For years, I had a dirty little secret about my business.

I would spend hours creating content, post consistently on LinkedIn, show up at every networking event in town. I was hustling hard.

And my business was...okay. Good enough. I was making money, getting clients, building something that looked successful from the outside.

But whenever things would slow down—when the referrals dried up or the networking events weren't converting—there was one thing I knew I should do but absolutely wouldn't:

Send DMs.

Not because I thought it was pushy or unprofessional. Hell, I respected people who could do it. I knew it worked.

I just...couldn't.

Instead, I'd find a million other things to do.

• I'd redesign my website (again).

• I'd create more content.

• I'd sign up for another networking event.

• I'd optimize my LinkedIn profile.

• I'd research new marketing strategies.

All very important business activities, right? Except none of them were actually moving the needle.

I was staying busy to avoid the one thing that would actually grow my business.

And it took me embarrassingly long to realize what was really happening: I was terrified.

The Sophisticated Procrastination Trap

Here's the mind-fuck that took me years to understand:

I wasn't avoiding outreach because I thought it was wrong. I was avoiding it because it felt impossible.

And instead of admitting that, I created elaborate workarounds.

• I told myself I didn't have time (while spending hours on content that got zero leads).

• I convinced myself I needed a better website first (and then redesigned it three times).

• I decided I needed to build my "personal brand" more (while my bank account stayed flat).

I was like someone lost in the woods who becomes an expert at making camp—setting up the perfect tent, organizing supplies, building elaborate fires—anything to avoid actually finding their way out.

The problem wasn't that I didn't know outreach worked. The problem was that I couldn't make myself do it.

And here's the really twisted part: I had started my career in sales. I was good at sales.

But there's a massive difference between selling someone else's product and selling yourself.

When you're selling for a company, you have scripts, training, and a brand backing you up. You're representing something bigger than yourself.

When you're selling your own services?

Every "no" feels personal.

Every silence feels like rejection.

Every message feels like you're saying, "Please validate that I'm worth your time and money."

That's terrifying in a completely different way.

The Real Cost of Terror-Based Business Building

Let's be honest about what this sophisticated avoidance was actually costing me:

Time Cost: 

I spent countless hours on activities that felt productive but weren't revenue-generating. Content creation, website tweaks, strategy research—all important, but none of them directly bringing in clients.

Opportunity Cost: 

While I was perfecting my LinkedIn bio, potential clients were hiring my competitors who were brave enough to reach out.

Energy Cost: 

Busywork is exhausting. I was working harder, not smarter, trying to build a business through everything except the most direct path to clients.

Confidence Cost: 

Deep down, I knew I was avoiding the thing that mattered most. Knowing that I was letting fear drive my business decisions chipped away at my confidence as a CEO.

The brutal truth? Most of my "strategic business activities" were just fear wearing a business suit.

Why Terror Feels Safer Than Action

The thing about sophisticated procrastination is that it gives you the illusion of progress without the risk of rejection.

When I was posting content or going to networking events, I could tell myself I was "building my business." I had something to show for my time. Metrics to track. Activities to report.

But outreach? That was binary. Either someone responded or they didn't. Either they were interested or they weren't. Either I was good enough or I wasn't.

There was nowhere to hide.

And if you're someone who built their career as an employee—where success meant following processes, hitting metrics, and getting approval from above—this kind of raw, unfiltered feedback can feel brutal.

Hell, when you’ve thrived in an environment that prizes rule following and obedience, even the action of putting yourself out there in that way can feel dangerous. Inappropriate, pushy, or desperate.

As an employee, you have layers of protection. Company policies, team structures, established relationships. You're rarely putting yourself completely on the line.

But as an entrepreneur reaching out to prospects? You ARE the product. You ARE the company. You ARE the entire value proposition.

Every message is a mini-test of your worth.

No wonder it's terrifying.

The Employee Programming That Keeps You Spinning

Here's what I've realized about why this shift is so hard for those of us who came from traditional careers:

We were trained to wait for instructions. 

In corporate, someone tells you what to do, when to do it, and how to measure success. But in your business? You have to create your own assignments. And reaching out to prospects isn't anyone's assignment but yours.

We were rewarded for following proven processes. 

Companies have sales teams, marketing departments, and established lead generation systems. You just had to execute your part. But now you have to figure out what the process should even be.

We learned to avoid risk. 

Making mistakes as an employee might get you in trouble, but they rarely threaten your livelihood. But business development? Every outreach feels like you're risking your reputation, your relationships, your future.

We were taught that good work speaks for itself. 

If you did your job well, you got promoted, got raises, got recognition. But in business, good work sits in silence unless YOU speak for it.

So, of course, you're doing everything else. Everything else feels familiar. Safe. Like the professional behavior you've been rewarded for your entire career.

But here's the problem: Those same behaviors that made you a great employee are keeping you a struggling entrepreneur.

The Terror Behind the Terror

Let's go deeper. Because the fear of outreach isn't really about outreach.

It's about being seen. Really seen.

When you reach out to someone, you're saying: "I believe I can help you. I believe my work is valuable. I believe I'm worth your time and attention and money."

That's a massive declaration. Especially if you've spent years in environments where you weren't supposed to think too highly of yourself, where modesty was valued over confidence, where you learned to let your work do the talking.

For many of us, especially women, we were taught that promoting ourselves was unseemly. That confident people were arrogant. That asking for what we want was selfish.

And now business success requires us to do exactly those things.

And that shit is haaaaaaaard!

The Mindset Shift That Changes Everything

Here's what finally helped me move through this: I had to stop making outreach about me.

Instead of thinking, "Will they think I'm worthy?" I started thinking, "How can I help them see what's possible?"

Instead of, "What if they reject me?" I shifted to, "What if they've been waiting for exactly this solution?"

Instead of, "Am I being too pushy?" I reframed it as, "Am I being helpful?"

I stopped thinking of it as sales and started thinking of it as service.

The truth is, your ideal clients are drowning. They're overwhelmed, stuck, and desperately seeking solutions to problems you know how to solve.

When you don't reach out, you're not being modest or professional. You're withholding help from people who need it.

That's not humble. That's selfish.

The Practice: Building Your Courage Muscle

Ready to start moving through this? Here's how to build your outreach courage, one small step at a time:

Week 1: The Observation Practice 

Just notice. When do you avoid outreach? What do you do instead? What stories do you tell yourself? No judgment, just awareness.

Week 2: The Reframe Practice 

For every person you think about reaching out to, write down: "How could I help this person?" Not "How can I sell to them," but "How can I serve them?"

Week 3: The Tiny Action Practice 

Send one message. Just one. To someone you genuinely want to help. Don't worry about being perfect. Don't craft it for hours. Just send it.

Week 4: The Integration Practice 

Make outreach a regular part of your business rhythm. Not something you do when you're desperate, but something you do because you're a CEO who creates opportunities.

I know you may be rolling your eyes or thinking I’m overselling the power of a practice like this, but truly, consistent effort over time can play a pivotal role to help overcome the decades of fear-based programming we all have.

If you want to deeper, consider checking out my Inventory and Flip framework that I shared a few weeks back when talking about The Silent Lie Costing Your $10k/month.

I break this exercise down when talking about money mindset, but it works for any limiting belief. It’s been a core resource in my personal transformation toolkit.

The Real Transformation

Here's what happened when I finally started doing this work:

My business stopped feeling like a rollercoaster and started feeling predictable.

I stopped waiting for good months and started creating them.

I stopped being at the mercy of referrals and networking luck and started building relationships intentionally.

Most importantly, I stopped feeling like a fraud who was hoping to be discovered and started feeling like a CEO who was solving problems.

The work didn't get less scary. I just got braver.

Your Turn

You have two choices:

You can keep perfecting your website, optimizing your content, and attending networking events—hoping that eventually, somehow, the right opportunities will find you.

Or you can acknowledge that the terror is real, normal, and not a reason to stop. You can start building the muscle of reaching out, one small action at a time.

Your ideal clients aren't going to break down your door. They're busy, overwhelmed, and probably don't even know you exist yet.

But they need what you offer. They're struggling with problems you know how to solve. They're looking for someone who can guide them to a better outcome.

The question is: Are you brave enough to let them know you're here?

Your business—and your courage—are waiting for your answer.

In love and growth,
Kasey

P.S. Ready to work through your outreach fears? I've created something special: an AI version of me that's available 24/7 to help you process your blocks, craft your outreach strategy, and build your CEO mindset.

Chat with my AI Twin here – she's got all my frameworks, strategies, and tough love, without the timezone constraints. Whether you're up at 3am wrestling with imposter syndrome or planning your outreach campaign over Sunday coffee, she's there to help you move from fear to action.

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