I used to think sales was about scripts, charm, and closing lines.
Nine years in, I know better.
The truth?
The lessons that actually stick aren’t in training decks... they’re in scars.
Scars from deals lost, calls fumbled, and pipelines that dried up overnight.
Here are 12 scars I carry; and the lessons I wish I knew from day one.
✅ What Sales Really Taught Me In 9 Years
1. Volume is crucial
Sales is math. Activity compounds. If the top isn’t full, nothing falls out the bottom.
2. The deal is won or lost when you’re not in the room
Your champion, your notes, your business case; they have to sell without you. If they can’t, the deal dies quietly.
3. Discovery is for disqualifying
The fastest “yes” starts with faster “no’s.” Don’t waste cycles on ghosts.
4. Cold calls are the fastest way to pipeline
I learned this the hard way after waiting weeks on automated sequences. Nothing beat the first live dial. Conversations > campaigns.
5. You’ll never be perfect
Ship the call. Then iterate. Consistency beats flawless.
6. You’ll fail more than you succeed
Rejection is not the enemy — it’s the gym. Every “no” adds weight to the bar. Lift it enough times and skill follows.
7. Create your own luck
Luck finds those who show up early, follow up late, and stay visible. I can’t count the number of “coincidental wins” that came from being findable.
8. Follow-up wins deals
Most reps stop after 2–3 touches. The gold usually shows up around 8–10. Outlast the competition.
9. Pipeline solves problems
When your funnel’s thin, desperation leaks into your voice. And desperate sellers make desperate deals.
10. Mindset is your real quota
Forget the leaderboard, your emotions are the true performance metric. Control those, and you stay in the game.
11. Challenging beats relationships
Being liked is nice. Being trusted as the person who pushes their thinking is what closes.
12. Speed matters
Set next steps on the call. Send recaps the same day. Momentum is the moat.
Before You Close This Tab...
Sales have never been a straight line.
It’s a cycle of wins and losses, of days where the phone feels light in your hand and days where it feels like lifting a hundred pounds.
The scars we collect along the way aren’t just reminders of failure; they’re the very proof that we’re still in the fight.
And if there’s one thing almost a decade in the trenches has taught me, it’s this: the best reps don’t rise because of talent alone. They rise because they keep showing up long after the excitement fades, long after rejection numbs the will, long after most people would’ve quit.
So as you read these lessons, don’t take them as rules etched in stone.
Take them as sparks... reminders to reflect on your own scars, your own journey, and the truths you’ve bled for in this game.
Because sales will never hand you certainty. It will only hand you choices: to shrink, to stall, or to keep pressing forward.
And the choice you make today… that’s the one that will define you.
See you next week.
— The Sheriff in Town
