We’ve all been there. We’ve created a product or a service. Or perhaps it’s someone else’s product or service. We know it works but when it comes time to sell…the proverbial light switch fails to turn on.


I’ve been there multiple times. Heck, multiple times every year.

The First Time I Tried to Sell

I remember the first time I tried to sell anything online. It was 2003 and I was flat out broke. I was 24 years old, still living with my mom, and living off of $1 frozen pizzas and Hot Pockets (to this day I can’t stand those things).

In other words, I needed the money. The next check wasn’t about getting to the next level or achieving my dreams. It was the difference between eating and not eating. I’d just been fired by my dad (yes that happened) and I was too driven (some say stubborn) to go on unemployment.

But I knew I had a good service to offer. In fact, at that time, I was the only person I knew of offering it. My problem was convincing potential clients that they needed what I offered.

Why I Sucked at Selling

Like most people, I sucked at selling. Here’s why:

I was selling scared.

That is the number one reason most people suck at selling anything. They sell scared.

The number one reason people suck at selling is because they sell scared.

Scared of what?

Scared of looking ridiculous.

Scared of being being rejected.

Scared of losing subscribers.

Scared of someone not liking you.

Scared of a little two-letter word the begins with N and ends with O.

Scared, scared, scared.

What Happens When You Sell Scared

When you sell scared, people instinctively know it.

Like a dog can sense fear, prospective customers know when you are selling scared. It comes through in person. It comes through on the phone. It even comes through in email. Yes, email.

It comes across in the way you look at people (or fail to). It comes across in your posture. It comes across in your voice. It comes across in the words you choose.

In a metaphorical and literal sense, you are transferring your fears to the potential customer. And no one wants that.

It feels weak. It feels slimy. It feels…well, scary. No one wants to buy from someone who is afraid to sell!

No one wants to buy from someone who is afraid to sell!

Overcoming Your Fear of Selling

So, how do you overcome your fear of selling?

Here are four steps to help you get past your fear and start selling with confidence.

1) Believe in your product

It almost goes without saying, but it must be said. Ask yourself this question:

Would I sell this product or service to my best friend? (Assuming they have a need for such a product or service)

If the answer is NO, don’t try to sell it to anyone. Period.

When you wholeheartedly believe in the product or service, whether it is yours or someone else’s, you will sell with authority.

2) Ignore the worst-case scenario

Often, we focus on the worst thing that could happen when selling.

Embarrassment. Rejection. Unsubscribes.

Yet we don’t do that in any other aspect of like (except for the rare people with extreme phobias). We don’t focus on the worst-case scenario.

When I get in the car to drive to the store, I don’t think to myself, “Worst case is I’ll die in a car crash.”

When I make a reservation at a nice restaurant, I don’t say to my wife, “Worst case is we’ll get good poisoning.”

Ignore the worst possible outcome, because it’s likely never going to happen. So why focus on that?

3) Go all out

When you go halfway, you get nowhere.

No offense to Kansas City (it’s a lovely place) but if your objective is to get from one coast to the other and you stop halfway in Kansas City, you have failed. You intended to see another ocean and instead you ended up with…well, I’ve only been there once and there was a lot of corn and not much in the way of elevation change.

When you go halfway, you get nowhere.

When you sell, go all out. In particular when you are selling online, that means sell with confidence and don’t be afraid to get in people’s faces if needed.

A good example of this is right now with my promotion of Michael’s Hyatt’s 5 Days to Your Best Year Ever. If you are currently on my email list (and you should be!), you might be almost to the point of being tired of me talking about his course.

But there is a reason why I am so strong of an advocate of his course. I believe in it because it worked for me so well. Last year, we paid more in taxes than we made in total income the year before. That is a remarkable transformation!

So why would I not go all out to share that with you? In fact, it would be a disservice to not do so.

Hey, while we’re at it, check out my full review of Michael’s course here and then go buy it.

4) Stop using weak words and phrases

When you are selling something, eliminate words and phrases like these:

  • I hope
  • Try
  • If you’d like
  • Maybe
  • Probably

In words, don’t sell in the hopes of someone buying, sell with the expectation that they will.

That single mindset shift makes all the difference.

Don’t sell in the hopes of someone buying, sell with the expectation that they will. 

Don’t ask they audience to try something. Ask them to make a commitment to buying. “Try” is such a weak word.

Don’t ask them to “check it out if you’d like.” Encourage – no, urge – them to get it now.

Use encouraging, action words when you sell.

Sell with authority. Sell with confidence. Sell because you have to tell the world about what you are selling.

What holds you back from selling what you know you should sell?

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4 thoughts on “The #1 Reason You Suck at Selling

  1. Sue Anne Dunlevie says:

    Great post! I spent my corporate life in sales and all this is so true!

    Thanks for the info, Matt.

    1. Matt McWilliams says:

      My pleasure and thank you Sue 🙂

  2. The words “try,maybe,hope” are words I’ve deffinately used selling at local flea markets. I feel when someone asks me for a price on an antique and I say ” I’m trying to get 60 out of it”. I’ve never got my asking price. Now I will say I want 60 or it’s 60 and engage on why it should be theres!

    1. Matt McWilliams says:

      Yep! It’s much better to justify the price and sell it’s value than haggle over a few bucks.

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