2 min read

Comfort Almost Killed Me

Picture of Dan Fisher Dan Fisher : Sep 2, 2025 8:45:00 AM

Sales Coaching Leadership

I almost let comfort destroy my sales career and my business.

And I know it’s trying to destroy yours too.

This isn’t about the economy. Or bad leads. Or your comp plan. Dan sitting on bench (1)

This is about the silent killer that creeps into every successful salesperson’s life. The one that feels good in the moment. The one that whispers you can “ease up” because you’ve made it.

I'm talking about comfort.

The Rise

A couple of years ago, I was untouchable (at least that is how I felt). Closing big deals. Winning logos. Customers were ecstatic. My MRR was north of $50K a month. Not bad for a one-man army. I’d roll out of bed and money was already waiting for me. And that’s when comfort showed up.

It leaned in and whispered:

“You can relax. You don’t need to grind anymore.”

And I believed it.

My Downward Spiral

It started small. Sleeping a little later. Cancelling "non-essential" prospecting calls. Neglecting networking. Telling myself, “I’ll make it up tomorrow.”

Then came long weekends. A little more time at the gym. Fewer demos, fewer follow-ups, fewer uncomfortable conversations.

I convinced myself I was still “working hard.” But I wasn’t.

Comfort doesn’t take you out with one punch. It bleeds you dry in small withdrawals. Until one day you wake up, and your pipeline is a ghost town.

That’s where I found myself. Prospects stopped answering. Customers didn’t renew. I’d stare at my CRM and feel my stomach drop. And then came the voices.

“You’ve lost it.”
“Everyone’s passing you by.”
“Maybe you should try real estate.”

When your business dries up, it’s not just your income that takes the hit—it’s your identity.
Every rejection feels heavier. Every silence feels louder. And you start to wonder if you were ever good at this in the first place.

The truth?

Rebuilding from zero is brutal. It’s humiliating. It’s lonely. And it makes you question everything.

My Wake Up Call

My turning point wasn’t a lightning bolt moment. It wasn’t a TED Talk or a podcast pep talk. It was the slow, sinking realization that customer after customer wasn’t renewing. That my pipeline was paper-thin. That my bank account was bleeding out, day by day.

That’s when it hit me: Comfort wasn’t just slowing me down. It was killing me.

My Climb Back

So I did the one thing comfort hates most. I started over.

And I built myself a path back brick by brick.

Here’s the playbook:

1. Mornings: Discipline First

Alarm at 5:30. No snooze button.
Coffee, notebook, and 30 minutes of planning before the world woke up.
Wrote down my three non-negotiables for the day. These weren’t “tasks.” They were moves that created pipeline.

2. Prospecting: Non-Negotiable Blocks

Two hours of cold calls before checking email. Every single day.
Tracked conversations, not dials. Conversations build pipeline—dials are the means to conversations.
Even on days I didn’t feel like it, I forced myself to pick up the phone.

3. Follow-Up: Ruthless Consistency

No prospect ever waited more than 24 hours for a response.
Promised info? It went out that same day.
Said I’d follow up? I did—no matter how uncomfortable it felt.

4. Skill Work: Daily Reps

Every night, I worked on one piece of my game. Just one.
Studied one objection, role-played one part of my pitch, listened to one recorded call.
Brutal, but it made me sharper.

5. Mindset: Discipline Over Motivation

Stopped waiting for “inspiration.”
Focused on stacking small wins—one call, one follow-up, one conversation at a time.
Build momentum through discipline, not hype.

It wasn’t glamorous. It wasn’t instant. But it worked. Slowly, the pipeline came back. Wins stacked up. And eventually, my confidence returned—not because I found a shortcut, but because I earned it back.

The Lesson

Sales isn’t about talent. It’s about discipline. It’s about showing up when comfort tells you to stay home. The moment you let comfort take the wheel, your career starts dying.