Why Easy Wins Might Be Your Biggest Loss

Welcome back to the 47th issue of Disrupting Conversations!

What if I told you that getting a "yes" could be the worst thing for your career?

I was recently asked what drove Lappin180's success. The person asking expected me to talk about persistence, dedication, or the uniqueness of our approach. Instead, I surprised them by saying it was timing and having really good people.

This got me thinking about a dangerous pattern I see everywhere: professionals getting comfortable with easy wins. When external factors align perfectly—new technology hits the market, regulations change in your favor, your company undercuts the competition—the yeses flow freely. 

But here's the trap: lazy yeses make us lazy. They cause us to take things for granted, create biases about why we're successful, and put blinders on that prevent us from seeing reality. We start believing our own press.

The hard truth? Easy wins often have little to do with our actual skills. And when the external factors change—which they always do—we're left unprepared.

That's why the best thing that ever happened to my business was nearly two years of "nos" after I started. Those rejections forced me to get better, to look inside myself, and to develop the skills that created our 15+ year successful run.

So here's the question: Are your recent wins making you better, or just more comfortable?

– Dan

Breaking Sales is my podcast to connect with those who are ready to break free from the chains of old sales methodologies that don’t work.

Title of Episode: If You Don’t Change - Nothing Changes with Emily Smith

🎙️What happens when a top performer realizes her formula for success might be holding her back? Emily Smith spent 12 years dominating commercial real estate by being the most prepared and knowledgeable person in every room. But when she started working with Lappin180, she discovered that her "expert" identity was actually creating barriers to reaching the next level. Her story perfectly illustrates this week's theme: sometimes our greatest strengths become our greatest limitations when we're not honest about what's really driving our success.

Stop Creating Pressure; Start Providing Perspective

Picture this scenario: You're crushing your numbers. Deals are closing left and right. Your pipeline is full, and everyone's calling you a superstar.

But what if those wins aren't about you at all?

What if they're about market timing, company positioning, or regulatory changes that created perfect conditions? What if you're riding a wave that has nothing to do with your actual selling skills?

This is the "lazy yes" trap, and it's more dangerous than any rejection you'll ever face.

Here's why: Easy yeses create a false sense of security. They make us believe we've cracked the code when we've simply benefited from our circumstances. We start taking credit for outcomes that were largely driven by external factors, setting ourselves up for a devastating wake-up call when conditions change.

👉 There's a neurological principle at work here: we tend to minimize our part in our failures and aggrandize our part in our successes. But high performers do the opposite. They minimize their successes and focus relentlessly on how they could get better. They ask tough questions: What external factors contributed to this win? What was actually within my control? How can I get better regardless of circumstances?

I learned this lesson the hard way early in my career. In the late '90s, I was consistently ranked in the top five among my company's national sales organization. But when I honestly analyzed what drove that success, it wasn't my selling prowess—it was perfect timing. New technology aligned with government deregulation of an industry, and my company was aggressive with marketing and pricing.

I was working hard and staying disciplined, sure. But my sales approach was completely traditional. There was nothing skillfully amazing about what I brought to the table.

The real test came when I started my own business. Those first two years were brutal—almost no revenue, tremendous stress, and a young family depending on me. But those "nos" were the best education I ever received. They forced me to:

• Examine my actual skills objectively

• Invest in real development

• Build resilience that served me for the next 15+ years

• Separate what I could control from what I couldn't

👉 Those hard-earned lessons became the foundation for everything that followed. They taught me that the most dangerous moment isn't when you're failing—it's when you're succeeding for the wrong reasons.

The next time you land an easy yes, don’t celebrate too quickly. Ask yourself: What really drove this outcome? Was it my skill, or was it timing? Was it my approach, or was it their desperation? Be brutally honest. Your future self will thank you. 

Because when the market shifts, the regulations change, or the easy conditions disappear—and they always do—you'll be the one still standing. Not because you got lucky, but because you got better.

QUOTE

"Success is a lousy teacher. It seduces smart people into thinking they can't lose." 

— Bill Gates, co-founder of Microsoft

Thanks for reading!

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