How does selling make you feel?

Do you feel gross thinking about pitching yourself?

I always think of Danny DeVito in the movie Matilda. He’s the epitome of disgusting salesperson. He runs a used car lot, of all things, and he runs cars backwards to get their odometers to reset.

And actually, come to think of it, I can’t think of a salesperson in the movies who is depicted honorably. The Wolf of Wall Street was just a different kind of shady character, and all the guys in Glengarry Glen Ross were so shady that the movie feels like a parody of a salesroom.

So it’s no wonder we feel gross when we think about selling. Especially if we’re selling ourselves.

That has a particular connotation, and it’s not pleasant.

My last corporate job was at a sales consulting company and one of the things the consultants said often was that “always be helping” should replace “always be closing” and sure, that looks good on a sticker, but what does it mean, and how can we do the helping without being ridiculously obnoxious?

Example from real life: the time I talked a friend out of working with someone else and into working with me

I do my best to talk to other entrepreneurs as often as I can (weekly, at minimum). It’s the only way I know how to ease the lonely solitude of working for myself online.

At one of these conversations, my friend brought up that they were looking to drop a bunch of cash on a very expensive coach. The person they wanted to work with was asking $25,000 for a six-month coaching package.

I couldn’t help myself. “That’s the price of a decent car!”

That was my knee-jerk response, but after I paused, I had something more helpful to say. “Look, I know that person’s style, and they’re really high pressure. What they’ll do is teach you how to use those same high-pressure tactics. Is that what you want?”

And then I felt really awkward about the next thing I said.

“Listen, I definitely didn’t schedule this call to pitch you anything, but you have to know that a 90-minute deep dive with me is less than $1500 and during that time, we’ll map out your path to profit for the next six to 12 months.”

My friend said, “I’m goal oriented but I’m too close to my business to know where I should go next. I just need someone to sit with me and tell me where to put my focus. If I could get that, I would absolutely be good to go.”

I told that friend I’d send a link with more information about these strategy calls I do.

And I followed up.

I really think if I’d scheduled the call with “I wonder how I can get more money from this person” intention, the call would have gone differently.

But that wasn’t my intent, and it never will be. As much as I like making money, I like working with people I know I can help even more.

Was it awkward to pitch my services like that?

You bet it was!

But more than wanting this friend to work with me, I wanted them to avoid figuring out how to finance working with a coach that wasn’t doing any implementation.

I’m proud of that coach, and I’m glad they can get those kind of rates. But that big of a package wasn’t the right fit for my friend.

It’s really easy in the world of “let me help you make more money” to get sidetracked by your daydreams of making it rain and somehow turning your digital products into a cash machine, which can lower your defenses.

If you believe someone when they say their way is the only way to make it, you’ll follow them.

Until their system starts to fall apart (which won’t happen until you stop working with them, of course).

Then what?