Sales Doesn't Have to Feel Like a Performance
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You've probably felt it before. That tightening in your chest right before a sales conversation. The rehearsed script running on loop. The sudden urge to send an email instead of picking up the phone. Most of us were never taught how to sell. We were taught to be helpful, to not be too much, and to definitely not talk about money. So when we started a business and suddenly needed people to pay us, the whole thing felt like a performance we never auditioned for.
In this episode, I sit down with Chris Castanes, a 30-year sales veteran, author of You're Gonna Be Great at This and Nearly Motivated, and host of his own podcast, to talk about what selling actually looks like when you strip away the pressure and get back to the human part of it. Chris started door-to-door in the mid-80s, survived some genuinely wild rejection stories, and came out the other side with a simple philosophy: people don't buy from companies, they buy from people.
What I kept coming back to in our conversation was intention. Not technique, not script, not the perfect closing line. Intention. When you walk in genuinely wanting to help the person in front of you, the dynamic shifts entirely. The pressure drops. The conversation opens. And the right people say yes.
Here's what this episode will help you understand and apply:
Why rejection in sales is almost never actually about you
How to move from a networking conversation to a real sales discussion naturally
The three-option pricing strategy that guides people toward yes
How to ask for referrals directly without it feeling transactional or awkward
Why confidence in sales is built through action, not mindset work alone
Meet Chris Castanes
Chris Castanes is the president of Surf Financial Brokers, a speaker, author and host of the "You're Going To Be Great At This!" podcast.
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Sales Doesn't Have to Feel Like a Performance
There is a particular kind of dread that lives in the body right before a sales conversation. It shows up as a tightened chest, a rehearsed script running on loop, a sudden urgent need to check your phone. Most of us have felt it. Many of us have let it win.
For a long time, I thought that feeling meant something was wrong with me. That I wasn't confident enough, polished enough, or cut out for the business side of business. What I've come to understand is that the feeling isn't a signal to stop. It's a signal that you care. And caring, it turns out, is actually the foundation of good selling.
I sat down with Chris Castanes, a sales expert with over 30 years of experience, author of You're Gonna Be Great at This and Nearly Motivated, and host of his own podcast, to talk about what selling actually looks like when you strip away the performance and get back to the human part of it.
Rejection Is Not About You
Chris opened our conversation with something that sounds simple but lands hard: people will not buy for a million reasons that make absolutely no sense. They don't like the kind of car you drive. They had an employee walk out that morning. The last salesperson who called them was a nightmare. None of that is about you.
This reframe matters because most of us treat rejection as data about our worth. It isn't. It's data about timing, context, mood, and a hundred variables you have no control over. The sooner you stop internalizing every no, the sooner you can actually show up fully in the conversations that do go somewhere.
The Intention Behind the Conversation
Chris has a phrase he comes back to consistently: your income is not in that person's wallet. That framing, the one that treats selling as extraction, is exactly where the slimy feeling comes from. When the goal is to get something from someone, people feel it. When the goal is to genuinely help, that comes through too.
The shift is surprisingly practical. Instead of walking in with a pitch, walk in with questions. What are your goals? What's standing between you and those goals? What would it mean to remove those obstacles? Let them talk. Find the opening. Then offer the thing that actually fits.
This isn't just feel-good advice. It's strategic. People buy from people they trust. Trust is built through listening, not presenting.
From Networking to a Real Sales Conversation
One of the most practical parts of our conversation was Chris walking through exactly how he moves from a casual networking interaction to an actual sales discussion. His approach is disarmingly simple: he doesn't try to have the sales conversation at the event. His goal is just to make an appointment.
He gets a business card, follows up the next day, and suggests coffee. By the time they sit down, both people know the purpose. The pressure of a surprise pitch is gone. The conversation can actually go somewhere.
At the coffee meeting, Chris brings a trifold brochure with a simple menu of everything he offers on the back. Not because he pushes it, but because he slides it across the table and lets curiosity do the work. More than once, someone has looked at that list and said, "Wait, I didn't know you did that. That's exactly what I need."
The Three-Option Strategy
When it comes to proposals, Chris always comes back with three: something lean, something premium, and something in the middle. The psychology here is consistent across industries. People don't want to look cheap, but they know they can't always justify the top tier. The middle option wins almost every time.
The lesson isn't just about pricing. It's about giving people a clear, contained choice rather than an overwhelming menu of variables. Decision fatigue is real. Three options respects the buyer's time and mental energy while still giving them autonomy.
Confidence Comes From Action, Not the Other Way Around
This might be the most important thing we talked about. So many people wait to feel confident before they take action in sales. They want to feel ready before they make the call, have the conversation, post about their business. But confidence doesn't arrive before the action. It arrives because of it.
Every conversation you have and survive, every rejection you walk away from intact, every yes you receive after a string of no's, that's what builds confidence. Not more preparation. Not more mindset work. Action.
A Final Thought
Chris has spent 30 years in sales and most of his clients have become friends. That is not an accident. It's the natural result of showing up in every conversation as someone who genuinely cares about the person across the table.
You don't have to love selling. You don't have to be naturally charismatic or fearless. You just have to care about helping people and be willing to get uncomfortable enough to start. The confidence will follow. It always does.
