GUEST SERIES: Confessions of an Introverted Entrepreneur | Part 4

Pitch, don’t kill my vibe.


A lot of health entrepreneurs and coaches hate the S-Word. Introverts definitely hate the S-Word. I spent thirteen years pursuing classical music just so I wouldn’t have to confront the S-Word.


It’s slimy, it’s disgusting, it’s used-car salesmen turning odometers back on cars.

It’s fibs and lies and stretched truths.

This is how we hear the word ‘selling’ these days.

Caveman exchanged stone tools for furs all the time, I’m sure. So what causes the modern-day aversion to exchange?

For starters, we’re in the age of the informed customer. You wouldn’t give up your stone tools without first trolling the shit out of Etsy to see if someone else’s furs are cooler. (You’re probably also doing this research while uber-ing home from brunch before your Instacart order arrives. We’re in the flattest information landscape ever.)

One could also assert the rise of social media has caused a drop in actual human connection when having an in-person conversation. You often hear society complain that millennials are addicted to their phones, social media has become an obsession, and people don’t know how to relate in person.

At first I thought this assertion was hearsay. Then I read a study that email marketing has an ROI of 4,300%. 4,300%. Email marketing far outweighs all social media marketing, btw.

So clearly people crave connection and millennials crave connection, and now the difference is salespeople are successfully replicating the feeling of connection and validation through the written word. The market is changing and connection can be shared through crisp, clean penmanship and written vulnerability.

I’m not saying you can never talk to anyone again and build your side hustle into a new career. 

What I will say is the structure of in-person persuasion and written persuasion boils down to the same three-part skeleton.

I need a step-by-step of how to have a conversation if I’m going to survive the freelance life, and this formula has already helped me a ton. You’ll find that inviting people to let you help them is much easier than you thought. 

So here is a double-secret, quadruple-awesome formula to get anything you want in life through the power of conversation:

Relatedness + Opportunity + Request = Results.

Let’s dig in.



First, people must relate to you. People often relate over a common affinity or scenario they find humorous, interesting, or enlightening.

This is why in my new opt-in video “The 5 Laws of Growth”, I begin with a fun quiz entitled, “Who said that – controversial yoga guru or professional wrestler?” It breaks the ice, it creates ease, it’s a silly spin in an otherwise-technical webinar.

This Fast Company article beautifully illustrates how NOT to establish relatedness. Businesses (and people, frankly) are spending way too much time attempting to engage. And social media is already such a minefield in terms of engagement.

(Footnote for the Goals Universe: “I am published in Fast Company on December 31st, 2016.”)

People are now immune to selling and shut off when they hear people sell, even when it’s a service or opportunity they really want. And it’s not their fault really – you’re exposed to 5,000 advertisements a day, compared to 500 a day in the 1970’s.

As a company, what do you do? Companies knew they were running out of real estate in people’s brains. So they began to explore a new way to get related to people: a muse. A muse is a fictitious person (or character) whom both you and your market find inspiring; this then gives the two of you a context of relatedness.

Sterling Brands calls the muse “the most dynamic and compelling archetype within a target audience. He or she is aspirational, not representative.” It’s important to note that muses are usually not real people. Muses are evergreen, which is great. The behavior of real people after having a taste of fame is not.

Subway played with fire in using an actual person as a muse when they brought Jared Fogle into the spotlight in 2000. Twelve years later reality surfaced with charges for child pornography, and J-Fog is now in a 13-year prison sentence.

It’s fascinating that companies now know they need to relate in order to even get the ear of people. This applies to everyday life, too – to cut through the noise and bombardment of our day-to-day, you must first build relatedness, or else people simply won’t hear anything you say.

Now you’re related – that’s great. Time to put your vulnerability pants on. The ones with extra built-in diapers.



Share yourself. Why are you up to what you’re up to? What will get you there? (If you’re struggling with that question, talk to a friend or hire someone to tease the awesomeness out of you.)

Paint a picture of a future that otherwise wouldn’t have existed – and why that’s important to you and the planet.

Note: this is not a long speech where people fall asleep. After you share, you check in – what do they hear for themselves?

Here’s an example:

I lost 100 pounds. I knew I didn’t know how to care of myself because when I looked in the mirror I started crying. I went for a walk one day for the first time in a long time, and that action was transformational. Even though I didn’t know what to do to lose weight, I had action on my side, and through action everything falls into place.

When you read that, what comes up for you as a stuck point? What’s the next action? You can tell me. 

Relatedness and opportunity are two-way streets; you must ask them what they hear as possible for themselves. Otherwise this formula doesn’t work.


Truthbomb comin’ in hot: Questions are more transformational than answers. The author Peter Block makes that statement in many of his works, and every time I go back to his work or books I become present to that.

Is your day full of questions or full of answers? Mine had become full of the latter, which is why I quit my job.

If you answered answers, don’t worry; you don’t need to resign, you just need a coach to put questions (aka transformations) back in the picture. If you can’t afford a coach, still get one – get a money coach or career coach first. Lead through action.



Now you make a request. The request is an invitation to act on the opportunity they now hear as available.

“We want a more love-filled life; let’s get a dog.”

“You could train with me 1-on-1 and start getting those results now.”

“Come on this vacation with me, the memories will last a lifetime!”

You ask them for an action. They’re clear how the action allows them to act on the opportunity they’ve seen for themselves. They act.

When the opportunity is in front of someone and they are truly in your world, their world shifts and moves – obstacles disappear. If it’s a sale or a request for someone’s time and commitment, and people truly see the opportunity, they find the necessary resources to make it happen. Period. 

Some of you feel people won’t make time for you or pay for you to help overcome their vices. If that’s the case, you need a confidence boost, so you should read about this lamp that doesn’t turn on unless you turn off your phone, and how people want to buy it just TO HELP THEM TURN THEIR PHONE OFF. Case closed. People will pay and make time for anything that occurs them as an opportunity to improve their quality of life.


The one part everyone fucks up


People sometimes accidentally sell through guilt, which establishes their selling from below the line. It can be effective – but only because shame is viciously effective. (Here are 40 ways NOT to invite action.)

The success-minded seller may resort to shame selling. But not us. So here’s the rule of thumb: When you make a request, the listener should feel they have power and authority to make a choice. They make the choice. They are then satisfied and confident with the choice they have made. You acknowledge their choice wholeheartedly and you both feel complete about the conversation.

If they’re left feeling ashamed or guilty with their choice, there’s cleanup to do. This causes buyer’s remorse and can strain relationships; you want requests and subsequent actions to feel good on both sides.

Try this formula out and tell me how it goes.


This series is entitled “Confessions of an Introverted Entrepreneur”, and here is one final confession: I truly believe introverts have caught up to extroverts in the entrepreneurial landscape through the levers of technology, vulnerability, and vision. There are many, many ways to elevate your brand, connect with people powerfully, and impact the world in our information age. 

Never hesitate to reach out. That’s an action too.

That’s all for now. I appreciate you.


Jacki Carr