If Selling Makes You Cringe, Read This



Be honest—when you hear the word “sales,” what’s the first thing that comes to mind?

  • The aggressive car salesman who won’t let you leave the lot.
  • The “Hey girl!” DM from someone you haven’t spoken to since high school.
  • The never-ending “limited-time offer” that somehow never actually expires.

Selling has been taught as something sleazy, manipulative, and pushy.

So naturally, we want no part of it.

Instead, we do everything but sell:

  • Post content, hoping people will magically ask to work with us.
  • Keep tweaking our offers, convinced the wording isn’t quite right.
  • Tell ourselves we need more followers, more confidence, more something before we can sell.

But let’s be real—none of that is actually selling.

It’s avoiding selling.

And the truth is, we’re not alone in this.

Most of us don’t struggle with selling because we lack something valuable to offer.

We struggle because somewhere along the way, we picked up the idea that selling means convincing, pressuring, or persuading people into buying something they don’t really want.

That idea keeps so many of us—especially women—quiet.

We don’t want to be “too much.”

We don’t want to bother anyone.

We don’t want to seem desperate.

So we hide.

We do all the behind-the-scenes busywork, hoping people will somehow just know about our business and decide to buy.

But here’s the thing: People can’t buy from us if they don’t even know what we offer.

This isn’t about becoming a “better salesperson.”

It’s about learning what selling actually is—and why it doesn’t have to feel so uncomfortable.


TL;DR

Selling feels uncomfortable when it’s framed as convincing someone to buy. But selling isn’t about pressure—it’s about making it easy for the right people to say yes. '
When we shift from “I need them to buy” to “I have something that can help,” everything changes.

Why Selling Feels So Hard (And How to Fix It)

Most of us assume selling feels awkward because we’re “not good at it.”

That’s not true.

The real reason selling makes us cringe? Because the focus is on us, not them.

The second selling comes up, our minds spiral:

  • What if they think I’m being pushy?
  • What if they say no?
  • What if I sound desperate?

Every single one of those thoughts is about us.

➝ Selling feels weird when it’s about us.

➝ Selling feels natural when it’s about them.

Think about it—if someone we knew was struggling with a problem we had the exact solution for, would we hesitate to tell them?

Of course not. Because we wouldn’t be “selling” them anything—we’d be helping them.

That’s what selling actually is.

Not manipulation. Not pressuring someone into something they don’t need.

Just showing up with a solution and letting the right people decide.


This Is Something I Still Struggle With Too

Even though I know this, I still find myself overthinking sometimes.

I worry about how I sound.

I wonder if I’m being too direct.

I hesitate before sharing something—just in case it comes across the wrong way.

But here’s what keeps me moving forward anyway:

I believe in what I’m doing. I know I’m not just selling for the sake of making money—I’m showing up with something that can genuinely help the right people.

I care more about my purpose than my fear of selling. When I focus on why I’m doing this, it becomes easier to talk about it.

I trust that the right people will see the value. Selling isn’t about chasing or convincing—it’s about making sure the right people even know my work exists.

That’s how I push past the discomfort.

That’s why I keep showing up.

And every time I do? It gets a little easier.

And you can do this too.


If you’ve been holding back because selling feels uncomfortable, I want you to remember this:

➝ You don’t need to be “better” at selling—you just need to believe in what you’re offering.
➝ You don’t have to convince anyone—just make it easy for the right people to say yes.
➝ You don’t have to wait until you feel 100% ready—clarity and confidence come from doing.

So what if, instead of overthinking, you simply started sharing?

What if you showed up today, trusting that the right people are out there waiting for what you have?

Because they are.

And they won’t know unless you tell them.


The Shift That Makes Selling Feel Effortless

Here’s what changes everything:

Instead of thinking,

“How do we get people to buy?”

Ask,

“How do we help them make the best decision for themselves?”

Because here’s the truth:

Selling isn’t about tricking people—it’s about connecting the right solution to the right person.

Selling isn’t about pushing—it’s about making it easy for people to say yes.

Selling isn’t about forcing—it’s about helping someone get what they already want.

The best sales conversations don’t feel like sales at all.

They feel like relief.

Because when someone sees the right offer at the right time, there’s no convincing needed.

They don’t need to be “sold.”

They just need to know it exists.


Final Thought: Why Selling Feels Icky (And How to Fix It)

Selling feels uncomfortable when we make it about us—but it’s never been about us.

It’s about the person who needs what we have.

When we shift our focus to them, selling stops feeling pushy and starts feeling helpful.

Instead of overthinking every word, we start speaking with confidence.

Rather than worrying about seeming pushy, we focus on being helpful.

And when we stop dreading sales conversations, they become opportunities to serve.

Selling isn’t about pressure—it’s about offering the right solution at the right time.

If it feels uncomfortable, it’s not because we’re doing it wrong.

It’s because we’ve been taught to see it the wrong way.

Selling isn’t the problem.

The way it’s been taught is.

Yours truly,

Kristina Portella, Business Strategist

Founder of Side Business Momentum

Because once you have momentum, everything changes.


From Messy Middle to Momentum: Side Business Clarity for Women

Your go-to Friday email for women in the messy middle of their side business. Get clear, practical tips to simplify your messaging, refine your offer, and confidently attract clients to build momentum and grow.

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