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Late Career Entrepreneur

Encore Career

+3

The autopilot did its job. That's what killed them.

Aug 18, 2026

•

6 min read

The autopilot did its job. That's what killed them.

What a 2009 plane crash can teach late-career professionals about handing judgment to AI.

Rob Norris
George Pillari
Rob Norris, +1

Encore Career

+3

Don't Fund the Bubble.

Aug 11, 2026

•

5 min read

Don't Fund the Bubble.

Most of what's happening is garbage. The infrastructure underneath it isn't.

Rob Norris
Rob Norris

Encore Career

+3

Design was always a Business Result

Aug 4, 2026

•

5 min read

Design was always a Business Result

Pretty got commoditized. Then usability. Here's where the value goes next.

Rob Norris
Rob Norris

Encore Career

+3

Drucker solved this in 1966

Jul 28, 2026

•

5 min read

Drucker solved this in 1966

Drucker got the diagnosis right sixty years ago. The cure showed up last year.

Rob Norris
Rob Norris

Encore Career

+2

Old folks rule (the data agrees)

Jul 21, 2026

•

3 min read

Old folks rule (the data agrees)

AI has made your experience worth more — not less.

Rob Norris
Rob Norris

Encore Career

+2

It's all your fault

Jul 14, 2026

•

4 min read

It's all your fault

The confession is the easy part. The turn is where it counts.

Rob Norris
Rob Norris

Essential Reading

+3

Start a Business Without Risking Your Retirement

Jun 30, 2026

•

7 min read

Start a Business Without Risking Your Retirement

Rob Norris
Rob Norris

Encore Career

+2

Become a Beginner Again (On Purpose)

Jun 23, 2026

•

4 min read

Become a Beginner Again (On Purpose)

Apprentice Yourself to Your Next Chapter

Rob Norris
Rob Norris

Entrepreneurship

+3

Don't quit your day job. Use it.

Jun 16, 2026

•

6 min read

Don't quit your day job. Use it.

How to launch your second act without blowing anything up

Rob Norris
Rob Norris

Innovation

+4

AI Didn't Fix the Bozos

Jun 9, 2026

•

6 min read

AI Didn't Fix the Bozos

The 2026 update on innovation — and why your experience is worth more, not less

Rob Norris
Rob Norris

Entrepreneurship

+3

Almost nobody uses AI

Jun 2, 2026

•

7 min read

Almost nobody uses AI

ChatGPT just hit 900 million weekly users. The math is more interesting than the headline.

Rob Norris
Rob Norris

Encore Career

+3

Everybody starts too big

May 26, 2026

•

4 min read

Everybody starts too big

Stop thrashing and do one thing

Rob Norris
Patrick McLean
Rob Norris, +1

Creator Economy

+4

Build your own door

May 19, 2026

•

5 min read

Build your own door

Don't wait for gatekeepers to let you in

Rob Norris
Rob Norris

Encore Career

+4

Your agency of one

May 12, 2026

•

5 min read

Your agency of one

How to build a screen porch side hustle

Rob Norris
Rob Norris

Creator Economy

+4

A Newsletter Became a Community Became a Fund.

May 5, 2026

•

5 min read

A Newsletter Became a Community Became a Fund.

What I learned helping my son build the audience he's now raising a venture fund on top of.

Rob Norris
Rob Norris

Encore Career

+3

You've Been a Copywriter for 30 Years. You Just Called It Something Else.

Apr 28, 2026

•

4 min read

You've Been a Copywriter for 30 Years. You Just Called It Something Else.

The flood is here. The filter is the part you already built.

Rob Norris
Rob Norris

Encore Career

+3

Sun Tzu didn't have a 5-Year Plan

Apr 21, 2026

•

5 min read

Sun Tzu didn't have a 5-Year Plan

And you don't need one either

Rob Norris
Rob Norris

Entrepreneurship

+3

Nobody Saw This Coming

Apr 14, 2026

•

9 min read

Nobody Saw This Coming

(Except the People Who Did)

Rob Norris
Rob Norris

Encore Career

+3

Listen to your father

Apr 7, 2026

•

8 min read

Listen to your father

80's advice holds true today

Rob Norris
Rob Norris

Essential Reading

+4

The Late-Career Entrepreneur: Why Starting After 50 Is a Competitive Advantage, Not a Handicap

Apr 4, 2026

•

8 min read

The Late-Career Entrepreneur: Why Starting After 50 Is a Competitive Advantage, Not a Handicap

Rob Norris
Rob Norris

Encore Career

+3

Mastery is in high demand

Mar 31, 2026

•

9 min read

Mastery is in high demand

Experience and judgement are exactly what the AI economy needs

Rob Norris
Rob Norris

Essential Reading

+4

AI Won't Replace You. But a 28-Year-Old Using AI Might.

Mar 24, 2026

•

13 min read

AI Won't Replace You. But a 28-Year-Old Using AI Might.

Rob Norris
Rob Norris

Encore Career

+3

Your biggest Business Idea is Already Solved

Mar 24, 2026

•

9 min read

Your biggest Business Idea is Already Solved

You've been sitting on it for decades

Rob Norris
Rob Norris

Essential Reading

+4

12 Encore Career Ideas for Executives (That Actually Use What You Know)

Mar 21, 2026

•

17 min read

12 Encore Career Ideas for Executives (That Actually Use What You Know)

Rob Norris
Rob Norris

Innovation

+5

Eat your own dog food

Mar 17, 2026

•

10 min read

Eat your own dog food

AI agent projects you can build this weekend

Rob Norris
Rob Norris
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