How to Actually Get Comfortable With Selling

Want to get comfortable with selling ANYTHING? Do these nine things.

You post about your offer once.

ONCE. 

And then you sit there for three days convinced you’ve become “that person.”

That person = the pushy creative, the salesy one, the one everyone’s secretly rolling their eyes at every time you show up in their feed.

Meanwhile, your actual offer—the one you built, the one that genuinely changes something for the person on the other side of it—has been mentioned exactly once and is now sitting quietly in a folder somewhere, unbothered, definitely not making you any money.

Soooo. Let’s talk about that.

That person is NOT you because your offer is too good to only be mentioned once a quarter.

If it actually does what you say it does—if it saves someone hours, or fixes the thing that’s been stressing them the frick out, or gets them to that level they’ve been dreaming about for monthsssss—then barely talking about it isn’t humility. It’s withholding.

It’s you withholding something truly useful from your target audience. And that is not good for you or for them.

I want you to know this:  

“You’re not selling a slot. You’re selling a transformation.”

Say that one again, slower.

You are not selling forty-five minutes of your time or a PDF template or a spot in that high-ticket program.

You are selling the version of your client that exists on the other side of working with you—the one who finally launched the thing, fixed their strategy, stopped guessing what the h*ck they should be doing, and slept better because the business finally makes sense.

That’s what you’re actually offering. The forty-five minutes is just the delivery mechanism.

So why does selling still feel so deeply uncomfortable?

Because most of us were taught, somewhere along the way, that wanting to be paid for something good makes you a bit much.

That if you really cared about helping people, you’d just… do it for free.

But that’s not true. You’re already giving a ton of FREE value. In your Instagram posts, in that TikTok from two days ago, in your emails, in your blog posts, in your freebies, in your most recent Substacks. 

Look, value creation should abso-frickin’-lutely be tied to fair compensation. You’re solving a problem. That’s a skill. You’re helping people achieve their dreams. That’s a skill!

And, I kid you not, there is a group of people out there who are willing (and some of them can’t wait) to pay you to help them out. Your target audience.

(If you don’t know who your target audience is, get the Ideal Client Development Workbook.) 

Sooooo, how do you actually get comfortable selling to these people? 

Mindset shifts first, because selling is 90% headspace. And at this point, selling isn’t the problem; your mindset is.

1. Remind yourself what happens if you DON’T sell

Every time you skip mentioning your offer because you’re worried about being “too much,” someone out there is still sitting with the exact problem you already know how to solve.

They’re still stuck.

Still Googling the same question at midnight. Still cobbling together a worse, slower version of the result you could’ve handed them directly. 

Not selling doesn’t make you humble. It just means the help arrives later, or from someone else, or not at all.

Don’t keep quiet in the name of “being considerate.” There’s nothing like that. As a business owner, I’m giving you the permission to sell it like you mean it.

2. Detach your worth from the “yes”

A NO is not a referendum on you as a human being, even though your nervous system will absolutely try to convince you otherwise.

Someone saying no to your offer might mean bad timing, tight budget, they’re not ready yet, they didn’t fully understand what you do, or forty other things that have nothing to do with your value.

You could get “no’s” that turn into “actually, yes” six months later. You could get no’s that would just be, well,… no’s, and the sky won’t fall.

The second you stop treating every pitch like it has a say on your worth as a person, selling stops being a personality test and starts being what it actually is. 

And that is:

Promoting an offer the best way you can while knowing that someone gets to respond to it however they want.

3. Talk about the transformation, not the technicalities

As a copywriter, if there’s something I genuinely believe will help you sell better. 

It’s this:

Stop leading with what’s included. Yes, your program has so many features—the calls, the templates, the deliverables, and the bonus workbook they didn’t know they needed. 

But nobody… literally, nobody is lying awake wanting “three 60-minute Zoom calls.” They’re lying awake wanting the problem gone. And if it’s those Zoom calls that will solve the problem, then they’d want it.

 So, lead with the results they get. The transformation that happens. Who they become after the offer.

For example, before working with me, someone’s staring at a blinking cursor, rewriting the same sentence for the ninth time.

But after? They’ve got copy that sounds like them and sells without feeling gross—and finally, they’ve stopped opening Google Docs with a small sense of dread.

That’s the sell.

But really, if writing better sales copy is something you want done for you, let me take it off your plate.

4. Borrow confidence from your past clients

You don’t need to manufacture confidence from nothing, which is good, because that’s basically impossible on demand.

Instead, borrow it—from the client who told you working with you changed their lives, from the person who messaged you four weeks later saying everyone is gushing over their design, or from the screenshots sitting in your camera roll that you keep meaning to do something with.

Every result is evidence.

When your brain starts spiraling into “who am I to sell this,” that evidence is your rebuttal.

Keep it close. Reread it before you hit publish anytime you feel a little scared of selling.

Now that we’ve tackled the mindset part, below are some practical action steps you can take right away.

5. Mention your offer more than you think is reasonable

Here’s the actual math nobody tells you: most people need to see an offer several times, in several different ways, before they’re ready to buy.

Depending on the type of offer and price point, they need to see it 7 to 28 times. 

Twenty-eight frickin’ times!

Mostly because life is loud and your one Instagram post from three weeks ago is long gone from their memory.

So if your gut says “twice a month feels like enough,” push it to weekly. If weekly already feels brave, aim for a few times a week in different formats—a story, a line in your newsletter, or a mention inside an unrelated post. 

You are not spamming people. You are giving the right person, at the right moment, one more chance to see the thing that could actually help them.

6. Build selling into content that isn’t “about” selling

You don’t need a big dramatic “ANNOUNCEMENT” post every time you want to sell.

Weave it in. Tell a story about a client win, and mention it happened inside your program.

Share a tip (in your blog post or newsletter or social post), and end with “this is exactly the kind of thing I dig into with clients inside ___.”

Selling doesn’t have to announce itself with a trumpet. In fact, it shouldn’t—unless you’re doing a launch. For a business owner, selling SHOULD be a regular thing. 

Some of the most effective selling I do isn’t a sales post at all. It’s a regular story or email or blog post (like this one) that just happens to mention, quietly and naturally, that there’s a way to get help with what they need.

7. Write down your mission statement and reuse it constantly

Sit down once, and actually write it out:

“I help ___ go from ___ to ___.”

For example, I help freelancers go from chasing clients to getting 5 leads per week. 

Not five versions. Just one.

Get it right, then weave that sentence (in different ways) into your bio, your email signature, your sales page, your captions, and your voice memos to yourself at 2am when you can’t sleep.

Just reuse it enough times till it actually sticks.

The purpose of this is to recite what you do enough times to:

• Understand it yourself
• Get known for it 

When you say the same thing so many times that people start repeating it back to you unprompted. That’s when you know it’s landed.

8. Make the ask actually clear

Don’t ask them to “check it out if they want.”

If you want someone to book a call, say “book a call” and link to it. If you want them to grab the template, say “grab the template here.”

If you want a reply, literally tell them what to type back.

Vague asks get vague, half-hearted results, and then you walk away thinking, “Guess nobody wanted it,” when really nobody understood what you were asking them to do.

Clarity isn’t pushy. Clarity is the kindest thing you can do for someone who’s already interested and just needs a nudge over the finish line.

9. Track the “they say” moments

Start a note, a folder, a screenshot pile—whatever works for your brain—and every single time someone tells you your content, your post, or your offer helped them, it goes in there.

This becomes your proof file.

I have one. I call it a SMILE FOLDER. 

It’s actual, receipts-based evidence that showing up and asking for the sale is doing exactly the job it’s supposed to do.

On the days selling feels genuinely hard, when your brain is convinced you’re bothering people, you open that file instead of spiraling.

So, what now?

Stop treating your offer like a secret you’re mildly embarrassed about, and start treating it like what it actually is—a real answer to a real problem that deserves to be seen by the people who need it, more than once, on purpose.

Selling shouldn’t be the icky part of business. I mean, it’s literally how you make sales. And if you follow the tips I’ve shared above, you will get way more comfortable selling your offer.

If you need help with getting the words right—the copy that makes your offer sound like the transformation it truly is—see how I’ll help you do that.

Or, if you want more budget-friendly options to write better copy, check out my shop for templates that make selling feel a whole lot less scary and a whole lot more you.

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