Confessions of a Sales Expert

fear of selling selling when you hate selling Oct 12, 2026

I started my career in sales and worked in it for 15 years, then taught it to others for another 20 years.

And here is my confession: I still don't love doing it.

Yeah, that's right.

Despite decades in the trenches, I still don't love it. I still do other things instead when I can.

But, I still sell when I should. I don't avoid it, entirely.

There is a massive difference between what I do and what I see so many others do.

I get it. Having that conversation and asking for the sale is asking you to be very vulnerable. It is asking you to not only hold up your baby for others to see it, which you think is beautiful, but also to ask if that person across from you also thinks it is beautiful. AND, it is asking them if they think it is beautiful enough that they would give you money to prove just how strongly they agree with you.

Of course, that is not what's really going on. But that is how it feels to many of us.

Because of this, I see so many entrepreneurs avoid the sales process altogether. They sit in their office (usually their second bedroom) and spend more money on Facebook ads or send another batch of emails. Or worse, do nothing.

They avoid the conversation.

I get it. We can always choose to do the marketing things that bring in sales that don't involve actually selling. But be honest with yourself. Where would I be if I did have that conversation more often? Could I bring in twice as much revenue? Maybe even 10 times as much? What would my life look like then? Who would I be if that happened?

So, don't avoid it altogether. Do what you can to build your business without it, sure. But still step up and do it when you know that you should. It is often the last required step to get many of your buyers across the line to actually buy. No amount of advertising, educating, and relationship building will get them to be a customer. Selling will. And you have missed a lot of them so far.

Finding the Balance

Knowing when you should engage can be a challenge. But when you do, arm yourself with the ability to handle it in a way that is comfortable for both you and the buyer. Approach it with real confidence. Find a way that ensures you won't avoid it entirely.

I use the N.I.C.E. sales method, and I've taught it to thousands of others across classrooms, workshops, and online cohorts. It is also the core of my new book, How to Sell When You Hate to Sell.

I teach it because it works, and because it feels damn good to see those people succeed.


This article first appeared in my LinkedIn newsletter, Approachable Entrepreneurship.

You don't have to love selling. You just have to stop avoiding it.

How to Sell When You Hate to Sell walks through the N.I.C.E. method step by step, so the conversations you've been putting off start to feel like conversations, not pitches.

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Approachable ideas on selling, confidence, and building a business that feels like yours. Short, practical, and written by a guy who also hates to sell.

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