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I Thought I Was Afraid of Cold Calling. I Was Afraid of Not Being Liked.

Years of dials, one honest realization about what the dread was actually about — and an experiment to test it.

Sep 30, 20262 min readsales · rejection · authenticity

For years I told people I hated cold calling. Everyone nodded. Sales people especially — it’s the most universal nod in business.

Then I started paying attention to when the dread actually showed up. It wasn’t at the dial. I could dial all day. It wasn’t the pitch either — I know the pitch cold. It was the moment the other person started forming an opinion of me. The pause before they decide if I’m a person or a pest. That’s where my chest got tight.

I was never afraid of the call. I was afraid of being judged with no chance to explain myself.

The tell

Once you see it, you can’t unsee it. Watch what a person does right after the fear spikes:

  • They over-explain. (Explanation is a request to be understood correctly.)
  • They apologize preemptively for existing in the prospect’s day.
  • They agree with objections they privately think are wrong.
  • They become noticeably more charming than they are in regular life.

All of those are the same move: trading the call’s outcome for the prospect’s approval. And it’s a bad trade! The prospect’s opinion of you is the one thing the call cannot purchase — but it’s also the one thing that doesn’t matter. They need the problem solved. You need the commission or the contract. Whether they’d grab a beer with you is not on the table.

Where it came from

I spent my early career doing VoIP consulting in Boston, and a huge part of that job was dials to business owners who did not know me. Hundreds and hundreds of first calls. I got good at them — which meant I got good at being likable fast. Charming, quick, agreeable, safe.

The skill worked so well it took me a decade to notice it was also a cage. Being likable on demand is exhausting, it flattens your actual opinions, and — the part nobody warns you about — it makes you forget what your opinions were.

What I’m doing about it

This stopped being an essay and became Experiment #001: stop trying to make prospects like me. The short version: sales calls where I drop the performance entirely. Say the honest read. Let silence sit. No preemptive discounting. Note every moment I want to trade an opinion for approval.

Early result, with the caveat that early results lie: the calls are shorter, more direct, and at least one went better specifically because I said “I don’t think you need this.”

The fear didn’t disappear. It just got correctly labeled. And a correctly labeled fear is a lot smaller than a vague one.