Coffee With Chris: Stories on Grit, Growth and Leadership

Coffee with Chris

Weekly reflections on life, leadership and finding peace in the chaos...from my pond straight to your inbox.

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50 Feels Different Than I Thought

I turned 50 this week. And for most of my life, I assumed that number would feel different. At 20, I thought success at 50 would be obvious. Big bank accounts...Fancy cars...Dream homes and vacations... External markers that told the world I had “made it.” Instead, what overwhelmed me wasn’t reve...

by Chris Errington — Feb 21, 2026

When failure feels louder than reality

There’s a specific kind of tired that shows up after disappointment. Not physical...narrative. It’s the exhaustion that comes from replaying moments you wish had gone differently. Conversations.Decisions.Silences. Failure doesn’t usually arrive with fireworks...it sneaks in quietly…and then your ...

by Chris Errington — Feb 14, 2026

Time Isn’t Patient

“Don’t behave as if you are destined to live forever.” Read it again. Not because it’s dramatic...but because it’s practical. Most damage isn’t done by bad intent...it’s done by delay. We postpone conversations.We defer decisions.We tolerate misalignment longer than we should. All because we assu...

by Chris Errington — Feb 07, 2026

Getting Up Matters More Than How Hard You Fell

Chris Errington | Your Sales Wingman Chris Errington...E2E Solutions Ltd...Network strategy... shipper and carrier partnerships... sales coaching... practical systems that mo... www.chriserrington.com There’s a moment most people don’t talk about. It’s not the fall. It’s the moment you r...

by Chris Errington — Jan 31, 2026

You Don’t Get Away With Things… You Just Delay the Receipt

Chris Errington | Your Sales Wingman Chris Errington...E2E Solutions Ltd...Network strategy... shipper and carrier partnerships... sales coaching... practical systems that mo... www.chriserrington.com There’s a belief floating around that karma is some mystical force... I don’t see it th...

by Chris Errington — Jan 24, 2026

Coffee with Chris...Maybe the Stoics Were Right About Time

I read a line from Marcus Aurelius that I just can't shake... “Am I afraid of death because I won’t be able to do this anymore?” It haunts me now... When I first read it, I thought about our kids...the girls chasing their dance dreams...Bubba chasing baseball glory... Most would call them long ...

Jan 10, 2026

Maybe So...Maybe Not...

There's an old story often told by Alan Watts... It's simple…almost too simple...and that is why it cuts so deep when you sit with it. A farmer lives with his son and a single horse. One day the horse runs away...the neighbors gather and say…“Such bad luck.” The farmer replies…"Maybe so…maybe not...

by Chris Errington — Jan 03, 2026

2026… The Year You Finally Build the Life You Keep Talking About

There used to be a moment at the end of every December where I felt that quiet tension in my chest... The year is almost over…the next one is knocking at your door…and you start asking the same question every person asks… “What am I going to do differently next year?” Most people answer with re...

by Chris Errington — Dec 27, 2025

COFFEE WITH CHRIS...Quiet Generosity…

I saw a video the other day that damn near broke my heart... An eighty eight year old man, retired military, working the front door at grocery store. Not because he wanted something to do...but because life had taken things from him that he never expected to lose. He had worked for GM, counting o...

by Chris Errington — Dec 20, 2025

COFFEE WITH CHRIS: The Politically Bulletproof Person

How a person becomes sovereign…stable…and unshakeable in any political climate There is a message whispered in every room lately. People feel it at work...at home...at the gym...at the dinner table...in the back of their mind when the house finally goes quiet. Something feels off. Uncertainty...p...

by Chris Errington — Dec 13, 2025

When I connect people...everyone grows

When I Connect People, Everyone Grows There’s a quiet truth I’ve learned nearly 30 years in sales, leadership, and life…the world opens up when you put the right people in the same room. I don’t mean networking events...I don’t mean trading business cards...I don’t mean “let me know if I can ever...

Dec 07, 2025 chris errington coffeewithchris

Coffee with Chris … The Standard You Live By

There’s a moment from my past that has shaped how I lead…how I sell…and how I carry myself as a man. I had a customer I respected...good man...good family...we built trust over time and he became more than a customer…he became a friend. We were in the middle of a project when my boss pulled me as...

Nov 29, 2025

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