Choose Your Pain Wisely

Welcome back to the 51st issue of Disrupting Conversations!

Here's an uncomfortable truth about high-performance sales: pain is inevitable. The only choice you get is when you experience it.

I've been watching this play out with clients all year. Some are riding a wave of success, closing deals, hitting targets. Others are drowning in anxiety, watching their pipeline dry up, feeling the weight of avoided discomfort compounding into crisis.

The pain of a weak pipeline six months or more later creates performance inhibiting stress.

The difference between these two groups isn't talent, market conditions, or luck. It's which pain they chose late last year or early this year.

Think about your prospecting time on the calendar. When that block appears, do you honor it—knowing it will feel uncomfortable—or do you find other "urgent" things to prioritize? When you're in a meeting and a tough question crosses your mind, do you ask it despite the tension, or do you stay in the friendly zone where it's safe?

These moments of choice determine everything.

The pain of prospecting consistently is manageable anxiety. The pain of an empty pipeline six months or more later is career-threatening stress.

The pain of asking hard questions today is temporary discomfort. The pain of leaving a meeting thinking "Why didn't I ask that?" is regret. 

You're going to feel pain either way. You just get to choose which kind.

– 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: Stop Making Outreach Decisions Based on How You Feel

🎙️ What separates high performers from everyone else when it comes to prospecting? It's not their message, their experience, or their market. It's how they think about the activity itself.

Most sales professionals make the critical mistake of allowing their feelings to dictate whether they follow through on their prospecting commitments. They convince themselves that how they feel in the moment—tired, unmotivated, or overwhelmed—should determine whether they make those calls or send those emails. But here's the uncomfortable truth: your best client is still out there, and they're not coming to you. 

In this episode, I challenge everything you think you know about prospecting by breaking down seven powerful mindset shifts that separate high performers from everyone else. If you're ready to stop letting your mood dictate your prospecting success, this episode provides the mental framework to build consistency in your outreach efforts.

The Real Cost of the Friendly Zone

Let me tell you about a pattern I see constantly: relationship-focused sales professionals who pride themselves on building rapport—who get energy from connecting with people, who can mesh with a prospect instantly—tell me their sales cycles run three to five years.

Is that really necessary? Or is it a story they tell themselves to avoid confronting an uncomfortable truth: they're choosing comfort and ease. 

Here's what's actually happening. When you prioritize being liked over being helpful, when you seek validation and approval from prospects, when you're distracted by thoughts about social connectivity instead of truly listening—you're avoiding the short-term discomfort of asking meaningful questions.

You get really good at small talk. You become skilled at sharing your expertise. But you never help your prospects gain the objective perspective they need to make a decision.

The result? Long sales cycles that make you feel better about avoiding tough questions, but keep you trapped in a cycle of anxiety about whether deals will ever close.

This is choosing pain tomorrow to avoid pain today.

Now consider a different definition of relationship selling. What if prospects are relationships you help, guide, or coach to make the best possible decision for their business—whether that includes you or not?

Suddenly, the relationship isn't about them liking you. It's about you serving them with the hard questions no one else is asking. You become a valuable part of their business - not simply someone that’s fun to have dinner with once or twice a year. 

Pressure vs. Perspective

Think about your own experience when someone tries to get you to change something. Maybe a manager, a spouse, or a consultant.

When they lead with their expertise—telling you exactly what you should do, how you should do it, what your mindset needs to be—how do you respond?

If you're honest, you're listening to disqualify them, not qualify them. You're thinking, "They don't really understand my situation," or, "That might have worked for others, but my circumstances are different."

This is what happens when someone creates pressure instead of perspective.

Your prospects do the exact same thing when you lead with your competency. When you jump to solutions before helping them think through whether the problem is worth solving, you trigger their natural resistance to change. They assess your expertise through the lens of their biases, searching for reasons to disqualify you so they can stay comfortable.

But when you help someone gain perspective—when you ask questions that make them reflect, think, and debate more objectively—everything changes. You're helping them discover insights themselves rather than forcing them to accept yours.

Questions like:

• "Is solving this challenge worth your time right now?"

• "What do you risk if nothing changes in the next 12 months?"

• "What could you gain if this improved?"

• "How does this align with your other priorities?"

👉 These questions don't pressure prospects to choose you. They help prospects see their situation more clearly. And when people gain perspective, they apply pressure to themselves to make a decision.

The irony is profound: The better you become at helping people gain perspective, the less you need to chase them. You stop being the person who’s trying to convince them and become the person who helped them think clearly about their situation.

This is the difference between professionals who close deals in three years and professionals who close them in far less time. It's not about harder tactics—it's about choosing the discomfort of asking better questions today rather than the anxiety of empty pipelines tomorrow.

The question is: Which pain will you choose?

QUOTE

"We must all suffer from one of two pains: the pain of discipline or the pain of regret. The difference is discipline weighs ounces while regret weighs tons."

– Jim Rohn

Thanks for reading!

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