How do you sell when you feel awkward selling?

When you have spent your whole life being scared of sales.

As a corporate I had to sell myself maximum once a year. This was the appraisal season either waiting for promotion or hikes. Once every few years again, when I was shifting jobs. And if you see these also did not need a lot of effort. Hiring managers see your experience and the journey usually flows very well.

But when I shifted to freelancing this had to become a daily ritual. And I feel this became my biggest challenge. How do I promote myself? What do I talk about? I felt icky. Because that’s what we have been taught our entire life. Sales people are scams and they take money, so naturally we all felt awkward. Sales as a profession itself is considered shady or scammy which is far from the truth right?

A few sales people should not tarnish the reputation of everyone who is trying to add value.

So I slowly started figuring out how to sell - I am still not great at it but I am learning.

What Selling Actually Means

I used to think selling meant convincing someone to buy. Now I see it differently. Selling is simply communicating value — helping someone understand how your skills, product, or service can solve their problem.

It’s not about pushing.
It’s not about closing.
It’s not about ego.

When I reframed it this way, everything changed. Selling started to feel like helping.

Where the Fear Comes From

Most of us grew up in homes where money talk was uncomfortable. We were taught to be humble, polite, and grateful and not to talk about our worth, not to “brag.”

So when it’s time to promote ourselves, we freeze. We feel like imposters. We underprice. We hope our work will “speak for itself.” But freelancing doesn’t work that way. If you don’t talk about your work, no one else will. If you don’t ask, you won’t receive.

Learning to Sell Like Yourself

For me, the biggest shift was realizing that I didn’t need to sound like a salesperson. I could sell in my own way — quietly, honestly, and with context.

I stopped thinking of it as “pitching” and started thinking of it as inviting.
I started replacing “Here’s why you should hire me” with “Here’s how I can help.”
It instantly felt lighter, more natural, and more human. Selling should never feel like pretending. It should feel like sharing something useful with someone who needs it.

Make It a Process, Not a Personality Test

When I first started freelancing, every sales conversation felt personal.
If a client said no, I took it as rejection. If someone ghosted me, I thought I had failed.

But over time, I realized — the more emotion I attached to every “yes” and “no,” the harder it became to keep going.

Now, I follow a simple process. Reach out, share what I do, listen to what they need, and if it fits — make an offer. If it doesn’t, I move on.

That shift from taking it personally to treating it as a system made selling less emotional and more sustainable.

I also try and speak to people every day to help overcome the shyness I used to feel earlier.

Start Small

You don’t have to land a huge deal right away. Start by selling something small, a one-hour consultation, a short project, a workshop, or a low-commitment package.

Every time someone says yes, it builds confidence. And every time someone says no, it teaches you something. I am making a small diary where I note down all my sales conversations.

Selling is Self-Trust in Action

At its core, selling is an act of self-trust. It’s saying, “I believe what I’m offering is valuable, and I’m willing to stand by it.”

When you genuinely believe in what you’re selling, you stop worrying about sounding pushy. You stop worrying about rejection. You just share what you know can help.

The awkwardness fades when you stop trying to “get” something from people and start offering something that truly serves them.

A Note for Creators and Freelancers Who Still Struggle

If you still feel awkward selling, remember, you don’t have to become a different person to do it well. You don’t have to force confidence or fake enthusiasm.

You just need to find your rhythm. The more you show up, the more natural it feels. Sales, like creativity, becomes easier with repetition.

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