What’s On The Other Side of Discomfort

Welcome back to the 60th issue of Disrupting Conversations!

When was the last time you did something that genuinely made you uncomfortable? 

Most high performers know what it feels like to push through discomfort. That willingness — to have the hard conversation, make the risky ask, or do the thing they’d rather avoid — is usually a big part of how they got to where they are.

But when was the last time you actually embraced and did it with confidence?

If it’s been a long time for you, you’re not alone. This is something many successful people struggle with, and the reason isn’t usually a lack of discipline or drive. The reason often comes down to success itself: The farther you progress, the easier it becomes to stay within your comfort zone. 

This issue is about that pattern, and what you can do about it.

– Dan  

Title of Episode: Choose Your Pain Wisely

🎙️ Pain today or pain tomorrow — that’s the choice every high performer has to make, especially in sales. Sales professionals often opt for the short-term comfort of avoiding prospecting, risk-taking, and asking tough questions… but at what cost? This episode explores why this choice compounds over time, and what it actually costs you when the discomfort you avoided today shows up as regret tomorrow.

What’s On The Other Side of Discomfort

High performers are skilled at breaking out of their comfort zones — that’s usually how they got to where they are.

But success has a way of working against you. The apartment becomes a house. The $100K salary becomes $350K or more. And somewhere along the way, as more success breeds more comfort in their businesses and their lives, the habit of pushing through discomfort starts to get rusty. 

Maybe you’ve experienced this yourself. You see the conversation you need to have or the decision you've been sitting on. You know you need to do it. But the voice in your head gets there first: This week’s going to be rough. Do I really need to deal with this right now? I’ll get to it later. 

And just like that, the thing that would have moved you forward gets absorbed into the week and disappears. This is a natural response… but it’s also how performance plateaus happen. 

The good news is that the ability to move through discomfort isn’t doomed to disappear once you become successful. You just need to maintain it. One simple way to build this mindset is by getting intentional about it before the week starts:

1. At the beginning of the week, sit down with your calendar and take a hard look at what’s coming up — both the things you’ll have to do soon and the things you’ve been carrying from last week. 

2. List every task, conversation, or decision you’ve been avoiding. Pay attention to the things that produce a specific internal reaction when you think about them — resistance, dread, tension — then write them all down. 

3. Notice your instinct to rationalize away each item. Sit with the voice in your head that’s telling you, This isn’t urgent or The timing isn’t right. Recognize that voice for what it is: your brain trying to keep you safely in your current comfort zone. 

4. For each source of discomfort, think about what’s on the other side of it. What will you gain once it’s done? More trust and clarity after a hard conversation? Less low-grade anxiety from putting off a chore? The satisfaction of having handled a difficult task? Whatever the benefit is, write it down.

I do this exercise every Sunday before the week begins, and it’s made a significant difference in how I approach things I’d otherwise look for ways to avoid — whether a tough conversation or something as simple as an early morning workout. 

The point isn’t to make these things feel easy; it’s to stay connected to what doing them actually creates for you. And chances are, you already know the answer. It’s just waiting on the other side of something uncomfortable.

Thanks for reading!

Want to know more about the work I’m doing? Follow me on LinkedIn.

Was this newsletter shared with you? Subscribe here.

Learn more about Lappin180.