Weekly newsletter + companion podcast.

WINNING AT WORK

Practical ideas for managers and operators 5–15 years into their careers — on leadership, organizational politics, and the strange realities of professional life.

Every Tuesday, one short essay on a real workplace situation — written by someone who spent 35 years in the room where decisions actually get made

Subscribe and get my free guide, "Reading the Room: A Field Guide to the Seven People You'll Meet at Work"
plus one short essay every Tuesday on how work actually works

5 min
to read

1 issue
every week

High signal
zero startup noise

WHAT YOU WILL RECEIVE

A Simple Idea From the Newsletter

The Career Triangle

Most people want three things:
✔ Meaningful work
✔ Good money
✔ Work-life balance
The uncomfortable truth? Most of the time you can only pick two. Understanding the trade-offs can make your career far less frustrating and much more intentional.
Subscribe to get ideas like this every week.

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What Winning at Work Covers

Most career advice focuses on motivation. Winning at Work focuses on reality.
Each essay and podcast explores one idea that helps you navigate professional life more intelligently.

Career Reality

The unwritten rules of organizations influence politics and decision-making.

Leadership

How good leaders build trust, protect teams, and gain influence.

Work Frameworks

Simple mental models like the Career Triangle or Managing Up vs. Managing Down.

Stories From Field

Lessons from real career successes, mistakes, and everything in between.

Recent Issues

Recent Newsletter issues from the Winning at Work newsletter that you can check

Professional Growth

The Wizard in the Blue Shirt - AI and your career, Part 1

I've seen this movie before — at the dawn of the consumer internet. Different technology, same story. And it's worth telling before we spend a bunch of time talking about AI.

John Caldwell

Franklin and the Long Game

Some people win by leaving. Franklin won by staying. They both take courage — but only one of them takes patience. And that might be the harder one.

John Caldwell

The Career Triangle - The Ultimate Tradeoff

Why you can have meaning, money, or balance — but almost never all three at once

John Caldwell

Managing Up: Charlie and the Oxygen Factory

Charlie Copper wasn't the boss. But, he controled the oxygen in any meeting he was in.

John Caldwell

View All Posts

About Winning at Work

Winning at Work is written by John Caldwell, who spent 35 years at the sharp end of music and gambling — selling 40M records as a label president and helping build the online poker industry

The Goal is Simple!

Help mid-career managers and operators understand how work actually works — the part no one teaches you between your first promotion and your first executive role.

Prefer To Listen?

Winning at Work is also a short weekly podcast. Each episode explores a single career idea's frameworks, stories, and observations about professional life. Short. Practical. Thoughtful. Listen on your favorite platform

FINAL INVITATION

Work is strange, winning at it shouldn’t be!

Subscribe and get the free guide — Reading the Room: A Field Guide to the Seven People You'll Meet at Work — plus one short essay every Tuesday..

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