Worse, it’s holding you back from making the bold moves your dream business and life deserve.
The Courage Paradox That Changes Everything
Here's a truth that took me years of failure to understand:
Everything you want in your business and your life is on the other side of doing something that feels "cringe."
That awkward first post where you share a vulnerable story? That's where connection lives.
That controversial opinion that makes you nervous to publish? That's where differentiation lives.
That genuine enthusiasm about something others might think is dorky? That's where magnetism lives.
We spend so much energy trying to avoid looking foolish that we forget: The people who seem most confident, most successful, most magnetic are usually the ones who were willing to look foolish first.
They didn't skip the awkward phase. They embraced it.
Because here's what I've discovered: The thing that feels most terrifying—being authentically weird on the internet—becomes the thing that makes you feel most courageous and alive.
Every time you hit "post" on something that feels a little too real, a little too you, a little too much...you're doing courage training.
And that courage starts to show up everywhere else in your life.
The Awkward Phase Is Where the Magic Happens
Let me tell you something that might blow your mind:
Your first 50 posts are going to be awkward. Maybe your first 100.
Your voice will feel forced. Your stories will feel clunky. You'll cringe at your own content and wonder if you should delete everything and pretend it never happened.
This is not a sign that you're bad at this. This is a sign that you're learning.
Because finding your authentic voice isn't something that happens in your head. It happens through your hands, on the keyboard, in the messy process of trying and failing and trying again.
When I was building my TikTok following, I posted dozens of videos that got 12 views and made me want to hide under a rock. But each "failed" video taught me something:
That joke didn't land. Okay, I'm not as funny as I thought.
(Seriously, I’ve learned that I’m reasonably funny in person, but all online attempts at humor are painfully bad)
That story felt forced — I need to find a more natural way to share that lesson.
That opinion sparked debate, conversation, and meaningful connection — interesting, maybe controversy isn't something to avoid.
I’ve learned that the awkwardness of this process isn’t a problem. It’s actually how you learn.
The Self-Discovery Journey Disguised as Content Creation
Let me shatter an illusion: You think you're here to build a personal brand. To grow your business. To establish thought leadership.
But that's not what's really happening.
This journey you're on? It's identity archaeology.
Every post is a dig site, every comment a buried artifact, every moment of vulnerability a precious discovery about who you really are and what really matters to you.
Every post you write forces you to ask:
What do I actually think about this?
What do I really believe?
What experiences have shaped me that might be valuable to others?
Every comment you receive gives you data:
What resonates? What doesn't?
Who am I attracting? Who am I repelling?
(And am I okay with that?)
Every awkward moment teaches you:
Where are my edges?
What am I afraid of?
What would happen if I pushed through this discomfort?
This is why damn near every person I've worked with who has stuck with building their personal brand experiences something fundamental that changes inside of them.
Not because they got more followers. Not because they made more money (though both often happen).
But because the daily practice of showing up authentically, consistently, courageously builds something in you that can't be built any other way.
It builds unshakeable self-knowledge.
It builds tolerance for discomfort.
It builds the ability to be yourself even when being yourself feels risky.
And that? That personal growth becomes the foundation of everything else you want to achieve.
Why I'm Back in the Awkward Phase (And Why I'm Grateful)
So here I am, trying to rebuild what I had on TikTok but in a new context, with a new strategy, for a new audience.
And it's awkward as hell.
My posts don't flow the way they used to. My voice feels rusty. I find myself overthinking things that used to feel effortless.
But here's what's different this time: I'm not fighting the awkwardness. I'm celebrating it.
Because I know something now that I didn't know before:
The awkward phase is something to embrace, instead of overcome.
It's where you get to be a beginner again. Where you get to experiment and play and discover who you're becoming. Where you get to remember that the journey of finding your voice is never really finished — it's an ongoing conversation between who you are and who you're becoming.
That idea alone is breathtakingly beautiful.
There's something inspiring about having a beginner's mindset, even when you're not actually a beginner.
It keeps you curious instead of certain.
It keeps you playful instead of precious.
It keeps you focused on learning instead of looking good.
And that is where the real growth happens.
The Ripple Effect of Digital Courage
Want to know the most fascinating part of this journey? The courage you build online refuses to stay online.
It spreads like wildfire through every area of your life:
LinkedIn courage becomes:
Unshakeable confidence in client calls
Fierce boundary-setting in your business
Bold decision-making in your life
Magnetic presence in every room
Each "small" act of bravery:
That vulnerable story you share
That controversial stance you take
That authentic truth you speak
That imperfect post you publish
They're not just content creation. They're courage creation.
And suddenly, you realize: You haven't just mastered a platform. You've mastered becoming that future version of yourself.
The person who was once afraid to post? They're now changing lives, leading movements, and building legacies.
Not because they figured out LinkedIn. But because they figured out how to be unshakably, magnificently themselves.
Your Next Brave Act
I want you to do something right now. Not tomorrow. Not when you feel ready. Now.
Open LinkedIn. Create a new post. Feel your heart rate increase. Notice the voice in your head listing all the reasons to wait.
And then, despite every instinct screaming at you to play it safe, I want you to do this:
Start where you are, with what you have, as awkwardly as necessary.
Pick one story from your professional journey that feels a little too personal to share. Share it anyway.
Pick one opinion you have about your industry that you worry might be controversial. Post it anyway.
Pick one thing you're genuinely excited about that others might think is nerdy or weird. Get enthusiastic about it anyway.
And then pay attention to what happens.
Not just the external metrics — the likes, the comments, the connections.
But the internal shift.
The moment when you realize:
I did something that felt scary, and I survived.
I was authentically me, and the world didn't end.
I shared something real, and people actually appreciated it.
That's when you start to understand what I've learned:
The thing that feels most terrifying — being seen for who you really are — is actually the thing that sets you free.
The Character Building You Didn't Know You Needed
Want to know the secret that transformed my entire approach to business?
Building an authentic platform will reconstruct your entire character.
Every time you show up, you're training:
Consistency: Posting when you're tired, discouraged, or convinced no one cares
Vulnerability: Sharing the story that makes your hands shake as you type
Resilience: Publishing again after a post flops, when the critics show up, when doubt creeps in
Courage: Standing firm in your truth when it would be easier to water it down
Authenticity: Choosing your messy reality over a polished performance
This isn't just about building a following. This is about building you.
And the person you become through this process — someone who shows up fully as themselves, who faces rejection with grace, who stays true under pressure, who owns their story without apology — that person is un-f*cking-stoppable.
That person? They don't just succeed on LinkedIn.
They transform every room they enter.
They elevate every conversation they join.
They inspire every person they meet.
Because they've done the hardest thing possible: They've become unshakably, unapologetically themselves.
The Beautiful Truth About Starting Over
Let me speak directly to the person who's been here before:
You had a moment of courage. You started posting. Maybe you even gained some traction.
Then life happened. Or fear crept in. Or perfectionism took over.
And you stopped.
Now you're sitting there thinking everyone else has figured it out. That you're behind. That you're broken. That you're living proof this doesn't work.
But here's the truth:
You're not behind. You're not broken. You're becoming.
And here's what I know about you:
Every false start has been preparing you for this moment.
Every time you begin again, you bring more wisdom, more self-knowledge, more clarity about what you actually want to say and who you actually want to reach.
Every "failure" has taught you:
What doesn't work (priceless data)
What feels forced (clarity through contrast)
What actually matters to you (your true voice)
Every return to the arena proves:
You're resilient enough to face the awkwardness again
You're committed enough to choose growth over comfort
You're brave enough to choose truth over approval
This isn't just about LinkedIn. This isn't just about content creation. This isn't just about building your business.
This is about becoming the version of you who:
Isn't afraid to be seen
Isn't afraid to be real — even online
Isn't afraid to be "too much" for some people
Knows they're exactly right for the people who matter
Everything you want is on the other side of doing something cringe.
Your voice — awkward, amazing, and absolutely essential — isn't just waiting.
It's ready.
The only question is: Are you?
In love and growth,
Kasey
P.S. I’m working on something new for Solo CEO…something really freaking big and beautiful. And I’d love to hear how I can shape it to help you.
So, hit reply and tell me: what is the big goal you’re shooting for, or what problem can I help you solve?
Whenever you’re ready, here’s how I can help you become a Solo CEO:
Want to land your first (or next) $10K+ client—without relying on referrals or working 24/7? Get my FREE 5-day email course, The Solo CEO $10+ client blueprint, and learn how to build a high-ticket, repeatable business.
Reach a highly engaged audience of experienced professionals and entrepreneurs. Sponsor ‘Becoming a Solo CEO’ to connect with decision-makers who are ready to invest in tools, ideas, and services that fuel their personal and professional growth. Learn more here.
Reply