Why discomfort is the secret to real confidence
Most people treat discomfort as a stop sign. David Engel treats it as a green light. After more than 30 years in marketing, from pressing vinyl record labels to building a retainer-based consulting practice for major Canadian banks, David has one consistent through-line: if you're not uncomfortable once or twice a month, you're probably not moving forward. "I view discomfort as a catalyst for moving forward or not," he told Ben. "You have no control over change. So you might as well accept it and make it work for you."
That's not a motivational poster. It's a operating principle David has tested across decades of real business risk, including selling a $10,000-a-month innovation platform to the Royal Bank of Canada before he'd figured out how he was going to deliver it. "First you make it up," he said, "and then you make it happen."
How to build real confidence when the outcome isn't guaranteed
Confidence, David argues, isn't certainty. It's the practiced willingness to act without a guaranteed outcome and to find value in both results. "There's value in succeeding and there's greater value in not succeeding," he said. "Some things work and some things don't work." He traces his own confidence back to a father who never said no, who sent him to New York at 24 to pick up printing film for Apple Records at midnight, who let him negotiate a 50% paper advance from a client to fund a press purchase the company couldn't otherwise afford. The safety net wasn't money. It was permission.
Dan Sullivan of Strategic Coach pushed David to formalize what his clients already knew: they weren't paying for equipment or deliverables. They were paying for wisdom. Sullivan's exercise, writing to your 10 best clients and asking them to name three reasons they work with you, produced the same answer every time: "You come to us with new ideas, you teach us things, you solve our problems, and you never let us down." That clarity became the foundation of a retainer model David still uses today.
Why failure is your greatest teacher in business
David doesn't hide his mistakes, he catalogs them. A $350,000 glue error on a print job that a client refused to pay for turned into millions of dollars of future work because David handled it with honesty and confidence in the relationship. An undercapitalized growth phase taught him that cash confidence matters as much as sales confidence. A bank that turned him down for a $100,000 line of credit when he had a Procter & Gamble order in hand taught him that banks aren't always your best friend, and that the client often is.
"Entrepreneurs don't tell you the times that they fail," David said. "They only tell you the times that they succeed. But the failures are the impetus to get up and go on." His skiing analogy says it plainly: you master the bunny hill, then you have to go to the intermediate run even though you know you'll fall. "The question isn't if you're going to fall. The question is how quickly you get up."
Why relationships define a meaningful life
Ask David for his top advice to a 25-year-old and the first word out of his mouth is relationships. Not strategy. Not capital. Not hustle. Relationships. He's been married 47 years. He has three kids who married people he considers his own. He volunteers. He reaches out to non-clients who said no just to ask what attributes they value in partners, because the relationship matters more than the transaction.
"The things that you think you've done wrong, nobody ever notices them," he said. What they do notice is whether you showed up, whether you were honest when something went sideways, and whether you brought them something new. That's the whole game. Confidence gets you in the room. Relationships keep you there.
The one thing you can't get back
Ben asked David to close with a ripple, one phrase to echo out. David didn't hesitate: "The only thing you can't get back is time. Use it well, respect it, and don't waste it." Every other resource in this conversation, money, confidence, relationships, even reputation, has a path back. Time doesn't. That's not a warning. It's an invitation to treat every uncomfortable moment, every hard conversation, every risky ask as exactly what it is: the thing you came here to do.
